WHEN A TRUSTED TEAM MEMBER TURNS DIFFICULT: Leading Through Personality Clashes with Clarity and Care

As senior leaders, we invest heavily in our people. We build trust, offer autonomy, and rely on our team members to deliver with integrity. So when a previously dependable employee starts pushing back, becoming argumentative or oppositional, it can feel like a personal betrayal.

This isn’t just a performance issue. It’s a relational one. And it requires a leadership response that is both courageous and careful.

The Shift You Can’t Ignore
You may have noticed the change gradually. A team member who once took initiative now questions every direction. They challenge decisions, resist feedback, and seem to be working against the grain. It’s tempting to rationalise the behaviour—maybe they’re stressed, maybe it’ll pass—but deep down, you know something’s off.

Avoiding the issue might feel easier in the short term, but it comes at a cost. Left unaddressed, this kind of behaviour can erode team morale, undermine your authority, and create a ripple effect of dysfunction.

Psychosocial Hazards: Why the ‘How’ Matters
In Australia, the conversation around psychosocial hazards in the workplace is gaining momentum. These are risks to a worker’s psychological health arising from the way work is designed, organised, or managed. Poor interpersonal relationships, unresolved conflict, and unclear expectations are all contributors.

When a leader mishandles a difficult conversation—especially one involving personality or behaviour—it can unintentionally cause harm. A clumsy or overly blunt approach might leave the employee feeling humiliated, isolated, or unsafe. This isn’t just bad for morale—it can be a breach of your duty of care.

Psychosocial injury can result from:

  • Embarrassment or public reprimand
  • Perceived bullying or exclusion
  • Unclear or inconsistent expectations
  • Loss of trust in leadership

So how do you have the necessary conversation without causing injury?

Step One: Prepare with Clarity and Compassion
Before you speak with the employee, take time to reflect:

  • What specific behaviours are concerning?
  • How are these behaviours impacting the team, the work, or your leadership?
  • What do you need from this person moving forward?

Avoid vague language like “bad attitude” or “being difficult”. Instead, focus on observable behaviours: interrupting in meetings, refusing to follow agreed processes, or undermining decisions.

Brené Brown’s mantra is worth remembering here: “Clear is kind. Unclear is unkind.” Clarity isn’t harsh—it’s respectful.

Step Two: Create Psychological Safety
Choose a private, neutral setting for the conversation. Let the employee know this is a check-in, not a disciplinary meeting. You might say:

“I’ve noticed some changes in how we’re working together, and I want to understand what’s going on. You’ve always been someone I’ve trusted and relied on, and I want to make sure we’re still aligned.”

This approach signals care, not confrontation. It invites dialogue rather than defensiveness.

Step Three: Listen Without Judgement
Give the employee space to speak. They may be feeling unheard, frustrated, or burnt out. They may believe the job should be done differently and feel disempowered by recent decisions.

Listening doesn’t mean agreeing. But it does mean showing respect for their experience. Ask open questions:

  • “How are you feeling about your role lately?”
  • “What’s been challenging for you recently?”
  • “Is there something you feel we’re not addressing?”

This is where Brené Brown’s concept of rumbling comes in—staying curious, grounded, and open to discomfort.

Step Four: Reaffirm Expectations and Boundaries
Once you’ve heard their perspective, it’s time to lead. Reaffirm your expectations for behaviour, collaboration, and decision-making. Be clear about what’s negotiable and what’s not.

If the employee believes the job should be done differently, explore whether there’s room for innovation. But also be honest if certain decisions are non-negotiable due to organisational priorities or risk.

Patrick Lencioni’s work on The Five Dysfunctions of a Team is useful here. When team members lack clarity around roles and authority, trust erodes and conflict becomes personal. Rebuilding trust starts with clear expectations and consistent follow-through.

Step Five: Revisit Autonomy and Accountability
If you’ve previously given this employee a lot of autonomy, they may be struggling with a shift in direction or oversight. Revisit what autonomy looks like in the current context. Clarify boundaries and decision-making authority.

You might say:

“I’ve always valued your independence and initiative. At the same time, there are some areas where I need things done a certain way. Let’s talk about how we can balance that.”

This helps the employee feel respected while reinforcing your leadership role.

Step Six: Document and Follow Up
After the conversation, document what was discussed. This isn’t about creating a paper trail—it’s about ensuring clarity and accountability. If the behaviour continues, you’ll have a reference point for further action.

Follow up with the employee. Check in. Reinforce progress. Address setbacks early.

Tips for Follow-Up Conversations
Follow-up is where trust is rebuilt—or lost. Here’s how to do it well:

1. Schedule a Check-In
Don’t leave it open-ended. Book a time to reconnect, ideally within 1–2 weeks. This signals that the conversation wasn’t a one-off—it’s part of an ongoing commitment to improvement.

2. Acknowledge Progress
If the employee has made changes, acknowledge them. Reinforcement is powerful. You might say:

“I’ve noticed a real shift in how you’re approaching things. I appreciate the effort you’re making.”

3. Address What’s Still Not Working
If issues persist, be direct but respectful. Refer back to the original conversation and the expectations you set.

“We talked about the importance of following agreed processes. I’ve noticed that’s still not happening consistently. Can we talk about what’s getting in the way?”

4. Keep the Tone Collaborative
Avoid slipping into performance management mode unless it’s necessary. Keep the tone focused on partnership, not punishment.

5. Stay Consistent
Don’t let things slide just because the conversation was uncomfortable. Consistency builds credibility.

The Risks of Avoidance and Mishandling

Avoiding the IssueMishandling the Conversation
Behaviour may escalate or become normalisedEmployee may feel attacked or unsafe
Team morale and trust may erodeRisk of psychosocial injury or formal complaint
Your authority may be underminedDamage to the working relationship
Performance issues may go unaddressedBreach of duty of care as a leader

Leading with Courage and Care
Difficult conversations are part of leadership. They’re not a sign of failure—they’re a sign that you care enough to engage. As Brené Brown puts it:

“You can choose courage or you can choose comfort, but you cannot choose both.”

Choosing courage means stepping into discomfort. It means facing the possibility that someone you trusted may not be coping, may not agree with your direction, or may be struggling with change. It means being willing to hear hard truths and still holding firm to your role as a leader.

But courage isn’t just about being bold. It’s about being deliberate, empathetic, and accountable.

  • Deliberate in how you prepare and communicate.
  • Empathetic in how you listen and respond.
  • Accountable in how you follow through and uphold standards.

Courageous leadership doesn’t mean avoiding conflict—it means engaging with it constructively. It means recognising that behind difficult behaviour is often a story, a pressure, or a fear. And it means being the person who can hold space for that, without losing sight of what the team and organisation need.

It also means protecting your team from the ripple effects of unresolved tension. When you lead with courage, you model what it looks like to have boundaries, to be respectful, and to take responsibility for the culture you’re shaping.

In the end, courageous leadership is about alignment—between your values, your actions, and your impact. It’s about showing up, even when it’s hard, and choosing the kind of leader you want to be.

Let’s chat. Reach out to The Workplace Coach today and explore how coaching can elevate your own leadership style and help you be even more effective in your role.

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