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.

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, 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!

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.

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!