Making the move into engineering leadership?
A coach for new engineering managers. Senior engineer to tech lead. IC to manager. If some version of that search brought you here, you’re in the right place. And what I do is different from what you’re probably expecting.
I’m Michael Greenspan. Seven years a software engineer, nine years an engineering manager — which means I made this exact move, and then spent nine years living with it. Now I coach technical leaders through it: new engineering managers, tech leads, staff engineers leading without authority, and senior engineers still deciding whether to make the move at all. I work 1:1, remotely, from Toronto. A three-month container: six conversations, every other week. It starts with a few free conversations, to figure out whether and how I can help.
What the move actually feels like
If you’re searching for help with this transition, some of this is probably true:
You were promoted because you were good at engineering. Then the job changed under you, and the skills that earned the title are not the ones the title needs.
Your calendar filled up and your sense of progress emptied out. At the end of the day you can’t point to anything you made.
People who were your peers a month ago now report to you, and every one of those relationships — including the friendships — needs renegotiating.
There’s a conversation you know you need to have with someone on your team. You’ve rehearsed it more times than you’ve had it.
You miss the code. Some days you wonder whether you’ve made a mistake.
And under it all, a question you keep to yourself: was I actually good at my job, or just good at my old job?
Most new managers land on the same plan:
The books are the easy part
Read them — this is the one stage of a career where the management books actually help. The mechanics of 1:1s, delegation, feedback: you can learn all of that, and you will.
What the books don’t cover is the harder part: on Friday you were an expert, and on Monday you’re a beginner, in front of everyone, with people depending on you. You’re making decisions about people that can’t be reverted, judging yourself on each one, and there’s nobody safe to admit that to — your team is watching you, your manager promoted you, and your old peers report to you now.
So the work isn’t a curriculum. It’s a slower kind of conversation: enough room to separate what’s actually yours to learn from the noise of being new, and to lead from your own judgment instead of an imitation of someone else’s.
From here, this goes one of two ways
I won’t promise you a transformation. Here’s the honest version, in both directions.
If nothing changes, the habit sets. You keep performing the manager you think you’re supposed to be — an imitation of the best boss you ever had, or a careful inversion of the worst — and each month you trust your own read a little less. Some engineers decide leadership isn’t for them before they’ve ever led as themselves.
If it does change, being new doesn’t stop being uncomfortable. You’re still new. But the discomfort stops meaning something is wrong with you. The rehearsed conversation gets had. The calls come a little sooner. You start leading as yourself, which is the only version of this job you can sustain.
Books, training, mentorship — or this?
An honest sorting, because they get blurred together:
Books and training are more useful here than at any other point in a career. They teach the mechanics, and I’ll happily point you toward good ones. What they can’t do is help you with the week you’re actually having.
A mentor inside your company is worth listening to, if you have one. But they sit inside your org chart, and some of what you need to say can’t go to anyone inside it.
Going back to IC is a real option. Some people I talk with work out that they’d rather build, and choose that with a clear head. That’s a good outcome.
This coaching is a recurring, confidential conversation with someone who made the same move and then ran engineering teams for nine years. Room to think out loud while you grow into the role — no org chart, no performance review, and no agenda but yours.
How it works
A three-month container: six conversations, every other week, remote. Confidential by default. Selective intake, small roster — and an honest “are we a fit?” page, because part of this work is helping people see clearly, and it would be strange to start by being unclear about that.
It starts with a few free conversations, no pitch, to figure out whether and how I can help. Once we have a clearer picture of what we could create together, we talk about what working together could look like.
Common questions
I just became an engineering manager. Is it too early for coaching?
No — the first year is when the habits form: how you decide, how you handle being new, which manager you imitate. It’s easier to shape that now than to unwind it later. And the first few conversations are free, partly so we can find out together whether this is the right moment.
Do you only work with new managers?
No. I work with engineering managers, directors, VPs, staff and principal engineers, technical founders, and CTOs. This page is about the transition; the engineering leadership coaching page describes the wider work. The common thread is carrying decisions you can’t fully talk through with anyone else.
Can you help me decide whether to make the move at all — or whether to go back?
Yes, and I have no stake in which answer you reach. Some of the most useful conversations I’ve had ended with someone choosing the staff-engineer path with a clear head. What matters is that it’s a decision, not an escape.
Will you teach me how to run 1:1s and give feedback?
Mostly no. The mechanics are learnable from books and training, and I’ll point you toward good ones. My work is the part the books skip: the deciding, the self-judgment, the being new in public. Though having run engineering teams for nine years, I won’t pretend I have no perspective.
What does it cost?
The first few conversations are free, and they’re not a pitch. We use them to get to know each other and figure out whether and how I can help. Once we have a clearer picture of what we could create together, we talk about what working together could look like, including the investment.
Where are you located, and do you work remotely?
I’m in Toronto, in the Eastern time zone, and all coaching happens remotely over video. I work with technical leaders across North America and beyond, and I’m flexible on scheduling across time zones.
Start with a conversation.
The first conversations are free and unscripted. I’ll learn what you’re carrying and what you’re hoping will be different. You’ll get a sense of whether my approach fits. No pitch, no decision expected.
Not ready for a conversation? The weekly reflection is the quiet way in: Monday mornings, a short reflection to sit with.
Send me the weekly reflection