Three Conversations Your Executive Team Needs—But Probably Isn’t Having

There’s a quiet paradox in executive life: the most pivotal conversations almost never appear on a calendar.

As someone who provides executive coaching, I’ve seen firsthand how easily a leadership team can cruise past the very dialogue that would move the needle. And it’s not for lack of intellect or commitment—these are smart, driven people, often with decades of experience. But when the pressure mounts, when there’s too much on the plate and not enough white space, certain conversations just don’t happen.

Instead, the agenda fills up with operational updates, performance dashboards, board decks, and budget revisions. All valid. All necessary. But rarely are they transformative. Rarely do they surface the invisible dynamics—the stuff that keeps leaders up at night or triggers the eye rolls once Zoom cameras go dark.

Let’s fix that.

Because the strongest teams I’ve worked with? They have a habit of asking the hard questions. Of naming the elephants. Of diving into the uncomfortable, and emerging clearer, stronger, and more aligned.

Here are three conversations your executive team needs to be having—conversations that don’t just manage your business, but actively shape its future.

1. The “What Are We Avoiding?” Conversation

It starts innocently enough. A topic comes up. A difficult personnel issue. A cross-functional tension. A long-delayed product decision. Someone raises it, half-heartedly. Another person nods. Then someone else says, “Let’s circle back on that.”

But you don’t.

I once sat with a leadership team that was grappling with its growth strategy. What struck me, just a couple hours into our offsite, was how carefully they skirted one key issue: the VP of Product wasn’t aligned with the CEO’s vision. It wasn’t just philosophical. It was personal. And everyone felt it. But no one named it.

Until I asked, “What are we avoiding?”

That question shifted everything. Within minutes, the team went from tight-lipped and guarded to expressive and honest. Was it messy? A little. But what came out was years of tension, finally aired. And once it was out in the open, alignment wasn’t just possible—it was inevitable.

Executive teams that thrive don’t avoid conflict. They invite it, thoughtfully. They build muscle for it. They recognize that avoidance is more costly than confrontation—because it erodes clarity, trust, and speed.

If you’ve never asked your team, “What are we avoiding?”—now’s the time.

2. The “Who Are We Becoming?” Conversation

Strategy isn’t just about where you’re going. It’s about who you are becoming on the way there.

In my executive coaching work I often pose this question to leadership teams: “Who are you becoming as a team?”

The initial answers are usually polished: “More aligned,” “More accountable,” “More innovative.” Good intentions, all of them. But not quite enough.

Because becoming something new requires unbecoming something old. It demands that you interrogate the behaviors, assumptions, and patterns that no longer serve. It demands clarity not just on where you want to go—but how you want to show up getting there.

So I ask follow-ups:

• What are we tolerating that contradicts the culture we claim to value?

• Where are we under-communicating expectations?

• Are our rituals—our meetings, our reviews, our decision-making—reflecting the kind of team we say we want to be?

One CEO recently told me, “I want us to be a team that tells the truth early, even when it’s awkward.” So we built in a monthly practice: 15-minute check-ins after every major meeting to rate—not the outcomes—but the candor. It changed the game.

Because here’s the truth: executive culture isn’t what’s written in the values statement. It’s how the top team behaves when things get hard. And if you’re not talking about who you’re becoming, you’re probably just recreating the past with better tech.

3. The “What If I’m Wrong?” Conversation

This one takes guts. It flies in the face of every executive instinct to project confidence and control.

But the most effective executive teams I know—especially those operating in complex, fast-moving environments—have one essential trait: they allow for uncertainty.

They make it okay to say, “What if I’m wrong?”

I remember coaching a founder and his leadership team during a volatile growth period. The CFO challenged the founder’s assumptions about a big expansion play. The room tensed. Defenses went up.

So I asked the founder to try something. I said, “Can you say, just for a moment, ‘What if I’m wrong?’ and let’s see what happens?”

He did.

And in that small moment of humility, something big shifted. The CFO relaxed. Other voices entered the conversation. The dialogue deepened. They didn’t reverse the decision, but they strengthened it—because they explored it more fully.

This isn’t about indecision. It’s about agility. Perspective. Wisdom.

In a team where no one can admit doubt, innovation dies. Risk-taking shrinks. And people stop telling the truth. But when it’s safe to say “What if I’m wrong?”—then it becomes possible to get it right.

Here’s the thing: executive coaching isn’t about adding more meetings or giving pep talks. It’s about creating space. The kind of space where the real conversations can breathe.

Imagine this:

• A leadership team that names the real problems early, without blame.

• A culture where identity is intentional, not accidental.

• A rhythm of reflection where doubt isn’t weakness, but wisdom.

Those teams? They outperform. They retain better. They move faster and smarter.

If your executive meetings feel full but not fruitful, if the real issues linger just beneath the surface, it might be time to ask a better question.

I’d love to help your team have the conversation it hasn’t yet had. Because what you talk about shapes what you become.

And your next level of performance? It probably starts with a better question.