Happy Saturday and happy Labor Day weekend to my US-based friends!
his week’s Letter from a Founder asks about knowing whether a role (specifically a COO role) is a fit for one’s skill set and career arc.
The writer asked multiple questions in their letter, which we’ll cover in upcoming newsletters. But for today we’ll focus on just the first one.
I hope you’ll share this week’s edition of the newsletter if you know someone facing the same challenges.
Let’s get to it.
Letter from a Founder
Hey BB,
How did you know if your role as a COO was either A FIT / NOT A FIT for your skillset and your career arc? Did you have any key systems or processes to succeed in the role?
Thanks!
An Ops-Focused Business Partner
Hey Ops-Focused,
Thank you for such insightful questions, and for also being willing to ask the thing that everyone experiences at one point or another — the existential dread as it relates to one’s role and career arc is real!
To be honest, I didn’t know if my role as COO was either a fit or not for my skill set and career arc!
Did I have concrete proof I was ready? No.
But I believed I had the background, training, and drive to do a great job. It was the first role of my career (other than founder) that felt equal to, or maybe even greater than, my capabilities.
I had a strong vision for where we could take the company. I believed in the mission. After years of studying what makes great company culture, I had many ideas I wanted to test in real life. The role would be challenging and require my best effort to do well.
Here’s the thing about a role as COO or any number two role at an organization: it’s primarily a matter of complementing the CEO. A COO’s job description can vary wildly across companies, often dictated by the gaps in the CEO’s background, knowledge, skills, and the overall needs of the company.
At my former company, we needed a COO who:
- Could easily dive in on and understand numbers — finances and metrics would be critical to scale
- Cared deeply about management and leadership of the team — both individually and in terms of developing other leaders
- Was interested in building a cohesive culture and communicating well
- Willing to run the majority of the teams so that the CEO could focus on his strongest skill set, which was product
- Could build systems — from forming and managing a board of advisors, to compensation, hiring, and performance management, to reporting on financials and analytics
- Would be responsible for setting strategy and goals, managing to them, and making sure we followed through or adjusted to reality
We needed what, in a more traditional non-startup company, looks a lot like a CEO. And those are all skills I either had, had interest in, or knew I could develop.
Part of the exercise of considering the role was writing a job description that highlighted all of the above. I wrote a six-month onboarding plan that would allow me to ramp up into the role by taking on one team within the company at a time, from the ones I was most familiar with to the least. It looked something like:
- Months 1-3: Backfill directors of marketing and customer success while managing the teams
- Months 3-4: Onboard new leaders and ramp up with sales and operations teams
- Months 5-6: Ramp up with engineering
- Months 7+: Continue to ramp with engineering and build data team
The biggest question mark for me was whether I would be an effective manager for the teams I was least familiar with, so once we got to that point in the plan, I invested heavily in the process.
I read books on engineering and engineering management. I traveled to the leader’s city to work in person. We did deep dive sessions to help me learn about our infrastructure, how we helped our teams set up their local environments, and how we shipped code on a weekly basis.
When I looked at the role and the timeline and worked with the CEO to confirm its merits, we knew what role we needed to fill, I was confident I could do it, and we had a plan on paper to make it happen. From that point forward, it was just a matter of following through.
By six months in, I was fully ramped up and running the majority of the company while our CEO was able to focus more on vision, strategy, and product. It turned out I was qualified for the job and the plan was a good one.
What I didn’t know at the time was what it would cost me to hang on to the idea of financial freedom with white knuckles. I didn’t yet know that being good at something and something pouring back into your life as a human being are completely different things. That’s for another day.
I’ll be back with another installment of this series on operations leadership next week.
Thanks for the note!
Much love and respect,
P.S. – Things to do next:
- Hit reply and write me a letter about a leadership challenge you’re facing. I might answer it in an upcoming newsletter.
- Listen to the latest Good Work podcast episodes with Kanyi Maqubela and Tamara Winter.
- Forward this newsletter to a friend who would enjoy it.
- Refer a founder friend to coaching and I’ll pay you $1,000 if we start working together.