Let’s talk about that conversation you have been avoiding.
I coach entrepreneurs, business owners, and leaders through the conversations that are critical to whether a business moves forward or fails.
No pitch. If it isn't a fit, I'll tell you.
You probably already know which one it is.
An employee who hides critical decisions that negatively impact the business.
The partner whose actions show a lack of respect for your role as a fellow owner.
A key employee everyone else has quietly built workarounds for.
A family member on the payroll.
The team member who was a friend before you became their boss.
A client who has become unprofitable, and doesn't know it.
A multicultural team you lead that can't seem to work well together.
Waiting is not neutral.
A conversation that isn't had doesn't go away. Worse, it gets more expensive. Not because the problem grows, but because the delay becomes part of the issue. Now there's the original problem, and there's the fact that you let it become part of daily life.
Others notice. They may not know the specifics, but they know something is being tolerated. That teaches them what the standard actually is, regardless of what you've said it is.
And you carry it. On the drive home, into the weekend, into the next hire you don't quite trust because the last one went sideways.
Most leaders don't avoid these conversations because they're weak. They avoid them because they care about the person, and they don't have the tools to address the issue while caring for the person.
One Hard Conversation
Roughly six weeks. Four sessions. A conversation you stop avoiding.
1. What's actually at stake
We don't start with what you'll say. We start with what you want on the other side of this, what you're afraid of, and honestly look at how it got here. Spoiler: most people discover the conversation they've been rehearsing isn't the one they need to have.
2. Preparation
We shape the conversation and then we pressure-test it. What happens if they cry. When they get angry. When they agree too fast to make it stop. You won't get a script, because scripts can fail the moment the other person throws a curveball. You'll have the tools to be ready for a conversation that doesn't follow one.
3. You Have the Conversation
This is your part, but I will be available that day.
4. Debrief
What happened, what surprised you, and what did you learn about how you lead. This is where the work stops being about them and starts being about you.
$2,500 — flat fee, paid as we begin. One price, no packages, no hourly rate.
I hold two spots each year at a reduced fee for people leading in hard places with thin resources — early-stage founders, nonprofit and ministry leaders, people doing this work overseas. If that's you, say so on the call. It won't be awkward.
When this isn't the right work
I'd rather tell you now.
You've already made the call (firing someone, for example) and want help feeling better about it. That's a decision, not a conversation.
You want a script to memorize. I don't work that way, and it doesn't hold up under pressure.
The situation needs an employment attorney or a formal HR process. Get that first. I'm happy to be useful after.
Most of the time, one is enough.
You'll have handled it, and you'll know how you handled it. That's a complete piece of work, and plenty of people stop there.
Sometimes the debrief surfaces something else — a pattern, where this turns out to be the fourth version of the same conversation and the common factor is you. That's what ongoing one-on-one coaching is for, and it's an option when you want it.
And sometimes what surfaces is simpler and harder: you're carrying all of this alone. That's not a coaching problem. I chair a Convene team of leaders who meet regularly for exactly that reason, and I'm glad to tell you about it.
Why I'm qualified to sit across from you
I spent twelve years at an investment firm that grew from $200 million under management to over $7 billion. I was there for the version of the company that had a handful of people and the version it grew into.
Then I left it. I moved to South Asia, founded SCALE Consulting, facilitated entrepreneurial training programs across eighteen countries, and watched the funding for that work run out. I co-founded the first coworking space in my Boston neighborhood, which survived the pandemic and is now thriving. I teach business courses at a local college and serve on the board of Equipping Farmers International.
I'm telling you this because I've had these conversations. I've had the one where I was wrong. I've had the one I waited too long to have and paid for the delay.
I'm not going to hand you a framework I read about. You are going to learn what I practice.
Questions, not answers
My working definition of leadership comes from Andy Crouch: being more concerned with the flourishing of the people around you than with your own — and flourishing meaning fully, abundantly, gloriously alive.
That framing rules out a lot. It rules out leadership as having the right answers. It rules out coaching as advice-giving. What's left is harder and more useful: asking the questions that bring what's already in you to the surface, and building the next step together.
I do this work because I believe the businesses we build and the people we lead genuinely matter — that how you handle a hard conversation with someone who works for you is not a small thing, and is not separate from the rest of your life.
“He asks pointed questions that cut through mental clutter to identify key themes. In each of our sessions, I have started with a jumble of thoughts and left with clarity to step into purposeful action.”
Start with the conversation about the conversation
Thirty minutes. Free. You describe the situation, I ask questions, and at the end I tell you whether I can help.
If I can't, I'll say so and point you somewhere better.