Category Archives: Personal Growth

Transition Reflections

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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!

Balancing The Many Hats Of A Startup CEO

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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 the following framework I’ve created to help them determine which hats to wear and when to wear them. While this article is largely focused on startup CEOs, the framework can also be an effective tool for other organizational leaders.

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The Hats

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

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

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

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

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

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

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

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

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

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

  • Finances – CEOs 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.

The Current Normal

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Our Current Normal, Amelia Austin

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

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

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

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

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

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

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

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

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

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

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

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

Self-Awareness & Asking For Help Are Super Powers!

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

My perspective on the many ways to get help…

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

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

MBA, Accelerator Or Just Go For It?

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You’re in your mid-to-late 20’s and your thinking about being a first time entrepreneur. Maybe you already have an idea for a solution to a problem that needs solving or perhaps you just know in your bones that the entrepreneurial journey is your destiny. You’re probably in your first or second job after undergrad and feeling like now’s the time to figure out how to make the most of this “prime time” in your life – this is the tail end of your defining decade. Perhaps this is the right time, before you have family or other life commitments; or maybe because you feel if you wait too long, you’ll never do it. 

Regardless of where you are in life, if you’re feeling like you are at a cross roads in the early part of your entrepreneurial journey, you probably fit into one of these categories:

Screen Shot 2019-07-23 at 2.44.18 PMI see aspiring entrepreneurs approach these categories in a few ways: Learning as they start their companies, enrolling in an MBA or certificate program and/or applying to a startup accelerator. Some also choose to join an early stage company while they noodle their idea(s) so they can see how others do it and learn from their successes and failures before they strike out on their own. There are pros and cons to each approach and each is a highly personal decision based on your risk threshold, what you’re building, and who you are as a human being. There is no “right” way to do it, but here are a few ways to think about each approach, noting that sometimes doing more than one can be the best formula. 

On the Job (OTJ)

I am a big proponent of experiential learning. Touch a hot flame, you know not to do that again. Take an active listening role face to face with a customer and you’ll learn more about their needs and how you can solve them vs. running a survey or doing passive research on-line. However, some might argue that OTJ learning is a “two steps forward, one step back” approach as you’ll make a lot of mistakes along the way. Some mistakes will be recoverable, but some may be life threatening to your business and almost none of these mistakes can be predicted. Many of the most successful startups got that way because of luck and timing or because they had made/raised enough money to dig themselves out of a hole or two until they got it right.

OTJ_Poll

Questions to ask yourself if you are thinking about this approach:

  • What is your pain tolerance in terms of how far you can stretch your money, lifestyle and idea? Your about to get on a roller-coaster. Do you think you can handle it? Are you ready to hear “no” a lot and live off of ramen noodles and pizza indefinitely?
  • Do you have a strong network of mentors, coaches, advisors, investors and friends to get advice (and potential capital) from? Do you know how to get that advice/money and will you take it or not?
  • How easily do you make decisions? Will the noise of endless advice, competition, differing opinions from employees/co-founders/investors thwart your progress?
  • Are you a good salesperson? Can you recruit talent, fundraise and acquire customers?
  • Do you understand the product development process for your idea? Have you fully explored the problem to be solved, who you’re solving it for and the potential solutions? Do you think you have an MVP that will get you off the ground as you work towards product market fit? How confident are you that there’s an addressable market worthy of you/your co-founder and/or investors taking a risk of time and money on this idea?
  • Are you as in love with the problem you want to solve and passionate about the possible solution as you are in love with being a leader/CEO? Where is your ego in this process? Starting a company is one of the most humbling experiences you’ll ever have – it’ll touch your insides in ways you never thought it could. Are you ready for that?

If a few of the above points give you pause, either figure out how to resolve them before forging ahead, or consider some of the other options below.

Applying To An Accelerator

I’m a big fan of well structured accelerators with strong reputations for developing entrepreneurs and their products (e.g., Y-Combinator (YC) or TechStars). The programming is usually very solid and the results are almost always positive – companies are typically much further along with their business plans and messaging by their usual culminating event, “Demo Day”. Fundraising is also a big part of an accelerator program and the better ones have a pretty strong network of investors eager to fund each cohort. That said, in my recent Twitter poll, 50% of the respondents said that the network was the top benefit. I’ve seen this firsthand from my years of experience as a mentor with TechStars. Whether it’s needing help with introductions, getting advice on business strategy, building products or even just a shoulder to cry on, these networks have proven to be invaluable for entrepreneurs who’ve gotten into a quality program.

accelerators

There are many accelerators out there. In addition big brand names like YC or TechStars, there are a myriad of others that range from niche areas (biotech, robotics, healthcare, fintech…) to city-specific, to those that cater to underserved populations, etc. The list is endless! Here’s how to think about applying to accelerators:

  • Figure out which accelerators are a fit for your idea/company and what you want to get out of their program. It’s no different than applying to college – everything from where you want to live to who you’ll hang out with 24×7 counts in the decision process.
  • Make sure your idea/company is far along enough to apply. I often see founders trying to apply way too early and while it can be a good experience just to go through the process, it’s a big time waster for you, your company and for the accelerator who is evaluating your application if you are not at the right stage.
  • Talk to alumni from programs you’re considering. Find out about their application process and any lessons learned (things they think they nailed, what was the program worth it to them, tips on how to get the most out of the program, etc.)
  • Understand program expectations while you’re running your business. Many founders who get into the more intense programs don’t appreciate how hard it is to keep the momentum of their business while going through the program. It’s like having two full time jobs!
  • If you are definitely applying to a program, line up your references in advance and try to get warm intros to the Managing Directors (MD) of the program. Warm intros are worth a lot in all parts of business, accelerators included. Also, you may find that a warm intro can serve you well if your timing was out of sync with the accelerator’s application process. Sometimes. a company drops out of a program last minute, just before the start date, and a warm connection with the MD could be the fast track to fill that open spot (several companies I’ve worked with have been accepted into programs because of this situation).
  • Apply to more than one and know that some may push you to another location of theirs or class depending on where you are in the process, stage of your company, other cohort needs, etc.
  • If you don’t get into a program, either decide if the time to apply was worth it (maybe it forced you to learn more about you, tune the story of your business or products?) and try again, or move on and keep on trying to accelerate your business on your own.

Getting Your MBA

There are countless reasons one should or should not get an MBA, all of which I will not cover here, but if you are thinking about how to learn about entrepreneurship or further your business, it can be a great way to go. Of course, in most cases it is very expensive and yes, it’s ~2 years “checked out” of the real world, but in the right type of program, it can be a great solution.

DISCLAIMER: I am on the faculty at Harvard Business School which I think has superior programming for entrepreneurs, but I try to be unbiased here and cover more general aspects of MBA programs with an entrepreneurial focus.

Screen Shot 2019-07-23 at 3.11.58 PM

Considerations for whether to apply to an MBA program with an entrepreneurial focus:

  • Cost – can you afford both your time and money?
  • Do you have an idea/company already in process that you want to move forward? How will the particular program help you do that? Are there specific courses for your stage of business, industry or problem you’re trying to solve? Are there faculty, peer mentors or other on-campus experts available to students starting businesses? Is there time during the program to actually work on you company (e.g., experiential courses where you build your business for credit, summer programming, etc.)
  • Do you want to be somewhere where you can find an idea and/or a co-founder? Are the programs you’re looking at known for incubating new ideas and/or fostering co-founder relationships?
  • Are you unsure if you want to be a founder, but would at least like to become a joiner to learn more about startups? Do the programs you’re evaluating offer opportunities for joiners to meet founders building their companies while in school? Do they offer courses that educate the joiners as much as the founders?
  • Beyond the curriculum, what e-ship programming is available in a given program? Do they run accelerator programs or have space for young companies to connect and incubate their ideas?
  • Is startup funding available such as contests, access to venture funds, loan forgiveness for startups coming out of the program, etc.?
  • What access do students have to the school’s network such as alumni, the local startup community, investors, other universities in the area etc.? How do they add value to the entrepreneurial experience of admitted students? Will this network fill in gaps in your current network?
  • If you’re considering the venture side of entrepreneurship, do the programs you’re looking at have an investment-oriented curriculum and/or opportunities for aspiring investors to experiment with investing and learn to work with founders while in school?
  • Finally, what is the entrepreneurship track record of a particular program? How many startups were founded by their alumni (either while in school or within five years of completing their MBAs)? What is their alumni companies’ funding track record? In what other ways are their alumni founders successful (revenue, social impact, focus on diversity & inclusion, strong and ethical business ethos, etc.)

In the world of entrepreneurship, there are so many variables to consider when making just about any type of decision – from what product to build, who to hire, how to sell and how to finance your business. The list is endless and extremely tied to the type of business you are building, your customers and who you are as a leader. Similarly, which route you take to develop your entrepreneurial skills is highly personal. The route one entrepreneur took that worked out well for them does not ensure the same will hold true for you. Consider all of the above and decide which one or combination of all options makes the most sense for you.

Have you done one or several of the above to help kick-start your entrepreneurial journey? Please share your experience and lessons learned in the comments!

Reflecting On The Intersectionality Of Today’s Pressing Issues

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I was so moved at tonight’s event at The Wing in SoHo that I had to write. In the spirit of the anniversary of Stonewall, we had an extremely thoughtful panel of rockstars:

  • Cecilia Gentili – Transgender activist, actor and someone who speaks with deep empathy from countless experiences throughout her lifetime.
  • E.M. Eisen-Markowitz  – Restorative (and Transformative) Justice Coordinator and public school teacher.
  • Wazina Zondon – Founder of Coming Out Muslim and sexuality educator.
  • Alex Berg – Panel moderator, and journalist covering national news, women’s issues, and LGBTQ+ culture. 

My twenty year-old daughter, who has been openly queer from a young age, joined me tonight as my guest. As we walked home, we processed key points from the discussion. A few worth noting:

  • We are privileged white women and we and our family, friends, colleagues, etc. are not doing enough to support real change in this country for the LGBTQ+ community. Putting strong light on the issue and companies changing logos and decorating storefronts to rainbows a few weeks a year is not enough. It’s a conversation and action that needs to happen every single day.
  • The majority of people who are speaking up and fighting for change are putting themselves at risk ahead of those of us who can afford to take real risk. Reflecting on Stonewall, Cecilia highlighted that it was the white privileged professionals who ran from the scene and the less privileged crowd that put their lives at stake to fight back – people who could not afford bail money if arrested or perhaps survive if they were to be imprisoned. 
  • Wazina gave us pause around how we’ve been talking about reproductive rights. This is an intersectional issue, not just a white feminist issue or about who can tell whom what they can do with their own bodies, it’s also a parenting issue: who is ready to be a parent and what that means (emotionally, physically and economically). I applaud her for the work she’s doing with young people around this and other important health, identity and sexuality issues.
  • EM spoke of transformative justice inside schools to change the narrative and behavior vs. the crazy spend in NYC schools to police the problem (over $700M/year!). This is an important issue well beyond our city schools. We need to transform society.
  • On D&I and hiring, we heard stories of companies seeking to be inclusive that are not removing barriers to allow a diverse pool of candidates to apply simply by creating exhaustive list of requirements in the JD (see more of my thoughts on this here). Provide training, mentorship and tuition reimbursement for applicants who have the aptitude and lack the experience. Make it happen vs. complaining “we can’t find the ‘right’ candidates”.
  • Finally, know your political candidates positions and vote for those who understand these issues and are motivated to take action. Now more than ever, we need the right people in office.

I’m definitely going to think deeply about how I can make a bigger impact on these points and take action; with my voice, my dollars and my body if I have to. I suggest everyone else do the same – educate yourselves, open your minds and take action. 

Thank you to the events team at The Wing for organizing this evening! My only constructive feedback (‘cuz you know I have it!) is that there were not nearly enough of your members there or PR around it. We can do better.

Beyond Their Funds, How Can Your Investors Be Helpful?

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An entrepreneur recently said to me “When it gets really hard, I feel like I’m doing it wrong.” She went on to say that sometimes she’s not sure how her investors could be helpful — even if it’s just validating what’s hard vs. advising on how to work through certain challenges. I’ve heard other entrepreneurs say they’d like to get help from their investors but worry that purely by asking for help it will signal a weakness. Conversely, I’ve heard investors say they wish the leaders of their portfolio companies would be more transparent about challenges they are facing and ask for help. As one investor said to me recently, “They already sold me on the business and have our money. It’s now our firm’s job to help them succeed.”

In an informal Twitter poll I recently conducted, 56% of entrepreneurs who responded said their most common ask of their investors is for hiring help. Second to that (31%) are asks for introductions to potential partners or customers and a small percentage (13%) tap their investors for financial management advice.

I also polled my investor friends on what questions they like to get from their portfolio companies. What they shared made it clear to me that they can and want to be helpful well beyond their funds!

“Good entrepreneurs are learning machines so they’re always asking for advice and guidance from multiple sources of expertise, including their investors. In fact, the best founders are outstanding at squeezing every bit of insight, advice and contacts from their network of investors and advisers.“ Jeff Bussgang, Flybridge Capital

Do you know how to get the most from your investors? Below, I have outlined what I consider to be basic asks (table stakes) as well as suggestions for deeper asks.

What To Ask For

Hiring

Table Stakes:

  • Referrals and warm introductions
  • Posting job links on their websites
  • Invitations to recruiting events

Beyond the Basics:

  • Seek examples of job descriptions (JDs) and/or critiques of those you’ve written. Most investors were operators once and have a good sense of how to write a good JD; they may also have a recruiting arm at their firm who can counsel you on specific searches. [See point on compensation in Financials, below]
  • New to hiring? Practice interviewing candidates with investors or their associates before bringing actual candidates in for the real interview.
  • Resume screening can be an easy ask and a quick job for someone who’s seen 100’s if not 1000’s of resumes. Experienced eyes can point out immediate red flags and give you specific areas you may want to probe for a particular candidate.
  • Invite an investor to help diversify an otherwise homogeneous interview team. This can be a game changer for a candidate who may otherwise feel like they are a token hire. Knowing the extended team around the business is diverse, can allay these concerns.
  • Ask your investors to help sell the business to prospective candidates. This can be especially critical if you’re trying to hire a senior team member or a start-up first-timer.

    “This is something we continue to do, even with mid-level hires in mid-stage companies when the founder feels like a highly desirable candidate could use an extra push. It’s not a huge burden on our side, but can have a very strong positive impression on the candidate who probably feels like getting board/investor visibility is a strong positive in their career development. “ Rob Go, NextView Ventures

  • Investors can also be helpful offering insights on how your company is perceived as a workplace from their own perspective or from feedback they’ve garnered in the market. (people talk…)
  • Finally, but very carefully, investors may be able to help you get backdoor references on potential hires. I wrote more about this particular topic here. Backdoor references can be helpful, but only if done right!

Marketing, Sales & Partnerships

Table Stakes:

  • Introductions to potential customers and/or partners
  • Putting your company logo on their website; putting their firm’s logo/board member on your website
  • Invitations to marketing & sales events
  • Tapping their social media presence for sharing news and events

Beyond the Basics:

  • Investors look at markets all day, every day, and have an objective perspective on not just current market forces, but patterns over time and how markets move and customers buy. They may not know your specific market details or the intimate buying patterns of your target customer, but as Bob Mason of Project11 says “We often ask the right questions informed by our opportunity to step out of the day to day urgency of running the business. We have enough knowledge to understand the big market forces, see patterns from other businesses and can help drive an engaged dialogue. For the engineering-centric founders, you can think about this as ‘debugging’ an issue. When coding, you might bang your head for hours trying to find the root cause of a hard bug. But you bring over a colleague and talk through the situation and often a solution will appear. They didn’t tell you the answer, but the process of conversation brought insight to your mind.”
  • Whether you are building an enterprise product and need access to a buyer inside a potential large customer or trying to develop partnerships for your business (B2B or B2C), investors can provide invaluable insights on what drives particular companies, who the “real” decision makers are and how their buy/partnership process works. They can reach out to execs at companies and get an early feel as to how important such a potential deal or relationship could be.
  • Investors are generally good at analyzing marketing or sales funnels. If they are former marketers or sales people, they should be able to help you understand the “magic moment”, points of stickiness, drop off, etc.. They also won’t have the biases you likely bring to the table and can look at the numbers objectively.
  • Investors can be helpful with developing your company and product story as well as speak with folks in the industry to see how the story resonates.
  • Beyond offering advice on digital marketing and leveraging social media, your investors may also be helpful with brand awareness and offer PR opportunities. Perhaps they are sponsoring an event where you or a key member of your team can be a speaker? If one of your investors is a blogger, ask for a mention in their next blog post about a topic you’ve been discussing, or perhaps even a guest blog spot. Be creative about how your investors can help shine a light on your brand, product and team!

Product

Table Stakes:

  • If they can use your product as a firm or as individuals, they better be using it! Whether it’s for testing the MVP or to dogfood the brand, no excuses. There’s nothing more compelling than an investor who offers you a cup of coffee made with one of their portfolio company’s new beans or the investor who has a “powered by” one of their companies on their website. Have you asked your investors to use your product?
  • When asked (or not), investors never lack for advice on how your product can improve. Just remember, you are in it every day, they are not. So, always weigh that advice against what your team is discovering with your customers and progress accordingly.

Beyond the Basics:

  • If your investor is a former operator, especially at an early stage company, odds are they have built/tested many an MVP. Engage them in the MVP discussion. Review product priorities and test plans. Again, their objectivity and experience could give you a fresh perspective. This will also help them understand the tradeoff decisions you are making and can be very informative when it comes to strategic thinking about the company’s product roadmap and long term direction.
  • Speaking of roadmaps, if you’ve got a former head of product or VPE on your investor team, invite them to a planning session. Same reasons as above — fresh perspective and added insight when it comes to bigger picture discussions.
  • Security and compliance is an area often overlooked and where investors can probably draw on their own or other resources to ensure your company doesn’t get tripped up on a sale or regulatory issue because an “I” was not dotted or “T” crossed. They may have access to pen testers or be familiar with compliance requirements for things like PIA, HIPPA or SOX through other portfolio companies’ experiences; even if it’s just asking when to worry about it vs. holding off on investing in this work.
  • Also helpful is tapping investors’ technical EiRs and/or network. When I was CTO at DigitalOcean, it was amazing to have someone like Martin Casado at a16z, our lead investor, to bounce ideas off of and even help us with some tricky architecture decisions. Similarly, my friend Jocelyn Goldfein of Zetta Venture Partners said she’s often tapped by her portfolio companies to help with developing data strategies and answer questions about data rights. Know who the experts are in these firms and they’ll probably love the opportunity to get into the details with you since it’s no longer their day job.

People

Table Stakes:

  • If they are involved with financial planning, investors should be helpful with basic headcount and organizational growth plans (what roles to fill, how many and when)
  • Investors are generally not shy about telling you (sometimes unsolicited) if they think a key employee they are interacting with is great, needs coaching or may not be successful in your organization. Just remember, if you have a board, other than the CEO, they don’t make hiring or firing decisions. That’s your job.

Beyond the Basics:

  • Whether they were former operators, or have just seen a large number of companies operate, investors can give helpful insight around people and culture. You can ask how to work through team challenges, enhance your company culture or even how to make remote teams work. If they’re not the experts in these areas, they likely have companies in their portfolios who are doing creative things or who maybe learned from mistakes and are willing to share tips and tricks to avoid pitfalls as you scale.
  • While it may make you feel vulnerable, asking your investors for guidance around your own personal development demonstrates your willingness to grow — especially if you are a first-time CEO, or other member of the C-Suite. I’ve seen investors coach leaders on everything from how to lead their teams and handle challenging employees to how to run a great board meeting. I’ve also seen investors support and sometimes even pay for executive coaches and training programs for high-potential leaders.

    “Drop your shields, if you think asking for advice or help from your investors is showing signs of weakness you have it all wrong. Your investors are by definition already on your side and any problem you are facing or any area of growth where you think they may be able to contribute to or connect you to someone who can be helpful, go for it. I want leaders to ask me ‘what am I doing wrong, where can I level up?’” Reed Sturtevant, The Engine

  • Beyond headcount and budgets, investors with experience leading teams at scale can be very helpful with how to think about organizational design through various stages of growth. Investors can also have a really good sense of leveling across organizations and have seen a lot of creative approaches used across companies.

Financials

Table Stakes:

  • Investment checks
  • Future rounds  —  financing strategy, valuation, etc.

Beyond the Basics:

  • It’s never too soon to get “budget religion”, especially if you have a capital-intensive business where you need to figure out working capital, financing with manufacturing, etc.. Ask for guidance on how best to manage your funds as well as how to track burn and prepare data for future financing to make the diligence process easier for new investors. They may even have models or frameworks other portfolio companies use that you can borrow.
  • Not sure whether your compensation packages are competitive or fair? Or how to think about equity vs. salary splits? Comping your sales team? Your investors have probably seen many different configurations and can help you get creative if you’re trying to land a key hire or to retain and motivate your current team.
  • Other financial areas where investors can be helpful are ways to think about marketing spend as a ratio of investment in engineering or sales/revenue, pricing models and tax considerations.

In all of the above cases, if your investors can’t help you directly, odds are very high that they know someone who can. Good investors won’t expect you, especially if you are a first-time founder, to figure it out all by yourself. For me personally, I always appreciate the humility that comes from anyone who knows what they don’t know and asks for help. It is impossible for anyone to know everything!

How To Ask

There are three ways I think every founder should interact with their investors outside of board meetings (if you have them).

  1. Investor update emails are always a good vehicle for asks. If you’re not sure if anyone on the investment team can be helpful, be specific: “Looking for advice on digital marketing strategies.” or “Would love to talk with someone in your network who can advise my team on HIPPA compliance.”.
  2. Routine 1:1 calls or meetings are a must. This establishes a good touchpoint with investors to establish a rapport and catch up informally instead of waiting for a crisis or issue to arise as a reason for a call. I suggest you always have at least one ask for these meetings and always follow up with a quick email with that ask in writing.
  3. Identify at least one domain area where each investor may serve you best (e.g., I am usually the go-to person for product & engineering or organizational planning for my angel investments and advisees). When the needs arise, set up face-time to dig into that specific topic with that investor.

Remember, your investors are not just here to provide cash. They are invested in you and your company’s success. As Jason Seats of TechStars says, when in doubt, “pretend that they are not an investor and figure out what you’d ask them. If you can’t come up with anything, they may not be a good investor for you.” This can also be a nice hack around targeting the right investors from the start.

Have other examples of ways your investors have been helpful beyond their funds? Please share in the comments.

 

Go Big, Or Go…Startup

big Fish Little Fish

Image source unknown

A common career advice question I get all the time is what the tradeoffs are between going to a startup vs. going to a big company. There are many things to consider and lots of “it depends” when it comes to where you are in your career, where you live etc., but when it comes to the general aspects of a startup vs. mature company, most of the situations don’t vary that much. I’ve done both, several times, so here’s a perspective on the tradeoffs based on my own experiences.

Startup vs. Mature Company

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(c) 2018 Julia B Austin

Putting aside for a moment industry and how you feel about the products the company is building (both of which are very important!), most of the differences between a startup vs. a mature company are pretty obvious. In a mature company, you will likely have more role models to learn from and stronger teams to collaborate with, a clear direction and a mature board. The role you consider may have a narrow scope, but could offer deeper learning and of course great benefits, compensation, etc.. You’ll also get exposure to what good (or bad) looks like at scale and possibly a nice brand for your resume.

Startups can offer a chance to do “all the things” which can be either a blessing or a curse depending on your interests. You may miss out on having peers to collaborate with, have to look outside of your company for mentors and role models or have limited budget to get stuff done, but you may get high value equity in exchange for lower than market-level pay. If you want to dig more into deciding which startup to join, I suggest Jeff Bussgang’s book Entering Startupland which goes deep on the different roles at startups and how to get your foot in the door.

Leadership

One thing often overlooked when considering a new job is the leadership of the company. Serial entrepreneurs will have a very different approach than someone who has limited real-world experience and mature company executive teams can be world class or “legacy” leaders who can’t move with the times. There are many tradeoffs when factoring in leadership into the decision process of startup vs. a mature company.

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(c) 2018 Julia B Austin

Startup founded by serial entrepreneurs: This can often be the best case scenario if you want to learn from those who have “seen the movie before”. They likely had no issue raising money and were selective on who their investors were and who sits on their board. They will know how to get the flywheel moving incited by past mistakes OR failures.

“When I started my fifth company I knew exactly how I wanted to build the team. So, on day one I hired a head of recruiting to get things off to a strong start. I also knew market adoption would be critical to fundraising so focused on growth very early on – before we even had a product!” – David Cancel, CEO & Co-Founder Drift

Serial entrepreneurs may also try to overcorrect in areas where they failed the first time, such as over analyzing or delaying decisions, being too conservative on cash flow or focusing too much on scalability too early in the product development process. If you’re interviewing with a serial entrepreneur, it’s always good to ask what lessons they learned in their last startup and how they’re bringing those lessons into their new venture.

“I joined Drift in part because I wanted to learn from the experience of the co-founders. They’ve seen it before so they anticipate issues, they know when (and how) to hire experts to level up the team, and they know what’s “normal” for a hypergrowth company. It’s the best of both worlds: you get the rollercoaster startup experience with some of the more measured leadership and strategic characteristics of a bigger company.” – Maggie Crowley, Product Manager Drift

Industry veterans doing their first startup: Founders coming from mature companies with no startup experience can have big company confidence, be great at hiring and leading teams, but lack scrappiness to get a Minimum Viable Product (MVP) out the door and work towards product market fit.

“At our first startup after a series of roles at large enterprise software companies, we tried to force a big company perspective on how we did employee feedback and reviews. We were too structured with this initially and quickly cut back to a more loose feedback and review process with our team.” Izzy Azeri & Dan Belcher, Co-Founders Mabl

They may also be too used to having teams of people and systems in place to cover the more mundane duties of running a company and don’t want to get their hands dirty. On the flip side, they often know how to implement those processes and know the people to hire to run them so once the flywheel is moving and cash is in-hand, they can get momentum quickly.

“Earlier in my career, I hired a small team within a large corporation that was scrappy and had entrepreneurial mentality. At my startup, I quickly realized the benefit of once having a corporation behind me when things weren’t working out. The impact of a bad decision or process was much greater with no safety net.” – Karen Young, CEO & Founder Oui Shave

Startup with limited leadership experience: Working with a skilled group of founders leading teams for the first time can be tons of fun. If you bring some experience to the table, it can be very gratifying to not only work from the ground up, but also work alongside these founders as they grow. However, it can be frustrating if you find yourself figuring out things on your own because there’s no one in the company to mentor you. These situations can be very rewarding if you’re patient and you can always get outside mentors and advisors if they’re not available at this type of startup.

“When we started, we got a lot of advice like: stay focused, don’t expand too quickly, be careful that experienced hires match your culture.  All good advice, but we discovered there’s no real substitute for learning the hard way. The lesson just doesn’t sink in until you feel the pain of doing it wrong.” Wombi Rose, CEO & Co-Founder LovePop

Mature company with inexperienced leadership: If they made it this far, they are either wicked smart, lucky or both! More likely they also have surrounded themselves with strong, experienced leaders, investors and/or board members. You can learn a lot from joining a company like this, but they are very, very rare! When companies scale too fast, they can also suffer from having people in roles that have outgrown their experience. Read more about the impact of Hypergrowth situations written by my friend at Reboot, Khalid Halim, for First Round.

Mature companies with experienced leadership: These organizations have all the standard things you’d expect. Probably more politics and process than you’d ever find at a startup, but the benefit of exposure to great role models and best practices can be invaluable. Sometimes, these bigger companies can also expose you to the “dark side” of leadership and processes which are also great learnings on what not to do in your next job or company you may start yourself.

Which comes first in your journey?

For those doing early career path planning and knowing they want to do both a startup and a mature company at some point, there’s always the question of which should come first. Hiring managers at early stage companies can get “spooked” when they see someone with too much time (5+ years) at mature companies; questioning whether the candidate will be able to transition to startup life. Not that it’s impossible, but it’s something to consider. For these candidates, I suggest highlighting any scrappy “ground zero” work they may have done at their companies to demonstrate they can handle ambiguity and take risks. I am also a huge (and very biased) fan of people who’ve joined companies early and scaled with them. They have learned a TON from those experiences and can often start scrappy, but know how to operate at scale. Win-win.

Conversely, someone with a lot of startup experience may have a hard time adjusting to mature company. A hiring manager at a mature company may question whether a candidate with only startup experience can handle a slower pace or won’t know how to navigate a complex organizational structure that requires political and communication savvy. You may have to sacrifice title and maybe some salary to get a foot into larger institutions who may view your past role, which may have been very senior at a startup, to being pretty junior if those around you have decades more experience. However, I always find those with startup experience can be invaluable to a team that needs to be shaken up, take more risks or explore new ground. Often, those who sacrifice title and pay when they joined, make it up fast as they move up the chain in a larger organization.

There’s no right or wrong place to start. A lot depends on how you define your skills and how willing and patient you are in either case to adjust. Much can depend on who hires you and their management philosophy. I’ve seen some people bounce between both types of situations over and over, some that just can’t handle startup life, and others who have startups in their DNA and should just stick with that world 🙂

“At a startup, every job matters and you can see almost daily that you are creating something that wasn’t there before. You have the ability to learn quickly and have a fast feedback loop to let you know how you’re doing. It’s very different working at an established company vs a startup, but you can learn a lot at both – you’ll just learn very different things.” – Rebecca Liebman, CEO & Co-Founder LearnLux

Questions To Ask

Regardless of whether you are a seasoned veteran or fresh out of school, as you ponder whether you want to join a startup or a mature company here are some final things to consider:

  • What tools do you want to add to your toolbox? Will the role allow you to hone skills you already have or add new ones?
  • Who do you want to learn from, and how do you want to learn? You can learn from experienced colleagues and mentors, but having bad role models can also teach you a lot about what not to do. Similarly, if you are an experienced hire coming into a company started by inexperienced founders, you may want to learn by mentoring or teaching these young leaders. Taking the skills you’ve developed over your career and applying them to a new situation in itself can be a very enlightening experience.
  • Who do you want to work with? How important is the size and culture of the team you’ll work with? Remember, you’ll probably spend more waking hours of the day with these people than anyone else in your life – regardless of the size and nature of the company you join.
  • What do you value? At the end of the day, love what you do and decide what role will allow you to maintain the integrity of who you are and who you aspire to be!

Do you have other tips on how to decide whether to join a startup vs. a mature company? Please share in the comments!

What Made You, You

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Let’s face it, last year was rough. Rough for our country, rough for story tellers exposing the truths no one wanted to hear and rough for the world we live in as we continue to face climate change, war, poverty, etc. Not to mention suffering through several tough Mercury in retrograde transitions! I had a particularly challenging year myself – personally and professionally – and was ecstatic to put 2017 behind me.

But just like our current president is SO BAD that our country is working towards finding its democratic voice again, and the stories that have been told (and will continue to be told #metoo) are teaching us to listen and act, we each face challenges that can transform who we are. These challenges inevitably make us, us – good, bad or perhaps just more enlightened. This became very apparent to me in 2017.

What made me, me….

Just over a year ago, a work colleague and I were hanging out in the office chatting about life. It was pretty routine for us to wrap up an intense week by unwinding with a short glass of whiskey and story telling. It was a great way for us to continue to foster the strong working relationship we had developed. After over a year of this routine, we had gotten to know each other pretty well and trusted each other to tell some very personal stories about our lives, families and hopes of the future.

That particular evening, I shared a story about something I experienced at a retreat I had recently attended. I won’t get into all the details about the experience, but the short story was that during one of the group sessions at the retreat, I had decided to let go of a toxic relationship with someone in my immediate family(*). I have always carried guilt, sadness and anger about that relationship  – hoping some day it would be different, but knowing in my soul that it would never be what I hoped for nor could I forgive for things said and done. The exercise at the retreat was to let go of something that no longer served us. At that time, I felt that the relationship with that family member no longer served me. (there was a burning ceremony…. it was super intense…)

I shared that experience with my colleague and his immediate response was “you must forgive that person and maintain that relationship because they made you, you.”. I was a little annoyed with that response because I was so damn proud of myself for letting go of a bad relationship that no longer served me, but he continued to push me to consider how even the negative aspects of that relationship undoubtedly had a positive impact on me (motivated me to improve my relationships with other members of my family, developed some of my better traits which were the weaker traits of this family member, etc.). It was pretty profound and hard to argue with.

Even though the conversation that evening was very impactful, it didn’t immediately change my mind and cause me to call the family member up the next day to forgive them. However, the conversation stuck with me. That person, no matter how toxic the relationship was, made me, me. It’s been echoing in my head ever since that conversation with my colleague.

In the past few months, I have created some space in my life to allow me to revisit this topic and consider how this family member made me, me. I have been made aware from other family members that this family member is suffering from age-related health and financial issues and lacks a good support system. They live in a subsidized housing facility with very little access to in-house services or transportation for services elsewhere. While I don’t have unlimited resources, I decided I could help this person have a more comfortable end of life then they would otherwise enjoy. It’s been a huge emotional leap for me to move forward and have compassion for this person and appreciate how they contributed to making me, me. I have also done some family research to develop a deeper understanding of what made them, them and have far more empathy for this person than I have ever had.

We’ve still got a ways to go to figure out how to forge a better, more positive, relationship, but I am confident I am moving in the right direction and both of us will be better for it. I am helping to arrange for better housing and services, helping them with health issues (driving to MD appointments, etc.) and I have started to reengage them in my own family’s lives. This, by the way, is also a huge opportunity to serve as a role model for my kids who are keenly aware of the hardships I endured with this family member. It is healthy to forgive.

I am not suggesting you should maintain a relationship with everyone in your life who made you, you. There are certainly some people in your life who truly put you at emotional and/or physical risk and regardless of whether they made you, you, may not be appropriate to restart or be in a relationship with. In my case, there was abuse in the past, but because it was family and I know how to establish boundaries, this one was safe.

So despite everything, I found my silver lining in 2017 and 2018 is looking good! To the colleague who pushed me on this (you know who you are!), thank you. I am forever grateful for having the time and the means to revisit this relationship and make things better while there is still time.

(*) Intentionally keeping this family member generic to protect their privacy.

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Do you have less than positive life experiences that have made you stronger or give more positive experiences to others? Who made you, you? Please share in the comments!