The one thing that changed how I work

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I didn’t come to leadership through a business school. I learned by building teams, shipping work, and making plenty of mistakes in a fully distributed environment.

That’s why, a few years in, Automattic’s CFO asked me a simple question: “How could the company help your development?”

Going back for a formal program sounded great in theory and impossible in practice. I was working full‑time; there was no realistic way to disappear for months into classes and case studies.

So we looked for something that would fit the work: coaching.

I had never done it and was really curious. I never thought it would change the trajectory of my career.

I found a coach in Vienna and we met regularly for about a year—roughly twenty sessions, almost every other week. (Automattic covered a block of sessions, which made it easy to start.)

Remote work wasn’t mainstream yet, so an amusing amount of our early time went into me explaining how a distributed company actually runs. In other words, my first coaching win was… onboarding my coach. Once we got past that, the value was immediate: coaching didn’t “install” skills; it pulled out what I already knew, revealed blind spots, and turned intention into action. The following year, we kept three or four check‑ins, then closed that chapter.

Then in 2017, Automattic launched a structured coaching program. That was a real unlock. Coaches were pre‑vetted and already fluent in our context—remote work, async decision‑making, written culture—so we could spend the full hour on outcomes instead of explaining how Slack threads work.

After a short sabbatical, in 2018, I chose one coach from the program and worked intensely with him through five or six cycles. Each cycle ran six to eight months: set a few objectives → do the work → measure → reset. These weren’t six years on the same topic; every cycle focused on different goals, and we kept moving the baseline forward. That cadence—clear goals, real work, honest measurement, reset—became the operating rhythm I still rely on.

By the end of 2024, that coach gave me a piece of feedback I appreciated: we were approaching mutual‑coaching territory. Not because everything was “done,” but because our conversations had become too familiar. To push further, I needed a different perspective.

So, in 2025, I switched to a coach with hands‑on experience in my exact role. Since then, the mode alternates deliberately: coaching when I need clarity (he draws answers out of me) and teaching when a proven method exists (we install it and move).

So, I guess I have some experience in coaching (more than 10 years at this point!).

There are a few practices that stuck with me:

• Work in cycles (6–8 months). Few goals, clear measures, reset.
• Pick the mode on purpose: coaching for clarity; teaching for repeatability; and, when the knot is human rather than technical, make room for counseling‑style reflection so the work can proceed.
• Choose fit over prestige. There’s no universal “best coach”; there’s the right one for your role and season.

I’m grateful Automattic invests in this. And I’ll repeat the simple lesson I’ve learned since 2014: nobody serious operates alone. Ask for help, pay for it when needed, and change the kind of help as your season changes.

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I also publish on paolo.blog and monochrome.blog.