You have a difficult employee. Before you label them as the problem, pause.
Here’s what most leaders miss: “difficult” employees often have unclear expectations or inconsistent feedback.
I’ve coached hundreds of leaders through this. The ones who succeed ask themselves hard questions first.
Try these quick shifts:
✔️ Get specific. Replace “you need to be more proactive” with “I need you to identify problems before they escalate and bring me solutions, not just issues.” Vague feedback creates vague results. When you’re crystal clear about what you need, you give people a real chance to succeed.
✔️ Name the behavior directly. Say “You’ve interrupted colleagues three times in today’s meeting” instead of “you seem aggressive.” Concrete observations are harder to dispute and easier to address than judgments about someone’s character.
✔️ Focus on impact, not intent. “When you miss deadlines, the team has to work weekends” hits harder than “you’re unreliable.” You can’t read minds, and debating someone’s intentions is a losing game. Help them understand consequences instead.
✔️ Ask what’s in the way. Sometimes “difficult” means frustrated. “What’s making this hard for you?” can reveal missing resources or unclear priorities. You might discover the problem isn’t willingness. It’s capability or context.
✔️ Give feedback in real time. Waiting weeks to address problems makes them harder to fix. Address issues when they happen, while the situation is fresh and correctable.
Here’s the reality check: some employees truly are difficult. Resistant, negative, or disruptive despite clear feedback and support.
When that’s the case, you need to act. Set clear expectations. Document what needs to change. Be willing to let them go if nothing improves.
Keeping a genuinely difficult employee tells your whole team what behavior you’ll tolerate. Your high performers are watching.
But make sure you’ve done your part first. Clear expectations. Direct feedback. Real support.
I worked with a VP recently who was ready to fire someone on her team. “He’s impossible,” she told me. “Always pushes back, never follows through.”
We spent time examining her role first. Had she been specific about what success looked like? Had she addressed issues in real time? Had she asked what was getting in his way?
The answers were no, no, and no.
She went back and tried the shifts I’m sharing with you. She got specific about her expectations. She started giving feedback immediately when things went off track. She asked what obstacles he was facing.
Within a month, the situation completely turned around. The employee wasn’t difficult at all. He was confused about priorities and frustrated by mixed messages. Once he had clarity and real-time feedback, his performance improved dramatically.
Not every story ends this way. Sometimes you do everything right, and the person still doesn’t change. When that happens, you need to act decisively. Document the issues. Set clear timelines for improvement. And if nothing shifts, be willing to let them go.
But start by looking in the mirror. Your clarity, your consistency, your willingness to have hard conversations in the moment… These things matter more than you think.
Every choice you make (how you show up, listen, follow through, give feedback) shapes the environment around you. You have more control than you think.
Then you’ll know whether the problem is them or you.
What difficult conversation are you avoiding this week?
If you’d like to talk through a challenging employee situation, schedule a call with me.
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