Articles

Thoughts on Leadership

Writing on leadership for executive directors, VPs, and senior managers in mission-driven organizations.

How Your Leadership Lands · Sep 24, 2026 · 3 min read

The Leadership Style That Backfired

A staff member pulled me aside and told me my most generous leadership move wasn't landing the way I meant it to.

I thought I'd found the most generous leadership style: ask, don't tell. Then someone on my team pulled me aside and told me it wasn't landing the way I meant it to. Here's what I learned about leadership presence, and what changed in how I read a room before I open my mouth.

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The Practice of Leadership · Sep 9, 2026 · 4 min read

The Meeting You’re Called Into After Vacation

A staff member asks for a meeting, and you don't know which way it's going to go. Neither did I.

A staff member asked me for a meeting soon after vacation. I didn't know which way it was going to go. That feeling is universal for anyone who leads people. Here's what it taught me about paying attention before you're surprised, not after.

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The Practice of Leadership · Sep 2, 2026 · 5 min read

Down Is the Easy One

A room full of executive leaders, and no direction on how we were to work out who got to decide.

Many of the meetings that matter in the NFP sector have a team in charge rather than a person. Everyone around the table is somebody's leader, everyone has a good idea, and by the end either nothing has been decided or the person who talked longest has decided it for you. Almost everything written about leadership assumes you have the authority to settle it. Here is what's left when you don't.

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Diagnosing Leadership · Aug 27, 2026 · 6 min read

A Game of Inches: The Six Domains of Leadership

A roofer once offered to drop my chimney with a shotgun. I said brick by brick — and that choice turns out to be the whole of how leadership actually improves.

A roofer once offered to bring my chimney down with a shotgun. One shell with the pellets removed (for safety), he said, blown at the bottom and the whole stack drops into its own void. I told him no; take it down brick by brick. That roof is still standing twenty years later, and somewhere in that choice is the story of how leadership improves.

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Mission-Driven Leadership · Aug 19, 2026 · 4 min read

Why Business Leaders Struggle When They Join Nonprofits

You came in capable, and three months later you're quietly failing. Here's the truth no one in the nonprofit will tell you — because they need what you bring too much to say it.

You've led teams. You've hit targets. You know how to move quickly and do things well, and that track record is exactly why the nonprofit wanted you. So the last thing you expected, three months in, was the quiet sense that you're failing. Here's the part no one inside that organization will tell you — because they need what you bring too much to be honest about it.

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Diagnosing Leadership · Jul 29, 2026 · 3 min read

I Was Right. That Was the Problem.

I was the board chair. I'd done the work and I had the evidence. I still couldn't see the one thing everyone else in the room could.

I was the board chair and we were planning to send interns into a complicated (dangerous) part of the world. One board member kept pressing on liability. I'd done the work — thoroughly. I had the evidence to prove it, So I did prove it. Again, and a little louder each time. It took a colleague pulling me aside after the meeting to show me the one thing everyone else except me could already see.

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Diagnosing Leadership · Jul 14, 2026 · 3 min read

Your Staff Are Listening Too Much

She wanted to know how to train her team to follow her. Then I asked what her business actually does, in one sentence.

A local business owner told me her staff wouldn’t listen. They didn’t sell the way she wanted, didn’t greet customers the way she wanted, didn’t clean the store the way she wanted. She asked how to train them better. Then I asked her what her business actually does — in one sentence. She couldn’t answer that either.

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How Your Leadership Lands · Jun 18, 2026 · 4 min read

You’re the Last to See How You Lead

You can read another leader’s form in a glance. Your own is the one run you never get to watch.

I was partway down a ski hill, watching two skiers below me — one smooth, one working harder for the same run. And the question hit me: which one am I? I could read both of them in a glance. The one skier I couldn’t see was me.

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Team Health · Apr 22, 2026 · 2 min read

What Island Health Taught Me About Culture

Real culture doesn't stay in the mission statement. It shows up in 10-minute interactions with strangers.

My 14-year-old was in surgery last month. I walked in ready to manage expectations — just get through it. What happened instead was a masterclass in culture. Not the kind on a wall. The kind that shows up at 4pm on a Tuesday with a stranger who’s worried and didn’t schedule the emergency.

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How Your Leadership Lands · Mar 18, 2026 · 2 min read

We’re Not All in the Same Boat

During transitions, people don't need their leader to be in the same boat. They need an honest captain.

I listened to a leader say "We're all in the same boat here." He meant to connect. I immediately tightened. Everyone in the room knew it wasn't quite true, and once you feel that gap, trust in the messenger starts to slip.

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The Practice of Leadership · Mar 3, 2026 · 2 min read

The Conversation You’re Avoiding

Kindness matters. But small talk does not equal kindness.

When you need to address a performance issue, don't open with "Hey, I just wanted to check in." It seems friendly. It isn't. The desire to reduce anxiety is often the very thing that increases it.

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Mission-Driven Leadership · Feb 5, 2026 · 2 min read

The Nondescript Wednesday

The pressure we're under as leaders always comes out somewhere. The question is where.

I once told my team that what I was most looking forward to was a nondescript Wednesday in the fall. A day I'd come in, do a normal day's work, go home. Nothing would happen. No crisis. Just a regular day. That fall turned out to be a mess. But the moment stuck with me.

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Diagnosing Leadership · Jan 27, 2026 · 2 min read

If It Ain’t Broke

Stability isn't always a sign of health. Sometimes it's a sign of stuck.

Nothing was really broken — but change simply hadn't been on the table for years. That kind of perpetual sameness starts to wear a place down. It has a name. And your most motivated team members are already feeling it.

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The Practice of Leadership · Jan 15, 2026 · 2 min read

The Three-Legged Stool

Titles can't make a leader. But at certain moments, titles protect them.

A colleague of mine was being asked to deliver results without the formal authority to require them. It's a common kind of leadership strain, and it has a structure. Remove one leg and things start to wobble.

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Mission-Driven Leadership · Dec 12, 2025 · 2 min read

The Daily Heroic Multitasking Trap

Mission-driven leaders get celebrated for doing everything. That's starting to look like a trap.

Most nonprofit leaders I know hold two or three jobs inside one role. That creativity is vital to the sector. But being celebrated for daily heroics can trick us into thinking that everything should require daily heroics.

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