Balancing The Many Hats Of A Startup CEO

Illustration by Amelia Austin (c)

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

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The Hats

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

BEFORE

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

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

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

AFTER

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

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

No Recipe Is Perfect

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

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

Conclusion

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

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

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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.

Welcome GFH Cohort Three!

I am so very pleased to announce that the third Good For Her (GFH) cohort has launched this week! Back in 2015, I noticed that there were a lot of male founders supporting each other. Some had informal monthly meetups for beers where they’d talk about leadership and fundraising challenges. Some were part of programs created by investors or startup accelerators. When I asked why there were so few women integrated into these groups, I got answers ranging from “I don’t know any women founders” to “It would be weird to have only one woman in our group”. I knew plenty of women founders, so I decided that if they were not getting invited to these groups, I’d create one for them.

The focus of GFH is to create an intimate community for like minded startup founders who identify as women. Each cohort of 8-10 founders is carefully curated to ensure a diversity of backgrounds, experiences, company stage and types of businesses. We have founders of B2B, D2C and B2C products. They’re bootstrapped to post series A. There’s no limit to where their businesses can go to be part of the group. The only requirements for a member are that they are a founder of their business (not all are CEOs), have a product in-market and they are good humans. All members are vetted by me and occasionally another GFH member before they are invited to join. Most of our cohort two and three members are in NYC, however with the pandemic, we’ve become more flexible and now have members based around the country.

Including an “Emerging Leader” in each cohort is something we started with cohort two and will continue to do for all cohorts going forward. These young women are aspiring leaders who would benefit from being among the incredible GFH women. They are part of the GFH family and included in every way.

GFH is fully funded by me. There is no fee, equity grant or financial obligation for any of our members. It is my way of paying-it-forward and I take great pleasure from watching these groups and individuals thrive. Pre-covid, I hosted events that ranged from dinners in my home to taking members to the theater and book signings to organizing pitch practices and how-to sessions (our most recent one was on the product roadmap process). I lead on topics I know well and bring in experts from my network as needed. During the pandemic, our connections are primarily in Slack and Zoom meetups – we’re hoping that’ll change some day soon! Meanwhile, in the GFH Slack, each cohort has its own private (and very active!) channel and there are open channels for cross-cohort connections around topics like fundraising, hiring and leadership. All members sign a code of conduct ensuring what happens in GFH, stays in GFH! I am also available (practically) 24×7 to every member for networking and coaching. Oh, and there’s a lot of fun too – the GFH community has a great sense of humor 🙂

When a new cohort starts, I am very engaged in pulling the group together and fostering discussions. It is my goal that, over time, each cohort becomes its own “thing” without my routine facilitation. With two cohorts now well on their way, it’s time to welcome cohort three! Herewith are our newest members (hover on images for name & company):

I am sooooo excited about partnering with this group! The buzz has already started on slack and they are receiving the much needed support they crave. Welcome cohort three!!

Check out our website for more information about GFH and pay attention to all of our members – they are doing amazing things!

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GFH Cohort Three Kick-off – July 2020!

The Fundamentals of Roadmapping

We are in an era of Objectives & Key Results (OKRs) and Key Performance Indicators (KPIs); tools companies use to track and measure their progress and ensure they are on track to reach strategic goals. In scaling startups, CEOs and co-founders have mixed feelings about delegating tasks they once owned to new layers of management. Some tasks, like perhaps managing the books to a new head of finance, they are eager to let go of, and some, like product decisions, can cause a lot of angst. In these times of transition, it’s not uncommon to implement OKRs/KPIs as a way to get comfortable with handing off these responsibilities. As management layers are added, there is a natural fear of no longer being close to the detail, of wondering whether a team can execute as well without a founder/top leader engaged in the day-to-day. I often hear CEOs/Founders of scaling companies ask how they will know if things are working if they are no longer in the weeds. These leaders want to trust their team and worry about micromanaging, but they also want accountability and the ability to track progress. 

Measuring performance and holding leaders accountable is indeed important, but what’s often missing is the holistic view of where the company is going and an organization-wide understanding of how it will reach its goals. Before setting those metrics, leaders must be clear about the True North for the business – the compass of your company’s identity and growth direction – and set a near-term vision with a roadmap to get there.

The 30K Foot View

Anyone that asks what your company’s 3-5 year roadmap looks like is clueless about how businesses – at any stage – really work. With constant innovation, new market entrants and potential black swans like a global pandemic, the best a leader can do is set a 12-18 month strategic plan that is directionally aligned with the company’s true north. That plan should be broken down by quarter with the assumption that the degree of confidence in achieving goals within each quarter will decline over time. You cannot predict the future, but you can build within a set of assumptions. Assumptions should be articulated for each goal as a means to establish confidence levels.  

Here’s a framework for thinking about the high level view of your company’s roadmap:

roadmapframework

High-level Roadmap Framework (c) Julia Austin 2020

The true north (or mission) statement should be at the highest level, a guiding principle of the impact your company is committed to making for the long term. When I was CTO at DigitalOcean, we coined the true north statement “To Empower Developers To Build Great Software”. This gave us focus on our target persona (developers) and latitude to evolve as needed to achieve that mission. While we were (and they still are) a cloud company, this statement said no matter how we evolved, markets change, etc. we would remain focused on what’s needed for developers to build great software. Google’s statement is “to organize the world’s information and make it universally accessible and useful.” Again, the focus is on the impact – the world’s information being accessible – not how the company delivers on that mission.

The 12-18 month vision statement should be a clear focus on near-term impacts. This may be to achieve a certain level of market adoption or to have a core set of offerings viewed as table stakes for the target audience. It could be the launch of a new product or service or a major financial metric like reaching Free Cash Flow.

Quarterly OKRs/KPIs should be brief (no more than 2-3 major goals), achievable, but with some amount of stretch. In other words, if you were using the traffic light rating system (red, yellow, green) not all of them will be “green” per quarter. More info here. Beware of over-adjusting OKRs every quarter – while they will definitely evolve, especially if the process is new to an organization, there can be a temptation to focus on changing the objectives vs. adjusting KPIs or accepting that the goals simply can’t be met for other reasons (poor leadership, systemic issues, market changes) which should be addressed outside of the rating process.

Expect each team across the organization to cascade their operational roadmaps from these strategic foci. Operational roadmaps should identify key initiatives and milestones. Some milestones may be a sum of parts (as in the Engineering roadmap below) and some may be more linear and timeline driven as the Operations and GTM roadmaps show below. Of course, each initiative can be broken down even further per team (see next section); that’s up to each team to decide how to manage from there. However this high level format is the right level of detail for broader communication across the organization and perhaps with your board or even your customers.

strategic_roadmap

Strategic Roadmap Example (c) Julia Austin 2020

The Process

I encourage a six-quarter rolling approach whereby each quarter the leadership team:

  • rates and reflects on last quarter’s results;
  • reviews upcoming quarterly goals;
  • adjusts assumptions and factors in any new information (market shifts, product/revenue changes, etc.) for the next 6th quarter;
  • communicates the updated company plan across the organization; and 
  • has each team create a tactical roadmap that lines up with the quarterly goals.

Below are representations of tactical roadmaps I’ve seen used in two very different organizations. In the first example, the product team and key stakeholders (sales, support and finance leads) review current priorities and drag and drop efforts according to their complexity and priority relative to company goals. They use a product like Mural to collaborate electronically (both when in-person and remotely). In the second example, a simple spreadsheet is used, projects are t-shirt sized using standard scrum methods, and there are links to each project’s details (in apps like Jira or Trello) for more information about relevant epics and user stories. PMs meet with engineering leaders each month to review and adjust as needed. In all cases, the details of each major initiative includes tie-backs to OKRs/KPIs. If they can’t be tied back, and measured, they should not be on the roadmap!

matrix_roadmap

Example One

 

spreadsheet_roadmap

Example Two

Considerations For Very Early Stage Companies – Pre-Product Market Fit

  • If your company is very early stage, expect to pivot the vision and the roadmap a lot as you learn and grow. Create guiding principles for when and how you would adjust a True North and/or Vision Statement. What factors must be true? What assumptions are you making about the market and/or target persona that may prove wrong or different than what was expected? Will you lean into these new findings and shift the direction of the business or keep testing those assumptions in different ways to learn more? Even the earliest staged companies should have a true north as they get started.
  • Avoid peanut buttering! One of my favorite terms, this suggests spreading many things across a broad surface vs. being focused on a few key initiatives. It is scary – especially for early stage companies – to commit to only 1-2 things when it’s so unclear whether either/both will be a success and there are so many other things to try. However, by spreading limited resources across too many things, it’s more likely nothing of substance will get done, or things will move too slowly OR each thing will be done with poor quality while possibly burning out your team. Pick those 1-2 focus areas and set time-boxed milestones that will drive next steps or a change in direction. For example, “we must reach 20-30% conversion rate with the current MVP over the next two quarters or shift to the other product idea.” Commit to these milestones and agree how close you’d need to be to reaching that goal to keep moving forward vs. cutting bait and moving on.

Considerations For Companies With Product Market Fit

  • Appoint a roadmap owner who can oversee the process across the organization. This is typically a senior product manager/head of product or Chief of Staff who is empowered to drive decisions and prioritize based on the 12-18 month vision. This role may be supported by a program/project manager who maintains the details in whichever tool or platform you use (e.g., updates the spreadsheet, inputs changes into Trello, etc.)
  • Be mindful of how much time your team is spending on roadmapping and the measurement process. If it’s taking more than a few hours per quarter to discuss, update and communicate the roadmap and OKRs, it’s costing your company far too much time and money. This process supports productivity, it doesn’t become the work itself! If it’s taking up too much time, it’s likely the goals and measures are far too detailed and/or there are too many people involved in the process.
  • Establish Rules of Engagement (ROE) for times when an opportunity or challenge may disrupt the roadmap. For example, what size/nature of a new customer opportunity would disrupt the roadmap? Can it only be for initiatives that were already on the roadmap, but further out? Will the sales team have points they can “spend” per quarter to reprioritize something? What about a major bug/performance issue? How bad would they have to be to disrupt the current plan? Once the ROE are set, these too should be managed by the roadmap owner. If the ROE are not adhered to, they’re useless, so only have a few and keep them simple. E.g., unless a new customer could grow revenue by x% and what they need is already on the roadmap, we won’t do it. OR if a bug is creating more than x% churn or denying service to a critical mass of customers, it’ll be fixed in accordance with the roadmap.
  • Prioritize the backlog and tech debt as part of the process. These are just as important as new features and the longer they are put off, the harder they will be to schedule and get done. Set aside anywhere from 3-10% of resource allocation dedicated to these efforts. It largely depends on how severe issues are, whether upcoming roadmap initiatives have dependencies on these issues and/or how long they have been festering. It can be useful to “age up” backlog/debt items to raise their priority.
  • A few finer points on this topic:
    • If a new request or critical issue bumps something else, always communicate the tradeoff(s) made and the positive or negative impact they will have on OKRs/KPIs.
    • Developers hate roadmap thrash! So try not to disrupt it too often.
    • Remember, for projects already underway, a reprioritization is not a 1:1 swap – there will be a J-curve in productivity each time a team has to stop something, start something new, and return to the old project later. 

Conclusion

There is no one best way to do the roadmapping process. How you lead, the type of product you build, organizational structure and culture all come into play to determine what will work best for your company. Having a roadmap process will improve the prioritization process and create alignment among teams, will provide transparency across the organization and should give leaders (including your board) the right level of visibility to ensure the work is getting done. Don’t create a process just for the sake of process or implement OKRs just because someone told you that’s what you’re supposed to do. Be thoughtful and implement whatever process works best for your company.

Do you have other suggestions on how to run a great roadmapping process? Please share in the comments!

Virtual Fundraising

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.

Virtual Pitches

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!

Overhauling Higher Education For Today’s World

University Nevada Reno (UNR) Living Learning Community (visual concept)

Around seven years ago, I had an epiphany that the delivery of higher education would change dramatically. This was triggered by the fact that we had shifted our hiring game in the tech community from caring about pedigree (MIT, Stanford, etc.) to “tell me what you have actually done”. While pedigree demonstrates academic aptitude, it does not speak to a candidate’s ability to execute. Now more than ever, especially in a time when building is going to be what stimulates the economy, those who can execute will excel.

My vision seven years ago (which still stands) is the disruption of higher education as we know it today. Instead of high school students aspiring to get into their top choice college or university and moving on campus for a singular experience, we will move towards a model where young people want to leave home, further their learning, but care less about the brand of institution(s) they attend, or even getting a degree, and care more about their ability to learn what they need to be productive in society. Parents will care less about brand and the degree too, but will want their kids to have a solid, post-secondary, education in a safe environment. College age students (18–22’ish) want to be with likeminded peers who are either focused on similar academic interests or they want a diverse community to expose them to other areas they may not otherwise know about. I loved living in a dorm at UMASS Amherst with peers pursuing all sorts of topics I knew nothing about. I still attribute my interest in marketing to having a roommate that was a marketing major while I was an art major.

Now that most colleges and universities are forced to teach online, and the cost of higher education is through the roof, we are primed to change the shape of post-secondary education. I believe young people in the next 3–5 years will want to move out of their homes (and their parents will be eager for them to do the same), to a city of interest and pursue further education by joining live-in learning communities vs. applying to a specific college.

The model would look something like this:

  • Live-in learning communities will be developed in popular college cities (Boston, NY, SF, Austin, etc. — perhaps eventually abroad as well). These will be dorm-like buildings with high bandwidth on-line learning capabilities like high-tech video rooms, Jamboards, and amenities such as gyms and community kitchens. There will be Resident Assistants and administrators to oversee safety concerns of parents and establish behavioral norms. There will likely be some sort of student-run government, clubs and special programming depending on the live-in learning community.
  • Qualified, remote educators will offer courses similar to how HBX delivers online experiences today (below) or simply via Zoom with smaller groups.

  • Prospective students will apply to live in these communities based on city of interest, peer group and other criteria (amenities, special programming, etc.). Applications will focus on diversity, inclusion and ability for students to contribute to the learning community vs. SAT/ACT scores and high school accomplishments. All applicants will be peer reviewed and cost will be commensurate with ability to pay. In a utopian world (one can dream), the government would subsidize these programs.
  • Live-in learning communities will provide cross-university, curricula based on skills development. For example, a computer science program may be a series of courses offered from not just local universities, but online courses from across the country. Certifications or hours of learning may replace degree programs. A foundational curriculum of core competencies such as public speaking, project management and financial skills will be woven into every program.
  • Most important, live-in learning community curricula will be focused on experiential learning. Most if not all courses will be project-based — some individual and many team oriented so students are developing real-world experiences that also demonstrate their ability to execute.
  • Study groups may form or be required in each live-in learning community or on-line. New opportunities for social connections and networking will be within and between learning communities.
  • Completion of programs may be based on committee reviews and a PhD-theses-like defense. Alumni communities will be fostered post-completion of any program.
  • Prospective employers will recruit from these live-in learning communities. Students’ inherent training to work remotely will be an asset to the growing number of companies establishing remote workforces. The foundational skills development would be seen as a key differentiator of these programs.
  • This will of course require current colleges and universities to partner with whomever creates these live-in learning communities. The question is when, not if, these partnerships will form. For many universities, this will ensure their survival and could enhance vs. dilute their brand.

While there will still be some professions, like doctors and lawyers, that may still need the discipline of a more rigid degree program, I can imagine many students (and parents) taking advantage of the ideas above. Perhaps there are entrepreneurs out there already developing this idea. If so, send them my way…I’d love to support their efforts! …and if you have other ideas about this concept, let’s riff.

The Current Normal

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Our Current Normal, Amelia Austin

A year ago, I was adjusting to moving out of Massachusetts for the first time in my life. I became a full time New Yorker and loving it. I had moved into an empty-nester apartment with an open floor plan. Other than the guest bathroom, my bedroom is the only private space, with a Murphy bed in the living area for occasional visits of my daughters and friends. The NYC startup community was thriving. I have many old and new friends here in the city and countless former students working and starting their own businesses scattered across Manhattan and Brooklyn. In the past year, between teaching in Boston once a week and conducting my coaching practice, my “new normal” was an endless stream of breakfasts, coffees, lunches, dinners, drinks…book signings, shows, galleries, music… It was the dynamic and stimulating environment I craved. As my good friend Bethany noted almost exactly a year ago in her own reflections about leaving Philly for NYC, it wasn’t that I didn’t love Boston (it had been my home my whole life, after all), it was that I wanted more.

[insert sound of car screeching to a halt, here]

My last in-person class at HBS was on March 9. My youngest daughter, Eliza, a senior in high school, had been sitting in on my course all semester as part of her Senior Capstone project (she’s building an app). It was a joy to see her once a week in my classroom as she is a boarding school student and other than weekends when she’d visit NYC or our college tours together, our weekly dinners in the Spangler cafeteria after class were a welcome opportunity to connect. I cherished those intimate times together before she headed off to college, when we discussed what she learned in my course, how her app development was coming along, college applications, her part time job and life in general. On that last day on campus, we ate together and then headed to South Station. It was her spring break and, because of the pending doom of Covid19, a class trip to Amsterdam had been canceled so she decided to hang out in NYC with me and the many friends from summer camp that she knows in the city. We thought nothing of it to have a couple of her high school friends come along for a few days too. Looking back, it’s funny to think about the anxiety we had of the four of us in my apartment for a few days. It would be tight, but we’d make it work.

Amid all of this, my elderly mother was showing signs of decline. The day before Thanksgiving, she had a fall. Falls are not uncommon for an 88 year-old with limited mobility and several health issues, but this fall resulted in breaking her ankle and finding out she had two serious cardiovascular blockages. Two stents later, she was shipped off to a rehab center to recover from the stent procedures and start PT for her ankle. Sadly, mom was not a fan of PT (“the exercise repetitions are so BORING”) and she didn’t appreciate that she had to commit to the physical work if she were to ever return to her apartment in an Assisted Living (AL) facility in Cambridge, MA. Weeks turned into months and mom continued to decline both physically and mentally; she had lost interest in eating (an early sign of dementia) and as a result, her energy was waning and her body was starting to atrophy. All the while, the pandemic was becoming real and we were worried for the possibility we might not be able to visit with her if things got worse. The last time I had seen her was March 2nd – a quick visit to the rehab center before class that day – and she seemed to understand that she was declining, but I’m not sure she fully understood death was near.

Meanwhile, my middle daughter, Amelia, was on a ship on the South Pacific sea off the coast of New Zealand. A Junior in college, her semester at sea program ended March 23 and her plan was to backpack with friends in NZ for a few weeks once the program wrapped up. The same week my youngest was making the most of NYC with friends as it began the pausing process with local shops and restaurants starting to limit hours or closing altogether, Amelia’s program was cut short and we were scrambling to get her back safely (and virus free) before she ended up stuck in NZ indefinitely. So many swift decisions to make – from where she should make safe connections (SF was optimal) to whether she’d be better off in NYC,  Boston with her dad or with my oldest daughter, Abigail, who normally lives in NYC but is temporarily based in Portland, OR for a film project (currently on hold). We decided NYC was Amelia’s best bet so she could at least be with me and her younger sister and close to her friends in NYC. Looking back, we still had no idea how severely life would change for us or how drastically NYC would be hit by Covid19.

Eliza’s friends got back to Boston before things started to get uglier here in NYC and Amelia arrived safely here a week later. There was a mild panic in my home towards the end of that week when it sounded like NYC was totally shutting down. The girls could have gone to Boston, where their dad had more space for them in his home, but we didn’t know whether they were asymptomatic carriers, potentially exposing their father to Covid19. He was caring for his elderly, immunocompromised, parents and the risk was very high. I was also deeply worried about being completely alone. I had moved to this city alone because it gave me so much outside my doors that it didn’t matter. However, the prospect of being totally alone (other than my elderly Maine Coon cat, Edgar), scared the crap out of me. What if I got sick? What if they got sick and I couldn’t care for them? No personal connections for weeks? I just couldn’t bear it. I’ve never been clinically depressed, but I thought about how being alone indefinitely could trigger something like that; never mind the anxiety of fearing for my children’s health. Undoubtably, with so many sheltered alone in place, a major side effect of Covid19 will be depression, anxiety, suicide and accidental death. This is a traumatic moment in time for many and I will be forever grateful my girls stayed here in NYC with me.

So, here we are. I’m referring to this time as our “current normal” because we don’t really know what life will be like day to day or month to month. We’ve adapted to a life of unpredictability; accepting that each day is what we make of it and what lies ahead is truly unknown with minimal structure. Amelia and Eliza are doing two-week rotations between the Murphy bed and the couch. Weekdays are somewhat defined by Eliza starting online high school classes around 8am and I’m on Zoom with coaching clients, students and my work colleagues. Both girls have started to go running along the Hudson river each afternoon; doing their best to socially distance, donning gloves and keeping a scarf handy. I am keeping up with yoga via my favorite studio‘s live and on-demand classes. We are cooking together a LOT which we haven’t done for years. I’m breaking out old favorite recipes and teaching my girls cooking skills. Amelia, our resident artist, is creating new works almost every day – collages, drawings (this blog’s heading pic is hers), and evening hours are filled with music, an occasional cleaning party, binge watching several different TV series and slowly making progress on an epic, 3000 piece puzzle. While Edgar the cat is delighted to have constant snuggle time, he’s exhausted by all the activity that comes with us being home all day. We’re very happy he’s here with us though.

The current normal means that at any time, things will change and we’ll just deal with it. This week, it was mom’s passing. We knew it was near, but hadn’t considered how it would feel to not be able to be with her in the end, to sit with her as her body shut down, to be graveside to say our goodbyes or grieve together as a family. My three, globally distributed, siblings and I had a complicated relationship with our mother and mine was especially difficult with long periods of estrangement, anger and pain. She was my mother though and I was so sad for how she had to leave this world – totally alone. She never left the rehab center. In her last two weeks, PPE was required for visitors and none of her local relatives felt comfortable going there. Her caregivers were kind to her and I am confident she was comfortable at the end. Her funeral involved a brief, live streamed graveside service conducted by a rabbi who knew our mother. Her nieces and a nephew attended – abiding by the five-person maximum allowed at the grave site and all standing ten feet apart. My siblings, our children and a few cousins, watched the live stream together on Zoom. It was surreal and I still don’t feel closure because it was more like watching a reality TV show than my mother’s funeral. Since we never had the habit of talking routinely – she had a hard time hearing on the phone and never became a cell/text user- it’s still hard to believe she’s gone.

Moms_Funeral_CovidThis week, we conducted virtual Shiva sessions with family and friends via Zoom. We prayed and we told stories of mom with a focus on her best self – when she was funny, supported us and how she served as a feminist role model. It still doesn’t feel real for me though. It also feels strange after the past year of a very high-touch relationship with my much older siblings navigating mom’s care, making arrangements, lamenting over her lack of progress in rehab, that we no longer have that forcing function to pull us together. We had been chatting daily on WhatsApp. My sister and I calling each other almost daily to strategize about mom’s care and finances while also discussing how she impacted our lives – for better and for worse. It’s been an intense time. That was our current normal and will somewhat return once we are allowed back in her AL facility to clear out her things – an event that may not be until this fall or even winter given the vulnerability of the community with whom she lived.

We broke the Shiva this week to celebrate Passover. Abigail, three hours behind us, was preparing her own seder feast as we did our abridged “30-minute seder” here in NYC. I found a local butcher who scored me a perfect, small, brisket for three and a shank bone. Amelia waited in line for an hour at Trader Joe’s only to be rushed by their staff to grab matzoh, apples for charoset and other much needed sundries and get out of the store as fast as possible. We left the massive puzzle in tact on the dining room table, carefully placing a computer atop scattered puzzle pieces at the center so Abigail had a view of our tiny spread. We were supposed to be in Portland with her this week – celebrating with dear friends who were kind enough to drop off “Passover in a box” for her earlier that day. I am so jealous she had home made matzoh balls for her chicken soup! We made it work. It wasn’t quite the same, but I was with my girls and we are healthy and safe and that, frankly, is all that matters right now.

My biggest take aways from this current normal is to lean into life as it is today and appreciate this time with my children in the moment. While a planner by nature, these times have shifted my mindset to accepting whatever happens as it happens. I truly believe “this too shall pass”, but I have no idea what the future holds…and I am ok with that. I am absolutely sure life will not go back to the new normal I had adjusted to in NYC. Some of my favorite haunts will not survive, new ones will appear. We will start connecting with friends again, but perhaps with more caution and preparedness. The markets will suffer, but eventually recover. My children will go on with their lives, but we will have new memories together of the time we were forced to live in a period of complete unknowns – grateful we had each other and our health during this time. We will say goodbye together as a family to my mother, likely at her Yahrzeit a year from now. We will embrace life with a new lens – appreciating the moment like never before and being grateful for what we have vs. what we’ve lost.

Each night at 7pm in NYC we hear the loud clammer of residents far and near. They are shouting out their windows, banging pots and pans, and celebrating the countless medical professionals and service people supporting the US epicenter of Covid19. This is the city I moved to; not thwarted by disaster. We’ve been here before during 9/11. We stand together, we will get through it. It’s our current normal.

Testing Leadership During Trying Times

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

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

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

To inspire trust: Lead by Example

To build trust among teammates: Suffer Together

To restore trust when it weakens: Hold People Accountable

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

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

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

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

A Pandemic’s Impact on Remote Work

covid19With the COVID-19 virus continuing to spread, there is a potential for many teams and whole companies to have to quickly shift gears from working in HQs and globally distributed offices to working from home. This will impact the operations of both the companies handling this rapid scale in remote work and companies unaccustomed to a remote work culture. It will also impact personal and family life at a broader scale; creating new demand for services and products that cater to at-home workers.

  • Remote-friendly software tools like ZoomSlackHangouts, etc. must not only ensure their products can function at scale with lumpy spikes in both adoption and usage, but should also ensure their teams can handle the stress on the company — from sales and user onboarding to customer support and billing. Teams need to prepare for growth they’ve never experienced. This is a chance for these companies to shine, but they could also easily implode (for anyone buying up their stock!).
  • If a company has not had a remote-friendly culture to-date, the shift will a big change — and could be sudden without time to prepare. HR and operations teams should start to get up to speed on trends and best practices for remote work, stat. This article has a great list of reads on the topic. Share with your managers and start talking about how you might operate if you have to shift to remote work for an extended period of time.
  • Assuming the dust settles and we will get past this impending pandemic, once you’ve opened the door to adopting a remote work culture, it may be hard to go back. My prediction is that there will be a higher demand for more remote-friendly software solutions, more workers looking for remote roles, more need for co-working spaces outside of urban settings and a lot of empty space in large office parks and urban towers.
  • In terms of personal and family lives, I could imagine even more demand for home delivery services, build-out of home offices and demand for in-home care givers. Those who have not traditionally worked from home will quickly realize that it’s not as simple as sitting at your laptop on your couch for the day. The new remote workforce will need private spaces away from family and life’s distractions (laundry, dishes, the dog!) in order to focus. They’ll need alternatives to daycare and possibly even need work spaces for children who cannot attend their schools for some period of time.

While there’s no need to panic (yet), it’s prudent to think about how the potential for a pandemic will impact our work and family life — beyond the worst possibility of ourselves and our loved ones actually getting the disease. Until then, be safe, get the facts straight, prepare for possibilities and PLEASE, if you are sick, stay home!

Self-Awareness & Asking For Help Are Super Powers!

What’s the difference between having an Advisor, external coach, internal coach, and/or therapist? Should I join a Peer support group? I get asked these questions a lot. The good news is that usually when I am asked this question, it’s because someone knows they need help. With so many options these days, it’s hard to know which to choose or how best to leverage each, or whether adopting a combination of any or all make sense.

My perspective on the many ways to get help…

  • Advisor: Most advisors are domain experts or experienced operators in a particular area (product, marketing, sales, finance, etc.). They are commonly called upon when domain-specific guidance is needed, to make introductions to customers, prospective partners or job candidates. Advisors may also mentor junior members of a team when you lack the funds or time to hire in an experienced leader. Advisors are usually given equity for their contributions, commensurate with their experience and the time they commit to the company. Some advisors work ad hoc as needed, others are more prescriptive with set number of hours per week/month that they are available for consultation. In some cases, advisors are involved so much that it warrants a mix of equity and consulting fees. My heuristic for these types of engagements are to assess whether they are performing a part-time role you’d otherwise fill with a full time employee (FTE) if you could find/afford them. These engagements should be time-boxed and outcomes measured as you would do for any FTE.I recommend nailing down expectations prior to any equity grant and using a template like the FAST agreement to solidify an advisor relationship. Most startups have at least 2–3 advisors filling in complementary areas, sometimes many more, but be cautious about too many overlapping interests or people who seek to be an advisor too early before you’ve established a rapport and figured out how they can be helpful. There are a lot of bad actors out there just looking for free equity.
  • External Coach: External coaches are objectively focused on professional (and often personal) growth. They work within the context you bring them. The best coaches guide individuals towards finding their own solutions using tools and frameworks they’ve developed themselves and/or learned from professional training. “A central tenet of coaching is a faith in your client’s inherent wisdom. Good coaching is about revealing their truth, not yours.” (Tarikh Korula) You should expect to commit a minimum of 2–3 hours per month with a coach and many offer email/text touch-points between a regular cadence of sessions. If properly trained and experienced, external coaches can be pricey. Most charge thousands of dollars monthly or quarterly, but if the chemistry is strong it can be a partnership – and an investment! – that’s well worth the money and time. My dear friend Steve Schlafman has great advice here on how to find the right fit with a potential coach.
  • Internal Coach: Internal coaches (sometimes called “Talent Development”) usually have the same skills/training as external coaches and are hired to develop executives, managers and occasionally individual contributors. They are a marvelous add to any team, but remember that they are employees and therefore have inherent bias as part of the inner workings of the organization. Internal coaches are accountable towards the overall success of the business vs. to an individual and may not always be objective — especially given that they know the players and may be coaching them as well. If you are hiring an internal coach(es), be thoughtful on who they will work with and how to measure their success vis-a-vis employees’ growth. Success metrics can be everything from basic employee retention numbers to frequency of/average time to promotions, employee satisfaction surveys and external recognition as leaders and contributors. Learn more about how internal coaching and talent and development is evolving inside organizations here.
  • Therapists: What used to be stigmatized, is now considered almost a right of passage for most entrepreneurs and leaders dealing with the stress of scaling their companies and balancing life’s demands. Therapists are medical professionals with extensive training who focus on an individual’s psychological, emotional and physical wellbeing. Most therapists lack business context or domain expertise, but may have some insights and empathy from other clients with whom they work. Therapists are wholly objective, can be very expensive, but also extremely worth it if you are under a lot of stress at work and/or at home. If you can afford it or have insurance to cover, I recommend being proactive and engaging a therapist even if everything seems “OK”. Establishing a relationship and providing historical context ahead of any stressors or crises will prepare both you and your therapist if those events arise.
  • Peer Support Groups: The ultimate in gaining empathetic support is being a part of a tight knit group of people going through the same types of challenges you are facing. I highly recommend finding a small, like-minded, group of peers to connect with on at least a monthly cadence. The group is ideally made up of a minimum of six (for breadth) but no more than eight individuals to encourage intimate conversations. They should be from a diverse set companies with varying personal backgrounds to allow for different perspectives and to avoid any awkward competitive conversations — although there should be an inherent “cone of silence” among the group. There may be some areas of commonality like all are at roughly the same stage in their careers, stage of company (e.g., pre-series A or post-IPO), or stage of life. Often, these groups are facilitated by a professional coach or peer mentors who ensure that conversations are meaningful and everyone has a voice. Reboot.io has a great program for CEOs as does the Inc. CEO ProjectYPO, etc. but there are also niche peer groups like VPE Forum that specializes in engineering leaders. It may take some time to find the right group, so be patient. You’ll know when you’ve found your people!

All of the above resources are valuable for anyone in an organization, not just to founders and executives. It is a sign of strength when I meet a leader who taps into each one to develop a healthy, well-balanced, support system. More and more CEOs and leaders are recognizing how critical this support is to their personal and professional growth. Being self-aware and asking for help is a super power, and no time is too soon to get started!

Time, Talent & Treasure

Bootcamp 2020

Bootcamp 2020 students, Faculty & TAs

I am a former Trustee, alumna, parent, donor and longtime community member of a non-profit organization that’s mission is “changing lives for good” through the the community’s gifts of time, talent and treasure. As a hundred-plus year old organization with a diverse group of alumni, staff and trustees, we strive for our community to give beyond dollars (treasure) and to pay it forward with their time and talents. This mission is something I deeply believe in beyond this particular non-profit and extends into my personal and professional life; and it’s something I value and look for in the people I work with. 

If you follow me on Twitter, you know we just wrapped up an eight day Startup Bootcamp at Harvard Business School (HBS). This program was brought to life four years ago by my mentor and friend, Professor Tom Eisenmann who recognized a growing need for our first year MBA students to explore their startup ideas and understand the world of entrepreneurship through experiential learning. First year HBS students enroll in a prescribed curriculum known as their Required Course year, and these students are referred to as “RCs”. RCs wanting to start companies, learn about joining startups and/or venture capital have limited time outside of classes and other school-related activities to pursue these interests in their first year. The advent of Startup Bootcamp created that time and programming to explore before their second (“Elective Course”) year. Approximately 200 students take time out of their January break to return to Boston to immerse themselves in startup land. Startup Bootcamp is free to enrolled students and is seen as a Pass/Fail course on their transcripts.

Those who know HBS, know our primary teaching approach is via the case method. This is an excellent way to help our students understand the complexities and challenges of business through the lens of a diverse set of protagonists and companies around the world. Many of our course sessions for each of the hundreds of cases our students read invite the protagonists into the classroom to discuss their perspective and “what happened after the case” with our students. This time with these leaders is invaluable to students and often the leaders get as much out of the experience as they impart their wisdom and share lessons learned.

In the past few decades we have introduced more field courses to complement the case method with a learn-by-doing approach. Like our live case discussion with protagonists, the HBS field courses tap into some of the top entrepreneurs and industry experts in the world. Startup Bootcamp is no exception! In order to pull off an intense eight days of programming, we drew in over 70 guests throughout the week. These guests did everything from keynote talks and serving on panels to offering hours of coaching time and workshops. Each guest donated their valuable time, treasure (many paying their own way to travel from all over the US) and immeasurable talent to be part of this program. Our students were blown away with the level of high quality content each guest provided and all were so grateful for every ounce of insight they received on their ideas, their teams and their future as entrepreneurs, joiners of startups and members of the venture capital community.

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Tagging over seventy people is well above the maximum limit for most social media platforms, so herewith, a hearty THANK YOU to all of the guests who joined us last week. We absolutely could not have done it without you!

Gil Addo
Gideon Ansell
Henry Ancona
Berlynn Bai
Jay Batson
Eliza Becton
Edward Berk
Ethan Bernstein
Peter Bleyleben
Jana Boruta
Jeff Bussgang
Bobbie Carlton
David Chang
Chuck Collins
Maggie Crowley
Karen Devine
Brian Doll
Richard Dulude
Doug Fox
Dave Gerhardt
Jodi Gernon
Shikhar Ghosh
Rob Go
Jamie Goldstein
Samara Gordon
Sean Grundy
Rohit Gupta
Christian Heim
Jason Hines
Sarah Hodges
David Hornik
Alex Iskold
Jennifer Jordan
Howard Kaplan
Stella Kim
Melody Koh
Brendan Kohler
Tarikh Korula
Karen Korula-Young
Jeremy Kriegel
Pascal Kriesche
Elizabeth Lawler
Sarah Leary
Elise Lelon
Rebecca Liebman
Jennifer Lum
Nate Maslak
Bob Mason
Devon McDonald
Bob Moesta
Jennifer Neundorfer
Eric Paley
Andrew Payne
Melissa Perri
Mark Pincus
Amira Pollack
James Psota
Vinayak Ranade
Christina Raymond
Jeffrey Rayport
Caty Rea
Carlos Reines
Laura Rippy
Mark Roberge
Bryce Roberts
Brendan Schwartz
Javier Segovia
Shereen Shermak
Caroline Sherman
Nancy Tao Go
Satish Tadikonda
Jill Ward
Christina Wing
Peggy Yu

Finally, it takes a village to pull off such an intense program that took months and many hours of planning and an average of twelve hours a day over eight straight days to orchestrate. Hats off to my co-instructors, Allison Mnookin and Martin Sinozich for being great collaborators, to Jacey Taft and Sneha Pham for their tireless support throughout many twists and turns and to our outstanding Teaching Assistants – now second year MBA students and Bootcamp alumni – Gaby Goldstein, Jad Esber & Ollie Osunkunle. Best team ever!

Interested in learning more? Listen to what our students and faculty have said about the program in this video and check out our Instagram page!