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.

  • mark gelband

    bravo!

    “The origins of corporate secrecy can be traced to executives who possessed the technical skills to scale the corporate pyramid but were not mature enough to handle the heights.”

  • Great post. Taking the mentorship model to a whole other level. We’re trying to accomplish something similar to this in Miami amongst local entrepreneurs in three ways: 1) mentoring 2) round tables 3) shadowing.

    The key thing you stated in the post was shadowing someone that is one stage ahead of you. They know where you are now and can help guide you to getting to the next stage.

    Thanks for the detailed suggestions as well. Very informative.

    • Zachary Rosen

      Thank you Darryl.

      Agreed: Shadowing someone who is a stage ahead is quite important.

      I’d love to hear and learn from other entrepreneurs who try shadowing..

  • David Parker

    Love this idea. As a CTO, I see a lot of parallels and think we should do something like this as well.

    • Zachary Rosen

      Thanks David.

      Totally agree, I think shadowing can be applied for all leadership positions.

  • Jason Portnoy

    This is awesome. Great idea and well presented. Can’t wait to share this with our portfolio company CEOs.

    • Zachary Rosen

      Thank you Jason. Would love to hear how it goes for your portfolio CEOs.