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!

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!

Product Discovery 101

As an entrepreneur, how confident are you that you fully understand your customer’s pain points and/or job to be done? When I first meet an entrepreneur, they tend to start selling me on their solution before explaining the problem they are trying to solve. I typically see or hear little evidence that they’ve done true discovery work to validate the problem or their target customers. While gut feel or personal experience with the problem can be a strong signal there’s a problem to solve, without proper product discovery work, you won’t truly know if you have a winning solution.

For those that profess they have done proper discovery work and have validated the problem, but don’t yet have a product, my follow-on question is “How do you know people or companies will use your product?”. More often than not, I get examples of interest tests such as hits on social media posts or answers to surveys that are so biased it’s hard to trust the results. Further, they may have a good hunch there’s a job to be done that needs improving/replacing, but they cannot describe where in the customer journey they can truly make an impact.

I’m a big fan of confident founders who are passionate about their idea, but a little humility and a lot of discovery work can determine whether there’s a winning solution and save a lot of time and money wasted on building the wrong thing. If fundraising is also a consideration, being able to have real data vs. gut feelings and biased test results can be the difference between a modest angel round and a strongly led seed- or A-round.

To that end, a few tips…

Interest vs. Problem Testing

“We had 1000 clicks on our Facebook ad in the first 48 hours”,
“Our conversion rate from click to sign-up was 50%”, OR
“We interviewed a bunch of people and they said they’d use our product if we built it”

When I hear these types of quotes early on in a product’s lifecycle, I do a mental facepalm. These quotes suggest they may have found an audience interested enough to click on an ad and to give their email addresses, but they still have not proven anything about the actual usefulness of their product or that it solves a real pain point for their target customer that they are willing to pay for to fix. These tests are OK to do, but should not be the only way you validate problems to solve. If you plan to do interest tests, consider these approaches:

  • Social Media: Great for finding your audience, should be done on multiple platforms and carefully crafted so as to answer only 1–2 hypotheses. These hypotheses are commonly “Is this where our audience is if we want to market to them at some point?” and “Are they interested enough to click and learn more”. These tests can be expensive so be thoughtful about where and when to do them (e.g., if you’re building a product for teens, test on Instagram or Snapchat where they are (vs. Facebook)
  • Landing Pages: The best way to capture interest, email and demographic data. If they found you through social media tests or googling,
    a) you’ve proven they were interested enough to learn more,
    b) that your SEO works and they found you; and/or
    c) that they trust you or care enough about the problem you wish to solve that they will give you insight into who they are.
    These future customers are great targets for problem testing and could be your early adopters. Be careful though, early adopters are great for testing, but don’t always guarantee a chasm-crossing to the mainstream. This too must be validated.
  • Surveys: Surveys are very hard to do right and often capture a lot of random and very subjective information instead of getting real data to inform your product. We have this tendency to think “while we have them, let’s ask them everything!”. Great surveys are:
    • Ten questions or less,
    • reflective in nature (Ex: how many times did you buy “X” in the last month?) and very data-centric (Ex: how often do you order takeout for dinner?). Reflective questions should have ranges to choose from that do not sway the prospect or suggest there’s a right answer; and
    • capture basic demographic information only relevant to the questions at hand (e.g., don’t ask age or gender or income unless that’s specifically something you need to know about your audience); as long as you have contact information, you can always follow up for more demographic data if needed.

More important than interest tests early on, are tests that validate there is a problem worth solving and where exactly a product can be most successful in solving that problem. Validating hypotheses about the problem through a variety of methods is going to lead to a far better outcome than clicks on a Facebook ad. The more ways you can learn about your target customer and discover where the problems are, the more likely you’ll get on the right path to solution building. This process takes multiple iterations and approaches to get to a minimum viable product (MVP) that begins to address the issue.

Consider trying these different types of problem validation tests in your discovery process:

  • Interviews: Similar to surveys, interviews are as much an art as they are science. It is incredibly easy to lead a witness, bias answers and hear what we want to hear in an interview. The best guide for conducting a proper discovery interview is Rob Fitzpatrick’s book “The Mom Test”, which I encourage every entrepreneur and product manager I work with to read. A few key takeaways:
    • PRIORITY: Talk with strangers! Any interview subject who is a friend, family member or member of an affinity group (e.g., student/alumni at your school), you bias the conversation. They are more likely to tell you what you want to hear and validate your idea vs. truly objective answers. If you’re not comfortable talking with strangers, don’t interview or hire an independent consultant/friend to do it for you.
    • Write a script and be clear about what hypotheses you are trying to validate before the interview. Sticking to a script ensures a clean comparison of results after interviews.
    • Start by setting the stage. You are learning from them vs. selling them on your idea, no answer is a wrong one and set a time expectation — 30–45 minutes are ideal. Always end by thanking them, asking if you can follow up AND if there’s anyone else they suggest you speak with about the topic.
    • Always ask open ended questions — Ex, tell me the last time you…
    • Always have someone serve as observer & notetaker not just to capture what’s being said, but to look for body language, expressions and any other “tells” about the problem you are trying to learn about.
    • Do more listening than talking — you’re there to learn from them, not sell to them.
    • Unsure what they were explaining or want to reframe their response into hard data? Echo it back and see where that leads them. Ex: “So what you said is, you usually eat out twice a week?”.
    • Always record the session — most interviewees will not mind being audio or video recorded (the latter is better), especially if you assure them it won’t be shared outside of your team.
  • Ethnography: Observing prospects performing the job you hope to improve/replace can be extremely insightful. You may see hacks they would never tell you about in an interview or discover there’s a whole new set of problems in their process that you had no idea existed.
  • Emotional journaling or mapping: Having a prospect journal or map out their process and highlight how they feel along the way can pin-point exactly where they are most frustrated in their process. This is also a great technique if you cannot observe the prospect in the setting where the problem exists. Ask them to journal or map and send you something within a set period of time.
  • Journey mapping: Bringing together all your discovery work to identify where you found patterns of highs and lows. These may surprise you; often where we hypothesized there was the most pain in a process may be somewhere completely different.
  • (Don’t do) Focus Groups: I am generally not a fan of this form of discovery. It lends itself to group think and can lead to false results. Focus groups can be useful later in the product cycle when you want to get reactions to branding or observe groups of people using your product if it’s a tangible item.

Prototype Testing
The best way to validate a problem exists is to actually insert yourself into the process and learn by doing. These tests lean towards solution building, but the idea is you’re doing tests without building anything or building very little to get clarity on the problem and the customer. The most common forms of these tests are:

  • Lo-Fidelity Concierge Testing: Jump right in and assume part of the role that your product might fill in the future. If you were coming up with a new restaurant reservation system, this may involve a phone conversation with the party needing a reservation and having you do the actual booking for them and perhaps texting them to confirm their reservation. By being the intermediary, you are fully embedded in the process to understand all sides of the problem. The key to success of these early tests is to resist the temptation to correct your customer or other players and just go with whatever they do to experience the process. You can tweak things as you learn more about what works and what doesn’t work along the way.
  • Wizard of Oz (WoZ) Testing: Unlike a concierge test which is transparent and prospective customers are aware you are part of the solution, a WoZ test allows you to intervene without a customer knowing you’re doing work behind the scenes. This is usually created by having a prototype of some sort that the user interfaces with, but involves manual labor that users don’t see. For example, In the early days of Uber, a dispatch team was used to direct drivers to pick up customers and text customers about arrival times before they had complex algorithms and a driver app.
  • Physical Prototypes or Competitive analogs: If you are building something non-digital that could be expensive to manufacture before you test, there are several creative ways to do discovery early on.
  • Prototypes: Small runs of your future product or handcrafted using freelancers to do 3D printing, sewing or even a pop-up restaurant are ways to get your idea concept tested and feedback on its use before spending too much money. One of my favorite examples of these is a former student’s idea for a smoothie making machine for offices. Before he even made the machine, he started making smoothies in offices just to see what employees liked, how visual aids helped (having fresh fruit nearby inferring a fresh product) or offering add-ins like chia seeds or protein powder to see if they made his smoothies more appealing. Not only did he learn what flavors were most popular to focus his MVP, but he also got a lot of insight into the operations of small to medium sized businesses, how much of a footprint he’d need for machines, maintenance requirements, etc. It was an invaluable experience for this entrepreneur.

Smoodi team testing mix-ins with their early prototypes

  • Competitive analogs: Having target customers use other, similar, products can be as telling as using the product you hope to create. Using a tool like UserTesting to have a prospect walk through their use of a current competitive product can be very insightful. Having target customers use a competitive product for a week or two can also be insightful. Just be careful not to start creating your product based on what these other products have/don’t have. The goal is to understand how these prospects interact with those products today — it’s not to get feature parity.
  • Expert Testing: Sometimes, you are working in an area where you may not be an expert, but you have a hunch it’s a white space ripe for disruption. If you don’t have access to the experts or their customers, find or create a space for them to connect and observe through their experiences. This could be as simple as finding them on Quora or Reddit and looking at threads of questions that are related to what you’re exploring. You could create a forum for them to chat if none exists (e.g., an affinity group Slack workspace or Meetup) or even create an event to gather the right people. Another one of my former students got her start with ElektraLabs by creating an event which not only informed much of the early product, but also connected her with experts who went on to both advise her company and evangelize her product.

A Few More Best Practices
All of the above tests should be explored whenever you are in the process of validating problems and target customers. Try many and do them often. Testing never stops! Here are a few more things to consider when designing your tests:

  • Eliminate Bias: I can’t emphasize enough how important it is to have as objective a test as possible. This means not asking your friends, co-workers or parents to participate. Find total strangers who can give you honest and authentic feedback.
  • The Rule of 5: If you keep your criteria very tight — who you are asking and very specific things you are testing — you need not do more than five tests before you know where you are trending. But limit your variables per test (see next bullet).
  • Limiting Variables: The Rule of 5 only works if every test you do is limited to a couple of key questions you want answered. The more variables in a test, the harder it will be to discern what influenced an outcome. For example, if you are trying to test whether women ages 18–20 vs. women 30–35 have a problem finding a great yoga class, design a test that is the same in every way, just test it with five of each of these two different audiences. Similarly, limit variables in prototype tests such as in the smoothie test noted above, where when the founder tested add-ins at one particular site, that was the only variable he changed; all other aspects of the test remained the same including the site itself.
  • Breadth of Demographics: You may be designing a product that you believe everyone in the world will need OR that you believe only one target audience needs. Gender, income level, geography, etc. may or may not have an impact on adoption but you won’t know that until you parse things out early on and test a few. How a 13 year-old uses a product may be completely different than a 45 year-old (Facebook is a great example of this). Also, if you don’t test different demographics, you may miss an audience that could be in most need of your product.
  • Measured Outcomes: Start with a hypothesis of what will happen per test, ideally in measurable outcomes such as % of people who accept a restaurant recommendation or number of smoothie customers who want an add-in vs. those who do not. Decide what you think success looks like for these tests. If your outcomes vary, then consider whether your test was valid and/or whether the learning lends itself to further testing or abandonment of an idea. In the case of the smoothie, the founder hypothesized that his target customer would want 5–6 flavor combinations, but found only 2–3 flavor combinations were most popular, thus he limited the flavor options in his MVP.
  • Leverage Existing Technology: Finally, in today’s highly tech enabled world there are a number of ways to engage your target customers using what’s already out there to your advantage before building anything yourself:
    • Typeforms, google forms, etc. can capture form data
    • Online payments can be simulated using Venmo
    • Texting can simulate alerts and notifications
    • High fidelity web prototypes from Figma, Sketch, Invision, etc.
    • 3D printed mockups & scrappy hand crafted prototypes made from supplies you can buy online

Another former student of mine with a software engineering background resisted the temptation to code a solution and instead created a WoZ test by cobbling together Soundcloud, Dropbox, texting and a high-fidelity mock front-end. Once she had experienced dozens of people using this method and understood what they needed, she officially built and launched the product.

Test Early, Test Often!
With all the options available, there is no excuse for weak validation of problems and target customers early on in your product development process. One test or even a few tests does not qualify a product as marketable or fundable. The more objective tests you do up front, and iterate on those tests often, the higher likelihood you’ll land on a great solution that people want to use and buy.

This blog post is largely inspired by my course, PM101 at Harvard Business School. We focus the most of the semester on best practices for discovery. I have open-sourced the syllabus for this course here.

Are You Being Strategic About Hiring?

If I had a nickel for every time I get an email or text asking if I know any full stack developers for hire, I could cover the cost of my next trip to SF. I’m also struck by the number of founders who say they’re raising more money simply because they need more engineers to code, yet they do not have a good hiring strategy.

For decades, there have been books and articles about building engineering teams. The infamous book The Mythical Man Month, by Fred Brooks should be on every software engineer and tech startup leader’s reading list (It should also be re-titled either “The Mythical Person Month” OR “Nine women can’t make a baby in one month”…just sayin’). There are also many blog posts explaining why full stack engineers are unicorns. Yet, when I did my latest poll on twitter on top hiring priorities this is the response:

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Sure, it’s fine to look for a generalist [or augmenting your team with an outsourced dev shop] to get basic stuff done, but being more strategic about your hiring process, is what could be the difference between a great product in the market vs. something basic that is slow to ship. Below are some tips on how to be more strategic about hiring:

  • Product prioritization leads to hiring prioritization: If you’re doing proper product prioritization via discovery – talking with customers and understanding what you need to get to product market fit or grow adoption – then these priorities set the hiring agenda. For example, if you’re realizing that your on-boarding process is too complicated, then hiring a User Experience (UX) person may serve you far better than someone who can code a fresh UI. If performance issues are causing churn, then hire a performance engineer; someone who knows how to diagnose and fix performance issues. Just like you are building a product to solve for the job to be done, hire the engineer for the development job to be done. 
  • Understand the roles: Do you understand the difference between a front end developer vs. designer vs. UX expert? (if you don’t, read this) Are you fluent enough in your architecture to know what type of engineer should be building which elements of your product? Many early stage companies are started by engineers who know exactly what they’re doing, but many are biased in the areas of which they are most familiar, even if that is the suboptimal choice for their current products. I’ve seen products built with .NET simply because the seasoned engineer-founder knows that platform best, without considering whether it is the best platform for their product and/or whether they’ll be able to hire engineers who are skilled in .NET (or want to learn it) to build it at scale. I’ve also seen many startups default to the language of choice for the full stack engineer they found to build their first prototype and then let that language dictate future work as their product gets market fit and scales. This rarely works out, unless that first engineer is a ringer, and most of the time the reality of having to refactor your entire codebase or port to a new language hangs over the product team…forever. 
  • Long term need vs. short term fix: Another common mistake is hiring a full time expert in an area that only needs occasional work. E.g., Performance engineering. Certainly, if you’re building a complex, distributed, application that has heavy computation or many API calls, then a performance engineer is a critical full time hire. However, it may behoove you to find a good contract engineer who specializes in performance tuning as needed; at least until you’re operating at scale. Same thing for a designer – unless you’re at scale and adding new features/products at a steady clip, then a contract designer may be prudent while you iterate on your MVP. You may pay a little more per hour for these contractors, but that far outweighs over hiring and paying a full time salary early on. 
  • Time Delay + J-curve: Just because you have cash in hand to hire, doesn’t mean you will find and hire the right people right away AND each time you add a new person to the team, there will likely be a j-curve impact on productivity.
    Screen Shot 2019-06-03 at 1.47.59 PM.png
    Therefore, when you prioritize hiring, factor in how long* some roles will take to fill (e.g., we don’t need a designer for a few months, but it could take three months just to find the right person) and be thoughtful about the cadence of adding new people to any team. Adding a bunch of new engineers at once is not going to accelerate development over night. Each time a new person comes on board, it’s disruptive to team’s flow – and this is not just about training them. It disrupts the whole
    dynamic of the team. If you’re doing a lot of hiring over a discrete period of time, set the right expectations (with yourself, your company and your investors) that a ramp in hiring will likely slow things down until new teams settle into new norms. If the ramp is constant, by the way, your teams will never settle into a groove leading to employee dissatisfaction, high turnover, product delays, etc.

    *This delay should also be considered in the budget exercise for these roles. Don’t front-load salary expenses for open jobs that may take weeks or months to fill. 
  • Humans are not robots: Hiring is hard, and even when you get really good at it, at the end of the day these hires are human beings that have their own unique needs, past-job baggage and career aspirations. Their added productivity, how they diversify and/or add to your culture is only part of the consideration. Having a strategy to prioritize manager, team time and money for their human needs (benefits, HR support, a strong on-boarding experience, ongoing training and mentorship, etc.) is just as important as having a strategy to prioritize these hires! 
  • Apply the 80-20 rule: A great product leader will tell you that if you invest 80% of effort to understand the problem, it should result in 20% effort to build the right solution. The same applies to hiring. If you take 80% of your effort to develop a great hiring strategy and program, it should lead to 20% of the effort to bring great people on board and retain them for the long term. 

There’s a severe opportunity cost that comes with bringing on the wrong people and/or at the wrong time and not having the right people programs in place. Even if you are a tiny early stage company, having to let someone go, or having them quit, and finding a replacement not only stresses out the manager and team, but there is a productivity hit to all while you go through the process. Even though it may feel like you’re moving slowly through the process of building a team, a strategic approach will pay off.

You can read more about my thoughts on hiring for startups here. Please share other ideas on this topic in the comments!