John Chilkotowsky
John Chilkotowsky is the Executive Coach at Northstar Coaching, LLC.
Retaining top association staff isn't just about compensation—it's about asking the right questions.
You’ve just had another one-on-one with one of your best staff members. You spoke about initiatives, membership goals, and the week's priorities. In 20 minutes, you both have clear action items. They leave, and you check it off your list. But here's what didn't happen:
You managed the work. You didn't develop the person. And six months from now, when they announce they’re leaving, you’ll be sincerely surprised. It’s one of the most consistent patterns in association leadership—and one of the most avoidable. Sound familiar?
Most association leaders are strong managers, but they often don’t focus on developing their people. This isn’t because they don’t care, but because their everyday responsibilities leave little room for the discussions that could truly transform those in the field.
Managing addresses daily needs: membership retention, event management, and board deliverables. Coaching is different. It’s about your team members’ understanding of purpose, growth, and staying engaged in the work they believe in.
When a staff member departs, they take member relationships, institutional knowledge, and momentum. Leaders who retain their best people are not always those with the biggest budgets, but those who invest in their people as intentionally as they invest in their members.
Your most seasoned employees are executing their programs well, members are satisfied, and, by every visible indicator, everything seems fine. Meanwhile, one of your most effective team members is quietly drifting away:
Then there is the conversation you didn’t anticipate. They're leaving. And their words stop you: "I stopped feeling like anyone here cared about my learning and growth about six months ago. I kept waiting for someone to ask. Nobody did."
You gave them ownership. You celebrated their wins. What more could they want? As it turns out, they wanted someone invested in where they were going, not just what they were delivering.
Your team is intentionally choosing this work, so it's easy to assume mission alignment is enough to sustain them. It isn't. Purpose matters. But it doesn't replace growth. When talented staff no longer feel challenged and don’t see any way to take that next step, they leave—often for associations with stronger development cultures.
The biggest obstacle to coaching, according to Michael Bungay Stanier in The Coaching Habit, is not skill—it’s habit. Most leaders default to advice-giving when what their people need are better questions and space to think. Staying curious a little longer changes the entire dynamic of a working relationship. So instead of falling back on those program updates, try asking:
These questions signal that this conversation is about the person’s future rather than the quarter's deliverables.
The expertise and skills you developed that enhanced your credibility are not the same skills that enable you to develop staff. The best association leaders make a conscious switch. In practice, that looks like:
These habits foster confidence and advance strategic thinking. They say you care about judgment and not just execution.
Developing your people takes genuine curiosity about their growth —and the discipline to ask about it consistently, even during your periods of peak demand. In practice:
You can’t always compete with the private sector for salary. But you can always compete on how well you invest in your people. What is a question that you would add to your next one-on-one, about the person, not the program?
And what would be possible for your association—and the members you serve—if your team knew that you were just as invested in growing and empowering your team members as you are in this year’s strategic plan?