The first 90 days are a lie

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I was talking with a friend recently about how long it really takes to feel settled in a new leadership role.

We like to use “the first 90 days” as this milestone. You’re supposed to be ramped up, making decisions, shipping impact.

But here’s the truth: most people still feel a little (or a lot) lost even after those first 90 days.

I'm 2.5 months into my new role at Zapier. Do I know more than I did last month? Absolutely. Am I still missing a ton of context? Also yes.

That “ramp-up” line isn’t a clean curve—it’s more like a series of spikes and dips.

You gain clarity in one area, and immediately uncover five new areas where you’re missing context. You start contributing in meetings, but still don’t understand half the acronyms people are using. You start to recognize who owns what, but the org chart still feels like a puzzle missing a few critical pieces.

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And if you’ve been in a leadership role before—especially at the same company for a long time—this transition can feel especially jarring.

You go from “I know how everything works, I know where the bodies are buried, I know how to get things done” to… “I don’t even know which Slack channel to ask this question in.” (Zapier has an async communications culture, and I have never been in so many Slack channels in my life. I know a year from now I’ll laugh at how few channels I’m actually in right now. It’s like that.)

It’s disorienting.

But what helps is remembering this:

• Everyone knows you’re new. You don’t have to pretend otherwise.

• Nobody expects you to have all the answers—they expect you to ask good questions.

• What people do notice is your willingness to listen, to try, to figure it out piece by piece.

You will make mistakes. You’ll probably send the wrong doc, or speak too soon in a meeting, or misunderstand a decision made 6 months ago that still has ripple effects. You’ll spiral over it (if you’re like me), and feel like maybe they’re regretting hiring you.

That’s your impostor syndrome talking. Don’t let it call the shots.

This part of the journey is uncomfortable by design. You’re stretching. You’re learning. You’re building your internal map of how this company really works—and it takes longer than any onboarding checklist allows.

Here’s your reminder for today:

You’re not behind. You’re becoming.
Trust that the competence will come. The confidence too.

Give yourself the same grace you’d give someone on your team.
You’re doing fine.

Want to work with me? Here are 3 ways I can help you:

1. Upgrade to a paid membership: You’ll get VIP access to monthly deep dives on newsletter topics shared on Tuesdays, as well as the archive of all free Tuesday posts. This includes scripts and templates you can put to use immediately.

2. Enroll in my Management Fundamentals course:

   • Looking for live interaction? Join one of my live cohort sessions for personalized guidance, group discussions, and Q&A. Next session kicks off the week of August 18.

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3. Sign up for 1-on-1 coaching: If you prefer to learn alone, I offer one-on-one coaching to aspiring and new leaders.