It is a great joy to announce that the fourth Good For Her (GFH) cohort has launched! With over forty applications this year, it was incredibly hard to select our next group of extraordinary women. Each cohort consists of only 8–10 members to foster the intimacy that we’ve learned creates a strong support network. This new cohort has ten members, including an Aspiring Entrepreneur which is a role designed to connect underrepresented women early in their entrepreneurial journeys with women further along who can serve as role models and mentors.
I created GFH as a pay-it-forward model for women founders who are often operating solo and/or with limited connections to peer founders. You can read more about my founding story of GFH here. While fundraising is not the only metric of success — it is a mortgage, after all — our current cohort members have raised over $70M in capital in the past year; with several closing $12M+ A-rounds (e.g., HumanFirst and Wagmo) and and one recently closing a $20M round. Beyond funds raised, these businesses are focused on being great employers with high retention rates, growing revenue exponentially, and building industry leading brands.
Our newest cohort members are centered in NYC, however with our renewed ability to travel and many opportunities to connect virtually, we have expanded our reach as far as the UK and LA. Our member companies represent a diverse range of industries — from fintech and martech to consumer products and services, biotech, social-environmental impact solutions and everything in between. These are not “cute lady companies”. They are serious businesses making an impact on the world. The combined GFH community identifies as 52% BIPOC and member ages range from early 20s to mid-fifties.
When a new cohort starts, I am very engaged in pulling the group together and fostering connections. Over time, each cohort becomes its own “thing” without my routine facilitation. While each cohort has a special bond, the GFH community supports all members with our “give as much as you get” philosophy. From quick responses on Slack to jumping on calls in the moment when urgent advice is needed, these women strive to support each other 24×7. Now, with three cohorts well on their way, it’s time to welcome cohort four! Herewith, our newest members:
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!
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!
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.
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.
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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:
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.
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:
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:
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.
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!
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NOTE: The balancing hat illustration at the top of this article was created by my daughter, Amelia Austin and is copy-written.
A number of the entrepreneurs I work with are in the middle of fundraising during this crazy pandemic. It’s unclear when we’ll ever be able to meet in person again, let alone travel to venture fund offices for live pitches. Therefore, most are pitching virtually via Zoom or other mediums. A common theme throughout their process has been the lack of face time with potential investors. Investors are expressing it’s hard to write a term sheet or know what it’s like to work with someone they’ve never met in person. It’s reasonable to think that an entrepreneur can accept that they’ll have to wait to meet the investor in person once it’s safe to move about the country again; they need liquidity and are quite used to making sacrifices to forge ahead. However, investors are less desperate and it increasingly unclear if the “I can’t write you a term sheet if I never met you in person” is valid or just another excuse to bow out of a deal.
This got me to thinking about the perspective of each in these times:
The In-Person Pitch
Consider what an entrepreneur worries about when fundraising in person:
Travel logistics: In addition to the cost of a flight and hotel expenses, if I can’t crash on a friend’s couch, I’ll be in SF for 48 hours and have to lock in meetings along Sandhill Road, ideally, back to back and with enough gaps to get from one to the next. OR…. Should I take the subway and risk ruining my professional look if there’s no AC or rack up ride-share fees that my startup just can’t afford right now?
I’m on their turf: Not knowing what to expect in the conference room, AV, who’ll be there and how they’ll perceive me as I am escorted through the office. Who’s watching, what physical attributes are they looking for, etc.
Who attends: We can’t swing all co-founders on the road financially or being out of the office for full days to pitch or for diligence. We have to keep the business moving!
There is certainly upside for entrepreneurs to get in-person face time with their future investors, but there’s not much downside for the investor to do in-person meetings.
Alternatively, the opportunities virtual pitches present to entrepreneurs include:
Schedule flexibility — Let me know what works for you! No travel necessary.
Cost savings — No flights, hotels or ride-share fees. No hit to the bottom line!
My turf — I’m in my personal space, representing who I am and feeling comfortable in my own chair. No one is scanning how I walk or what I’m wearing. I am authentically me!
My team — Need to chat with my CTO? She can jump on a video call whenever you’re free. Want to walk through our financials? My finance leader is happy to screen share our pro-forma to review with you.
From an investor perspective, one could imagine that the schedule logistics are the biggest plus for virtual pitches. But there are also some clear potential downsides of virtual pitches for both parties — many related to basic remote work challenges highlighted here, but I’ll call out a few:
Attention span — will both parties be fully engaged or distracted by other screen activity? (although I have seen many VCs looking a their laptops/cell phones more than engaging with entrepreneurs in a boardroom pitching right in front of them)
Eye contact — it’s hard enough to make eye contact in person let alone tracking gaze awareness and looking for social cues. There is no opportunity to catch a side glance or reaction from one party to the other. The post-meeting debrief won’t include observations like “did you notice when we shared our financial projections that they all looked at each other like ‘WOW’?” or when two partners notice body language between co-founders that suggest they may not be aligned on the company’s go-to-market strategy.
Cognitive load — not only does constantly looking at yourself while you are presenting create a lot of emotional pressure, but trying hard to track all of the social cues in 2D can be exhausting for all parties and could cloud the focus of the discussion.
Informal connections — the post-meeting socializing one often experiences is completely lost. The casual walk out of the conference room, chat at the coffee area or even the bio break that may lead an entrepreneur and investor to be washing their hands at the same time. Each of those situations are opportunities to form informal connections that don’t happen in the boardroom. You find out you have kids the same age or that you both like the same brand of lipstick. Your college roommate is in their soccer league or you both prefer oat milk over soy milk. While these are minor details, they make these connections more personal and build trust in what may become an important working relationship.
Optimizing For Our Current Normal
We won’t likely be going back into boardrooms for pitches any time soon, so herewith some suggestions to ensure the virtual-only rounds have a better chance of success:
Turn off your self-view and expand your screen to just video so you are fully engaged. Put aside your phone and resist texting with your co-founder/partners during the call. You wouldn’t do that in the boardroom (would you?!), so don’t do it on video.
For both sides, focus on facial reactions and body language (like leaning back or arm folding). Pause when you think “I really want to text my colleague to get their reaction to what’s going on right now” and consider how to incorporate that into the conversation. For entrepreneurs, this may be saying “Pat, I noticed you looked surprised when I mentioned we have large traction with such a unique audience. Would you like me to explain that further?” Or, “Sam, you seemed taken aback when we shared our unit economics. I have a backup slide with more detail if you’d like to dig into it.”. For Investors, it could be “Tyler, I noticed a long pause when I asked you about your engineering team. I am happy to discuss that further after this call if it’s a longer conversation or you’d like your CTO to be part of the discussion.” [Note: All of these examples could happen in person too, but may be done with more intention when on a video call.]
If the pitch is an hour or less, consider tacking on 10–15 minutes post-meeting to allow for more informal conversations. If it’s a longer, diligence or full partner meeting, consider scheduling a mid-point break for the entrepreneur to do a breakout with partners/team members they haven’t met yet. Or schedule these less formal chats as short meetings that follow the main event. Be explicit that these are more personal connections (“tell me more about YOU”) and not for deeper business dives. Yes, it’s more time on the calendar, but that’s the time the entrepreneur may have used to travel to your office or that you used to drive to the office or walk from your office to the board room.
Create opportunities for reference checking — Investors, make intros to other entrepreneurs in your portfolio who can share what it’s been like to work with your team after the money was wired. Entrepreneurs, make intros to customers, angel investors, mentors or others who can speak to who you are beyond your business. [NOTE: It’s no secret that backchannel references will happen on both sides, regardless, but being proactive about this is always a good thing!]
For entrepreneurs with physical products vs. software that’s easy to demo online, send prototypes or latest products in-market to investors in advance. Allow them to see and feel your product! You’d likely have brought it with you if you were in person, so why not send in advance? If you have limited supplies, ask the investor to send it back post-pitch. Any decent investor should be trustworthy enough to do that…on their dime…even if no term sheet comes of it.
Finally, investors, stop using lack of face time as a reason not to invest. Your investment theses are still valid whether you meet a founder in person or not and pattern matching can still happen on video. Trust your instincts and consider how incredible these humans are to be able to run and scale their businesses even during a pandemic with most if not all virtual teams. They are resilient and determined not to be thwarted by fully remote work environments. The strong survive and prosper, and so will you!
Do you have other tips to enhance the virtual pitch process for entrepreneurs and/or investors? Please add in the comments!
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
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
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!
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 PIA, HIPPA 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.
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.
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).
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.”.
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.
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.
A common career advice question I get all the time is what the tradeoffs are between going to a startup vs. going to a big company. There are many things to consider and lots of “it depends” when it comes to where you are in your career, where you live etc., but when it comes to the general aspects of a startup vs. mature company, most of the situations don’t vary that much. I’ve done both, several times, so here’s a perspective on the tradeoffs based on my own experiences.
Startup vs. Mature Company
(c) 2018 Julia B Austin
Putting aside for a moment industry and how you feel about the products the company is building (both of which are very important!), most of the differences between a startup vs. a mature company are pretty obvious. In a mature company, you will likely have more role models to learn from and stronger teams to collaborate with, a clear direction and a mature board. The role you consider may have a narrow scope, but could offer deeper learning and of course great benefits, compensation, etc.. You’ll also get exposure to what good (or bad) looks like at scale and possibly a nice brand for your resume.
Startups can offer a chance to do “all the things” which can be either a blessing or a curse depending on your interests. You may miss out on having peers to collaborate with, have to look outside of your company for mentors and role models or have limited budget to get stuff done, but you may get high value equity in exchange for lower than market-level pay. If you want to dig more into deciding which startup to join, I suggest Jeff Bussgang’s book Entering Startupland which goes deep on the different roles at startups and how to get your foot in the door.
One thing often overlooked when considering a new job is the leadership of the company. Serial entrepreneurs will have a very different approach than someone who has limited real-world experience and mature company executive teams can be world class or “legacy” leaders who can’t move with the times. There are many tradeoffs when factoring in leadership into the decision process of startup vs. a mature company.
(c) 2018 Julia B Austin
Startup founded by serial entrepreneurs: This can often be the best case scenario if you want to learn from those who have “seen the movie before”. They likely had no issue raising money and were selective on who their investors were and who sits on their board. They will know how to get the flywheel moving incited by past mistakes OR failures.
“When I started my fifth company I knew exactly how I wanted to build the team. So, on day one I hired a head of recruiting to get things off to a strong start. I also knew market adoption would be critical to fundraising so focused on growth very early on – before we even had a product!” – David Cancel, CEO & Co-Founder Drift
Serial entrepreneurs may also try to overcorrect in areas where they failed the first time, such as over analyzing or delaying decisions, being too conservative on cash flow or focusing too much on scalability too early in the product development process. If you’re interviewing with a serial entrepreneur, it’s always good to ask what lessons they learned in their last startup and how they’re bringing those lessons into their new venture.
“I joined Drift in part because I wanted to learn from the experience of the co-founders. They’ve seen it before so they anticipate issues, they know when (and how) to hire experts to level up the team, and they know what’s “normal” for a hypergrowth company. It’s the best of both worlds: you get the rollercoaster startup experience with some of the more measured leadership and strategic characteristics of a bigger company.” – Maggie Crowley, Product Manager Drift
Industry veterans doing their first startup: Founders coming from mature companies with no startup experience can have big company confidence, be great at hiring and leading teams, but lack scrappiness to get a Minimum Viable Product (MVP) out the door and work towards product market fit.
“At our first startup after a series of roles at large enterprise software companies, we tried to force a big company perspective on how we did employee feedback and reviews. We were too structured with this initially and quickly cut back to a more loose feedback and review process with our team.” Izzy Azeri & Dan Belcher, Co-Founders Mabl
They may also be too used to having teams of people and systems in place to cover the more mundane duties of running a company and don’t want to get their hands dirty. On the flip side, they often know how to implement those processes and know the people to hire to run them so once the flywheel is moving and cash is in-hand, they can get momentum quickly.
“Earlier in my career, I hired a small team within a large corporation that was scrappy and had entrepreneurial mentality. At my startup, I quickly realized the benefit of once having a corporation behind me when things weren’t working out. The impact of a bad decision or process was much greater with no safety net.” – Karen Young, CEO & Founder Oui Shave
Startup with limited leadership experience: Working with a skilled group of founders leading teams for the first time can be tons of fun. If you bring some experience to the table, it can be very gratifying to not only work from the ground up, but also work alongside these founders as they grow. However, it can be frustrating if you find yourself figuring out things on your own because there’s no one in the company to mentor you. These situations can be very rewarding if you’re patient and you can always get outside mentors and advisors if they’re not available at this type of startup.
“When we started, we got a lot of advice like: stay focused, don’t expand too quickly, be careful that experienced hires match your culture. All good advice, but we discovered there’s no real substitute for learning the hard way. The lesson just doesn’t sink in until you feel the pain of doing it wrong.” Wombi Rose, CEO & Co-Founder LovePop
Mature company with inexperienced leadership: If they made it this far, they are either wicked smart, lucky or both! More likely they also have surrounded themselves with strong, experienced leaders, investors and/or board members. You can learn a lot from joining a company like this, but they are very, very rare! When companies scale too fast, they can also suffer from having people in roles that have outgrown their experience. Read more about the impact of Hypergrowth situations written by my friend at Reboot, Khalid Halim, for First Round.
Mature companies with experienced leadership: These organizations have all the standard things you’d expect. Probably more politics and process than you’d ever find at a startup, but the benefit of exposure to great role models and best practices can be invaluable. Sometimes, these bigger companies can also expose you to the “dark side” of leadership and processes which are also great learnings on what not to do in your next job or company you may start yourself.
Which comes first in your journey?
For those doing early career path planning and knowing they want to do both a startup and a mature company at some point, there’s always the question of which should come first. Hiring managers at early stage companies can get “spooked” when they see someone with too much time (5+ years) at mature companies; questioning whether the candidate will be able to transition to startup life. Not that it’s impossible, but it’s something to consider. For these candidates, I suggest highlighting any scrappy “ground zero” work they may have done at their companies to demonstrate they can handle ambiguity and take risks. I am also a huge (and very biased) fan of people who’ve joined companies early and scaled with them. They have learned a TON from those experiences and can often start scrappy, but know how to operate at scale. Win-win.
Conversely, someone with a lot of startup experience may have a hard time adjusting to mature company. A hiring manager at a mature company may question whether a candidate with only startup experience can handle a slower pace or won’t know how to navigate a complex organizational structure that requires political and communication savvy. You may have to sacrifice title and maybe some salary to get a foot into larger institutions who may view your past role, which may have been very senior at a startup, to being pretty junior if those around you have decades more experience. However, I always find those with startup experience can be invaluable to a team that needs to be shaken up, take more risks or explore new ground. Often, those who sacrifice title and pay when they joined, make it up fast as they move up the chain in a larger organization.
There’s no right or wrong place to start. A lot depends on how you define your skills and how willing and patient you are in either case to adjust. Much can depend on who hires you and their management philosophy. I’ve seen some people bounce between both types of situations over and over, some that just can’t handle startup life, and others who have startups in their DNA and should just stick with that world 🙂
“At a startup, every job matters and you can see almost daily that you are creating something that wasn’t there before. You have the ability to learn quickly and have a fast feedback loop to let you know how you’re doing. It’s very different working at an established company vs a startup, but you can learn a lot at both – you’ll just learn very different things.” – Rebecca Liebman, CEO & Co-Founder LearnLux
Questions To Ask
Regardless of whether you are a seasoned veteran or fresh out of school, as you ponder whether you want to join a startup or a mature company here are some final things to consider:
What tools do you want to add to your toolbox? Will the role allow you to hone skills you already have or add new ones?
Who do you want to learn from, and how do you want to learn? You can learn from experienced colleagues and mentors, but having bad role models can also teach you a lot about what not to do. Similarly, if you are an experienced hire coming into a company started by inexperienced founders, you may want to learn by mentoring or teaching these young leaders. Taking the skills you’ve developed over your career and applying them to a new situation in itself can be a very enlightening experience.
Who do you want to work with? How important is the size and culture of the team you’ll work with? Remember, you’ll probably spend more waking hours of the day with these people than anyone else in your life – regardless of the size and nature of the company you join.
What do you value? At the end of the day, love what you do and decide what role will allow you to maintain the integrity of who you are and who you aspire to be!
Do you have other tips on how to decide whether to join a startup vs. a mature company? Please share in the comments!
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!
A 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.
Consider 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:
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.
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 heads 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.
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!
So, you’ve decided to hire some interns this summer. Well done! Often, early stage companies shy away from hiring summer interns because they dread the idea of “babysitting” on top of everything else that needs to get done. If you’re bringing one or several interns on, you know it is well worth the effort because interns:
are potential future full-time hires;
can work on stuff no one has time to do, but would be great to have (often referred to as “gravy projects”); and
they are walking advertisements of your company and your product(s).
Whether your company is fully established or just getting started, having a well thought out program for your interns will ensure that you get the most out of them and that they get the most from their experience at your company. A great experience means they’ll be talking up your company and your product(s) when they head back to school. Thus, they will be walking advertisements for future hires and future customers.
A Guide to a Great Internship Program
Let’s assume you’ve already made great hiring decisions for the summer and students are coming to work for you for approximately 10 weeks. I’m not going to get into salaries, temporary housing, or other pre-hire logistics in this post, but I will walk you through an outline for a solid internship program. It’s geared towards engineering types of interns, but most applies to any intern role.
If you have more than one intern coming on board this summer, try to have them start around or on the same date. This eases the burden of on-boarding processes by orienting everyone as a group and gives them a sense of belonging to a cohort from the get-go.
After orienting them to the office and getting them all the necessary logins, etc., do a kick-off lunch with founders and mentors to welcome them to your company.
Outline a weekly schedule for the intern program. Many interns have not worked in a business setting before and will need structure with a clear beginning, middle and end to their program. As much as they’ll appreciate a clear understanding of their summer schedule, this should also help your team balance their time around intern commitments. A sample schedule is below (click on the image for a larger view).
Every intern should be assigned a mentor. This is not typically their hiring manager, but rather a peer or someone slightly senior to them who can guide them through project specifics (e.g., coding standards or pricing models) and help them assimilate to the company culture or maybe even to a new town if they’ve temporarily relocated for this job.
Mentors should be briefed on HOW to be mentors. Make sure they understand the difference between being a guide and being a boss. No one wants two people telling them what to do all the time. Also make sure you pick someone who wants to be a mentor – this is a great growth opportunity for your team, but if they’re not up for it, it could make for a suboptimal experience for your intern.
Mentors should be generally available over the summer for ad hoc questions as well as weekly 1:1s. If someone is taking more than 2 weeks off this summer, they should not be a mentor.
While it’s nice to do, a mentor does not have to be a domain expert for the intern’s summer project. As long as they know how to help the intern get access to the experts and can guide in other ways, they are qualified!
Mentors should be expected to give feedback to their intern’s manager on performance and possible offers to return to your company for another summer or full time role. Mentors should not make such offers themselves. This is the intern’s manager’s role!
It’s good practice for companies to keep a running list of possible intern projects throughout the year. Again, gravy projects are ideal – meaningful and useful projects, but if they are not completed, it does not put your company at risk.
Try to offer projects to your interns that will:
Allow them to stretch beyond their comfort zone.
Result in something tangible that others will use such as code that ships, content on a public website or even a tool that helps an internal team be more productive. Ideally, it has a result that can be listed as an accomplishment on their resume and added (or strengthened) a skill.
Encourages them to get to know your company/products (remember, walking advertisements). For example, one that lets them dig into customer data or one that requires them to work with people from other parts of the company such as sales or support.
There are two different approaches I like to assigning intern projects. Either have a list of projects to offer when they start and let them ask questions and explore them a bit in the first week, then they pick one. Or, in advance of their start date, ask them questions about what skills they’d like to develop this summer and before they start, you and their mentor can pick the one best suited for their skills and goals.
Try to offer one or two meaty projects at most for the whole summer vs. several small projects that could limit their learning experience.
Pre-reads: Whether you have a project in mind before they start or a list of possible projects for when they start, it’s nice to send a suggested reading list and some company info to your hired interns a month or so before they start. Don’t overdo it since they are probably cramming to finish the semester. Just send things that will give them a leg up. Even with an NDA they still may be a bit clueless about what not to share, so don’t send them secret sauce information!
Learning and Having FUN
Interns chose to be interns instead of scooping ice cream this summer because they want to learn. Invest in them and expect that they want to understand as much as they can about how everything works at your company.
Beyond what interns learn doing their project, consider offering weekly lunch-n-learn sessions where food is brought in (or they get their own if your company is being careful about burn!) and have someone do a talk. Change it up and do everything from a technical talk to a business talk to maybe inviting a guest speaker like one of your company advisors or a customer or partner. Also, talks should be relevant and understandable whether you’re a coder or a marketing intern.
Look for opportunities for interns to have a unique experience. For example, tagging along on a customer visit or helping out in the company booth at a sales conference. Not only is it nice to have an extra set of hands, but interns will be SO appreciative for these extra opportunity to get different perspectives of your business.
Include interns in routine company meetings and off-sites. They are employees of your company and these are also learning experiences.
Make time for fun. Take them bowling or a baseball game. If your interns are new to the area, show them the city via a Duck tour. Mentors should come along as well as part of the bonding process. The summer at your company should be memorable for interns beyond the work they did.
If your company is based in MA, enroll in TechGen, a program from the NEVCA, which has lots of professional development and social resources for your interns and is also a great place to source talent.
Throughout the summer, you should schedule time to give your intern feedback on their performance and for them to let you know how they think they’re doing. In addition to weekly 1:1s with their mentor, there should be a mid-summer review and end of summer exit interview. You don’t want to find out at the end of the summer that your intern had a horrible experience! They’re at a startup, so things will undoubtably change unexpectedly. Course correct throughout the summer as needed and help them understand that this is the nature of early stage companies.
In preparation for the mid-summer review, ask mentors to feedback to managers how interns are doing. Factor this into a potential decision to re-hire interns for the following summer or offer a full time job for when they graduate. Interns should be told that this is a possibility OR NOT. Do not set false expectations. If your company cannot commit, then make it clear that good interns will be the first people you’ll call when you are hiring.
The last week of the internship should be for closing things out. Checking final code in, writing documentation and/or tests, doing a code-walk for whomever will take over when they go, and maybe doing a demo day or poster session so interns can see each other’s work. Also, plan for one last fun outing so people can say goodbyes and feel all warm and fuzzy about their experience. Schedule this last event when most/all of your interns are still around. Even if a student is returning to a nearby campus, it’s not reasonable to expect them to come back to work even if it is for something fun.
If you are offering a sign-on bonus for a full time position when they graduate, give 50% of it in their last paycheck with no strings and hold the other 50% for them if they are to return. The second half will be in their first, full-time, paycheck. Start to finalize your plan to offer or not around two weeks before the intern leaves.
If your intern(s) are returning to local schools, consider offering them part-time work during school (with potential for full time during breaks). It’s a great way to maintain the relationship and further lock them into a future full time position.
Your company does not have to be big and profitable to be thoughtful about the internship experience. In fact, starting when you’re small and nimble will ensure that a strong internship program is part of the fabric of your company as you grow. Just envision smiling interns back at school raving to their friends about their best summer ever and the returning faces and quality resumes you’ll see next hiring season!
Have you worked (or currently work) for a company with a great internship program? Share tips and tricks that made it great by replying with a comment.