The 4-Step Process to Dealing with a Difficult Coworker

Are you struggling to work with a difficult coworker, leader, or customer who makes collaboration feel impossible? The kind of person who seems to thrive in chaos, breeds toxicity, and makes everyone around them feel as stressed as they are? Yeah, same. And one of my coaching clients is experiencing it right now too.

She landed a job she loves after we worked together nearly three years ago. Now, she’s on track for a promotion, but there’s a big obstacle in her way: a difficult leader (not in her direct reporting line) who could derail her progress. This leader:

• Demands her immediate attention
• Sets unrealistic expectations and deadlines
• Pushes back hard anytime she does
• Doesn’t respect her boundaries or workload

At first, she saw him as a roadblock, someone negatively impacting her experience and growth. But instead of staying stuck in frustration, we worked together to flip the script, shifting the dynamic from conflict to collaboration. Read below to understand how she’s doing it. 

Reframing the Situation 

She’s taking a step back to consider what might be driving his behavior. Is he under pressure from the C-suite? Navigating personal stress? Working with his own difficult personalities? My client and I talked about this and she acknowledged he was a father of three under three, and his recent child was born just a few months ago. If you’re a parent, you know postpartum is challenging on all family members, especially when other children are in the mix. Even though his demeanor feels personal, my client is reminding herself: it likely isn’t.

Scheduling a Courageous (and Candid) Conversation 

Instead of avoiding the tension, my client is proactively scheduling a 1:1 to level set with this leader. She’s planning to start with: “I understand you’re probably under a lot of pressure from leadership. My goal is to help you succeed while I balance competing priorities.” This sets the tone for empathy and boundaries. Trying to relate and meet a difficult coworker halfway (and sometimes more than halfway) seems simple enough, but can often lead to healthy, productive conversations.

Aligning on Goals and Priorities 

My client is using that private conversation to understand what this leader needs most. I advised her to be genuinely curious, asking respectful but direct questions that show empathy but also address the conflict. Some of the questions we brainstormed are as follows:

• What are the key goals you’re focused on this quarter?
• What can I do differently to support you and meet your deadlines?
• Since I report to a different team, how can we align earlier on upcoming priorities?

These build trust and shift the conversation toward mutual success.

Building a Relationship Beyond the Work 

She’s taking small steps to connect beyond just “asks.” It’s hard to do when someone isn’t pleasant, but humanizing the relationship can help. She’s starting informal Slack check-ins and weaving in light, thoughtful questions like:

• “What was the highlight of your weekend?”
• “What fun things is your baby doing these days?”
• “Can we set up time to walk through the program you built at [previous company]? I’d love to learn from it.”

Now, instead of being steamrolled, my client is working toward turning a critic into a champion – someone who respects her time, communicates proactively, and supports her success.

If you’re dealing with a difficult person at work right now, try this:

• Seek to understand their world before changing yours.
• Open the door to honest conversation.
• Shift from frustration to curiosity.

It won’t change everything overnight. BUT it just might change enough to make progress, preserve your energy, and turn that dynamic around. You don’t have to go it alone. I’m here if you want to talk through your situation!