You've Been Doing Difficult Conversations Wrong (& It's Costing You) 💸

The conference room had that unmistakable tension you could cut with a butter knife.

My VP was convinced our product launch should target enterprise customers first. I had six months of market research screaming that mid-market was our sweet spot. We'd been going in circles for twenty minutes, and I could feel my jaw tightening with each rebuttal.

Then he said something that stopped me cold: "Harvey, you're so busy being right that you've forgotten we're on the same team."

Ouch.

He was absolutely correct. I'd turned a strategic discussion into a courtroom drama where I was both prosecutor and judge. The moment I shifted from "How do we crack this market?" to "How do I prove my research is better than his instinct?" - I'd already lost the conversation.

That was twenty-five years ago at Microsoft, and I still think about it weekly.

Because here's the uncomfortable truth: most of us are chronically terrible at difficult conversations. Not because we lack intelligence or eloquence. But because we're so focused on winning the argument that we forget the actual objective is to move forward together.

Let me show you how to stop fighting and start connecting.

The Paradox Nobody Tells You About

The best conversationalists aren't the most articulate people in the room. They're not the ones with the cleverest comebacks or the most comprehensive arguments.

They're the ones who make others feel safe enough to be honest.

Think about that for a moment. The person who "wins" difficult conversations isn't the one who demolishes the other person's logic. It's the one who creates enough psychological safety that both parties can actually hear each other.

This is particularly crucial in corporate environments where hierarchies, egos, and career pressures turn every disagreement into a potential landmine. I've watched brilliant people torpedo their credibility by treating every conversation like a debate tournament they need to win.

Don't be that person.

The Mental Script That's Sabotaging You

Whilst they're still talking, you're already three sentences deep into your rebuttal. You're not listening to understand - you're listening to identify weak points you can dismantle.

I know this because I've done it roughly a thousand times.

The problem is that the other person can sense this. They can feel that you've mentally checked out of understanding mode and shifted into attack mode. And the moment they sense it, their walls go up, and you're both now just performing at each other rather than communicating with each other.

Drop the script in your head. Properly listen. It's harder than it sounds, but it's the foundation of everything that follows.

Why Emotional Temperature Matching Matters

Picture this: your colleague is visibly frustrated about a missed deadline, voice raised, clearly emotional. You respond with ice-cold logic and a monotone delivery.

Congratulations, you've just told them their feelings don't matter.

Or flip it: they're trying to have a calm, measured discussion about resource allocation, and you come in guns blazing with passion and urgency.

Now you look unstable.

Emotional temperature matching isn't about being fake. It's about meeting people where they are. If they're heated and you need to de-escalate, you don't go from zero to zen - you start at 70% of their intensity and gradually bring it down. If they're calm and you're fired up, take a breath before you speak.

This isn't manipulation. It's basic emotional intelligence.

This newsletter edition is sponsored by the Influence Anyone Newsletter

The Word That's Destroying Your Credibility

"But."

Three letters that erase everything you just said.

"I hear you, but here's why you're wrong" is functionally identical to "I'm not actually hearing you at all."

Replace it with "and."

"I hear you, and here's what I'm experiencing" keeps both perspectives valid. It doesn't create a winner and a loser. It creates space for multiple truths to coexist whilst you work toward a solution.

I've seen this single word swap transform relationships between product managers and sales teams, between executives and their reports, between colleagues who thought they simply couldn't work together.

The Permission Principle

Here's something that took me embarrassingly long to learn: nobody wants your unsolicited advice. Even when it's brilliant. Even when you're absolutely certain it would solve their problem.

Unsolicited advice feels like criticism wrapped in helpfulness.

Instead, ask permission: "Would it help if I shared what worked for me in a similar situation?"

This tiny bit of agency - letting them choose whether to hear your wisdom - changes everything. If they say yes, they're mentally open to it. If they say no, you've just saved yourself from wasting breath on advice they were going to reject anyway.

The Vulnerability Hack

When you feel yourself getting defensive - and you will - name it out loud.

"I'm feeling defensive right now, and I want to stay open."

This is bloody uncomfortable the first few times you do it. But it's genuinely magical.

Vulnerability disarms aggression. When you admit your own emotional state, you give the other person permission to acknowledge theirs. Suddenly you're two humans trying to navigate a difficult conversation together, rather than two adversaries in an ideological battle.

I've used this everywhere from board meetings to family dinners. It works.

Your Action Plan: Three Timeframes

This Week:

• Pick one difficult conversation you've been avoiding

• Before you enter it, write down: "My goal is to understand their perspective, not to win"

• Use the "and" instead of "but" at least once

• Notice when you're rehearsing rebuttals whilst they're talking - catch yourself and refocus on listening

This Month:

• Practice the permission principle: ask before offering solutions at least three times

• When you feel defensive, name it out loud once (just once - start small)

• After each difficult conversation, write down what you learned about the other person's perspective

This Quarter:

• Master emotional temperature matching: pay attention to the energy you're meeting people with

• Build your "2% agreement" muscle: find common ground even in total disagreement

• Track your difficult conversations: how many ended with both parties feeling heard vs. one person "winning"?

The Truth About Influence

The irony of difficult conversations is that the person who's trying hardest to win usually loses the most.

They might win the argument. They might even get their way in the short term.

But they lose trust. They lose collaboration. They lose the willingness of others to be honest with them in future conversations.

And in corporate environments - hell, in any environment - those losses are catastrophic over time.

The person who focuses on connection over correctness? They build relationships that can withstand disagreement. They create psychological safety that leads to better ideas. They become the person others want to work with, rather than the person others avoid.

That VP who called me out in that conference room all those years ago? He taught me that being right is vastly overrated. Being someone whom others trust to navigate hard conversations together? That's the skill that's served me through five major career transitions.

Which of these approaches will you try in your next tough conversation?

Keep on rockin',

Harvey