Coaching the Reluctant Leader: How to Inspire Growth in Someone Who’s Still Figuring It Out
In every organization, there comes a moment when you look at someone on your team and think: They could be great. But they’re not there yet. Maybe they’re not even sure they want to be there.
They’re bright. Capable. Maybe even quietly ambitious. But uncertain. Tentative. Stuck between who they are and who they could become.
And yet—you need them to step up.
Whether you’re leading a real estate team, building out a property operations group, or grooming your next asset manager or leasing lead, the question is the same:
How do you coach someone who’s not sure if they belong in leadership—yet still give them space to grow into it?
The Truth: Not Everyone Starts with Vision
Some people enter this field with clarity and drive. Others stumble into it, unsure if it’s their long-term path. That doesn’t mean they’re unworthy of investment. In fact, some of the best leaders I’ve worked with were late bloomers—quietly absorbing, resisting, evolving.
What they needed wasn’t pressure. It was belief.
The Coach's Role: Guide, Not Push
When you’re coaching someone who hasn’t yet bought into the long game, your role shifts. You’re not there to demand excellence. You’re there to:
Spot potential they can’t yet see in themselves.
Frame their work in a broader context so it feels meaningful.
Give them wins they can own to build confidence.
Create a safe space to explore whether this path could actually fit.
This kind of leadership takes patience—but it’s often the most rewarding.
How to Inspire Growth in an Uncertain Team Member
1. Focus on transferable value.
If they’re unsure whether real estate, operations, or leadership is their forever path, show them how the skills they’re building—strategic thinking, clear communication, accountability—are valuable everywhere. This reduces fear and increases engagement.
2. Lead with curiosity, not assumption.
Ask questions like, “What part of this work energizes you?” or “Where do you feel like you’re just checking the boxes?” Their answers will tell you where to coach—and where to challenge.
3. Connect their role to outcomes.
People grow when they feel what they do matters. Help them see how their daily work affects residents, investors, team morale, or property value. Make it real.
4. Give them low-risk leadership opportunities.
Let them lead a meeting, own a project, or coach a peer. Leadership grows through practice, not titles.
5. Be transparent about their potential.
Sometimes people don’t step up because they don’t think they’re invited to. Tell them what you see in them. Tell them what’s possible. Be the mirror they don’t yet believe.
What to Avoid
Don’t guilt them into growth (“The team is counting on you”).
Don’t treat hesitation as failure (“Why aren’t you more motivated?”).
Don’t write them off too soon.
Coaching is a long game. Planting seeds. Creating conditions. Letting people bloom in their own time.
The Win-Win
When someone uncertain rises into leadership, it changes both of you. They learn they’re capable. You learn to lead with trust, not control. And your organization gains someone who leads not because they were told to—but because they chose to.
That kind of leadership is earned. And it lasts.
