Looking for engineering leadership coaching?
Executive coaching. Leadership development. A coach for engineering managers. 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, now a coach for technical leaders: engineering managers, directors, staff and principal engineers, technical founders, and CTOs. 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 you’re probably looking for
If you searched for leadership coaching, something specific is usually underneath it:
A decision you’ve been circling for weeks. A team that’s looking to you for a direction you’re not sure of yourself. A promotion that added weight faster than it added support. The performance conversation you keep postponing. Pressure from above, pressure from below, and nowhere to put your own thinking.
And the quiet conclusion most leaders reach:
Here’s the thing: the frameworks aren’t the bottleneck
You’ve read the books. You’ve run the 1:1 templates, tried the delegation matrices, taken notes in the leadership workshop. You’re a technical leader. Absorbing frameworks is not your problem.
What I notice in conversations with senior leaders is different: the hard part isn’t knowing what to do. It’s that you’re deciding alone, under pressure, while quietly grading yourself on every move.
So the work isn’t a curriculum. It’s a slower kind of conversation. Slow enough to separate the real decision from the pressure around it, see what’s yours to carry and what isn’t, and respond on purpose instead of defaulting to pressure or self-attack.
Not a framework. Not five steps. Not advice from someone who’s never led.
From here, this goes one of two ways
The job doesn’t change. The team doesn’t. The pressure doesn’t. And I won’t promise you a transformation. Here’s the honest version, in both directions.
If nothing changes, it doesn’t hold steady. It compounds. The decisions keep circling, because making them alone and under pressure feels too risky, and you trust your own judgment a little less each time.
If it does change, the pressure doesn’t vanish. It stops running you. The decision you’ve circled for weeks gets made on a Tuesday. You make the call without spiraling first. You stop grading yourself on every move. Clients describe recovering confidence after a hard job change and detaching their self-worth from external validation. Their words, on the coaching page.
Coaching, training, mentorship. or something else?
An honest sorting, because these get blurred together:
Leadership training teaches competencies to a room. Useful early. But your situation stopped being generic a long time ago.
Mentorship is advice from someone further down your road. It assumes the problem is not knowing what to do. For most senior leaders, the problem is the weight of deciding, not a missing answer.
Executive coaching can be excellent, and much of it runs on frameworks, assessments, and accountability. Usually from someone who hasn’t carried a team, a pager, or a production incident. If that’s what you need, it exists, and I’ll happily say so. It isn’t what I do.
Therapy treats and heals. The right place for the heavier weight, and coaching doesn’t replace it.
This coaching is closer to what I call a thinking partner: a recurring, confidential conversation with someone who’s sat where you sit. the thinking you can’t do alone, with 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
Is this executive coaching?
Not in the usual sense. Executive coaching often means competency frameworks, 360 reviews, and accountability structures. My work is reflective: a recurring, confidential conversation where you slow your situation down, separate the real decision from the pressure around it, and hear yourself think with someone who can reflect you back honestly. No method, no homework.
Do you only work with engineering managers?
No. I work with engineering managers, directors, VPs, staff and principal engineers, technical founders, and CTOs. The common thread isn’t the title. It’s carrying decisions you can’t fully talk through with anyone else. Not your team, not your manager, not your peers.
Is this mentorship? Will you give me advice?
Mostly no. Mentorship hands you answers from someone further down your road, and it assumes the problem is not knowing what to do. The leaders I work with usually know more than they trust themselves to act on. My job is to help you find and trust your own judgment. Though having sat in the engineer’s chair and the manager’s chair, I won’t pretend I have no perspective.
How is coaching different from therapy?
Therapy treats and heals; it’s the right place for anxiety, depression, and real crisis, and coaching doesn’t replace it. Coaching looks at how you’re leading and deciding right now. If what you actually need is therapy, I’ll say so and point you toward the right support.
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.
No pitch. No script. No follow-up sequence.
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