Surviving the Human Cactus: How to Work with Someone You Don't Like

Sometimes “collaboration” is just a nice word for a forced group project.

You’ve got a tight deadline, stress levels are in the red zone, and then boom: You’re paired with someone whose communication style is… not your favorite. They talk over you, ignore nuance, and send emails like they’re writing from a bunker. You try to meet them halfway, but it feels like you're bringing a white flag to a sword fight.

And yet, collaboration isn’t optional.

In the last quarter alone, I worked with three senior leaders navigating situations just like this. One described their colleague as “a human steamroller in a Patagonia vest.” Another said simply, “We do good work, but I dread every interaction.” These are not junior team members—they’re executives. And still, the friction is real.

Top-performing teams don’t necessarily like each other. They just know how to work together.

Chemistry Is Overrated

We tend to assume that good collaboration starts with a natural connection, such as similar work styles, shared values, and mutual respect. And sure, when it happens, that’s great. Like free guac at Chipotle—always welcome.

But effective collaboration isn’t built on chemistry. It’s built on clarity.

Clarity about roles. Clarity about expectations. Clarity about what’s worth fighting for and what you can let slide. And this kind of clarity doesn’t require a personality match. It requires leadership.

Let me explain.

You Don’t Need to Like Each Other—But You Do Need to Respect the Work

Sarah is a client of mine who is the VP of Strategy at a financial services firm. She said something recently that stuck with me: “We didn’t get along at all. But we respected what the other could deliver. Once we stopped trying to like each other and focused on what needed to happen, we became a great team.”

This is the shift. You don’t have to manufacture rapport—you just have to build functionality. That means:

• Understanding what the other person values (speed? accuracy? control?).

• Respecting what they contribute, even if the delivery makes your eyes twitch.

• Being crystal clear about what success looks like together.

Let’s walk through how to do this.

6 Real-World Tactics to Make Collaboration Work (Even When the Vibes Are Off)

1. Start With the Work, Not the Relationship

Instead of trying to “fix” the interpersonal tension first, reframe the situation: What do we both want to achieve? Center conversations around goals, timelines, and deliverables. Don’t start with trust. Start with task clarity.

2. Name the Tension—Gently

You don’t need to throw shade. But acknowledging the awkwardness (with humility) can defuse it. Try: “I know we’ve had different styles—I’d love to find a way to work more smoothly on this project. Open to brainstorming how we can do that?”

This takes guts. But it also takes leadership.

3. Use Collaboration as a Constraint

Instead of viewing collaboration as a fluid dance, treat it like a constraint. Set boundaries:

• Who’s the final decision-maker?

• What’s the cadence of communication?

• Where do we not need to agree to move forward?

Think of it like cooking with limited ingredients. The structure helps.

4. Work Through, Not Around

Don’t loop in five other people to “soften” the interaction. It dilutes accountability and fuels resentment. I had a tech executive tell me she created a “work-around web” of three direct reports just to avoid working with a peer. It looked productive—until it wasn’t.

5. Zoom Out (Metaphorically)

Ask yourself: If I were mentoring someone through this, what would I advise them to do? That perspective shift often dissolves the emotional charge. It’s not about you. It’s about the work.

6. Track What’s Working

In strained collaborations, we tend to only notice the misfires. Counter that. Keep a running list of things that went well, no matter how small. A quick approval. A clean handoff. A surprisingly thoughtful email. You’re wiring your brain to see collaboration as possible.

One More Thing: Stop Expecting Ease

If you’re leading at a high level, odds are you’re working with other strong-willed, smart, and opinionated people. Conflict isn’t a glitch—it’s a feature.

So maybe the goal isn’t to create a team where everyone gets along. Maybe it’s to build a team that can get through misalignment without losing momentum.

And if that sounds hard—well, you’re not wrong. But it’s also a hallmark of executive maturity. I’ve helped leaders build the skills that got them promoted, not because they were the smartest in the room, but because they knew how to navigate the messy middle of collaboration.

If you’re in that middle right now? Keep going. Don’t wait for harmony. Build the habits that let you lead through tension—and still deliver.

Because in the end, that’s what real leadership looks like.

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Need help coaching a team through conflict without sugarcoating or sidestepping? That’s exactly what I help leaders do. Reach out if you’re ready to make collaboration work—even when the personalities clash.