At some point, almost every leader encounters a team member they can’t quite reach.
It’s not the underperformer or the obvious problem employee. It’s the person whose work is solid enough, but with whom the relationship never quite clicks. Feedback doesn’t land. Conversations feel strained. Over time, something subtle happens: you begin leading around them instead of leading them forward.
It’s understandable. When you can’t identify the problem, it feels impossible to solve. But avoiding it limits not only that employee’s growth, but your own leadership.
What happens when we start leading around someone
Most leaders don’t consciously avoid tackling difficult issues. But when things just don’t seem to click with a team member, we often pull away gradually. It shows up in small ways. You stop asking for their perspective. Initiate fewer coaching conversations. Quietly lower your expectations.
As the distance grows, disengagement follows. The rest of your team notices who receives your attention, who gets challenged, and who gets overlooked. Avoidance rarely solves a leadership challenge. It usually reinforces it.
Look at your leadership first
When a relationship feels stuck, it’s easy to focus on changing the other person. That’s a recipe for frustration for both parties. Strong leaders activate their curiosity mindset and examine their own piece of the puzzle first.
Start by identifying the person you can’t reach. Don’t think about “challenging employees” in general. Identify the one individual who you most struggle to connect with. Then ask yourself: What, specifically, do I want to be different about working with this person? Drill into specifics:
When and why do I avoid engaging with them?
What do I spend more time on with them than with others?
Am I expecting them to communicate the way I do?
What assumptions am I making about them?
How do my feelings about this relationship affect how I see my leadership?
Pay attention to your workarounds. Are you communicating through someone else? Adding unnecessary check-ins? Taking work off their plate instead of addressing the issue? Those workarounds usually point to the real issues behind the disconnect.
Interrogate the story you’re telling
Sometimes the biggest blocker isn’t the employee. It’s the story we’ve started telling ourselves. That narrative can oversimplify your assessment of the person you can’t reach. If you’ve concluded someone is difficult, resistant, or disengaged, you’ll show up differently around them, and they’ll respond accordingly.
But the story doesn’t stop there. We also create a story about ourselves: I’m not getting through to them. Nothing I do makes a difference. This is simply who they are. Those beliefs can quietly become self-fulfilling. Leaders who continue to grow stay curious about how changing their own approach might change the relationship.
Unpack what parts of your narrative are grounded in reality and which are built on assumptions or distortions.
Shift how you engage
Experiment with small changes. Start exploring how different approaches can change results. Before your next interaction, choose one small change: ask a genuine question instead of making an assumption or address an issue directly instead of sidestepping it. Afterward, reflect on what changed and adjust your approach again before your next interaction. Small experiments often create new possibilities.
Have the big conversation you’ve been avoiding. Soon, you’ll have enough insight for a productive, big-picture discussion. Remember that managing difficult conversations calls for a collaborative approach. Instead of leading with conclusions, lead with curiosity.
Try questions like:
I’d like to understand your experience of working together lately. What’s feeling effective, and where do you think we could work together differently?
What’s helping you do your best work right now? What’s getting in the way?
What difficulties do you face that I might not know about?
Share observations rather than judgments, and listen more than you talk. You may discover unclear expectations, different communication styles, or challenges you never knew existed. The goal isn’t to fix everything in one meeting. It’s to build a shared foundation so you can move forward in the same direction.
Improve one relationship, amplify your leadership
The person you’ve been managing around may be your greatest opportunity to become a better leader. Leadership isn’t about connecting effortlessly with everyone. It’s about expanding your ability to lead people who aren’t naturally like you. When you finally connect with someone you haven’t been able to reach, you wind up with deeper self-awareness and more capacity to lead across differences.
When you’re struggling to connect with someone, ask yourself: What is this relationship asking me to learn about how I lead? That question has the power to transform not only one relationship, but every relationship that follows.