New company, old playbook?

Beginner's mind, expert's toolkit: navigating your first 90 days.

Welcome to the March subscriber edition. Thank you, as always, for being a paid subscriber, and remember that you can get in touch with me any time you like via the chat. I’m always open to hearing ideas for things to write about.

We’ve got a mailbag question this month, and it’s one whose situation I suspect will resonate with many of you. Once I received it, I knew it would be a great idea for an article, because it’s something I’ve only recently come out the back of in my new CTO role.

Here’s the question, edited for brevity:

I’ve been at my current company for 12 years, where I grew from a backend engineer through to Staff and then pivoted to the leadership track, becoming an EM four years ago and more recently a Senior EM. It’s time to finally leave and I’ve accepted an EM role at a really great company. I’m looking for ways to hit the ground running and get effective as quickly as I can, all the while concerned that all the things I do know won’t translate to the new place (though I know that’s illogical). Clearly The First 90 Days is going to be a general recommendation, but I’m looking for something more specific to tech leadership.

I suspect many of you, including myself, have felt this tension before. As you’re leaving your old role, you’ve built up years of experience, developed strong instincts about how teams should work, and earned the credibility that comes from a track record of getting things done.

And then you step into a new company and... none of that is visible. You’re effectively a stranger; a new transplant in a foreign body, if you will. You don’t know where anything is, who to talk to, or why things are the way they are. It’s a paradox: you’re simultaneously an expert and a complete beginner.

As mentioned above, I went through this recently when I joined Nordhealth as CTO in early 2025. I’d spent years at Shopify, a company known for operating without traditional KPIs and thinking in hundred-year timeframes, and suddenly I was starting over. What follows is what I learned through trial and error: a framework for those first 90 days that’s specific to engineering leadership, grounded in my own experience and supplemented by research on what actually works.

My intention with this article is to wrap my recent experience into a playbook that you can take away and follow, adapting it to your own situation as you see fit.

Here’s what we’ll cover in this article:

• The expert beginner problem. Why your years of experience are simultaneously your greatest asset and your biggest liability when you walk through the door.

• Days 1-30: See things clearly. Running a listening tour that actually works, and the simple two-question survey that reveals what really matters to your new team.

• Days 30-60: Pick your battles. Picking your battles wisely, learning to steer without doing, and understanding the cross-functional work that is a key part of leadership and critical to your “transplant” working out long term.

• Days 60-90: Land the results. Landing visible results, celebrating wins in a way that reinforces the right behaviours, and setting the tone for what comes next.

• What transfers and what doesn’t. The crucial difference between principles you can bring with you and prescriptions you need to leave behind.

• When this doesn’t apply. The situations where you should throw out everything I just said and act immediately instead.

If you’re interested in the backstory of how I ended up in a CTO role in the first place, I wrote about that journey in two parts last year: Part I covers the random walk of my early career, and Part II covers how executive roles actually get filled and the decision to make the move.

So without further ado, let’s get into it.

The expert beginner problem

So let’s start with the gigantic paradox. When you join a new company as an experienced leader, you’re in a strange position: you know how to do the job, but you don’t know where anything is, who to talk to, or why things are the way they are.

In a slightly gross phrase, Michael Watkins, author of The First 90 Days, calls this an organ transplant: you’re the new organ (kind of weird, right?), and if you’re not careful, the organisational immune system will reject you. There are so many ways for this to happen, from conflicts in how you work, to how you communicate, and generally how you fit in both up and down the management chain.

The problem is compounded by something researchers call “earned dogmatism“: the more expertise you accumulate, the more likely you are to close your mind to new information. For example: you’ve seen this pattern before, you know what works, so why question the same solution that’s served you well in the past? It’s System 1 thinking, as we covered in a previous article, at its most seductive. But what worked at your last company may not work here, and the confidence that comes from your experience can blind you to that fact.

The antidote is something Zen Buddhists call shoshin, or beginner’s mind: approaching a situation with openness and curiosity, even when you have experience. The goal isn’t to pretend you don’t know anything; it’s to hold your expertise lightly, staying curious about what might be different in the here and the now. It’s easy to understand in principle, but very hard to continually implement in practice, since you have to fight your own brain’s default mode.

So keep this approach close as we go through the plan in this article. Remember: beginner’s mind. So, let’s start with your first 30 days.

Days 1-30: See things clearly

Some executives assume they were hired to fix things, and therefore feel pressure to prove their worth quickly. Then they start making changes from day one.

When I joined Nordhealth, I didn’t want to go so quickly. I used my first 30 days as a pure assessment period: listening more than acting, and resisting the temptation to propose solutions to problems I didn’t yet fully understand. I wanted to see things clearly.