The Stockdale Paradox hit my radar screen this week and completely changed the way I think about how organizations approach change. The concept comes from Admiral Jim Stockdale, who spent eight years as a prisoner of war in Vietnam. When asked who didn't make it out, he famously answered: "The optimists." Not because optimism is bad. Quite the opposite. The problem was that some prisoners convinced themselves they would be released by Christmas, then Easter, then the next hol

It’s easy to jump to conclusions. Easy to make assumptions. Easy to decide we already know what’s happening. Easy to predict how a conversation will go or what someone “really meant.” What’s harder is recognizing how much of that interpretation might be based on incomplete information. The truth is, we rarely have the full story. One of the most important leadership skills isn’t having the answers. It’s recognizing how much you don’t know yet. That can feel deeply uncomfortab

When people hear: “You don’t have to do this yourself anymore.” They rarely respond by saying: “I’m uncomfortable because this role is tied to my identity and value.” They respond by saying: “It’s okay, I’ve got it,” or “Honestly, it’ll just take longer to explain it.” Which is sometimes true. But also sometimes a shield. Because the “it’s faster if I do it myself” reasoning often becomes the socially acceptable explanation for something much deeper. I’ve been thinking about

“People just want to feel heard.” We’re told that a lot as leaders In feedback discussions. In strategic planning sessions. In coalition work. In team meetings. In conversations about trust and culture. There’s truth in it, but we rarely stop to ask what that phrase actually means. Because “being heard” is often treated like a vague leadership nicety – something soft and polite that good leaders are supposed to do. Listen more. Validate people. Make space for input. Sure. But

Getting the right people in the room is only the beginning. What happens next—how that group functions, what it’s there to do and whether people leave with any clarity—determines whether the work moves forward or quietly stalls. And to be fair, not every group is meant to “move work forward” in the same way. Some groups are meant to share information. Some are meant to build relationships or create space for discussion. Some are meant to coordinate action and drive progress.

I’ll be spending time this week talking about coalitions and stakeholder groups—how they start, why they matter and where they tend to go sideways. But this isn’t just about coalitions. These are the same challenge that show up when: You’re pulling together a project team Trying to get alignment across departments Or figuring out who actually needs to be in the room for a decision In other words…leadership. Whether you call it a coalition, a project team or just “the people i

We had just finished a strategic planning session with a volunteer-led organization. They had spent time talking through where they wanted to go—stronger programs, better engagement, clearer identity, a more sustainable structure. Then we reflected it back to them. A set of draft goals that captured what they had said. Clear. Aligned. Reasonable. And they agreed with all of it. Every goal made sense. It matched their vision. It felt like the right direction. But at the same t

When someone on your team isn’t quite where you want them to be yet, the instinct is usually to act. Adjust your communication. Give them a different kind of opportunity. Lean into what you know about how they prefer to work. Those instincts are rooted in a genuine effort to support people well. But they can also lead us to move too quickly to a solution—before we’ve fully understood what’s actually going on. It can be easy to look for the quick fix. To make assumptions about

I’ve heard some version of this a few times this past week: “We’ll know good leadership when we see it.” And every time, it makes me pause. Because on the surface, it sounds reasonable. Flexible. Experienced. Maybe even intuitive. But in practice? What we each see might be very different. In one conversation, we were talking about trust, accountability, and commitment—big concepts that everyone strongly agreed were key to being a good leader. But then I asked, “What would we

I’ve been in more rooms than I can count where a strategic planning conversation starts the same way. We frame the vision. We tee up the discussion. And within about 30 seconds…someone says, “We should start a newsletter.” Another jumps in: “What about more regional events?” Someone else is already halfway into how we’d structure a new program. And just like that, we’re off. Because in the excitement of the ideas, we forget to keep coming back to the real question: What are w

What Leaders Get Wrong About Developing Their Team I came across a concept recently that made me pause. Not because it was brand new. But because it gave language to the way I think about leadership training and development. It’s called Bloom’s Taxonomy—a framework for how people learn. At its core, it’s a progression: Remember → We’ve heard this before. Understand → That makes sense. Apply → I tried it. Analyze → I see what’s working (and what’s not). Evaluate → We made

I’ve had several conversations lately that circle around the same pattern. Organizations juggling new ideas, new tools, new projects — and yet somehow feeling like they aren’t moving forward. Busy? Absolutely. But making real progress? They aren’t quite sure. Sometimes it’s because we’re chasing too many new ideas. Sometimes it’s because we’re not investing enough in the priorities we’ve already chosen. When that happens, I sometimes describe it as shiny object syndrome. You’

Runners sometimes talk about the loneliness of the long-distance runner. When you're training for a long race, there are miles you simply have to run on your own. No one else can log them for you. The early mornings, the steady pacing, the quiet discipline — the work of preparing ultimately belongs to the person chasing the goal. But if you’ve ever had a good training partner, you know something else too. The miles feel different when someone is running beside you. They don’t

Most organizations know how to assemble good pieces. Talented people. Clear mission. Experienced board members. Dedicated staff. On paper, it looks solid. And yet… You can have great bricks — and still feel like the wall is wobbling. You might be thinking: Why is decision-making this hard? Why do meetings feel circular? Why do we keep revisiting the same conversations? Why does every issue feel heavier than it should? When that happens, it’s tempting to swap out a brick. Blam

“A positive workplace culture is critical to organizational success.” You’ve read some version of that sentence before. Probably more than once. And it’s not wrong. But how does “positive workplace culture” actually show up on a random Tuesday morning? What does your culture look like: When someone makes a mistake? When a new idea gets proposed? When a deadline slips? When a team member challenges a senior leader? When a new employee is onboarded? That’s where culture lives.

Lately, I’ve been noticing something about relationships. In new coach training this week, the value “assume positive intent” landed differently for me as I thought about interactions I observe in my world. Around the same time, a colleague reviewing my 90-day framework pointed out that while I included “meet key stakeholders,” I hadn’t emphasized the work of deepening and sustaining those relationships. Two different settings. One consistent lesson: Relationships aren’t buil

At some point, most leaders have an uncomfortable realization: The work keeps coming, but their capacity doesn’t magically expand. That’s usually when “developing the team” slides to the bottom of the list — not because it isn’t important, but because it feels optional when everything else feels urgent. Deadlines loom. Emails pile up. The "quickest" path forward is often to just do the thing yourself. The quiet truth of leadership is this: success isn’t measured by how much y

Facilitating Meetings Without Losing the Room Running a meeting is often treated like a logistical task: set the agenda, keep time, move things along. But anyone who’s ever been in a well-run meeting knows there’s more going on than logistics alone. The conversation flows. People feel heard. Decisions feel clearer by the end than they did at the beginning. That doesn’t happen by accident. Facilitation is a form of leadership — one that often goes unnoticed when it’s done well

Most of us can picture our first day in a new role. You meet with HR. You fill out paperwork. You get a tour of the building. IT sets up your computer and email. Maybe you’re taken out to lunch by your new team. And then, at some point — usually by mid-afternoon — you find yourself staring at your screen thinking: Okay… now what? Too often, organizations treat onboarding as a series of logistics to get through rather than a system designed to set someone up for success. We

Why One-on-One Meetings Matter — and How to Make Them Useful Instead of Dreaded Ever been in a meeting where you can almost hear the collective thought: This could have been an email. For many people, that’s exactly how they feel about one-on-one meetings — and that’s a problem. When one-on-ones are done poorly, they feel like wasted time, awkward small talk or a weekly dose of micromanagement. When they’re done well, they’re one of the most effective leadership tools you hav