Tag: mentor

Feb 7 2019

Mentors 18/18: Have Empathy. Remember That Startups Are Hard

This is the final post (18) of the Techstars Mentor Manifesto. As with item 17, Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up and wrote a draft from his perspective. Following is item #18 of the Techstars Mentor Manifesto, in Jay’s words.

During one of the Techstars Boston cohorts where I’ve been Mentor-in-Residence, I worked with a 20-something CEO founder (code named Mary) who, shortly after raising a seed round of several million dollars, hired a high-powered exec, granting a significant equity option. This new hire was a commercial hustler (code named Scott), moving quickly and broadly to try to secure customers and partners, including some of the tech industry’s largest companies.

Mary had never managed somebody a decade senior to her and was struggling to manage Scott. Further, Scott tended to work autonomously, sometimes doing things outside his remit that was not well-communicated to Mary. As a result, Mary was worried about how this looked to her board. A massive sense of imposter syndrome started creeping in, especially since Mary felt investors had bet on her, yet Scott was having a notable impact, for better and worse, on the strategy and success of the business.

Mary was concerned that the investors thought she wasn’t being effective. A fear was brewing in the pit of her stomach and she worried that everything was going to come apart.

Pause for a moment. Recall the last time you had a consuming passion. Remember how it felt. Think about that incredibly exciting idea that grabbed you and took over your mind, time, priorities, and emotions. Remember how excited you were as you imagined all the threads of what could be, and how your heart beat faster and your adrenaline surged.

And then … you had an existential crisis. A moment when you feared that this awesome future might come crashing down because of a particular situation or the actions of one person. Your heart beat faster again, but this time out of worry, anxiety, and fear.

I want you to replay your joy and fears again for a moment. Having empathy requires you to feel what the other person is going through. To put yourselves in their shoes and feel their fear. And to not immediately try to fix it. Remembering your own hopes and fears will help you have empathy. And this is critical as a mentor because startups are extremely hard.

In the situation above, I could relate to Mary feeling imposter syndrome. My first venture-backed company was not a big exit, and neither I nor my investors fared well. So I felt some imposter syndrome when founding my second venture-backed company (which, happily, has done well.)

So what Mary needed from me as a mentor was to talk to a neutral third-party who understood how technology companies worked and who had felt the expectations placed on a founding CEO. She needed to talk openly about how she was feeling to someone not on her board or exec team, and to whom she could be fully and safely transparent.

Doing that first allowed us to get around to eventually discussing ways to handle the situation. I reminded Mary that first and foremost, Techstars mentors are here to coach her on how to manage athletes like Scott, so she should relax and look for help. She had time to handle the situation if Scott was indeed a problem, as his option grants had a one-year cliff and he was only a couple of months in. So, instead of feeling anxious and pressured into reacting, I encouraged Mary to focus on helping Scott be successful and assess things again in a quarter.

Several years later, after the company, led by Mary, was acquired and had a very successful outcome, she told me that the most memorable and important thing I did for her at that moment was to simply sit, listen, and relate to the feeling she was having. I hadn’t immediately replied with a solution to her problem. Instead, I started with empathy.

As a mentor, be aware when to suspend, or defer, your advice or judgment. The entrepreneur you are mentoring may not be in a head space to hear your solution. Mentoring is often an emotional rather than a functional or intellectual role. Take a breath and be empathetic, instead than jumping in to solve the problem. And never forget that startups are hard.

Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.

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Feb 6 2019

Mentors 17/18: Be Challenging/Robust, but Never Destructive

I wrote 16 posts detailing each item of the Techstars Mentor Manifesto. However, there were 18 items and, for some reason, I never got around to writing the final two.

Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up. I kept saying “I’ll get to it” but never did. So, he did it for me, with the added motivation of getting it up prior to the kickoff to this year’s Boston program. Following is item #17 of the Techstars Mentor Manifesto, in Jay’s words.

This item on the list might sound very similar to #4, “Be Direct. Tell the Truth, However Hard.” But, it’s different. This item (#17) has to do with you, not the companies.

You have been asked to be a mentor at Techstars because you’ve been successful as an entrepreneur and/or a leader. The managing director for your cohort trusts that you’ll help the founders. And those founders are betting – with stock in their company – that you’ll be good for them.

Because of your expertise, you are likely to quickly spot areas in their businesses that need work urgently.

Because you’ve read all the posts here about the Techstars Mentor Manifesto, you dutifully start by being socratic and digging into the fundamental thing that is broken. You are direct, telling the hard truth that you are deeply concerned about some area.

But at some point, you sense the entrepreneur isn’t simply following your lead. They aren’t changing some element of their business to align with your direction. So, you are more direct. You push harder and more forcefully because you think it’s important. But the entrepreneur continues to “not get it”.

And, just like that, you’re irritated. You shut down, you quickly end the meeting, or you push even harder. After the meeting, you vent to the Techstars managing director that this company is in real trouble because the founders aren’t paying attention to this element you find important.

We’ve now reached the point of this post: Never Be Destructive.

The moment you go beyond trying to get your point across to the entrepreneur and do something outside that moment that is less-than-supportive, you’ve stopped being a mentor. You are now simply a judge. Or, worse, a detriment to the company.

You have let your desire to succeed as a mentor become paramount. Your actions can easily shift from being helpful as a mentor to being hurtful to the entrepreneur.

If you let this state persist, your frustration will leak outside the safe space of Techstars. It might be something you say to an investor; which means you’ve now affected the company’s ability to raise capital. If you vent to another founder, you either hurt your own reputation or the mentee’s reputation. At worst, you may end up affecting their relationships with potential partners or future hiring candidates.

Being a Techstars mentor does not mean being 100% dedicated to being a successful mentor. It means being 100% dedicated to helping founders build great companies.

So, be robust if you have to in making sure they hear what you’re trying to make them aware of.

But when you leave the room, make sure you flip the switch and remain 100% dedicated to making them successful, whether or not you think they heard what you had to say.

Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.

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Jan 22 2018

Techstars Mentor Manifesto In Detail

I’ve been working on my next book, #GiveFirst, again. There’s a lot in it about the Techstars Mentor Manifesto and how to be an effective mentor.

Yesterday, I got a note from Jay Batson, longtime Techstars Boston mentor and now the Mentor-in-Residence for the program, asking if I had ever compiled the lists I posts I wrote about the Techstars Mentor Manifesto.

I hadn’t. He had conveniently done it in a Google doc so it was easy for me to list out the posts with links. They follow.

1/18: Be Socratic

2/18: Expect nothing in return

3/18: Be Authentic – Practice What You Preach

4/18: Be Direct. Tell the Truth, However Hard.

5/18: Listen, too

6/18: The Best Mentor Relationships Eventually Become Two Way

7/18: Be Responsive

8/18: Adopt At Least One Company Every Single Year. Experience Counts.

9/18: Clearly Separate Opinion From Fact

10/18: Hold Information In Confidence

11/18: Clearly Commit to Mentor, or Do Not. Either Is Fine

12/18: Know What You Don’t Know. Say “I Don’t Know” when you don’t know.

13/18: Guide, Don’t Control

14/18: Accept and Communicate With Other Mentors That Get Involved

15/18: Be Optimistic

16/18: Provide Specific Actionable Advice

17/18: Be Challenging/Robust but Never Destructive

18/18: Have Empathy. Remember That Startups Are Hard

Jay also reminded me that I hadn’t written posts on #17 and #18. They are now on my list to do. Thanks, Jay!

2/6/18: Jay wrote 17/18: Be Challenging/Robust but Never Destructive which is now posted.

2/7/18: Jay wrote 18/18: Have Empathy. Remember That Startups Are Hard which is now posted.

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May 16 2017

Mentors 16/18: Provide Specific Actionable Advice

There’s a tenuous balance between telling someone what to do and giving advice. It’s especially difficult as a mentor, especially if you’ve previously been a CEO and are used to being “the decider.”

As a mentor, you aren’t the decider. The CEO you are mentoring is the decider.

This dynamic is also true for many board / CEO relationships, where the board wants the CEO to make the ultimate decision. As I’ve often said, my goal as a VC is only to make one decision about a company – whether or not I support the CEO. If I do, I work for the CEO. If I don’t, it’s my job to do something about the CEO.

While this is nice in theory, it’s difficult in practice. One of my strengths is that I tell a lot of stories. One of my weaknesses is that, according to my wife Amy, my stories go on 20% too long (she is correct.) Here’s an example.

I’m at a board meeting. The CEO, which I love working with, is trying to figure out what to do about a particularly thorny issue. I tell a story. He reacts with a little more data. I tell another story. Another board member asks a question. I tell another story. This one goes on a bit too long.

The CEO looks directly at me and says, very firmly, “Will you just tell me the fucking answer for once?”

I tell him the answer.

He was looking for specific, actionable advice. I was telling him stories. If he spent enough time processing the stories, he might be able to come up with the right answer. Or, since they are stories, he might draw the wrong inference and decide to do something different from where the stories were leading him. This CEO was aware of that and, in real time was having trouble processing the point of the stories in his context.

Fortunately, this CEO was self-aware enough to ask for specific, actionable advice in a moment where he needed it.

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May 2 2017

Mentors 14/18: Accept and Communicate With Other Mentors That Get Involved

Two mentors in one of the Techstars programs were both people who I knew well. They hated each other as a result of being co-founders of companies that had been bitter rivals.

Each company was successful, but their paths ended up being very different. These two co-founders hadn’t interacted with each other, but the CEOs of each of their companies had some rough interactions. As a result, each of these co-founders thought the other was an evil person.

Each of the co-founders was technical, extremely smart, and capable. Not surprisingly, they gravitated toward mentoring the same companies.

After a few very awkward moments, I encouraged the two co-founders to let their pasts be history and to move on. I knew them each pretty well and expected they’d like each other and get along if they had an opportunity to reset things. Being mentors to the same company gave them this opportunity.

It turned out that they loved working together. At some point, the co-founders talked about their past. They had never actually met, and each realized that their emotions were a function of the hostile relationship between the CEOs. Since they were channeling these emotions, they realized this was a self-limiting perspective.

They became friends. In a few cases, they’ve been mentors for the same company. It’s been a great example of moving beyond whatever your past is and accepting each other as a mentor in a new shared context.

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Apr 21 2017

Mentors 15/18: Be Optimistic

Last month I took two weeks completely off the grid. As part of it, I spent some time working on my next book, Give First. As part of that, I finished up the sections on Deconstructing the Techstars Mentor Manifesto. While I wrote a draft of this post over a month ago, It felt appropriate to publish this, and the next few Mentor Manifesto posts, after a wave of Techstars Demo Days that just happened.

#15 is “Be Optimistic.” It sounds simple, but it can be incredibly difficult.

As a mentor, your job is not to solve a founder’s problem. It’s to help. It’s to listen. It’s to provide feedback and data from your experience.

You can do this from many different perspectives. However, given the stress on a founder, it’s best to do this from an optimistic frame of reference.

Here’s an example of the challenge. You are a mentor to Maria, who is struggling with her co-founder Stephan, who has become unpredictable, inconsistent, and subdued. Maria feels alone, both on a day to day basis as well as in dealing with Stephan (there are only two founders in this case.)

As a mentor, you had a difficult co-founder experience in your last company. While the dynamics were different, it ended poorly with your co-founder leaving the company. While you haven’t spoken since you split up, your business was successful and acquired for a life-changing sum of money for each of you.

Your co-founder struggle is one that didn’t work out between you and your co-founder but was ultimately financially rewarding for each of you. You carry around this conflict in your head. On the one hand, you are pessimistic about where things between Maria and Stephan will end up. On the other, you know that even if their relationship fails, the company can still be a success.

You also learned a lot from your experience with your co-founder. Each of you made mistakes in approaching things during your conflict period. This hurt both of you and negatively impacted the company for a while. Your struggle with each other was public, and it ruined several other relationships with people who felt like they needed to choose sides.

Being optimistic in this context is difficult. But it can be done. Start from a positive frame of reference. Talk openly with Maria about the things that you and your co-founder did wrong as you tried to address your conflict. Be clear about how things could have turned out differently. Be introspective in your discussion and speak from experience, instead of giving advice. Remember to reinforce that even though your relationship with your co-founder ended up failing, your business was successful.

Let Maria have her experience as she tries to resolve things with Stephan. Try to be a positive influence in the mix to encourage her to do the work involved, even if they end up parting ways.

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Oct 4 2016

Mentors 13/18: Guide, Don’t Control

It’s been a while since I wrote a post deconstructing the Techstars Mentor Manifesto. The last one I wrote was number 12 of 18: Know What You Don’t Know. Say I Don’t Know When You Don’t Know. Since I’m now working on the first draft of my next book #GiveFirst (or maybe it’ll be called Give First, or GiveFirst – I haven’t decided yet) it’s time to get my shit together and write the last six posts.

Throughout Techstars, we tell the founders that “it’s your company.” The implication of this is that they make the decisions about what to do. Everything they hear from mentors is just data.

A lot of mentors are successful CEOs. As CEOs, they are used to being in control. However, in the context of being a mentor, they don’t control anything. The best they can do is be a guide.

Interestingly, the best investors understand this. One of the lines my partners at Foundry Group use regular is that we only want to make one decision about a company – whether or not we support the CEO. If we support the CEO, we work for her. If we don’t support the CEO, we need to do something about this, which doesn’t necessarily mean fire the CEO.

In the context of being a mentor, you still get to make one decision, but it’s a different one. You get to decide whether or not you want to keep being a mentor. Assuming you do, your job is to support the founders, no matter what.

Ponder the following situation. The company has three founders. While one of them is CEO, it’s not clear that the right founder is the CEO. In addition, two of the founders (the CEO/founder and one other founder) are struggling with the third founder.

It would be easy to size up the situation and tell the founders what to do. But that’s not your job as a mentor. Instead, your job is to guide them to an understanding of the situation. The best mentors will invest time in each founder, keeping an open mind about what the fundamental problems are. You’ll surface the issues, guiding the founders to understand that there are real issues, what they are, help them talk about them, and help them work through them to a resolution or a better situation.

You won’t try to solve the problems. That’s not your job as a mentor. But you will be a guide. At some point, it will be appropriate, as a guide, to say what you would do if you found yourself in a similar situation. But, as a great guide, you won’t force this outcome, nor will you be judgmental if the founders go down a different path.

Remember – you get to make one decision – whether or not you want to keep being a mentor.

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Sep 8 2015

Mentors 12/18: Know What You Don’t Know. Say I Don’t Know When You Don’t Know

Techstars Boulder Demo Day is this week. It always marks the true end of summer for me and it’s a reminder that I stalled out on my Techstars Mentor Manifesto series of blog posts.

The last one I wrote was #11: Clearly Commit To Mentor Or Do Not. Either Is Fine. It’s an important life rule – either commit or don’t commit – but choose! Mentor Manifesto #12 is also a good life rule: Know What You Don’t Know. Say I Don’t Know When You Don’t Know.

We all know Mr. Smartest Guy In The Room. I find him insufferable and have nicknamed him Mr. Smartypants. Unfortunately, there are a lot of Mr. Smartypants in my world as he inhabits the bodies of some entrepreneurs and the souls of a lot of investors. Regardless of who he manifests himself in, he’s still tiresome and when there are two of him in the room, watch out.

The best mentors are not Mr. Smartypants. While a great mentor knows a lot and has had plenty of experiences, she’s always learning. The best mentor/mentee relationships are peer relationships, where the mentor learns as much from the mentee as she teaches the mentee. There’s no room in this relationship for Mr. Smartypants.

I know a lot about some things. And I know very little, or nothing about a lot more things. My business and technology experience is deep in software, where even the hardware companies we are investors in (Fitbit, Sphero, Makerbot, Glowforge, littleBits, and some others) are what we like to refer to as “software wrapped in plastic.” At the essence of it all is software and that’s what I know best.

But I don’t know all software. And I especially don’t know vertical markets. We’ve consciously stayed horizontal in our investing, being much more interested in our themes which apply to many different vertical markets. But ask me about a vertical market, whether it be entertainment, real estate, insurance, auto, food, energy, or financial services and I’ll often approach it with a beginners mind.

In some cases I think something generic will apply to a vertical market. But when asked about something structural, even though I’ve had lots of different experiences, read a zillion magazine articles over the years, and might have some opinions, as a mentor I’m quick to say I Don’t Know, unless I’m confident that I do.

When I find myself in an “I Don’t Know” situation as a mentor, I immediately start trying to figure out who I can refer the entrepreneur to who might know something about the situation. And, just because I don’t know doesn’t mean I’m not curious about finding out more. I’ll often stay engaged and hear what the mentor has to say, just so I get the benefit of having more data in my head to play around with in the future.

I say “I don’t know” or some version of it at least daily. How often do you say it?

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Apr 9 2015

Mentors 11/18: Clearly Commit To Mentor Or Do Not. Either Is Fine

I’m hanging out with Morris Wheeler and his family for a few days in Cleveland. I first met Morris through my friend Howard Diamond, currently the CEO of MobileDay (which I’m on the board of). Both Morris and Howard are extraordinary Techstars mentors, so I was motivated this morning to knock out another post in my Deconstructing The Mentor Manifesto series as foreplay for me starting to work on my next book, #GiveFirst.

When we started Techstars in 2006, the concept of a mentor was very fuzzy. There were many people who called themselves “advisors” to startups, including a the entire pantheon on service providers. While the word mentor existed, it was usually a 1:1 relationship, where an individual had a “mentor”. It was also more prevalent in corporate America, where to make your way up the corporate ladder you needed a “mentor”, “sponsor”, or a “rabbi.”

We decided to use the word “mentor” to describe the relationship between the participants in the Boulder startup community who were working with the founders and companies that went through Techstars. We had our first program in Boulder in 2007 and had about 50 mentors. Many were local Boulder entrepreneurs, a few were service providers who were particularly active in the startup community (including a few investors), and some were non-Boulder entrepreneurs such as Dick Costolo (ex-Feedburner – then at Google) and Don Loeb (ex-Feedburner – also then at Google, now at Techstars as VP Corporate Development). Basically, I reached out to all my friends and said “would you be a mentor for this new Techstars thing we are doing?”

At the time, we had no real clue what the relationship between mentor and founder would be. We knew that we wanted real engagement – at least 30 minutes per week – rather than just an “advisor name on a list.” We expected that engaging local mentors would be easier than non-local mentors. We defined rules of engagement around what mentoring meant, which did not preclude early investment, but did preclude charging any fees during the mentoring period.

Over time, we realized – and figured out – a number of things. When I talk about the early days of Techstars, remember that the concept of a “mentor-driven accelerator” didn’t exist and that the idea of an accelerator was still in its invention phase.

One of the biggest lessons was encapsulated in this part of the mentor manifesto. As mentorship became a thing, we suddenly had a supply of mentors that overwhelmed us. Everyone wanted to be a mentor. In 2008, we knew a little about what was effective and what wasn’t, so we continued to try to be inclusive of anyone who wanted to be a mentor, although I’m sure we blew this in plenty of cases. But we started seeing lots of mentors who did a single flyby meeting with the program, but never really engaged with any of the founders or companies in a meaningful way.

It probably took us until 2011 to really understand this and put some structure around it. By now, we had programs in multiple cities and managing directors who had different styles for engaging the local mentor community. And, mentorship was no longer a fuzzy word – it has shifted over into trendy-language-land and everyone was calling themselves a mentor, even if they weren’t. And being a mentor for a program like Techstars suddenly started appearing as a job role on LinkedIn.

Today we’ve got deep clarity on what makes for effective mentorship. And, more importantly, what makes a mentor successful and additive to an accelerator. A fundamental part of this is a commitment to engage. Really engage. As in spend time with the founders and the companies. It doesn’t have to be all of them – but it has to be deep, real, and with a regular cadence (at least weekly) over the three month program.

If you aren’t ready or able to commit, that’s totally cool. Don’t be a mentor, but you can still engage with the program and the companies through the philosophy I’ve talked about many times of “being inclusive of anyone who wants to engage” (principle three of the Boulder Thesis from Startup Communities).

And yes, this one is a hat tip to Yoda’s “Do or do not, there is no try.”

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Mar 22 2015

CEO Shadowing

Following is a guest post from Zack Rosen at Pantheon about his experience shadowing Jud Valeski, founder and then-CEO of Gnip for a day in 2012.

Behind the stories of most first-time venture-backed CEOs building startups and attacking markets at breakneck speed, there is usually a tight network of mentors and peers showing them the ropes of company building. That’s certainly been my experience at Pantheon—we likely would not exist if not for the crucial help of James Lindenbaum, Adam Gross, Steve Anderson, Ryan McIntyre, Brad Feld, and all of the advisors who have assisted us on our journey.

However, I’ve found there is a hard limit to how much you can learn about building a company from speaking with advisors. Before deciding on how to go about building your company, it is critical to build an understanding of other companies’ paths to success and learning from their mistakes along the way. I’ve found to really do that, often times you need to be there—out of your own office and physically present in theirs—to see with your own eyes how a company actually works.

That is the goal of CEO shadowing: to put you in the shoes of another CEO, let you observe, ask questions, and form a rich and detailed mental model of how another company operates. I’ve done it twice so far, and both times have learned more in a day of shadowing than I do in months of working sessions with mentors and peers.

My first time CEO Shadowing: Jud at Gnip in 2012

The first CEO I shadowed was Jud, who then ran Gnip which has since been acquired by Twitter. Foundry Group is a mutual investor of ours, and Jud and I met at an event in Boulder that they organized for portfolio CEOs.

In Boulder I ran around asking a number of CEOs and Foundry Partners for company management advice—how to run one-on-ones, structure executive meetings, manage my board, etc. Three times in row an answer to my question was prefaced by:

“You should really ask Jud this question because they just did this at Gnip and did a fabulous job.”

We were a 20-person company at the time, and Gnip had hit its stride and was growing very quickly. They were 50, soon to be 100—about a year and a half ahead of us in terms of scale. Gnip was known for being a very well-run company.

I cornered Jud at the event and soaked up as much data from him as I could. Then I went home, and realized how much more I really needed to learn from him and Gnip. The only way I thought I could really get answers to my questions was to go to Gnip and observe how Jud and his team ran the company.

So I sent this email:

“Can I fly to Boulder and shadow you for a day, and be a fly on the wall in yours and your team’s meetings?”

This was his response a couple of hours later:

Fun! You bet! Only question is timing. Thoughts?”

Jud invited me to attend his management meetings and let me interview anyone on his entire team at will. In one day on-site I was a part of his exec kick-off meeting, attended a company product strategy meeting, and interviewed two executives, two engineers, and individuals from their sales and marketing team. I took notes, asked questions, and tried to fit in. I approached it like a journalist whose goal it was to write a profile on how Gnip, the company, worked.

I found the Gnip team to be incredibly focused and busy—while still gracious, helpful, and happy to talk at the same time.

What I learned

At the time I shadowed Jud, Pantheon had a very early executive team and not much in terms of process or structure. We operated on tribal knowledge and had the benefit that everyone implicitly knew what the others were doing. We knew we needed to build our team and create more structure, but how were we going to do that without screwing up what was working so naturally?

What I learned at Gnip was:

1) It was absolutely possible to build a 100-person company that operated as efficiently, or even more efficiently, than our 20-person company.

2) Process and structure could be additive to company culture, because it forces you to get specific about implicit assumptions that are so important to a company’s future (values, strategy, management philosophy, etc.)

3) There is good management and bad management, and you need effective leadership and stiff penalties when you fail to lead. It was up to us to build the company right. Gnip was built right, and it worked.

On top of that, I learned many, many small tactical things—from how to structure the agenda of an executive meeting, to how to arrange teams and desks, to optimizing how the people worked together.

But the tactics were built on the big learnings, which were important for this reason: seeing how Gnip worked gave me confidence to trust my gut in building my company. To be clear, Pantheon is built very differently from Gnip. Many of the things that worked for them won’t work for us—we picked our own path. But there are so many internal obstacles to building structure in a startup as it undergoes massive change, and to know that it could work because I saw it work enabled to me to keep my head down and keep working towards my goal without getting blown off course.

Visiting Gnip in 2012 was like visiting the hopeful, successful, parallel future to Pantheon. It was like getting to travel to a foreign, and more advanced planet, and then getting to return and apply what I learned.

Want to do this? Here are my suggestions for how to get the most out of CEO shadowing:

  • Find a CEO at a company that is approximately 1-2 years ahead of yours (if you are $1M ARR, then $5-10M; if you are $10M, then $30-$60M). Ideally this is a CEO you admire, and one you already have a relationship with.
  • Confidentiality is incredibly important. You should probably sign an NDA.
  • Book a full day in the office with the CEO. I highly recommend visiting the day the CEO does the most “management” in a workweek—when executive meetings, planning, strategy, etc are scheduled.
  • Get yourself invited to everything. Everywhere the CEO goes, you go. This requires the CEO to warn their company ahead of time and get the OK of their execs and team members.
  • Spend half of your time observing in meetings, and half in one-on-ones with their team.
  • Meet one-on-one with execs, managers, and individual contributors, ideally from numerous different teams.
  • Ahead of time, prepare a list of questions with the CEO that you can ask of their team members, or research topics you can report back on that CEO wants to know (while respecting anonymity). Example questions:
    • “What do the values of this company?”
    • “What are the company priorities? Your team’s priorities? Your priorities?”
    • “What did this company get right that has enabled it to succeed?”
  • Take copious notes during all meetings and interactions. Anonymize feedback and send a full report of what you learned back to the CEO (this can be partial repayment for letting you shadow them).
  • Keep asking questions and observing until you feel like you could give a valuable five-minute presentation on “how the company works” to your team and the CEO you are shadowing.

Asking to shadow a CEO of a company is a big ask. It’s out of the norm, and it takes time from their team. You can repay some of that by offering to share useful observation or doing outside research as part of your time there, but at the end of the day this may be the ultimate “pay it forward” generous act the startup community is willing to take on for fellow CEOs.

Investors: I believe this could be one of the most valuable things you could help facilitate for your portfolio company CEOs. If anyone else has shadowed a CEO, I’d love to hear how you approached it and how well it worked for you.

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