Transition Reflections

Monarch chrysalis (Danaus plexippus) in its “neutral” phase.

Over the past year, I have had several clients going through periods of transition. Some have been co-founders who realized that it was time for a more experienced leader to take their business to the next level. Some were just ready for something new. Others have shifted their roles from leader to individual contributor and in one recent case, a CEO-founder sold their company and is now transitioning to a leader within a very large organization. In each of these cases, these were not overnight changes, but rather they were thoughtful shifts that each managed with intention. By transitioning with intention, we are more likely to come out on the other side with more clarity, less stress and with a higher likelihood of success – in whatever way each individual defines success.

The book Transitions, by William and Susan Bridges, outlines the three stages of transition – The Ending, The Neutral Zone and The New Beginning – and encourages the reader to pause and understand each of these phases during their own transitions. This is something most of us do not do with intention – whether it’s ending a relationship, changing a job or transitioning from a household of kids to an empty nest. When it comes to our employment, we have our last day at an old job on a Friday and start our new job on Monday; perhaps taking a week or two in between to decompress. Most people do not have the luxury of long breaks between jobs or extended periods of time to think about their transition before they step into the next thing. Additionally, as Bridges points out, we often don’t see when we are in a neutral zone – that time when we have officially “let go” of who we were before things ended, before we fully embrace the new beginning. Think of it as that time between how you associate yourself with “we”. When you stop saying “at my last company, we…” but you have yet to associate yourself with the “we” of your new role and still refer to your new team as “you”. E.g., “How do you do things here?” It is in this neutral zone where we are truly able to start our transition to a new beginning.

With this neutral zone in mind, I encourage my clients to take a moment – even if it’s just an afternoon – to consider the impact of a transition and what lies ahead. This is usually in the form of journaling where they write their responses to the prompts below and then we discuss them together. Whether or not you have a coach with whom to process your answers to these prompts, you should find journaling your responses to be a useful exercise. You might also consider asking a friend or partner to be your listening guide as you talk them through; be sure to encourage them just to listen and be curious about insights vs. helping you try to solve things.

The prompts below are very career-centric, geared towards startup founders. However, one can easily apply this guide to any type of transition.

Document Your Feels

There is lots of research proving that writing what’s going on in our brains is an important way to process and organize our thoughts. Whether you keep a journal or are just taking a moment in transition to write your thoughts, consider the following:

Highlights & Lowlights

  • What are 1-2 highlights from your experience? This could be a memory of your first big product launch, closing a hard funding round or even just that night that all hell broke loose and you fixed a hairy bug at 2am. What made these experiences great? What do you remember about how you felt – physically and emotionally – about these events? How did they motivate you going forward?
  • What are 1-2 lowlights from your experience? It could be that one time you really thought the company was dead or when one of your best employees quit because they just couldn’t adapt to the frenetic startup life. What made these experiences awful? What do you remember about how you felt – physically and emotionally – about these events? How did they motivate you going forward?

Learning

  • What have you learned as…a leader, partner, employee, peer, innovator, business-person? Most leaders wear many hats and it’s important to use these different lenses to fully embrace all the learnings that came from your journey.
  • What specific skills have you developed or mastered? Consider all functions within an organization – financial, sales, product, hiring, etc. These are typically your marketable skills and are often very transferable for the next gig.
  • What are you more aware of about yourself that you may not have known at the start of this journey? For example, you may have thought you were not technical, but after having to build your company’s first app because you couldn’t afford to hire a developer, you now know you are more technical than you thought you were at the start!

Evolution

  • How have you evolved? Consider phases in your journey – by role or “eras”. For example, perhaps who you were as a strategic leader was very different when you were bootstrapped vs. once you raised your A-round and had a board of directors. Or, perhaps you have shifted in the way you approach the work day as you went from being single to being married with children. 
  • Who have you become? Think about your key characteristics, your behavioral patterns and attitudes. How is the current “you” different from who you were when you first started this journey? Do you feel differently about things (family, relationships, career) or have changed your reaction to certain situations (more/less triggered, sensitive, focused, caring)?

The Future

  • What new tools do you wish to ADD to your toolbox? For example, a product-oriented CEO may wish to learn more about creating a sales playbook or experience venture from an investor’s perspective vs. as the fundraiser. What tools are missing from your toolbox?
  • What existing tools in your toolbox do you wish to HONE? For example, a founder may have led a small team and might want to know what it’s like to lead a larger team at scale. Or perhaps you were great at building a social media campaign, but want to learn more about the broader elements of marketing and brand functions.
  • What do you wish to leave behind? Consider elements of your role that you didn’t enjoy and that you don’t want to do again (e.g., finance or maybe even management!). Similarly, consider behavioral characteristics that no longer serve you. Were you a micromanager who spent too much time in the weeds? Did you spend too much time on product and not enough time on the rest of your business? Think about what drove you to develop these behaviors, why they did or didn’t serve you in your role and how they will or won’t serve you going forward. 
    • NOTE: The act of physically releasing things can be very healing. Start by writing a few sentences or drawing pictures on a piece of paper and (safely) burn it or fold it into a paper airplane and toss it from a city window or into the sea. Instead of writing, you could also use natural objects to represent things (e.g., an acorn to represent your tough outer shell or a dried leaf to represent being fragile in certain situations). State your intentions – out loud or in your mind – as you let these things go. What will be different once you let them go?
  • What do you wish to teach others? Whether your transition is related to a great exit or awesome promotion or because you feel you failed in some way – your business imploded or you were fired – you have lots to teach others! My father called any learning, even if we failed, “money in the bank”. Take time to reflect on what you learned (above) and how you might be able to mentor others to grow or avoid pitfalls. Not only will this help others following your path, but this will also help you further process your transition.

When journaling the above, I encourage writing full sentences and fully expressing your thoughts around each. Don’t worry about being legible – you may never go back to read them – it is the act of writing that is key here. As you write, look for themes or patterns – do these further inform your transition? Do you see new patterns and/or growth opportunities?

Other Opportunities To Reflect And Reach Closure

If your transition involves others such as cofounders or partners, consider conducting a group reflection process in addition to your individual process. This can be a great way to recognize how the sum is greater than its parts. While each team member played a role in your efforts, it is almost always how the team worked together that led to where you are now. Schedule a couple hours to be together – ideally, face to face and out of the office/home – and share the following with each other:

  • Highlights & Lowlights of the work you did together. Consider specific wins you had as a team and what made that work together special. Name one or two times that the team was not at its best. How did these moments affect the trajectory of your business/relationship?
  • What are you most proud of as a team? Are there events or elements of your business that could not have happened without the team coming together?
  • Key learnings for each individual. Have each person speak to one or two key learnings. It is OK to “+1” someone else’s key learning, but that should not supplant one’s own learnings. Try to acknowledge each of your team members as they cite a learning. “You crushed that big deal. I learned a lot from watching you navigate such a tricky negotiation.” OR “Firing that great engineer who was a bad teammate was so hard. I really admired the way you handled that situation.”
  • State what you wish for each other to encourage their path forward. For example, wishing them a great new partnership or a challenging new role.
  • Finally, commit to each other. This may be very tactical like committing to getting together once a quarter for beers or a family gathering. Or, it could be committing to supporting each other in their journeys going forward (networking, job reference, a place to crash when they are in town, etc.…).

These prompts work best when they are spontaneous vs. prepared in advance, so I recommend sharing the prompts when you come together. This certainly depends on the type of relationship you have with your partners, but if you are the CEO with co-founders all going through a transition, I recommend you do the above with a facilitator OR at the very least encourage your partners to speak first so as not to bias their reflections. Further, if you and/or your partners have significant others, do not lose sight that they too are going through this transition. A partner who’s significant other is all of a sudden more available than they were when they were running a company, or who is feeling insecure because their partner just lost their job, needs to reflect as much as you do. Make the space for this and include them in any group processes that will serve these important adjunct members of your group.

The New Beginning

You may know exactly what your New Beginning is – e.g., your company was acquired and now you’re in a new role at the acquiring company – you’ve got a new business idea or you have no idea what’s next. When you are unsure about what’s next, it can be easier to think about what you don’t want in your next role vs. what the perfect next role might be. Here are a few prompts to consider for the next thing:

  • What types of roles do you know you definitely don’t want? This could be a level of responsibility (e.g., a founding CEO may know they never want to be a CEO again) or within a function of an organization. (e.g., an engineer who became a product leader may prefer to go back to coding).
  • What industries are off the table for you? Maybe you spent the last decade in e-commerce and you’d like to try an adjacent area like MarTech or retail?
  • What type of people do you prefer to not work with? E.g., extroverts or introverts, micromanagers, jerks, etc.
  • What stage of business disinterests you? E.g., does the thought of inheriting a team vs. starting a team from scratch sound miserable? Or perhaps you never want to have to fundraise again.
  • What would you have to see in your future role to signal potential? Often, when in transition, we overcorrect for the things we didn’t enjoy in our last role. You may cut yourself off from something you might enjoy based on fear from your past experience. Consider what characteristics are important to you in a new role that may allow you to step into discomfort in an effort to grow and learn.

Whichever route you take, if you have less urgency to get employed ASAP, take as much time (if not more) to consider what’s next as you do with your reflections about what was. I suggest a ninety day period – yes, I know, that may be an unaffordable luxury – where you take at least 30 days to reflect, 30 days to consider your new beginning and then 30 days to gear up for the next thing. Even if you are working through the next thing during this period, try to recognize that you are still in transition and journal new insights as they arise.


Transitions are not always easy and we often don’t give ourselves the time to fully process our endings before we jump into the next thing. Take the time if you can and I am almost certain you will find it helpful. Have you tried other techniques to help you process a transition? Please share in the comments!

Good For Her Welcomes Cohort Five!

It’s that time of year when we get to announce that we have a new cohort at Good For Her (GFH). Cohort five has launched! We get an average of forty new applications each year and it was incredibly hard to narrow it down to this select group of exceptional women. This new cohort consists of nine extraordinary entrepreneurs as well as one aspiring entrepreneur. Our members are all founders, primarily in the c-suite, of operating businesses. We bring in a new cohort each year and intentionally keep each cohort small to ensure strong bonds form between members. Our cohort members are selected based on how they will complement the diversity of our current members as well as their willingness to contribute their experience and skills back to the community.

While fundraising is not the only metric of success, our current members have raised over $100M capital since January 2021 — including several $12–20M Series As. Beyond funds raised, these businesses are focused on being great employers with high retention rates, growing revenue exponentially, and building industry leading brands. Our newest cohort members are based in NYC, Boston, Miami, Chicago and Los Angeles. Our newest member companies represent a diverse range of industries — from B2B SaaS, FinTech, EdTech and Digital Health to consumer products and services. While each cohort has a special bond, the GFH community supports all members with our “give as much as you get” philosophy. From quick responses on Slack to jumping on calls in the moment when urgent advice is needed, these women strive to support each other 24×7. We meet as a community in-person a few times a year and cohort members regularly meet with each other one-on-one and in smaller groups off-line.

Herewith, our newest members:

GFH Cohort Five — 2022
Good For Her Cohort Five — 2022

(Listed from top row to bottom row)
Rave Andrews — Aspiring Entrepreneur
Wana Azam — Ullabelle
Lillian Cartwright — ShelfLife
Tiffany Faith Demers — Upkeep
Cindy Estes — Rapt
Ngoc Le — Phase Zero
Kait Margraf Stephens — Brij
Rebekah Wilson — Source Elements
Brittany Wright — Endex
Peggy Yu — Stack Education

Welcome cohort five!!

GFH operates as a registered 501(c)(3) and, in addition to the latest cohort, the organization recently added Monique Jean to its board of directors. ”I’m excited to support an organization dedicated to helping women entrepreneurs connect and build a community. As women, many of us have been in situations where we are the “only”, having a community built by women, for women, is not just about engagement or mentorship, it’s about being intentional in facilitating the progress of women entrepreneurs and supporting them in their journey.” We couldn’t be more thrilled to have you on board, Monique!

About GFH

Julia Austin started GFH to pay-it-forward after her three decades as an operator in the startup industry. “While we still have a long way to go, there has certainly been major progress since my early years in startup land when I was often the only woman in the boardroom. I didn’t feel I could fully celebrate my success without ensuring that the next generation of female leaders had access to the resources and support systems I never had.” You can read more about the founding story of GFH here.

GFH has had tremendous support from valuable women in the community. Jenny Fielding, General Partner at The Fund says “It is critical for underrepresented members of the startup community to have a trusted network like Good For Her to give them the best possible opportunities for success. I have personally seen how this community has supported their members as they build and scale their businesses and I am delighted to see this new group of entrepreneurs welcomed into the GFH community!”

Best selling author, coach and mentor Kim Scott was an early advocate for launching this non-profit when Julia decided to leave the operating world. She encouraged Julia to turn the energy around her frustration with the “injustice that surrounded the underrepresented MAJORITY” into efforts that empowered them to overcome adversity. “When underrepresented leaders come together in solidarity, we can confront bias, prejudice and bullying effectively and create teams where everyone can “just work” — in both the justice and the get sh-t done senses of the phrase.”

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

If you are interested in joining cohort six in 2023, apply here.

Walk The Talk…Every. Damn. Day.

On March 8, 2022’s International Women’s day, from social media posts with the year’s theme of #breakthebias to the New York Times Crossword puzzle theme of women in history, we saw friends, colleagues and leaders across the country proclaim their respect for and commitment to women. It was inspiring to see. However, let’s remember it is what comes after the day of celebration that really matters. The #metoo movement got the ball rolling beyond a special day or month for women in many ways, but are we still talking about it? My friend Susan’s callout of Uber in her famous blog post in 2017 lit a fire that led to lawsuits and the start of some regulatory changes in the heat of the moment, but when the party is over and we’re sweeping up the confetti, are we still keeping the momentum?

Image credit: Imobi Group

Recently on social media, I saw several fundraising announcements that made it all too clear that many companies are talking the talk but not walking the walk on creating equitable working environments. The dichotomy between the images of those who raised extreme amounts of cash for a pre-PMF (product market fit) company to those who raised modest seed rounds for their post-PMF company was infuriating. The posts about someone’s upcoming participation on a “mannel” (all male panel) or their new Crypto team (left) are cases in point. Why don’t they notice what they are doing?? How do companies allow this to happen? Has anything really changed despite all our efforts for equal rights?

This image was posted on Twitter on International Women’s Day ’22 — It has since been removed.

This morning, one of my coaching clients sent me a picture of how he planned to show up at his board meeting today (below, right – shared with permission). It was great to see his solidarity in this moment. In this case, I know Nick’s business, Help Scout, is on the bleeding edge of striving for equality. The company has made conscious efforts to prioritize hiring, culture and product decisions to be sure they remain 100% focused on a diverse team and providing an equitable and inclusive environment for their employees and their customers. They are transparent about how they do this and the metrics they track to stay on top of this focus. More importantly, they keep the beat every single day. Not just during International Women’s Day or Women’s History Month or Black History Month. Every. Damn. Day. 

As I looked at the t-shirt Nick was proudly displaying, I asked myself “Do people know that Nick truly lives the slogans on his t-shirt? Are other companies doing what Help Scout does, but not sharing it broadly to inspire? Do other companies that are announcing mannels or their 5th, homogenous, executive hire despite public proclamations that they understand the practical and ethical importance of diversity simply not believe what they are saying?? Do I give them a pass and hope they’re working hard every day just like the team at Help Scout? Or, do I call it out when I see it? Do I run the risk of getting dismissed as a “salty old broad” or keep challenging this behavior because I just have to do what it takes?” Every. Damn. Day. 

My dear friend Kim Scott’s voice rings in my head frequently reminding me to care personally, to challenge directly and not to display obnoxious aggression. I try to embrace Radical Candor every chance I can (I promise, Kim!), but there are days where I don’t care personally. I am fed up. Tired. Pissed off. I’ve been at this business of combatting bias, sexism, gaslighting and outright discrimination for over three decades. It’s exhausting! I have hope, though. I see more action than I have ever seen. Part of what gives me hope are, to borrow a phrase from Kim’s new book Just Work, “upstanders” like Nick. I don’t have to do all the work, leaders who identify as men understand that they will find more success and also do the right thing by hiring and promoting more diverse people. 

The young people I work with also inspire me. I was conducting office hours with an exceptional student of mine the other day who is a Freshman at Harvard and cross-registered in my graduate-level course. As a young woman of color, she is breaking barriers in many ways. She aspires to be an entrepreneur and can actually believe that this is possible for her. When I was her age, few women dared to have the hopes and dreams that she has. The stories about how I was treated in the executive conference room when I was a college intern would  shock her. The kinds of egregious things that happened all the time 30 years ago are unimaginable to young people today. 

I have tremendous hope for her and her generation of women; for my own three daughters who are already fighting this fight in their early adulthood, and have far more options (and regulations and guardrails) than I ever did at their age. We are shifting, albeit slower than I’d prefer. What can I say, anyone who really knows me knows that I am impatient as hell!

So I ask you, what are you doing on March 9, the day after International Woman’s Day, to affect change? How about on April 1, when Women’s History Month is another moment in the history books? How will you continue to foster growth of your teams and embrace diversity “Every. Damn. Day”? For me, I will continue to push every daily, but also remind myself that change is happening, and celebrate it.  It’s a marathon, not a sprint. I just hope I am around long enough to see what broken bias really looks like. When this topic is no longer a “thing”. That the shift has happened and things ARE in fact as they should be. Equal and just.

The Co-Founder Courtship

Co-founding teams from Wistia, CodeSee, Pandium and Rubicon MD

Recently, I was listening to the Huberman Lab podcast where Dr. Huberman interviewed Dr. Buss, a founding member in the field of evolutionary psychology and Professor of Psychology at UT, Austin, whose research centers around How Humans Select & Keep Romantic Partners in Short & Long Term Relationships. In the podcast, Dr. Buss describes his research on how people select mates and the dynamics of courtship. While the podcast was focussed primarily on heterogeneous relationships, marriage and monogamy, I couldn’t help but think of the parallels with co-founder relationships. My brain is in the entrepreneurship space most of my waking hours, after all, and it made me think about how many entrepreneurs I know are looking for co-founders, yet many don’t appreciate that this is a similar courtship to mating and partnership. 

Many entrepreneurs believe they must have a co-founder and some are pressured by investors to have a particular type of co-founder. The conviction to have a co-founder is often based solely on complementary skills and experience vs. the softer, and often more important, relationship criteria. While there are some working papers out there, I have yet to see definitive research that proves whether one absolutely must have co-founders vs. going it alone as a solo founder. This is a highly subjective situation dependent on many factors; some of which I’ll discuss below. 

Do you need a co-founder?

I’ve worked both for and with hundreds of entrepreneurs in the last few decades and on the topic of co-founder relationships, my observation is that each situation is highly dependent on the chemistry, the experience each brings into the relationship, leadership styles and many other internal and external factors. While having co-founders can de-risk the business and/or complement skills, forcing these relationships can result in bad “marriages” that create more harm to a business than help. Certainly, when a great match happens it can be magic, but just like any marriage, one should not enter the relationship rashly.

When thinking about whether or not you need a co-founder, consider:

  • How could a co-founder balance your skills and experience? For example, if you are a technologist, but lack management or operating skills (marketing, sales, etc.), you may benefit from a more seasoned business leader as co-founder who’s seen the movie before. While many operating skills can be learned, early stage founders may underestimate how critical these skills are to have early on and rookie mistakes can set back (or kill) a business before it’s barely out of the gate. Read Khalid Halim’s thoughts on Hypergrowth and The Law Of Startup Physics for more on this point. Conversely, expertise and experience can be additive to the business without a co-founder title and compensation. Unless you are doing hard science that is your core business, building a business that is technology-forward or relies on tech to some degree is not nearly as hard as it once was. Having a strong first-hire who is technical can suffice; the same holds for someone with strong sales, marketing or other operational skills.
  • Is domain expertise critical for your venture? Unless you are already the expert in the particular field your venture intends to address, you may need a co-founder with domain specific expertise. Having domain expertise will not only inform the product strategy, but will also help the venture gain credibility in the market and potentially open doors on the sales side. Investors may expect or even require there be a domain expert on the co-founding team, but similar to the point above, you may also be well served with a first hire or even an advisor who could serve you in this way vs. a co-founder.
  • Most importantly, ask yourself whether you value partnership, shared risk and collaboration with others. It can be great to have someone to brainstorm with, share the workload and to commiserate with during your journey, but having co-founders – like a committed personal partnership – is also a big test of your ability to be vulnerable, handle conflict and willingness to compromise. There will be many times your co-founding team will disagree on things – from product and hiring decisions to operating procedures and a fundraising strategy – and how you process these decisions together is fundamental to a healthy co-founding relationship. Self awareness, a willingness to lean into conflict and ability to thrive in ambiguous situations will be critical in a co-founding relationship. If you question whether you are up for sharing these experiences with one or more co-founders, you may need to do some introspective work before taking on a co-founder or, perhaps, go it alone.

Anyone thinking about having a co-founder must go beyond the skills and experience aspects and consider the fact that they are entering into a deep, personal relationship. Whether it’s because you couldn’t find “the one” and time is of the essence or because you are self aware enough to know you are better off going it alone, taking the solo route is perfectly doable by rounding out your team with necessary skills and expertise. You might also consider a second in command (COO, CTO, etc.) who plays a key role in the business without the official co-founder title and compensation. These individuals can still receive founding team worthy equity grants and, in earlier stage businesses could be anointed as “co-founder” down the road if the relationship blossoms over time.

The Co-Founder Courtship

If you’ve decided that you really want and/or need a co-founder, you’ve basically decided to seek a mate for a long term partnership. Just like a personal relationship may result in children, big financial decisions (like buying a house), running a household, etc., a co-founding relationship will force you to commit to how you will nurture employees, manage finances and run your business. There are big decisions to make – “how will we educate our kids?” is similar to “what kind of company culture will we have?”. There are philosophies on which to reach alignment – “where will we raise our family?” is similar to “will we have a home office or remote-friendly work environment?”. You can’t have a few coffee meetings with a prospective co-founder to discover how you will answer these deeper questions. It’s a courtship and despite the urgency you may have to get going with the venture so you can raise money, hire people, etc., I can’t emphasize enough how important it is to nurture these prospective relationships.

Herewith a few suggestions on how to court your co-founder(s):

  • Conduct a listening tour by meeting other startup co-founders. Talk with them about their own courtship process. Ask if there were questions they wish they had asked and hurdles they had to overcome early in their relationship. Even the greatest co-founding teams have war stories to tell about stressful situations in their relationships and what they learned from these experiences.
  • Using insights from the listening tour, along with your personal preferences, write a co-founder job description (JD) and include experience, skills and your ideal, softer, characteristics for this person. If you already have someone in mind, try to stay objective and not write this JD to ensure they can fill the role (confirmation bias). Use this as your guide as you meet prospective co-founders and adjust as you go. It’s very likely that the more prospects you meet, the more tweaks you’ll make to that JD and finding “the one”.
    • NOTE: If more than two of you are thinking about becoming co-founders, do the JD method as a “diverge-converge” exercise. Discuss potential roles each may fill and have each of you, independently (diverge) write the optimal co-founder JDs for each role. Once each has taken a stab at this exercise on their own, share these JDs with each other (converge) and discuss where you were all coming from for each role. Not only will this better define each role, but it will allow you and your prospective co-founders to expose perceptions and expectations of each other and how the leadership of the business will play out.
  • Experienced hiring managers know that it is rare they’ll hire the first candidate they interview for a newly created role because they may not be clear on the right fit for the role until they’ve met a few types of candidates. The same holds for co-founders. You may have to test a few potential co-founder candidates before inking a co-founder agreement. Try to meet at least a half-dozen people who may solve for the gaps you are hoping to fill (expertise, experience, chemistry, etc.). Yes, this may mean you are “dating more than one person at a time”, but you’ll be far more clear about fit through this series of conversations.
    • NOTE: Finding a half-dozen candidates may not be easy. Tap into your network, ask prospective investors, former professors, etc. and tell them what you’re looking for. Share the JD. Attend conferences, talks etc. and be clear you are in the market for a co-founder. YC also released a co-founder matching tool that may be helpful.
  • Test the relationship beyond coffee chats and dinners. As noted in the Huberman podcast noted above, relationships are truly tested when the parties engage in experiences that allow them to see more dimensions of their personalities. For example, go on a road trip or partake in an activity that neither of you have done before. See how each of you make decisions together like where to eat lunch or which trail to hike. Even a game of mini golf at a course neither of you have visited or playing a video game together can test how you collaborate and/or handle competition. You might also consider working on a start-up related project together to see how that feels, such as co-creating a pitch deck or conducting customer interviews together.
    • NOTE: If you are considering a first time co-founding relationship with someone you’ve worked with at a company in the past, this does not give you a “pass” to skip this part of the process. Co-founding a business with a former coworker is like going from dating to living together. You are sharing responsibilities you likely did not have when you were colleagues at a business where someone else was accountable for the overall successes and failures and, likely, making more strategic decisions than you were privy to.
  • Have vulnerable conversations. One of the most popular sessions in my course at HBS is the discussion around one’s relationship with money. Most adults have very different perspectives on money and typically this is rooted in deep family or personal experiences, sometimes starting in early childhood. A parent losing a job, having to work at a young age to support family, credit card debt, anxiety about school loans, etc. Understanding how you and your co-founder think about money will give you a lot of perspective when it comes time to raise capital, price your product, pay employees, etc. Similarly, it’s important to talk about any peak moments in past jobs, school, etc. that inform your attitudes about leadership, culture and how products are designed/built, etc. While these conversations may feel very uncomfortable, it’s a step towards a solid working foundation in what will almost surely be a roller coaster of a journey together. Being able to have these conversations also tests how you’ll handle and support each other during conflict and stressful moments. You will have context and better understand where you are each coming from. Most importantly, these types of conversations don’t stop once you agree to be co-founders; they should be ongoing throughout the life of your venture as each co-founder and the relationship matures.
  • Finally, I recommend that prospective co-founders meet each others’ partners/families/BFFs. Not only does this further uncover the broader context of who these individuals are, but it also helps these important people in your lives understand this new relationship you may be entering. So, when you are up until 2am slacking with your co-founder about the upcoming pitch or how to deal with a customer issue, they know who that person is and how they are partnered with you. 
    • NOTE: For those considering co-founders who ARE your partner/family member/BFF, I encourage you to enter with a mindset around taking a personal partnership from no kids to four kids. It brings the relationship to a whole new level. This can be an incredibly rewarding experience for you, but it can also test the relationship to the max. While this person/people know and probably trust each other better than strangers co-founding a business together, it also means there is likely baggage that can create more emotion and triggers around certain issues than the average partnership. I have worked with incredibly endearing and high performing co-founding teams made up of siblings, married couples and BFFs, but I have also seen these types of co-founding teams erode due to irreparable events rooted in their personal history. Do not take this choice lightly. Consider getting a coach early on who specializes in working with co-founders who also have personal history together. I guarantee you will not be able to put your personal stuff in a box outside your business. Personal tensions will come up – either overtly or subtly – and having the support to work through it will be crucial to your long term success.

One cannot rush the co-founder courtship process. The most successful co-founding relationships I’ve seen inevitably end up being far more than co-workers. They are practically family and while that means potentially more emotions are at stake, it’s their mutual understanding and deep respect for each other that allows them to traverse this often treacherous journey. They have mutual trust and are committed to ensuring the success of their business, together.

There are many other articles and videos published on this topic, but a few I like are here and here.

Do you have lessons learned from your co-founder courting and/or working relationships? Please share in the comments!

Good For Her Announces Cohort Four!

It is a great joy to announce that the fourth Good For Her (GFH) cohort has launched! With over forty applications this year, it was incredibly hard to select our next group of extraordinary women. Each cohort consists of only 8–10 members to foster the intimacy that we’ve learned creates a strong support network. This new cohort has ten members, including an Aspiring Entrepreneur which is a role designed to connect underrepresented women early in their entrepreneurial journeys with women further along who can serve as role models and mentors.

I created GFH as a pay-it-forward model for women founders who are often operating solo and/or with limited connections to peer founders. You can read more about my founding story of GFH here. While fundraising is not the only metric of success — it is a mortgage, after all — our current cohort members have raised over $70M in capital in the past year; with several closing $12M+ A-rounds (e.g., HumanFirst and Wagmo) and and one recently closing a $20M round. Beyond funds raised, these businesses are focused on being great employers with high retention rates, growing revenue exponentially, and building industry leading brands.

Our newest cohort members are centered in NYC, however with our renewed ability to travel and many opportunities to connect virtually, we have expanded our reach as far as the UK and LA. Our member companies represent a diverse range of industries — from fintech and martech to consumer products and services, biotech, social-environmental impact solutions and everything in between. These are not “cute lady companies”. They are serious businesses making an impact on the world. The combined GFH community identifies as 52% BIPOC and member ages range from early 20s to mid-fifties.

When a new cohort starts, I am very engaged in pulling the group together and fostering connections. Over time, each cohort becomes its own “thing” without my routine facilitation. While each cohort has a special bond, the GFH community supports all members with our “give as much as you get” philosophy. From quick responses on Slack to jumping on calls in the moment when urgent advice is needed, these women strive to support each other 24×7. Now, with three cohorts well on their way, it’s time to welcome cohort four! Herewith, our newest members:

Clockwise from top left:

Mae Abdelrahman — Aspiring Entrepreneur
Yuliya Bel — Notus
Allie Eagan — Veracity
Gina Levy — Kindra Connect
Julia Fan Li — Micrographia Bio
Shelly Xu — Shelly Xu Design
Amy Tang — Folio
Rachel Soper Sanders — Rootine
Tiffany Ricks — HacWare
Helen Lin — Discern.io

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 four!!

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

Founder Separation Anxiety

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

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

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

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

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

CEO: “Totally, no worries, friend.”

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

CTO: “You got it, friend.”

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

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

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

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

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

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

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

On Hiring: Beyond the Interview

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

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

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

The First 90 Days” Test

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

What good might look like: 

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

Engineering and Design Tests

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

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

What good might look like: 

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

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

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

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

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

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

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

What good might look like: 

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

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

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

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

Paving The Way For Less Experienced Hires At Early Startups

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

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

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

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

For the Manager

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

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

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

For The Less Experienced Candidate

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

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

If all else fails…

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

Tips on this concept:

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

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

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

Balancing The Many Hats Of A Startup CEO

Illustration by Amelia Austin (c)

Startup founders wear many hats that they take on and off as company priorities ebb and flow; especially, but not exclusively, CEOs. 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 founder 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 entrepreneurs 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, the framework can also be an effective tool for other organizational leaders.

* * * * *

The Hats

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

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

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

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

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

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

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

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

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

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

  • Finances – CEOs may be good at doing the accounting for the business and it has to be done, but often 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 when 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!
  • Hiring – Inexperienced CEOs may be managing people and leading teams for the first time. They 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. However, this may be a skill they have to develop vs. hand off to someone to do for them.

If a company has the runway, the CEO can usually move swiftly to swap or delegate hats with the support of their co-founders and leadership team. 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 and 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. 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.

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 more 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!