The Conversations You’re Not Having Are Costing You Your Best People

Empty office chair at a desk July 7, 2026 By: John Chilkotowsky

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 didn't ask what energizes them about their work right now.
  • You didn't ask what's wearing them down.
  • You didn't ask where they want to contribute beyond their current role.

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?

Managing the Work Versus Developing People

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.

The High-Performer Trap

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:

  • Showing less energy in staff meetings.
  • Bringing less enthusiasm for work that they used to drive.
  • Sharing fewer thoughts on how to grow membership or better serve members.

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.

When Mission Is Your Excuse

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:

  • “What part of your work right now is giving you the most energy?”
  • “What’s wearing you down that we haven’t talked about?”
  • “What other work experiences do you want to have, and how can I help?”

These questions signal that this conversation is about the person’s future rather than the quarter's deliverables.

The Shift From Expert to People Developer

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:

  • Asking, “What’s your instinct on how to approach this?” before delivering your own viewpoint.
  • Saying, “What would you do if this decision were yours?” and meaning it.
  • Letting staff deal with problems themselves, even when you could solve them faster.

These habits foster confidence and advance strategic thinking. They say you care about judgment and not just execution.

What This Actually Requires

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:

  • Treat one-on-ones as development conversations, not only task check-ins.
  • Ask, “What are you proud of this month?” before focusing on deadlines.
  • Make space for team members to talk about their careers, not just job duties.

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?

John Chilkotowsky

John Chilkotowsky is the Executive Coach at Northstar Coaching, LLC.