How to Onboard into a New Leadership Role: 7 Lessons from 25 Years

Gathering context is only the beginning. Here's the playbook I've kept evolving.

Photo by Niklas Jonasson on Unsplash

👋 Hi, I’m Jeff. I’m back from some traveling (maybe in another post). I write weekly about lessons I’ve learned leading product teams and working to lead well in chaotic environments, drawing on 25+ years of building.

1:1 exec coaching: I work with a small number of senior product leaders one-on-one as a coach. These are typically six-month engagements. If that’s you or someone you know, let’s talk.

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⏱ Read time: 6 minutes

In December 2017, I transitioned from LinkedIn to lead a small product team at Facebook building for creators. It started with the standard, not-great onboarding you’d expect.

But there was an unexpected gift of onboarding in December: this frenetic company slowed down. For a couple of weeks, Building 20 in Menlo Park was unusually quiet and mostly empty. I remember some Facebook employees walking their visiting families around the office, showing off the campus. They’d walk right by my desk.

Given the quiet, I used the time to start gathering context and, more importantly, think about what I’d learned from past onboards. I built a short playbook of notes for myself in those two weeks that I’ve kept evolving ever since.

Onboarding well is more than gathering context quickly. It’s forming points of view fast enough to shape what should come next. AI is making it easier and faster to understand context in a new role. But forming your point of view, connecting dots, deciding what needs help, choosing where to push and how — is still your most valuable human work. If you’re a VP, this shows up in how quickly you define strategy or assess a team. If you’re an IC, it shows up in how you frame problems and earn trust early.

Across internal moves, large companies, and startups, I’ve done onboarding well and also made mistakes. When I look back, the biggest mistake is almost always the same: I should have moved faster. And that’s even after times I’d moved fast.

Here are seven onboarding themes I use:

1. Treat the organization like a product. Most leaders go deep on the product early on, but make sure to spend time on the product that produces that product. That’s the team. Like any product, a team has inputs, ways it works, and outputs. It has users, problems to solve, and jobs to be done. Thinking about teams this way creates a lens for new ideas. Some of the most meaningful work I’ve done in new roles was about product managing the org itself: understanding how it worked before I arrived, where it was getting stuck, and how it needed to work differently to get better.

2. Protect your beginner’s mind. Avoid the lobster scenario: the water is heating up slowly, and before you realize it, you’re captive and adapting to the very culture you were hired to help evolve or change. Extend how long you think like a new person. Fresh eyes are valuable. Lean into your early lack of context as a source of interesting insight and unencumbered questions. Ask “why do we do it this way?” too often. New observations happen early. Notice them, write them down, and use them. One exec I worked with at Facebook kept a category of observations called “Huh?”

3. Seek patterns: Use structured listening and try the ‘doc test.’ Move through the org one 1:1 at a time, asking everyone the same questions: what’s going well, what’s not going well, where can I help, and what would you focus on if you were me.

AI tools with ambient transcription can help compare all these notes for you. You’re building trust by listening, and the team is pointing you at the context that matters most. Disagreement in what you hear is itself a signal. It means people aren’t aligned.

Pair this with the doc test, a useful question to ask even when AI can help find the answer for you. Ask different people to share the single doc on an important topic. You’ll get one of three signals:

• Everyone sends the same doc. Good sign.

• No doc exists. A flag.

• You get five different docs. An opportunity to create clarity.

4. Start bigger changes sooner than feels comfortable. Have a clear point of view on what type of org you’re joining and then act sooner than feels comfortable. A rocket ship wants you to keep things going, enhance and improve. A transformation wants you to help them change. There’s a continuum here, but don’t use a posture built for one scenario when you’re living in another.

Start bigger changes sooner than conventional wisdom says. Standard onboarding advice is to seek quick wins, avoid changing too much too soon, and think in terms of a 90-day or even one-year horizon. I’ve learned to go faster. The biggest changes that generate real impact: strategy, talent, growth, or how an org operates, all need time to unfold. The sooner you start, the quicker you see impact. Deep listening (see #3) is what lets you move sooner with more confidence. A clear point of view can arrive faster than you expect. As it does, lean into it.

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Also see:

• Answer First: A Simple Framework for Executive Communication

  People often ask me how to communicate more clearly with senior leaders. Some quick thoughts...

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5. Make your thinking visible. As Jeff Weiner has said at LinkedIn, citing David Gergen: Effective communication is repeating your message more times than feels natural. Writing helps. Write and share your observations early, and more often than feels comfortable. Sharing your writing in Slack, docs, or email will help you scale beyond the rooms you are physically in. I’ve seen this work well for individual contributors as well as leaders. One mistake I’ve made is writing less in cultures where writing isn’t the norm. Lesson: write anyway. Treat internal communication like a political campaign. Repeat your core message far more than you think.

6. Uncomfortable truths. Be prepared to state them. In my experience, there is a near linear correlation between your directness (from a place of deep listening and care) and building trust and creating success. You may learn early on that a person, process, or leadership pattern is part of what needs to change. Don’t shy away from articulating what you see and learn. Be kind, but clear. Your new point of view is part of why you are there.

7. Set boundaries: Go as you intend to travel. Whatever boundaries you need to be effective, set them from day one. At times, I’ve let myself react to how a company or team behaves, and later regretted not being clearer about time, weekends, and operating expectations sooner. Don’t confuse activity with progress or fall into meeting creep because you’re new. Some of the most effective people I’ve worked with — often working moms — state what they need clearly and work backwards from there. Be uncomfortably clear here. It will pay off.

If I were onboarding into a new role today, I’d do all seven of these sooner and more boldly. The biggest mistake I’ve made is not moving faster. AI is making context-gathering more efficient than ever. But you still need to listen deeply, form a point of view, decide what needs help, and say the uncomfortable thing.

If you’re onboarding soon, the doc test is a simple place to start. Pick one topic that matters. Ask three different people for the single doc on it. The pattern in the replies will tell you more than the docs.

Work the rest as you go.