Written by: John Chilkotowsky, Strategic Thought Partner, PCC, NorthStar Coaching, LLC
You've just had another one-on-one with one of your best marketing or strategy team members. You spoke about campaigns, growth goals, and the week's priorities. In twenty 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 for another health system or a consulting firm, you'll be sincerely surprised. It's one of the most consistent patterns in healthcare strategy leadership—and one of the most avoidable. Sound familiar?
Managing the work vs. developing people
Most healthcare strategy, marketing, and communications leaders are strong managers, but they often don't focus on developing their people. This isn't because they don't care, but because the daily demands of consumer growth targets, brand campaigns, and physician relations leave little room for the conversations that could truly transform a career.
Managing addresses daily needs: campaign performance, market research, digital engagement, and board reporting. Coaching is different. It's about your team members' sense of purpose, their growth as strategists, and staying engaged in work they believe genuinely improves their community's health.
When a strategist or marketer departs, they take physician relationships, market knowledge, and institutional memory. Leaders who retain their best people aren't always those with the biggest budgets—they're the ones who invest in their people as intentionally as they invest in their market position.
The high-performer trap
Your most seasoned team members are executing their campaigns well, leadership is satisfied, and by every visible indicator, everything seems fine. Meanwhile, one of your most effective strategists is quietly drifting away:
- Showing less energy in planning meetings
- Bringing less enthusiasm for work they previously used to drive
- Sharing fewer ideas about how to grow market share or deepen community trust
Then there's 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 chose healthcare strategy work on purpose, 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 strategists no longer feel challenged and don't see a next step, they leave—often for systems 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 campaign 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 experiences do you want, 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 marketing and strategy expertise that enhanced your credibility is not the same skill set that enables you to develop staff. The best healthcare strategy 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 your team work through a challenge themselves, even when you could solve it faster
These habits foster confidence and advance strategic thinking. They say you care about judgment, not just execution.
What this actually requires
Genuine curiosity regarding growth in your team—and the discipline to ask about it consistently, even during your busiest planning cycles. In practice:
- Treat one-on-ones as development conversations, not only project check-ins
- Ask "What are you proud of this month?" before focusing on deadlines
- Make space for your team members to talk about their careers, not just their job duties
You can't always compete with consulting firms or larger systems on salary. But you can always compete on how well you invest in your people.
What is a question you would add to your next one-on-one—one about the person, not the project? And what would be possible for your organization, and the communities it serves, if your strategy team knew you were as invested in growing them as you are in this year's strategic plan?
John is an executive leadership coach and speaker with over 10 years of experience helping leaders become more effective coaches themselves — unlocking communication, collaboration, and fulfillment across their teams and organizations.
Drawing on a background that spans Fortune 500 consulting and nonprofit leadership, John specializes in developing the coaching mindset and skills that allow leaders to inspire authentic engagement and sustainable high performance in their teams.