Founder Separation Anxiety

You’re the founder of a growing startup and it seems like just yesterday that you were a team of five, sharing a co-working space with one table and five chairs. There was an open flow of communication in the room and unless someone’s headphones were on to signal they were “in the zone”, anything was fair game to chat about.

Full Stack Engineer: “I’m thinking of moving the ‘Learn More’ button to the bottom right of the home page.”

CEO: “Sounds good. What do you think about what that potential customer said yesterday about our pricing? Should we push harder”?

CTO: “I d’no. Maybe we should talk to a couple more prospects and compare reactions?”

Full Stack Engineer: “Just so y’all know, I am probably going to revamp the pricing page layout in the next few days so if you’re thinking about changing things, lmk sooner vs. later, cool?”

CEO: “Totally, no worries, friend.”

Customer Support Rep: “Keep me in the loop too, all. I want to be prepared if customers start asking questions about the new layout or pricing changes.”

CTO: “You got it, friend.”

Operations Tech: “Yo, after lunch today can we talk about how capacity is doing with all these new customers? We might need to buy more cloud storage.”

CEO: “Ugh, I was hoping to keep our spending down before we close our A round next quarter, but I guess that’s a good sign that we’re selling. Revenue, yay!.”

It wasn’t unusual for the whole team to know every facet of the business. Where you were with sales, fundraising and how customers were feeling about every little change you made to the product. You saw each other’s work on your screens or perhaps, if all remote, you were in a non-stop thread in Slack with very few separate channels. It was intimate and cool….intoxicating. Even as the team grew from five to twenty five, there is this sense of deep connection that the early employees had with the founders of the business. A unique badge of honor which often garnered the respect of newer employees eager to hear the lore of those early days. However, with that growth, there becomes less intimacy and these early employees often find themselves with managers between them and the founders. This can create separation anxiety which manifests in different ways — from temper tantrums in meetings to disengagement and generally bad behavior — and can be the root of cultural issues or worse, unwanted attrition.

While many early employees will adjust to the scale of the business and the founders letting go of the details, some can become frustrated. They no longer feel “in the know” or are recognized as the CEO’s trusted advisor on particular decisions for the business. They are scolded for going around their new manager’s back to get the CTO’s opinions on their work or they try to undermine a decision made by the new head of a department by complaining to the CEO. Even finding time to just chat with the founder is a game of calendar Tetris for them. “They don’t have time for me anymore.” is a common sentiment. For these employees, you (or they) may feel that a scaling business is not a fit. Early stage is their sweet spot and a transition may be necessary. However, before concluding that it’s time for some of these early team members to transition, here are a few suggestions to manage Founder Separation Anxiety:

  • Openly discuss this situation with your team. It is a natural aspect of growth and success, but it requires managing expectations. “Good news, we’re growing! But this means we are going to be shifting how we work and some of us will be less in the know than we used to be.” This can be a great opportunity to ask the team what they need and where they are feeling the biggest gaps. Address what you can, but accept that you may not be able to honor all their asks. For example, being less in the know on board-level or financial issues as they may have in the “old days”.
  • Make sure you are accessible to your entire organization as much as you can be in both structured and unstructured ways. Create open office hours or lunch-n-learns for team members other than your direct reports to get time with you. Open office hours can be a standing block on your calendar (1–2 hours per week) where anyone can pop into your office (or jump on a zoom if you’re remote) and chat. Be clear that this time is to chat or bounce ideas around, not for decisions or setting strategy. Some newer employees might just want the time to get to know you better — your founder’s story or background (or theirs). These are invaluable opportunities to build a connection with your team. Unstructured time is simply ensuring you’re not tied up in meetings all day and have blocks of open time to walk around the office or pop into different Slack channels or Discord or whatever your business uses for remote communication.
  • Offer suggestions on how and when team members should book time with you outside of office hours. E.g., “Office hours are a great way to bounce ideas around with me or share ideas or thoughts about the business, but if you want to go deeper on a topic, let’s schedule a specific time to discuss and include others as needed.”
  • Set boundaries for early-timers when they try to end-around new bosses. Be open to listening to their ideas/complaints, but redirect them to their new bosses to make decisions. Coach them on how to express their concerns with their new bosses vs. offering to talk to their boss on their behalf or (worse) commiserate with them. Just because you used to sit next to them in a WeWork a year ago, does not afford them the privilege of undermining their leadership. Hold the line.
  • Be mindful of perceptions that come from “special relationships” between founders and early employees. It is not unusual for early employees to form personal relationships with founders outside of work. Late night beers or weekend family BBQs may have become routine. With a larger team, consider how these special out-of-work connections reflect on your leadership. Optically, it can infer special treatment or that some employees are privy to deeper business details. This does not mean you should end these friendships, but you should set clear boundaries and be transparent about them to the rest of your organization — especially if one of these individuals now reports to someone who reports to you. “Lisa, let’s be sure we don’t talk about work when we get our families together this weekend.” For the team, even just naming this, can allay concerns, but again, transparency is key. To Lisa’s new boss, you might say: “Lisa and I became BFFs in the early days of the company — our kids are BFFs too — but we’re committed to not discussing work when we connect outside of the office”.

This may seem like a lot to manage, but the time investment should result in team members better adjusting to the growing separation between them and the founders and having less anxiety about their roles in the business. You may not retain all of your early employees, but these tactics should mitigate some loss and will likely contribute to fostering a healthy culture of transparency, trust and respect among team members.

What creative techniques have you employed to mitigate Founder Separation Anxiety? Please share in the comments!

On Hiring: Beyond the Interview

There are no books you can read or blog posts you can scan that will guarantee that you make the right hire 100% of the time. From bad chemistry to misunderstandings about role expectations, even the strongest candidate may not work out. Also, despite best efforts, early stage companies or new teams inside scaling business often don’t know what they need until they have someone in a particular role. You might realize “oops, this person is great, but their skills are not what we need!”. It happens at every company. Hiring is HARD.

While you can’t prevent occasional mis-hires, you can try to minimize the possibility by including a project or testing phase in your hiring process. This is the stage beyond the standard interview questions and reference checks that gives you a sense of who this person really is, their skills and how they will approach their role. The goal of these tests is to allow the candidate to demonstrate what they are capable of and what it might be like to work with them once they are on board. These tests are critical and will either help you dodge a mis-hire or give you a higher degree of confidence that this is “the one”. I recommend that these tests are performed when you have 1-2 finalists and just before you are ready to do reference checks and make an offer. This can be an especially helpful step if you are down to two finalists you really like.

With this in mind, below are some tips on how to do these tests. For each of these tests, it’s about how the candidate approaches the test and the problem vs. getting correct answers. Build alignment with your team on what “good looks like” for each test and plan to debrief once the assignment is complete and/or presented. Examples of what good might look like are included below.

The First 90 Days” Test

This is a good general test for any new hire, especially an executive, but also for a people manager or technical leader. Have the candidate explain what their first 90 days on the job will look like. Either leave it wide open or offer a few prompts like “Who will you spend time with?” or “How will you get to know the business?” or “What accomplishments do you hope to make by the end of the first 90-days?”. Avoid being overly prescriptive or leading questions like “Name all the team members you’ll want to get to know” or “Will you spend time with marketing and sales?”. An experienced candidate should have a good sense of how they would spend their first 90 days based on the research they’ve done on your company and insights they’ve gained from interviews with the team.

What good might look like: 

  • Thoughtful about talking with the right stakeholders and when – align with your team on who they’d expect to see on the candidate’s list and when they’d expect to meet with this new hire within the first 90 days
  • Organized and realistic about what can be accomplished in 90 days – align with your team on what you’d expect
  • Asks good questions to get a feel for the assignment – shows they are comfortable with getting clarity on situations (not arrogant)
  • Articulates assumptions made (if any) – often a requirement of leadership roles and demonstrates strong communication skills
  • Cites examples from conversations they’ve had with team members/research they’ve done on the company, market, etc. – demonstrates they listened, interested and have taken the time to understand the opportunity

Engineering and Design Tests

While there are some nifty tools out there that can test coding skills for engineers, I am a strong advocate for testing the human side of these skills. Those who design and/or build your product should be able to demonstrate their work beyond coding or portfolio samples. The best tests here are brief scenarios that demonstrate not just depth of syntax knowledge or design best practices, but also how they will work on a problem with your team. These types of tests can be done as “homework” although it’s nice if it can be done in-person as part of an onsite/video interview. Present a scenario and ask the candidate how they will approach it. You could give them some alone time to think it through and then ask them to talk you (or a domain expert) through it. Ask them to cite how they thought about it and explain the direction they took and why. Prepare to have another approach or idea for the scenario when they walk through their work. This can help gauge how the candidate handles feedback and if they are willing to collaborate on ideas.

Try not to give an assignment that takes more than 1-2 hours to do unless you pay them for the work. I know a company who always pays for the time taken to do the test and if the candidate declines payment, they make a donation to their charity of the candidate’s choice for their time. (So cool!)

What good might look like: 

  • Asks good questions to get a feel for the assignment
  • Articulates assumptions made (if any)
  • Able to explain their work and creative approach; approach aligns with how your team operates and/or offers new ideas that will expand the possibilities for your team/product
  • Comfortable receiving feedback; bonus points if they’re willing to riff on the idea and take it to a better place.

Scenario Tests For Functional Teams (Marketing, Sales, Product, etc.)

Functional leaders are often asked to present a past project they did as a way to demonstrate their work. While this lends insight into the candidate’s past work, I prefer scenario tests. While the former does tell you an experience they had and what worked or not, it will not expose their work on something new. Further, a walkthrough of a former project may not give you insight into what they (vs. other team members) actually did to achieve success. In those cases, I listen for “we did this…” which begs the question “what part of that did YOU do?”. Here are some quick examples of scenario tests for a few functional areas:

Product: Our CTO just came back from a “listening tour” with some of our customers and wants to explore a new set of features to expand our product offerings. These offerings are not on the product roadmap. What steps would you take to understand these new features and how would you approach the prioritization process?

Marketing: We’re about to launch a new product for our customers. It is the first new product we’ve launched in a year. What steps would you take to plan for this product launch and how will you measure its success?

Sales Leader: We are building a product to attract new customers in a new vertical. What information do you need to prepare your team to sell this new product and how will you set sales goals for the team?

You could imagine similar scenarios for finance, customer support or other functional roles. Remember, they still don’t know how your business functions day to day and this isn’t whether they have a perfect plan, but more about how they approach the problem. For functional roles that will require strong communication and presentation skills, have them present their assignments as they would if they were doing it for your team, board or customers, depending on the scenario. For presentations, the ideal flow is interviews, assignment for finalists, and then a presentation to all those who interviewed the candidate. Other key stakeholders could sit in on the presentation, but to mitigate overwhelming the candidate, I suggest only those who interview them do Q&A after the presentation. Q&A should probe what’s being tested (what good looks like) and not to have candidates try to get correct answers.

What good might look like: 

  • Demonstrates research they’ve done to prepare the assignment
    • Including people on your team they may ask to speak with to prepare their preparation
  • Presentation skills – both oral and written. Focus more on content and less on pretty graphics on presentation decks unless that’s an important element of the role
  • Articulates assumptions made (if any).
  • Scenario solution is thoughtful, logical and realistic – align with your team in advance on what this would look like
  • Bonus points if they add insights that the team can learn from (e.g., I once had a VP Marketing candidate tell us what was broken with our SEO and how to improve it as part of his presentation of a hypothetical scenario. It was brilliant!)

With all of the interviews and testing, you still may not get it right every time. Again, hiring is HARD. For some roles, a “try before you buy” is often the best way to go for both the candidate and the company. Not every candidate can opt out of benefits or other things they need from a full time job to do a trial, but if it’s possible or they can do it outside of work, go for it. Pick a project that’s reasonable to do in 30-45 days and agree on what good will look like before they get started. Pay them an hourly rate and set the candidate up for success so they can hit the ground running (e.g., security access to your code repo, slack, etc,) and continue to test the soft skills as they go. if applicable, tell the candidate in advance that if they are hired, equity vesting will start when they started their project vs their actual start date. It’s a nice incentive for them to take the project seriously and know you are invested in their success. 

Finally, if you’re hiring a role for the first time and no one on your team has experience with that role – no one knows what good looks like – ask an advisor, investor or friend with experience to be part of the interview process. They should not only be able to interview the candidate, but also help you formulate the tests!

Do you have other tests or projects you like to use as part of the hiring process? Please share in the comments!

Paving The Way For Less Experienced Hires At Early Startups

Photo Credit From: https://hfaplanning.com/

So many of the early stage companies I work with are struggling to hire talent. Despite the pandemic, they have raised capital and are looking to hire everything from engineering and UX to marketing, sales and support. You’d think with the pandemic there’d be a lot of people looking for work, but in startup land (tech or not), it’s definitely a candidate’s market…unless you are considered too inexperienced for a role. I especially see this for candidates in underrepresented talent groups where there are less opportunities to develop strong networks. Further, less experienced candidates coming from first jobs at a big company where they hoped to gain mentoring and experience before going to a startup can be boxed out before they even get their careers of the ground. These candidates are often viewed as unable to work in a more scrappy, smaller scale organization.

The most common reason for not hiring less experienced talent in a very early stage company (say, less than 20 people) is lack of time to manage and mentor these team members. I get it. If you are a startup leader, you want an A+ team of people who are self-starters and have seen the movie before. While also more expensive, experienced hires should know how things work and in theory should hit the ground running. That said, even experienced hires rarely work effectively and that independently on day one. Further, I don’t know a single startup that has hired an all senior team and never had to let someone go (or they quit) within their first 90 days. This can be because of a mismatch in expectations, lack of alignment or often it’s because the more senior team members had become accustomed to managing more than doing in their prior roles; they were potentially “startup curious” and couldn’t scale down and/or they had lost their player-coach edge.

It is rare that any startup gets their first twenty hires right. Iteration, learning what you need in your team and evolution as your product changes and company grows is a likely cause for lots of refactoring of teams in the first few years. Therefore, hiring a few less experienced folks could net the same result as one senior hire – some will work out, and some will not. Yes, letting someone go or having them quit and starting over is a total time suck, but that’s part of the game and most companies get better and better in finding and keeping great talent over time. From my personal experience working for several startups early on, each of which had insane growth, I found having a mix of seasoned and less experienced team members can be a super power. Less experienced team members were hungry and eager to learn and the senior team members enjoyed mentoring and handing off the more menial tasks so they could focus on meatier and often more strategic work. It was a win-win and many of those junior team members have had incredible careers after we gave them their first shot.

For the Manager

Here are a few things to consider for those anxious about hiring less experienced talent:

  • Pipeline: In this candidates’ market, hiring managers need to treat recruiting like a sales exercise. Fill the funnel! Overly prescriptive job descriptions will limit applicants (especially women) – this includes being too specific about the number of years of experience required which may not translate well for someone who’s been coding since middle school, but has only been in the workforce for 1-2 years. Get the resumes in, then decide how you want to weed out less relevant candidates.
  • Pre-Interview Screening: Don’t judge a resume by it’s timeline! As noted above, many inexperienced candidates – especially engineers – have been doing relevant work well before they went to college or may be understating their contributions in their current roles. They may lack the confidence to promote their work, but that doesn’t mean they can’t get the work done. Consider having a screening question about how long the candidate has been doing relevant work that may not appear on their LinkedIn/resume.
  • Interview: Size the questions and/or the coding exercise with the experience. Determine if the candidate can learn quickly, whether they ask good questions and whether they can deliver on time. Early on in their careers, these are the key skills that will assure they will thrive vs. showing you their perfect coding capabilities in an interview or through a take-home exercise.
  • Potential for hire: If all that is keeping you from hiring a less experienced candidate who shows tons of potential is having the time or talent to mentor these candidates, look beyond yourself and your more experienced team. Have advisors who can sign up to serve as mentors for inexperienced folks. This can range from doing code reviews before check-ins to helping an inexperienced salesperson practice their pitch. These mentors do not have to have full context on your business or the details of the work; if they are seasoned, they know what to look for and should be able to offer objective guidance (and you should offer them some equity and have them sign an NDA, obvi!).
  • On the job: Yay! You are ready to hire a less experienced team member. Set the right expectations and scale the work. As with any hire, they won’t be up to speed on day one. Their 30-60-90 day onboarding process may look different than a more senior hire though. Start small and work up to more challenging tasks. As my favorite leadership coach Brené Brown says in her amazing book Dare To Lead “Paint what ‘done’ looks like.” The most common reason for failure between employees and their leaders in any job – regardless of experience – is misalignment about what the endpoint should look like. Always define and communicate measurable, clear, goals.

NOTE: If you will hire for a role within the next six months, but are not actively filling it, and a current candidate shows promise for that future role, hire them! You don’t want to kick yourself in a few months that you didn’t hire that candidate when you had the chance. This of course assumes you have the budget to do so.

For The Less Experienced Candidate

For folks dealing with the catch-22 of needing experience, but not getting job interviews or offers because you lack enough experience, here are some things to consider:

  • Highlight Transferable Skills: Look deeply at your resume and try to tease out skills you have gained in past roles that are applicable to the job you wish to land. Were you a camp counselor while in college? You likely have strong leadership skills, can multitask and work well in teams. Worked as a waitperson in college? You have sales and customer service experience! Were you on the robotics team or helped friends build their first websites in high school? You started building your technical skills earlier than you think! This also works for job shifters – pull out the buzzwords that highlight your transferable skills. Be explicit under each role such as “Product Management Skills:…” or “Sales Skills:…”.
  • Get Help: Find someone in your network to help you further tease out your experience in your resume and help you practice your interviewing skills. Tap into former bosses, advisors and college professors. If they can’t help directly, they may know someone who can! Practice both technical skills and general communication skills. Both are important.
  • Continuous Ed: Continue to develop your skills outside of school or your day job. Take coding classes online (there are tons) or participate in one of a gazillion webinars designed for core skills like sales, growth marketing and design. A silver lining of the pandemic is that there are now so many great online resources! If you complete these courses, list them on your resume; this shows initiative, willingness to learn and the ability to multitask if you did this work outside of your day job or school.
  • Never Assume: Finally, never assume that just because a company doesn’t have a job posting commensurate with your experience that should not apply. This could be a stretch opportunity or the chance to get a warm introduction to the hiring manager for a future opportunity. Taking steps like this is a first sign that you are ambitious and creative and many people will hire talent despite a position lining up perfectly or even being open. As noted for hiring managers above, good people are hard to come by! I have personally hired many talented people without a perfect fit or a role open at the time because someone showed promise or I knew I’d need them within the next six months.

If all else fails…

Still not sure you can bring someone less experienced on board or can’t get a young startup to take a chance on you? Get creative and offer a “try before you buy” option. Even if part time, it can be great for both the company and the candidate to do a small project together – for pay. The manager can get a sense of a candidate’s work and the candidate can get a sense of what it’s like to work at the company. 

Tips on this concept:

  • Agree on a project that is no more than 2-3 weeks worth of work for a junior team member and with a clear deliverable.
  • Use the time working on the project to meet other members of the team. Schedule a quick meet and greet on Zoom or join team meetings to get a deeper sense of the company culture.
  • If the trial goes well and an offer is made, the equity vesting/cliff start date should be from the start date of the trial project. 
  • Be careful about competitive situations. If a current employer has a clause in their employment agreement that says any relevant work done outside of business belongs to them, don’t do a trial role like this for a related business (sounds obvious, but I have seen this happen too many times!).

I am truly hopeful that more young companies will take chances on less experienced hires. This is where magic can happen for all involved and I can’t tell you how amazing it is to see some of my most junior hires “back in the day” now in senior leadership roles or starting companies of their own. Hopefully, they are now paying it forward!

How have you figured out ways to hire less experienced people or find a role as a less experienced hire yourself? Please share in the comments. You can also read more about my thoughts on hiring here.

Balancing The Many Hats Of A Startup CEO

Illustration by Amelia Austin (c)

Startup CEOs wear many hats that they take on and off as company priorities ebb and flow. One moment they are the CFO and raising capital and the next they are the Head of Product and making critical roadmap decisions. As a quarter-end nears, they become heads of Sales and as the company expands (or contracts) they’re running HR. There can be tremendous stress when a CEO tries to wear too many hats at once or struggles to decide which to wear, which to remove, and which to hand off to someone on their team – if such a team exists! The startup CEOs I coach have used following framework I’ve created to help them determine which hats to where when. While this article is largely focused on startup CEOs, framework can also be an effective tool for other organizational leaders.

* * * * *

The Hats

The most common array of hats that a CEO may wear at any given time fall into the categories below, but no CEO – early stage or not – can split their time and attention so perfectly as the chart denotes.

Before deciding which hats to wear and when, a startup CEO should first identify with what their hats (categories) are in their current role. Using the visual above, here’s how I define these very common categories:

Product (What & When): This is what the company produces. It includes customer discovery, design, building, shipping and support. It also includes prioritization and tradeoff decision making for features, new products and services. Many startup CEOs are product people and this can often be one of the hardest hats to take off completely – if ever. Note that being a product visionary and/or a great coder or designer does not necessarily mean one is a great Product Manager – knowing how to make tradeoffs, analyze customer requirements or develop a product roadmap. Be sure to fully explore this “hat” before deciding it’s one to wear or take off.

Culture & Process (How): I was inspired recently by a coaching client of mine who combined these two into one category. If the culture doesn’t work, then the processes won’t work either. Creating high performing teams goes well beyond what workflows, policies and procedures are in place. It is how the team communicates, operates and evolves as a living organism. Never underestimate the value of focusing on culture with process starting from day one! Some CEOs are natural culture builders and system thinkers, but if this is not a strong suit, it’s definitely a hat that should be worn by an in-house culture expert or by someone with natural team-building/program management skills.

Strategy (Where, Why & When): Determining the company’s True North, setting direction for at least the next 12-18 months and making critical decisions about the company’s mission for things like fundraising, revenue growth and human capital. This is also about defining and communicating why the company is doing what it does which is as important as where it is going. Employees and investors/board members all perform better when there is clarity on why the company is moving in a particular direction. This hat is quite commonly on the CEO’s head forever.

Talent & Development (Who & How): A company will not succeed or grow without hyper focus on the growth of their employees. It is vital to the success and stability of an organization to establish best in class hiring practices and programs as well as to develop each person’s skills as individuals and leaders. As companies grow, CEOs must be thoughtful about where to focus hiring efforts, how to provide incentives to retain top performers and how to grow those with high potential. In addition, as companies grow, there will always be tradeoffs on when to promote from within, when to hire more experienced talent and when it’s time for some team members to move on. CEOs often wear this hat more often than others, but many have COOs or strong HR leaders on their teams who wear this hat permanently.

Back Office (How): A company can have the best product and team in the world and mess things up royally because the back office hat was on the wrong individual’s head. This is mostly finance (accounting, receivables, payroll, etc.) and legal (employee contracts, partnerships, etc.). I’m amazed at how many CEOs wear this hat for too long. It’s ok early stage, but let the professionals do this work once the company hits product market fit and is beginning to operate at scale. Some CEOs are former CFOs who are perfectly capable of leading back office teams, but data shows that CFOs often lack “Outside-in” thinking (a strong mega-trend and customer focus)” and lack the creative and inspirational leadership qualities of a great CEO.

Marketing, Sales & Business Development (What, Why & When): Brand identity, target audiences, community development, filling the pipeline, closing deals and creating strategic partnerships. These tasks often require CEO leadership – especially early stage. Some CEOs are very marketing/sales oriented which can derive huge benefits for the business as long as there are capable leaders on the team wearing other hats. However, many CEOs are not marketers and, like the Back Office hat, should leave that work to the experts.

The Have-to-dos, Want-to-dos & Good-ats

Rather than being stressed out trying to balance all hats at once, it is best to focus on wearing 1-2 hats at a time. These 1-2 hats are those that HAVE to be done. It’s great when these prioritized hats also happen to be hats a leader wants to wear and require skills that they believe they are good at, but that is not always the case – especially for early stage CEOs who often need to do a lot of things that they may be good at, but don’t necessarily want to do. Similarly, there can be things a CEO is good at and wants to do, but the business doesn’t require them to do it. Finally, there are times when something has to be done, the CEO wants to do it, but they lack the skill to do it well (self-professed or not!). Here are a few examples:

  • Finances – CEOs are good at doing the accounting for the business and it has to be done, but usually very willing to give that up as soon as they can hire a head of finance. They don’t want to do it!
  • Product/Technology – No matter how much a founder/CEO wants to design or code – and they may be good at it – there is a point as a company scales that CEOs have to take off this hat. They are no longer “have to-dos” at their level. Note, I have seen a number of CEO-Founders take their CEO hats off to dive back into the product – they not only want to do it, it’s their passion!
  • Hiring – Inexperienced CEOs managing people and leading teams for the first time both have to hire and want to hire, but are often unskilled when it comes to sourcing, interviewing and managing the onboarding experience. This is a skill they are not good at.

If a company is well funded and/or profitable, the CEO can usually move swiftly to swap or delegate hats with the support of their leadership team or investors. They may hire more seasoned leaders or team members and/or offer training for those who need to develop their skills. However, for the fledgling teams who can’t fund these improvements, it is even more important to make hard choices about which hats to wear…even if that means letting some things slide or not executing perfectly. The tradeoffs can be hard, but the focus of this exercise can allow a leader to move quickly from one to the next so things don’t slide for too long. In fact, it is extremely common for CEOs to become so paralyzed about which hats to wear that the performance of the company is suffering more than if they had just picked 1-2 hats to focus on and move forward.

To get started on assessing “have to-dos (HTDs), want to-dos (WTDs) and good-ats (GAs)”, I recommend a two-pronged approach:

  1. Using the categories or hats identified, rate the HTDs, WTDs and GAs today and what the HTDs should be in the future. This exercise requires self reflection and a large dose of humility.
  2. Define what measurable goals must be achieved to remove a particular hat OR issues that need to be resolved to put on a particular hat. Include an action plan (with timeline) that ensures goals can be met. 

Using a framework like the chart below, begin to outline and rate the categories, 1-5. 1=low (this is a hat not being worn, not wanting to do, or something one is not good at ) and 5=high (absolutely something that has to be done, there’s strong passion to do it, self-assesses* that it is a strong skill).

*Self assessed skills are different than how others perceive one’s abilities. If unsure, do a 360-feedback survey with your team or seek outside help!

An optional third step is to color code each row to visually identify hats that are critical to wear (red), not urgent but important (yellow) and the hats that are satisfactory at this time (green).

I’ve created two charts below – before and after – as examples of how a CEO of a post series A startup with modest revenue might perform this exercise:

BEFORE

In the above example, the rows in green show where the CEO is satisfied with their current involvement (“hat wearing”). The rows in yellow are places where they need to adjust their involvement, but not urgent. The two red rows are urgent and where the CEO wants to put their focus. 

  • In the case of Culture & Process, the CEO only rates their hat wearing as a “2” and there are serious issues in the organization to address. The CEO has identified what is going on in the “HTD Achieved/Needed When…” column which requires them to put on the hat and what actions they will take to ensure they are wearing that hat at least at a “4” (HTD Future). 
  • In the second case, the CEO knows the Back Office work is important, but does not want to do back office work, nor do they feel they are good at it. Thus, they are working to remove the Back Office hat and reducing their involvement from a 4 to a 1. In this case, the bullets in the “HTD Achieved/Needed When…” column clarify what will be happening when the CEO has officially taken off that hat, moving it to a “1” (HTD Future).

Identifying what hats need wearing – and how firmly to wear/remove said hats – is step one. Taking actions to add or remove the hat(s) is step two. In the case of ramping up on Culture & Process noted above, the CEO would kick off the action items and set a timeframe of when they would be able to remove that hat. They would then update the chart to be clear what will need to be in place for them to remove/loosen that hat. Similar with Back Office work, once the key actions are achieved, the chart is updated to reflect that the Back Office hat no longer needs wearing. The updated chart may look like this:

AFTER

With the updates above, the CEO has removed their Back Office hat and is firmly wearing the Culture & Process hat. They can now continue to focus on the Culture & Process hat until it can be taken off (“1”). They can also decide which of the two yellow rows – Product and Talent & Development – they want to focus on next while the other areas of the business require less of their attention. 

Most CEOs who follow this process use months or quarters to time-box focused efforts and update the charts, but it all depends on how one works and how fast change is happening inside the organization. Choose what works best for you!

No Recipe Is Perfect

The exercise above is one way of thinking about how to balance many hats a CEO – or any leader of a large team – might wear. There’s no perfect algorithm and while one might aim to only wear a maximum of two hats at a time, there will be times when many hats will have to be worn. I’ve also seen CEOs who find that once they’ve mastered a new skill, the hat they didn’t want to wear is actually one that they enjoyed wearing more than they expected.

There are of course sometimes when CEOs realize that no matter how much training, coaching or mentoring they get, they are not able to wear any of the hats well or they just don’t enjoy wearing them. This is often when the company is achieving a level of scale that requires more experience than the CEO’s own professional experience. Some CEOs recognize this and work with their boards to find a successor, but sometimes this can be a decision taken out of a CEO’s hands when their board/investors decide the business can’t wait for the CEO to grow into the role. I’ve also seen many CEOs who find a great partner (President or COO) to run the business with them and augment some of the skills they have yet to or want to master. This not only keeps the company on the rails, but gives the CEO a role model to learn from along the way.

Conclusion

CEOs should be performing a regular assessment of where their time is focused, identify measurable results when changes are made and what actions to take to get there. Even a simple visual like the Before and After on the balance wheels below can kick start the process. Identifying what the current focus areas are (before) and where should they be (after).

No matter how a leader decides to assess and prioritize their hats, leaning into the balancing process will likely mitigate stress and potential burnout. What processes have you seen that are effective towards balancing hat wearing? Please share in the comments! Meanwhile, if you are thinking about trying this exercise, I have created a google sheet template for anyone to use to start this process. Feel free to save a copy of the template for yourself and dig in!

* * * * *

NOTE: The balancing hat illustration at the top of this article was created by my daughter, Amelia Austin and is copy-written.

Testing Leadership During Trying Times

The stress created by the global spread of the Coronavirus is an opportune time to take stock of how leaders, well….lead. Now more than ever, employees are looking to their leadership teams for strength, guidance and direction. Some leaders may have already had led their teams through storms — perhaps financial, operational, or otherwise — and are tapping into what they learned prior. However, many are leading through a storm for the first time and are being tested.

In the early days of Akamai circa 1999, ~200 of us were learning how to run what was then called the world wide web and manage a newly public company. Many of us were learning how to lead at scale and at an extreme pace with little-to-no experience. One of our founders was an academic, one a business school student and the other a computer scientist. The C-suite included seasoned leadership from outside the company, but it was the founders who were setting the tone for leadership across the organization — especially the computer scientist (Danny Lewin, RIP) who regularly tapped into his military background as an officer in the Israeli Defense Forces. He could be abrasive at times, barking out orders and demanding our attention to mastery, but he was smart as f-ck and his passion for the company was infectious, so we obeyed and tolerated his occasional tirades.

Before 9/11, the company was undergoing tremendous scale challenges while the internet bubble was showing signs of an impending burst. Danny knew we were all feeling the strain and one day decided an inspirational message was in order to rally the troops. The company was distributed across the globe — in the time before Zoom or Hangouts. So, he wrote a long email to the entire company about leadership that today most of us who were leading at that time can summarize in three main points:

To inspire trust: Lead by Example

To build trust among teammates: Suffer Together

To restore trust when it weakens: Hold People Accountable

When September 11, 2001 hit us hard both personally and as a business, most of us had never managed teams through a crisis. So, when the world was in crisis (and we lost Danny on the first plane that hit the towers), the points he made about leadership were absolutely brought to light. We did our best to lead by example, we suffered together and we held ourselves and each other accountable. The trust built among our teams was like no other I had experienced and many of those young leaders — some of my dearest friends — are now master leaders of teams and companies; quite surely in part from what we all experienced together in 2001.

With the world in crisis today, leaders should consider Danny’s advice.

  • Lead by Example: If you tell people to self-isolate and work from home, then you too should work from home. If you are restricting travel for employees, abide by those same restrictions. If team members are clueless about how to work effectively from home, demonstrate how it’s done or appoint experienced employees as mentors to guide the newbs. If you expect people to communicate clearly and often, do the same. During times of confusion and ambiguity, leaders are the guiding light — even if the only thing you can say is “I don’t know”. Being vulnerable and not having all the answers can be as powerful as having a perfect plan. It also allows others to do the same.
  • Suffer Together: Now more than ever is when teams need empathy; that you’re in this together. Employees are not just worried about personal illness; they are worried about their family, trips they have planned in the future, their personal finances and how business will fare during a volatile time. No one will be unscathed from this current crisis. You are all suffering together. Create forums for people to talk with each other, offer support and listen. Even if many people in your organization do not get sick or have ill family members, they are dealing with a crisis that is very real. The news and social media is in their faces and they will not ignore it. Accept this and share your own worries and concerns. Show your vulnerabilities and they will do the same. From my 9/11 experience, I can say that crying with co-workers was one of the most transformational moments in my career. No matter our differences, we had a shared experience that strengthened ties and allowed us to rise to the challenge and succeed.
  • Hold People Accountable: Times of crisis are when leaders show their true colors. Great business leaders during tough times are decisive and put the company, their employees, their customers and investors ahead of themselves. They are not seeking friends or trying to win a popularity contest and may make unfavorable decisions. Decisions like closing the office, cancelling a conference or back-burnering projects to accommodate business disruptions are not consensus building exercises. Decide and move forward. Once those tough calls are made, communicate very clearly who is accountable to execute on next steps. Set clear expectations on how everyone is expected to move forward; including communication protocols (cadence, timing and audience). Employees want leaders who can make calls — especially during tough times — even if they don’t like the decision.

If you are old-hat at dealing with times of crisis, reach out to the less experienced leaders in your network and offer a hand. If you are a first-timer, seek counsel from mentors, coaches and peers. You don’t need to figure this all out on your own. This is not time for heroics. Great leaders get help. We’ll get through this, just like we have in the past, and we’ll be ready for the next one. Be safe, lead…and wash your hands!

Beyond Their Funds, How Can Your Investors Be Helpful?

An entrepreneur recently said to me “When it gets really hard, I feel like I’m doing it wrong.” She went on to say that sometimes she’s not sure how her investors could be helpful — even if it’s just validating what’s hard vs. advising on how to work through certain challenges. I’ve heard other entrepreneurs say they’d like to get help from their investors but worry that purely by asking for help it will signal a weakness. Conversely, I’ve heard investors say they wish the leaders of their portfolio companies would be more transparent about challenges they are facing and ask for help. As one investor said to me recently, “They already sold me on the business and have our money. It’s now our firm’s job to help them succeed.”

In an informal Twitter poll I recently conducted, 56% of entrepreneurs who responded said their most common ask of their investors is for hiring help. Second to that (31%) are asks for introductions to potential partners or customers and a small percentage (13%) tap their investors for financial management advice.

I also polled my investor friends on what questions they like to get from their portfolio companies. What they shared made it clear to me that they can and want to be helpful well beyond their funds!

“Good entrepreneurs are learning machines so they’re always asking for advice and guidance from multiple sources of expertise, including their investors. In fact, the best founders are outstanding at squeezing every bit of insight, advice and contacts from their network of investors and advisers.“ Jeff Bussgang, Flybridge Capital

Do you know how to get the most from your investors? Below, I have outlined what I consider to be basic asks (table stakes) as well as suggestions for deeper asks.

What To Ask For

Hiring

Table Stakes:

  • Referrals and warm introductions
  • Posting job links on their websites
  • Invitations to recruiting events

Beyond the Basics:

  • Seek examples of job descriptions (JDs) and/or critiques of those you’ve written. Most investors were operators once and have a good sense of how to write a good JD; they may also have a recruiting arm at their firm who can counsel you on specific searches. [See point on compensation in Financials, below]
  • New to hiring? Practice interviewing candidates with investors or their associates before bringing actual candidates in for the real interview.
  • Resume screening can be an easy ask and a quick job for someone who’s seen 100’s if not 1000’s of resumes. Experienced eyes can point out immediate red flags and give you specific areas you may want to probe for a particular candidate.
  • Invite an investor to help diversify an otherwise homogeneous interview team. This can be a game changer for a candidate who may otherwise feel like they are a token hire. Knowing the extended team around the business is diverse, can allay these concerns.
  • Ask your investors to help sell the business to prospective candidates. This can be especially critical if you’re trying to hire a senior team member or a start-up first-timer.

    “This is something we continue to do, even with mid-level hires in mid-stage companies when the founder feels like a highly desirable candidate could use an extra push. It’s not a huge burden on our side, but can have a very strong positive impression on the candidate who probably feels like getting board/investor visibility is a strong positive in their career development. “ Rob Go, NextView Ventures

  • Investors can also be helpful offering insights on how your company is perceived as a workplace from their own perspective or from feedback they’ve garnered in the market. (people talk…)
  • Finally, but very carefully, investors may be able to help you get backdoor references on potential hires. I wrote more about this particular topic here. Backdoor references can be helpful, but only if done right!

Marketing, Sales & Partnerships

Table Stakes:

  • Introductions to potential customers and/or partners
  • Putting your company logo on their website; putting their firm’s logo/board member on your website
  • Invitations to marketing & sales events
  • Tapping their social media presence for sharing news and events

Beyond the Basics:

  • Investors look at markets all day, every day, and have an objective perspective on not just current market forces, but patterns over time and how markets move and customers buy. They may not know your specific market details or the intimate buying patterns of your target customer, but as Bob Mason of Project11 says “We often ask the right questions informed by our opportunity to step out of the day to day urgency of running the business. We have enough knowledge to understand the big market forces, see patterns from other businesses and can help drive an engaged dialogue. For the engineering-centric founders, you can think about this as ‘debugging’ an issue. When coding, you might bang your head for hours trying to find the root cause of a hard bug. But you bring over a colleague and talk through the situation and often a solution will appear. They didn’t tell you the answer, but the process of conversation brought insight to your mind.”
  • Whether you are building an enterprise product and need access to a buyer inside a potential large customer or trying to develop partnerships for your business (B2B or B2C), investors can provide invaluable insights on what drives particular companies, who the “real” decision makers are and how their buy/partnership process works. They can reach out to execs at companies and get an early feel as to how important such a potential deal or relationship could be.
  • Investors are generally good at analyzing marketing or sales funnels. If they are former marketers or sales people, they should be able to help you understand the “magic moment”, points of stickiness, drop off, etc.. They also won’t have the biases you likely bring to the table and can look at the numbers objectively.
  • Investors can be helpful with developing your company and product story as well as speak with folks in the industry to see how the story resonates.
  • Beyond offering advice on digital marketing and leveraging social media, your investors may also be helpful with brand awareness and offer PR opportunities. Perhaps they are sponsoring an event where you or a key member of your team can be a speaker? If one of your investors is a blogger, ask for a mention in their next blog post about a topic you’ve been discussing, or perhaps even a guest blog spot. Be creative about how your investors can help shine a light on your brand, product and team!

Product

Table Stakes:

  • If they can use your product as a firm or as individuals, they better be using it! Whether it’s for testing the MVP or to dogfood the brand, no excuses. There’s nothing more compelling than an investor who offers you a cup of coffee made with one of their portfolio company’s new beans or the investor who has a “powered by” one of their companies on their website. Have you asked your investors to use your product?
  • When asked (or not), investors never lack for advice on how your product can improve. Just remember, you are in it every day, they are not. So, always weigh that advice against what your team is discovering with your customers and progress accordingly.

Beyond the Basics:

  • If your investor is a former operator, especially at an early stage company, odds are they have built/tested many an MVP. Engage them in the MVP discussion. Review product priorities and test plans. Again, their objectivity and experience could give you a fresh perspective. This will also help them understand the tradeoff decisions you are making and can be very informative when it comes to strategic thinking about the company’s product roadmap and long term direction.
  • Speaking of roadmaps, if you’ve got a former head of product or VPE on your investor team, invite them to a planning session. Same reasons as above — fresh perspective and added insight when it comes to bigger picture discussions.
  • Security and compliance is an area often overlooked and where investors can probably draw on their own or other resources to ensure your company doesn’t get tripped up on a sale or regulatory issue because an “I” was not dotted or “T” crossed. They may have access to pen testers or be familiar with compliance requirements for things like PIAHIPPA or SOX through other portfolio companies’ experiences; even if it’s just asking when to worry about it vs. holding off on investing in this work.
  • Also helpful is tapping investors’ technical EiRs and/or network. When I was CTO at DigitalOcean, it was amazing to have someone like Martin Casado at a16z, our lead investor, to bounce ideas off of and even help us with some tricky architecture decisions. Similarly, my friend Jocelyn Goldfein of Zetta Venture Partners said she’s often tapped by her portfolio companies to help with developing data strategies and answer questions about data rights. Know who the experts are in these firms and they’ll probably love the opportunity to get into the details with you since it’s no longer their day job.

People

Table Stakes:

  • If they are involved with financial planning, investors should be helpful with basic headcount and organizational growth plans (what roles to fill, how many and when)
  • Investors are generally not shy about telling you (sometimes unsolicited) if they think a key employee they are interacting with is great, needs coaching or may not be successful in your organization. Just remember, if you have a board, other than the CEO, they don’t make hiring or firing decisions. That’s your job.

Beyond the Basics:

  • Whether they were former operators, or have just seen a large number of companies operate, investors can give helpful insight around people and culture. You can ask how to work through team challenges, enhance your company culture or even how to make remote teams work. If they’re not the experts in these areas, they likely have companies in their portfolios who are doing creative things or who maybe learned from mistakes and are willing to share tips and tricks to avoid pitfalls as you scale.
  • While it may make you feel vulnerable, asking your investors for guidance around your own personal development demonstrates your willingness to grow — especially if you are a first-time CEO, or other member of the C-Suite. I’ve seen investors coach leaders on everything from how to lead their teams and handle challenging employees to how to run a great board meeting. I’ve also seen investors support and sometimes even pay for executive coaches and training programs for high-potential leaders.

    “Drop your shields, if you think asking for advice or help from your investors is showing signs of weakness you have it all wrong. Your investors are by definition already on your side and any problem you are facing or any area of growth where you think they may be able to contribute to or connect you to someone who can be helpful, go for it. I want leaders to ask me ‘what am I doing wrong, where can I level up?’” Reed Sturtevant, The Engine

  • Beyond headcount and budgets, investors with experience leading teams at scale can be very helpful with how to think about organizational design through various stages of growth. Investors can also have a really good sense of leveling across organizations and have seen a lot of creative approaches used across companies.

Financials

Table Stakes:

  • Investment checks
  • Future rounds  —  financing strategy, valuation, etc.

Beyond the Basics:

  • It’s never too soon to get “budget religion”, especially if you have a capital-intensive business where you need to figure out working capital, financing with manufacturing, etc.. Ask for guidance on how best to manage your funds as well as how to track burn and prepare data for future financing to make the diligence process easier for new investors. They may even have models or frameworks other portfolio companies use that you can borrow.
  • Not sure whether your compensation packages are competitive or fair? Or how to think about equity vs. salary splits? Comping your sales team? Your investors have probably seen many different configurations and can help you get creative if you’re trying to land a key hire or to retain and motivate your current team.
  • Other financial areas where investors can be helpful are ways to think about marketing spend as a ratio of investment in engineering or sales/revenue, pricing models and tax considerations.

In all of the above cases, if your investors can’t help you directly, odds are very high that they know someone who can. Good investors won’t expect you, especially if you are a first-time founder, to figure it out all by yourself. For me personally, I always appreciate the humility that comes from anyone who knows what they don’t know and asks for help. It is impossible for anyone to know everything!

How To Ask

There are three ways I think every founder should interact with their investors outside of board meetings (if you have them).

  1. Investor update emails are always a good vehicle for asks. If you’re not sure if anyone on the investment team can be helpful, be specific: “Looking for advice on digital marketing strategies.” or “Would love to talk with someone in your network who can advise my team on HIPPA compliance.”.
  2. Routine 1:1 calls or meetings are a must. This establishes a good touchpoint with investors to establish a rapport and catch up informally instead of waiting for a crisis or issue to arise as a reason for a call. I suggest you always have at least one ask for these meetings and always follow up with a quick email with that ask in writing.
  3. Identify at least one domain area where each investor may serve you best (e.g., I am usually the go-to person for product & engineering or organizational planning for my angel investments and advisees). When the needs arise, set up face-time to dig into that specific topic with that investor.

Remember, your investors are not just here to provide cash. They are invested in you and your company’s success. As Jason Seats of TechStars says, when in doubt, “pretend that they are not an investor and figure out what you’d ask them. If you can’t come up with anything, they may not be a good investor for you.” This can also be a nice hack around targeting the right investors from the start.

Have other examples of ways your investors have been helpful beyond their funds? Please share in the comments.

 

Mastering The Team Meeting

No matter how much we hate going to meetings, there’s a generally accepted best practice that teams should meet with their manager as a group on a regular cadence. More often than not, I hear leaders and/or their staff dreading their team meeting. Instead of these meetings being the least favorite time suck of the week, wouldn’t it be great if these were the meetings we looked forward to? That we felt it was time well spent with our colleagues and added value to our roles in some meaningful way?

There’s no reason you have to suffer or make your teams suffer through another tortuous hour or more. A while back, I shared protips on Mastering the 1:1. Now, herewith my tips on Mastering the team meeting…

Meeting Purpose: Set a clear purpose for your team meeting. What do you want your team to get out of the time spent together? Do you want them to stay informed about larger topics in the organization? Get to know each other and their respective work better? Whether you are rebooting a long standing meeting or you are a new leader of a team gearing up for your first routine meeting, talk with your team members about what they want out of the session. This time is much more about their needs than yours, so align the purpose with their needs. A fun way to get this dialogue going is to ask each team member to complete this sentence: “My favorite meeting of the week is my manager’s team meeting because……” What would they say?

Agenda: I am a firm believer that if a meeting is important enough to have, it should have a time-boxed agenda and always be followed up with notes and action items (“AIs”). Protips on setting the agenda:

  1. As the team leader, you should solicit 1-2 “hot” topics per meeting from your team. I recommend you do this no more and no less than 48 hours before it is scheduled so ideas are timely and content is fresh. Topics should not be tactical – that’s what stand-ups and 1:1s are for. Instead, focus on strategic discussions and information sharing. On the latter, do not make it a status reporting meeting. Information sharing could be a product demo, or draft of a presentation someone is preparing for a conference or a preview of a big announcement to solicit feedback before it goes out.
  2. Always send the agenda for the meeting 24 hours in advance. This sets expectations and ensures no surprises and attendees are well prepared.
  3. Prepping for the meeting should take less than 15 minutes. Solicit agenda items – prepare agenda – communicate agenda. Long slide decks and spreadsheets created just FOR the meeting is a total waste of time. If those materials already exist and can add value to the discussion, then owners of said content should A) share these materials ahead of the meeting for pre-reading and B) bring said materials with them and be prepared to share them at the meeting.
  4. Lead by example for your team and read all materials sent in advance before the meeting. If you have not read them, no one else will and again, you’re wasting people’s time. If you’re prepared, everyone else will be prepared.
  5. Finally, always carve out 10 minutes at the end of the agenda to take a pulse on your team. My method is “share thumbs at one”. Three, two, one and on one have everyone in the meeting give a thumbs up, down or sideways. I do a quick read of the room and video screens to gauge if we’re trending in a particular direction and, if so, take time to discuss. People feeling really up? Share why! People feeling down? How can we work together to make things better? This simple, transparent, way of sharing how the team is feeling is a great way for you to lead and for them to support each other. I also find doing this at the end vs. the start of a meeting tends to be a better read because no one is bringing the stress from a prior meeting into their pulse check.

Meeting Engagement: No one wants to listen to a monologue at the team meeting and no one wants to be in a meeting with other people who are checked out. Several protips to avoid this:

  1. Ask 1-2 members of your team to take the lead on the hot topics in each meeting. They do not need to be the experts on the topic, just the topic leader. This includes having them facilitate getting pre-reads to team members ahead of the meeting. The more they have ownership in a topic, the more engaged they’ll be.
  2. The team’s leader should not speak more than ⅓ of the time throughout the meeting. Other than updating your team about broad company topics, your job is to facilitate the discussion and LISTEN. If you’re a bad facilitator (not every leader’s strong suit), then appoint or bring someone in to facilitate. I’ve seen everything from EAs and HR leaders to program managers serve as facilitators of meetings – they keep the meeting on topic, on time and pay attention to the room. I don’t recommend one of your team members be the facilitator – they are there as an engaged participant, only.
  3. READ THE ROOM. Are people reading their email, checked out on a remote phone or video line or rolling their eyes at each other (visibly or under the table on their cells via text…)? Pay attention to what’s happening in the meeting and pause if you see this kind of behavior. If you’re losing people, you’re wasting everyone’s time and you’re costing the company money. (do the math, the average team meeting can cost a company thousands of dollars every week!). Tell people to put their phones or laptops away if they are checked out. Ask people called in remotely if they have anything to add to the conversation. Pull them in. If the topic is falling flat, be direct and ask why or solicit suggestions on how to make it more engaging. E.g., budget discussions are rarely engaging so even a simple “bare with me as we get through this” can go a long way.
  4. Have fun! It’s great to start a meeting with a funny anecdote or personal story to wake up the room. Maybe someone on your team has a good customer story or had someone on their team get a “win” worth sharing. Perhaps you have a fun personal story to share that shows your human side. Keep it light where you can, but serious during some of the tougher topics (budget, staffing, etc.). This fortifies the culture of your team both inside and outside of the meeting.

Tactical Stuff: When you meet and who goes to the meeting is just as important as the agenda and the content. Protips:

  1. Timing: Got a distributed team in multiple timezones? Find a time that’s mutually convenient for all team members. Do you find the meetings always run over? Schedule it for an extra 30 minutes and if it ends early, everyone gets time back – you’re a hero. Does the team have family responsibilities in the morning or after work? Don’t schedule the meeting such that it disrupts their lives outside of work (if it can be avoided). I also generally discourage team meetings on Mondays (frequent holidays/long weekends means rescheduling or skipping too often) and Fridays (long weekends and if hard topics, no time to debrief/process offline before the weekend).
  2. Decision making: If a meeting has >8 people attending, it is an “information sharing” meeting. Less than that, and decisions can be made at the meeting. If you have a team greater than 8 people, tee up decision topics for discussion and, unless it’s a layup, take the actual decision off line. Otherwise, there are “too many cooks”.
  3. Assign and rotate a note taker at every meeting. You and/or the facilitator cannot read the room and take notes at the same time. Further, by rotating the role across your team, you foster engagement and get fresh perspectives on the meetings each time. Notes should be distributed no later than 24 hours after the meeting while things are fresh. Always call out AIs with owners and deadlines in the notes.
  4. Guests: An agenda should always build in intros for guests and should be time-boxed for cameos. For example, if the head of HR is a guest at your meeting to talk through the next review cycle with your team, the team should know that person will be there and why. Further, unless there’s scheduling trickiness, have guests come at the start or end of the meeting so as not to disrupt the meeting with people coming and going throughout. My personal preference is guests at the start. Then we get into our regular routine.

Most important, don’t set it and forget it. If you do change things up, be clear on why you’re doing it and give it time to settle. Starting or overhauling your meeting process won’t necessarily show positive results the very next meeting and changing it too often will not only cause unrest with your team, but can create distrust if the rules of engagement keep changing. Have at least 4-6 meetings for a new routine to set in and then evaluate whether the changes are effective and adjust as needed. Solicit feedback from your team regularly too – after all, it’s their meeting!

Do you run a kick ass team meeting? Or, do you have ideas on how to improve the team meetings you attend? Share your protips in the comments!

Hard To Do, And Easy To Screw Up; A Primer On Hiring For Startups

One of the most popular conversations I have with entrepreneurs I work with is how to improve their recruiting and hiring strategy. I love when they dive into this topic early on because it’s one of the hardest parts of running any company, no matter how small or big, and super easy to screw up. It’s also extra hard these days for tech companies when talent is sparse and you’re trying to create a culture of diversity. The blog post below is definitely not comprehensive and also not a replacement for a company-specific conversation tailored to your business, products and team, but in most cases these tips should be useful.

Herewith, a primer on hiring for startups.

business-people-sitting

Your Hiring Strategy

How much time have you put into thinking about what roles you will hire and when? It’s easy to say “we just raised x-million dollars, let’s hire!”. Then, oops, twelve months in you realize you have a bunch of people you don’t really need or worse, you’re running out of cash. Take some time to think about your hiring strategy. Don’t just plot out how much money you’ll spend per quarter on “heads”, but consider what roles they’ll play and how senior or junior each one will be. Also think about what roles could be filled by contractors vs. full time hires.

One exercise I often ask entrepreneurs to do is to draw an org chart of what their company might look like 12 months from now. Then, plot out the growth stages in hiring along the way. While their company will almost certainly change a lot between when they start and what it will look like along the way, having some idea of which and when roles may be added, and what they will cost, is a good way to think about how to prioritize your hires.

org_phase1

Org. Phase 1 (first 6-12 months)

org_phase2

Org Phase 2 (Months 12-18)

Beyond budgeting for growth (and compensation – including equity – each role may require), you should also consider time invested in getting those hires and lead time to fill the positions. Assume you and/or your team will spend a lot of time finding the right people, interviewing, selling candidates on the opportunity and getting them on board. Ask any first-time founder and they’ll tell you hiring consumed way more of their time early on than they ever expected. Further, just because you’ve got a position open, doesn’t mean you’ll fill it right away; especially if you keep the bar high and don’t settle for just anyone for the role. Resist the temptation to hire too fast for key positions. The opportunity cost associated with letting the wrong hire go and starting over is extremely high.

The Job Description

Once you know what roles you want to fill and when, you should write a basic job description (JD). This not only gives you a tangible to market the position, but it also serves as a communication tool with your team to be clear on what the role is and what you’ll be looking for in the candidates they may be helping you interview.

No matter where you post or share the JD, if it doesn’t attract the right people to apply for the job, you’ve failed right out of the gate. You want as many candidates to apply for the job as possible. Some tips on writing a good JD:

  • Avoid overt and subtle gender bias
    • Don’t use specific pronouns. Just don’t.
    • Test your job description for gender themed words and other potential biases. Try to keep it neutral.
  • Highlight a need for aptitude and attitude over must-have tech skills
    • Fast learner, dedication, multi-faceted skills – all good ways to suggest you care about potential.
    • Research shows that women, specifically, generally won’t apply for jobs where they don’t meet all the required skills. Don’t create an exhaustive list. Only highlight critical skills. You can always prod for more specifics once they’re in for an interview.
  • Highlight training opportunities – this suggests you can get them there vs. absolute required skills.
  • Avoid superlatives – “Ninja” “Expert” “top in their field” can all be deterrents to someone applying for the role. While we all want to hire people with high self esteem, some people are very humble and may not think they are an expert. Even if they are!

Sourcing

Sourcing candidates is a complex process that goes well beyond just posting the JD on your website or AngelList.

  • Make your “jobs” or “careers” page GREAT. Candidates who go there should feel like “I want to work with those people!” Two of my favorite career sites right now are DigitalOcean and Wistia. Both convey a strong sense of culture as well as make it very clear what positions are open.
  • Think about posting on other sites that are related to your industry. Perhaps affinity or user group sites. For example, She Geeks Out has a Slack site that has a jobs channel. Only women geeks are on that site and many are looking for jobs! Or maybe a hardware meet-up site or industry association site.
  • Your best hires will come from people you know. Consider using a networking tool like Drafted to tap into your network and your friends’ networks to find the right people. Even a small bounty can be a big incentive to get the right referrals.
  • Think about having a BIZZpage or post on the Jobs Board on VentureFizz (Boston) or similar sites to get more local visibility.
  • Most VCs have job postings on their website for their portfolio companies. If you’re venture backed, leverage this!
  • Don’t just promote the job on your social media channels but ask your network (including advisors, mentors and your board) to do so as well. Make it easy for them by creating the tweet, FB post, etc, with the appropriate text and links.
  • Campus recruiting is an awesome way to get young talent – especially here in Boston! Try to get resumes of students who will be at job fairs in advance. If you see some you like, reach out ahead of time and make contact. Maybe ask them their t-shirt size (if you have wearable swag) and tell them you’re exited to see them at the job fair. It’s a great way to get candidates to actually stop by your booth. Have swag at your booth and, most importantly, have people who know your company and understand the roles you’re trying to fill.
  • On whether to use outsourced vs. in-house recruiters, it depends on what your hiring strategy is.
    • If you think you’re going to have a regular cadence of hires over the next 1-2 years or more, hire a permanent recruiter who can manage the entire lifecycle – from helping with job descriptions, to sourcing, managing the interview process and on boarding your new hire. Someone who’s in-house will understand your product, your culture and the kinds of people you hire. They will save you gobs of time and energy when it comes to finding and hiring the best candidates.
    • Outsourced recruiters are great for targeted, high ranking, positions like a head of sales or a VP of Engineering. Don’t waste your time combing your network for these people unless you find someone right away. That’s what these guys are good at. Have them work on a fee for placement contract vs. a retainer up front. This is a good way to motivate the recruiter and the best ones will be happy to work this way.
  • Finally, leverage your team. Remind everyone at your company that they are on the hook to always be looking for talent and selling your company as a great place to work. The best hires often come from internal referrals. Consider offering a referral bonus for referrals who are hired and stay on board >90 days. Remember, though, some cash or cash equivalents (e.g., gift cards) are considered taxable income!

Resume Review

Fewer candidates are relying on paper resumes these days in favor of LinkedIn, but you will still see the standard resume for awhile. Here’s what I look for when I read resumes, as well as LinkedIn and Github profiles and Google searches:

  • A summary paragraph should help me understand a candidate’s brand. Are they a builder and leader of teams? A technology architect that knows how to build something from the ground up and to scale? Can they close a deal or build a relationship with strategic partners?
  • Track record is important. These days, it’s not unusual to see someone 1-2 years one place and then another. I look for “jumpers” though – people who have been <1 year in a few places tells me they either can’t fit in or they have made a lot of bad judgment calls on the companies they’ve joined. One or two jumps among longer stints are OK though. Especially if it’s someone who had a long track record somewhere else, and is now trying to find their next home.
  • resume_reviewI want to see more about what someone has accomplished than their responsibilities – ideally with metrics. For example, they wrote a coding standards guide or implemented a scrum process that improved code release velocity by X% or created a sales strategy that improved MRR by Y. What someone was/is responsible for is not as powerful as what they actually got done!
    • Unless they just graduated or I’m hiring for a research position, I don’t want to see education on the top. I care more about what they’ve actually done than where they’ve been educated or their GPA. Anyone with no work experience, even if a recent grad, is suspect for a startup. It questions how hungry this person is and how hard they’re willing to work.
  • If it is a research type of role, then I do look for publications with others, patent filings (even if provisional) and conference experience. This tells me they’re serious about their work, can collaborate, can bring something to a conclusion and present their ideas. Without all of this, I’d worry they are more into experimenting and not getting anything of significance done and/or able to work with others.
  • On LinkedIn, I often get the general resume/CV info I need, but more importantly, I look for how the candidate has chosen to present themselves; like a good summary and a full story of their job history, education and groups they’re a part of. If they are an active candidate looking for a job (vs. a passive candidate I’m trying to lure away from a comfortable job), then I expect their profile to be up-to-date and clean. They should be savvy enough to know that hiring managers and recruiters will be searching for them on LinkedIn. I expect to see alignment with the resume/CV they provided. I also expect to see a few, current, recommendations for active candidates. Finally, I look for mutual connections who could be good back door references (more on this below).
  • Regarding Github, it’s a nice way to see how an engineer contributes to open source projects or their coding style or community followers. However, keep in mind it is a not always an indicator of someone’s professional work. For a very technical role, I still have engineers provide real coding samples and/or do a small coding exercise with one of my engineers to see how they code in the real world.
  • Finally, Googling a candidate for anything “suspect” never hurts. Bigger companies do background checks. As a startup, a good check can be just looking to see if you can find arrest records or other behaviors that may not gel with your company culture. However, not every bad find on a web search is a flag not to hire. Some people drank too much in college and have gone on to have wonderfully successful professional lives 😉

The Interview and Candidate Experience

So many companies underestimate how important candidate experience is to landing the best hires. From the first blush with the candidate in an email or phone screen, to their onsite and offer process. This is as much about you finding the right person as it is them falling in love with your company and the opportunity.

  • Phone Screens: Whether you have a recruiter do it or you’re doing them yourself, you should have phone screen standards to ensure there’s consistency across candidates. Your goal with a phone screen is to not waste anyone’s time – yours, your company’s or the candidate – and to decide whether someone should come in or not for a full on interview. There are some good tips here on phone screens.
  • The Onsite Interview:  Be organized!job_interview_woman-smiling
    • Line up the right people to interview the candidate. No more than 2-3 people who will work with them.
    • Be clear to each of the interviewers on what their role is for the interview – for example, Joe will test their coding skills, Mary will talk with them about their teamwork and collaboration, and Bob will dig more into accomplishments at last job(s) and what they want out of this role. All interviewers should see the JD and candidate resumes at least a day before the interview.
    • Everyone is responsible for A) assessing culture fit and B) selling the job, company and opportunity. Make sure less experienced interviewers know the basics around what they can and can’t share about your product roadmap, financials, etc. Drill into their heads that if they don’t know the answer, tell the candidate they or someone else will get back to them. Don’t make stuff up!
    • Make sure everyone who interviews candidates knows what’s illegal to ask!
    • Optional: Have them sign a NDA before they come in or before interviews start so you can share more with the candidate about the role and what you’re building.
    • Have an agenda for the candidate when they come in. The recruiter or hiring manager should walk them through it and explain who they’re meeting with and why (e.g., “Joe is a developer you’d work with” or “Mary is the team leader from our product team).
    • Make sure the last person they meet with knows what to do in terms of walking them out, handing them back off to the recruiter, etc.
    • Whomever wraps up should NEVER make any promises. Just tell them it was great to meet them and whomever is the hiring manager or the recruiter will be in touch soon.
    • Only the recruiter and/or hiring manager should inquire about compensation requirements, start dates, etc.
    • Nice touch: Give them materials/swag they can take with them after the interview. Perhaps a white paper on the space you’re going after or a fun t-shirt to remind them how cool your company is.
    • NOTE ON REMOTE HIRES: If at all possible, have them come in for face-to-face interviews and pay the expenses associated with this visit. If not, all the same rules apply for a video interview as in face-to-face.
  • After the Interviews:
    • Have everyone send feedback to the hiring manager/recruiter without biasing others. Don’t walk by the next interviewer and say “she’s awesome!” or roll your eyes.
    • Keep feedback consistent: Strengths, weaknesses, opportunities and a Hire or Not Hire statement. No neutrals! Each interviewer either wants to work with this person or not.
    • If there is a big divide on a candidate (50-50 hire/not hire), then have a roundtable discussion so everyone can understand each other’s point of view. The hiring manager should read back everyone’s feedback and then ask people to share more details on concern or passions about the candidate. Ultimately though, it’s the manager’s call.
    • Fast turnaround is important! Do not leave a candidate hanging more than a day or so. Immediate follow up and next actions can make or break landing someone good and it leaves an impression on your company that can travel with the candidate. Follow up with a thank you for their time. If you’re passing, just say they are not a fit for the role and move on. If an offer is coming, ask for references and be specific on when you plan to make a decision. Let them know when they should expect to see an offer as well.

Regular and Backdoor Reference Checks

Although it did happen to me once where this was not the case, most references are going to be with people the candidate can trust to say great things. So, use those references as an opportunity to learn more about the candidate. A few key, but not all, questions I usually ask:

  • Confirm the role they were in with the reference and how they worked with the candidate (manager-employee, peer, etc.)
  • Ask them to highlight a particular accomplishment or contribution the candidate made and why it stuck out.
  • As their potential manager, what areas you should focus on to help grow the candidate in this role. (this is a great way to uncover weaknesses without asking directly!)
  • Would you hire him/her again if you had the chance?

Note that some companies have strict rules about references and won’t let someone do more than confirm title and dates of employment. The only time I read into someone not wanting to give details as a negative is if they explicitly say they prefer not to give a reference or have nothing they can share. I will usually ask if it’s company policy and if not, read between the lines!

Finally, on backdoor references, I highly recommend them. Be respectful of the candidate though – especially if they are still employed – and don’t blow their cover. Only ask someone to introduce you to someone who knows the candidate if they can trust that the person will respect the candidate as well and give you honest feedback. I rarely make a hire without at least one backdoor reference.

Your First Experienced (Senior) Hire – Don’t Be Ageist

A lot of startups come from young, inexperienced, founders with little to no prior work experience. It can be a little daunting when you decide (or your Board tells you) that you have to start hiring people 10+ years older and more experienced than the founding team. The idea of someone older or with more experience than you can cause all sorts of worry about culture fit, being patronized or steamrolled into doing things you don’t want to do. The best advice I can offer is experience and culture fit trump age. Many older candidates have worked at companies with much younger people before and if they’re hired to be the expert in a particular field, let them be the expert, but you are still the boss. It may mean they’re not keen on beer pong on Friday nights or can’t relate to the cat GIFs your team shares on Slack, but if they get along with everyone and meet the needs of your company, get past it. Those senior hires are going to take your company from good to great.

Making the Offer & Closing the Deal

Making the right offer for a startup hire is HARD. An experienced candidate has to make tradeoffs between salary and equity and no two candidates are the same. I could do a whole blog post just on this topic! Instead, I will give you a few things to think about and point you to a few resources:

  • Decide what kind of company you will be in terms of compensation. Is equity something you want your employees to value more than salary? Is parity among team members important? (because they will talk, trust me!).
  • Are you willing/able to pay market rates for a couple of key hires? If you can’t, can you set expectations that you will adjust salaries upon future fundraising/revenue growth? Will you be able to explain to earlier hires who have more equity than comp that an experienced key hire is getting market rates when they’re not? job_offer
  • How much equity will you put aside to refresh grants/hire future team members?
  • How willing are you to negotiate? Will it be a take it or leave it offer, or will you build in some room to adjust comp/equity up/down depending on the candidate’s needs?
  • What other compensation will you offer like healthcare, 401K or maybe Uber and food reimbursement for late night work? Not all startups can afford perks, but if you have some to offer it can make a huge difference for some candidates.
  • Resources: Understanding Equity, AngelList Salary Data, more tips on startup salaries and equity from my buddy @payne92.

A Quick Note on “Try Before You Buy”

A more common practice is to ask someone to work on a small project as a consultant so you can try each other out before either party commits. This can be very helpful – especially if they get some work done for you in the process! Be super clear on expectations here. Hire them as a contractor and pay them. Make sure they sign a simple contract that makes it clear they assign all of the work to your company and it’s under NDA. Set a timeline and agreed upon outputs (code check in, documentation, white paper, whatever…). Make sure they understand what you expect to see and that if it passes, they will get an offer. Do not be the company that keeps hiring “temps” to get work done with no intention to hire.

On-Boarding

Your candidate has accepted the offer! Hurray! You are so close to being done, but not quite over the finish line yet. Make sure your company is everything you promised and more:

  • Send a welcome “package” with general info, maybe some pre-reads about the company, the technology or market. Also include any benefit information (if applicable) in advance so they can think about what they’ll sign up for.
  • Get some info up-front to make the first day easier – like what email address they want (if they get to choose) and maybe a heads up on tools your company uses like Slack, Trello, Github, Intercom, etc, so they have a chance to familiarize themselves if they are new to these tools.
  • Order them a desktop, laptop, or whatever other tools they’ll need (if you cover that expense for your employees) so, ideally, these items are onsite when they start. It’s also nice if you can set them up on various tools, email, etc. before they arrive so they can jump in right away.
  • Figure out where they will sit and who they’ll have lunch with on their first day! So basic, but so welcoming and so often forgotten! Also, tell them what are normal work hours for your team and when should they arrive on their first day.
  • Make their first day and first week feel warm and fuzzy. Take them to lunch, introduce them to the team (locally and on Slack or the like if you have remote peeps). Give them opportunities to get familiar with tools, content and processes. Check in with them at the end of the first week and ask how it went.
  • Most important, ask them how their candidate experience was throughout the process so you can improve things for the next set of hires.

It’s crazy to think this is not what I consider to be an exhaustive list when it comes to the whole hiring process, but I hope it will get you and your company on a good path towards hiring top talent! Have some tips of your own on this topic? Please share in the comments below.

[Updated Nov 2017]

The Three P’s: Lenses to Assess Your Startup’s Performance

I took a bit of a sabbatical this summer and now, refreshed and with a few new topics brewing, it’s time to get back to writing!

LunettesA recurring theme I’ve encountered this summer is which lenses you should apply when evaluating the performance of your growing organization. As an advisor and executive coach to early stage companies, I’m finding more often I am preaching the concept of the “Three P’s: People, Processes and Programs”. Looking at your company or department through each of these lenses and asking yourself how you’re doing in each area can be very telling. It helps you understand where you may need to improve to continue to scale and reach success.

Lens #1 – People

The best leaders of any organization know that their people are what makes or breaks the success of their company. This isn’t just about performance and productivity metrics of each member or as a team, this is about people being in the right roles, having the right training, career path and great peers, bosses and teams to work with. When you ask yourself “are my employees happy?”, consider if you are doing everything you can to ensure greatness. This is well beyond great pay and company perks or weekly beer bashes. Most people want to feel challenged in their roles, but also supported and set up for success. They want equally smart (or often smarter) people to work with and they want to see you get rid of people who don’t work as hard as they do or who are jerks.

Great employees want to work towards growth either as an individual contributor or as a leader. They want to know that they will be rewarded for making solid contributions and for being team players. Growth should not always come from taking on more responsibility or more people to manage. Growth can also come from broadening their knowledge through exposure to new things such as customer visits, interactions with your board, or maybe going to a conference or speaking on a panel with other domain experts. When an employee is not growing or rising to a new challenge, ask yourself if this is a limitation of the individual, or is the system limiting them? Do they need mentorship from someone who’s been in their shoes before to guide them to the next level? Are you micromanaging, thus not giving them a chance to step up and show what they can do?

Happy employees also feel like they have visibility into the vision and direction of the company. They don’t need to know every detail of a product roadmap or the revenue strategy, but they want to understand where the company is headed and how leaders of the organization are measuring success. As a leader of an organization, do you have weekly or monthly all-hands and/or quarterly reviews that include vision and strategy? Do you routinely communicate through company email or on-line forums (e.g., Slack) on big company news like closing a big deal or a great new hire and include why these are important? The more understanding each employee has about the big picture, the more they can calibrate their actions and contribute towards success.

This first lens – evaluating if you are setting up an environment for happy, growing and informed employees – is probably the most important thing you can do to set your company up for long term success.

Lens #2 – Processes

As much as any startup loves being small, nimble and usually pretty organizationally flat, the reality is that implementing processes can be useful. I’m not talking about three ring binders full of protocols and standards. I’m just saying that having a general process for key parts of the business is important. There was probably a time (or maybe your company is there now) where everyone sat around one table and could just talk through how to get something done. Then, all of a sudden, one table becomes a few desks, maybe a few remote employees and a field sales person or two and what used to be a simple chat becomes harder to navigate.

ProcessConsider what processes are in place today that grew organically vs. with intention. If the organic processes work, that’s cool, but keep an eye on them because over time they may not scale. For those set up with intention – e.g., a hiring process or maybe your weekly sprints – reevaluate them on a regular basis. Are they repeatable and do they scale with more people in the company or more bugs to fix? Resist the temptation to keep a process because “that’s how we’ve always done it” or because “our Founder set it up, so how can we kill it?”. Companies that evolve have processes that evolve and what once worked then, may not work now.

Think about how decisions are made, information is disseminated and loops are closed for critical processes first. The most common areas where processes comes more and more into play tend to be product roadmap and execution plans, hiring strategies and go to market strategies. Here are some suggestions for each:

Product Roadmaps

  • Consider monthly, three-months-out roadmap reviews to prioritize new products, major features and release plans. Do not lose sight of the fact that this is not just which designers or engineers are building what, but also how you’ll market and support these products and features.
  • You may have weekly reviews to ensure you’re tracking to the meta-plan and make adjustments if needed. Have some sort of process in place to deal with surprises like a critical bug that bumps a feature or a customer opportunity that may change the priority of a future feature. Set criteria that justifies this type of change so you don’t have to analyze each one on the fly. For a critical bug to bump a priority feature, it might be something like “must impact >50% of our customers or degrade performance more than “20%”. For a customer opportunity it could be “must be a deal worth >$(?) revenue or a customer that will provide undeniable street cred for >50% of our current prospects”.
  • If/when the roadmap changes, have a process for letting people know. Don’t just update Trello and assume everyone will see it – have some sort of change management message that goes out via email/slack that tells the team what and why.
  • It also doesn’t hurt to have a process to track changes to the roadmap so you can see the impact on your initial plan over time. This will contribute to better planning going forward.

Hiring

  • I highly recommend a quarterly hiring plan – not just how many new heads, but actual roles you intend to fill. Given today’s climate where hiring is SO hard, it could take 2-3 months to get that right candidate. So have a process in place to assess where you are with hiring and what new roles you need to ramp on filling.
  • Get in the habit of a regular job description (JD) writing process. Don’t always wait for a role to open up. If people are in the role now, have them write their own job descriptions. This not only helps when it comes to review or promotion time, but you then have these JDs on file if/when needed. I’ve seen major delays with filling a pipeline with good candidates or terribly inefficient candidate interviews simply because no JD exists.
  • Have a hiring process in place that starts with the JD and ends with the on-boarding of this new hire. I’ll write a future post on this with more details, but the short story is that it should include how you’ll post and market the opening, handle phone screens, on-site interviews, making an offer, negotiating terms and how you’ll get that new hire on board and productive as fast as possible.

Go to Market

  • It’s one thing to have a product roadmap that outlines what you’ll build, but it’s another to say how you’ll get those things out there. With every product roadmap, there should be a parallel process for laying out how and when new products/features are publicized, priced (if applicable) and sold.
  • Have a process for content updates such as your website, marketing materials, and demos.
  • What process will you have for telling the world about your new stuff? Do you have a regular list of press or industry bloggers who write about your company or trends in your market? When should they hear about your new product/feature and what’s your plan to share what they write through social media or other channels?  How do your current customers and/or prospects hear about the latest new thing? These are not afterthoughts once the engineering is done, they are just as important processes to get in place as your code check-ins and testing procedures (which you have already, right?).

Looking through the lens of processes and seeing what you have and don’t have in place should tell you whether your company will be able to scale or is heading for a train wreck. Don’t be afraid to pause when you see a gap where a light process could relieve a bottle neck or better prepare your team for future scaling challenges.

Lens #3 – Programs

The Program lens is not used as often as it should. Granted, as a former Program Manager in a past life, I’m a little biased. However, what I often see missing in growing organizations is someone looking across the organization, programmatically, to ensure all the pieces are coming together including people, schedules and money.

A great example of this is the processes I mentioned above around new products or major feature releases. These are often multi-pronged activities involving engineering, sales, support, marketing and maybe finance and operations. You may have program_managerheads of each of these groups, but who is overseeing how they all work towards a common goal or launch date? For many small companies, that’s the CEO or CPO, but (oh by the way), these same people are running your company or out in the field selling or closing your next round of funding.

In the early stage, you may consider rotating the role of Program Manager between different leaders in your organization. Keep in mind, though, not everyone has the knack for project plans and cross-company communication. Make sure you pick the right people to be in this role.  As your organization grows, consider hiring an actual Program Manager. A Program Manager is often one of the unsung heroes of a company because they are in the background instead of on the front lines. They quietly prod and check things off lists. They communicate what’s happening and where there are possible gotchas. Program Managers beat the drum so everyone is marching in the right direction and at the right pace. They are masters in GSD (Getting Sh-t Done) with no task too small or ask too big.

So, don’t just look through the process lens, but also ask yourself what programs are cutting across more than one part of your company and who is orchestrating them. You’d be amazed how productive and efficient your startup will be when programs are well managed.

In Summary….

Startups, when they’re working, develop very quickly – often without enough attention given to people, processes and programs. It’s one thing for an Advisor or Investor to tell you what your company or department is lacking or how you could be doing better, but in the end, you need to ask yourself how YOU think it’s going. Applying these three lenses should help bring things into focus [pun intended].

Have you been using any of these lenses to assess performance or have different lenses that you’ve found effective?  Please share in the comments below!

Just Be Excellent

“Hi, my name is Julia, and I used to be a Grey’s Anatomy fan.”

I stopped watching the show sometime after season 4 or 5, but there was a scene in an early episode that has stuck with me ever since (and if someone can find the clip, I’ll buy them a fine dinner!). One of the female characters – Yang or Grey, I think – was feeling the classic pressure of needing to do more to succeed than just be a surgeon. She was stepping out of her comfort zone because she thought that’s what she needed to do to excel in her career. In this case, she was vying for an administrative type of role that required lots of paperwork, scheduling and managing staff – all non-surgical skills. While she was learning new things and stretching herself, she was not loving or doing well at this new type of work. In the memorable clip, one of this woman’s mentors lays it on the line with her and tells her to stop trying to be something she’s not or do something she doesn’t love and to just “be excellent”.

I often reflect on this scene when I coach leaders of early stage growth companies who are striving to grow professionally. keep-calm-and-be-excellent-8Sometimes it’s a salesperson who has become a CEO or a programmer who is now a VP of Engineering. Often, when one starts a new company, they are still doing their day job (sales, programming, market analysis…) not just because there’s no one else but them to do it, but because it’s their passion and the reason they started their business to begin with. The catch 22 of a successful startup can be that the job you loved and got you this far is a job you no longer have time to do. You are meeting with investors, managing people, closing deals, looking for space or just paying the bills. In many cases, there’s great satisfaction in learning how to run a company and domain experts become great leaders across and outside of their organizations. They are being excellent! Sometimes, however, they are being anything but excellent. They are poor people managers or suck at managing investors and they find themselves in a role that makes them miserable. This can have a negative impact on everything from the happiness of their customers, employees and the overall bottom line to their personal self-worth and esteem.

I have taken pleasure in seeing some great founding CEOs and CTOs step down from their roles early into their company’s success to go back to their true passion. Whether it was programming, a business development or sales role, they chose to be excellent so that they can make an impact on their company and found someone with the right skills and experience to do the job they did not want or were good at doing. So, when I am advising leaders in early stage growth companies about scaling their organization, I walk them through an exercise that forecasts what their company might look like in 12, 18 and/or 24 months. Then, I ask them a series of questions that include some of the following:

  • Do you feel prepared to manage an organization at that size?
  • What tools do you think you are missing in your toolbox to be good at that role?
  • What daily tasks and responsibilities are you willing or eager to give up?
  • What daily tasks and responsibilities are you loathe to give up?
  • What criteria will you use to know when you need to delegate something to a new or existing team member?
  • What criteria will you use to decide if you are still happy in your role?

Even with the best planning, most leaders have no idea what their companies will look or feel like at scale, never mind how they will feel about their own roles. However, being self aware and having some ideas in mind of what one will do at that juncture can be vital to their success. Lining up advisors and/or coaches who can help add those tools to your toolbox or to find the right people to delegate to, or perhaps hand the reins to, can be critical to the overall success of the company.

A good leader/founder is not a failure for admitting they suck at their job or that they can’t do it all. The best leaders are those who acknowledge what needs to be done and by whom and they make it happen. They know they need to just be excellent.

Have you stepped down from a leadership role so you can be excellent or know someone who has?  Please share your story in the comments!

Author’s note: After posting, I realized I should have called out that this mindset is applicable for ANY role. If you’re a great programmer, be an excellent programmer. If you’re a great designer, be an excellent designer, etc…