Five Questions Every Leader Should Ask When Things Get Messy

By Dan McCarthy

A colleague I respect made an pointed observation in conversation this week.

“I think there are only two kinds of people,” he said. “The kind who speed up when things get complicated and end up tripping over themselves. And the kind who slow down, pull out to a wide view, and make things more simple.”

I like the simplicity of that construct. Its power is that it is true.

Fast Isn’t Always Good

We’ve all seen leaders who, when things get uncertain, start moving faster.

I know I’ve fallen in the trap.

We default to solving, acting, proving. We’re in control, we’re competent and we’re going to solve the problem.

But when the ground starts to shake, speed can be a form of avoidance. What we really need—though it’s rarely intuitive—is to slow down. Not stop. Not drift. Just pause long enough to ask better questions.

The right question doesn’t just clarify the problem. It reveals how we’re showing up in the middle of it.

That’s why I created a short set of prompts I return to whenever things get messy. I call them the Five Questions to Center Your Leadership. They’re deceptively simple, but they do something important: they help shift you from reactive to reflective, from scattered to grounded. Here they are, with a few thoughts on what they unlock.

Five Questions to Center Your Leadership.

1. What am I solving for, really?

In the churn of a high-stakes moment, we often solve the loudest problem—whatever is generating the most heat. But leadership asks us to step back. This question reframes the moment. What outcome matters most here? What’s the signal underneath the noise?

Clarity comes when we move from symptom to source.

2. What do I know—and what am I assuming?

Pressure accelerates our certainty. But certainty is often the enemy of accuracy. This question helps leaders separate facts from inferences, and opens space for curiosity. What’s real? What do I wish were real? What might I be missing?

Assumptions are shortcuts. Sometimes helpful. Sometimes costly.

3. What’s not being said?

In complex environments, silence often carries more weight than what’s spoken. This question helps you tune into interpersonal dynamics—fear, confusion, politics. It invites you to look for the hard truths beneath polite conversation.

Leadership isn’t just about what you say. It’s about what others are afraid to.

4. Where is the energy—forward or backward?

Sometimes a team is moving toward a vision. Sometimes it’s stuck in resentment, regret, or legacy expectations. This question helps you sense the direction of momentum. Are you building? Or are you bracing?

Energy tells the truth faster than words.

5. Who do I need to be, right now?

This is the centering move. Not what do I need to do. Not what do I need to fix. Who do I need to be? Present? Bold? Steady? Open? Asking this helps you reconnect to your role as a signal-setter. Your way of being is contagious.

Teams respond to energy before they respond to strategy.

Have the Fortitude to Meet Yourself

When you sit in a leadership role, your ability to ask yourself tough questions is as important as your ability to challenge the team.

During crucible moments, when the pressure is mounting, you need to the fortitude and discipline to meet yourself.

I remember one critical meeting with my leadership team. One segment of our customers was sending clear signals that we were falling short in serving them. The issue was elevated on multiple fronts: process, people, product and technology. The team was frustrated with each other. It was challenging to set priorities, and each leader had critical issues that they had to address in their team. I took the lead in designing the process, sensing that I had to break up the logjam.

One of the key team members was getting increasingly frustrated. I asked her to voice her concern, but even as she began to lay out her issue, I pushed her to articulate it within the framework that we were approaching the problem.

We broke for lunch. I watched the team scatter around the meeting area to eat and work without interacting.

That wasn’t their normal energy.

I worked through the Five Questions. And when I got to the last one, I realized that I was showing up with too much force and power. When we came back together, I asked the key member to revisit her frustration. I listened carefully, made space for the other team members to engage. I understood that her point was valid, that our prioritization design was flawed, and that we needed to set a different starting point.

We came out of the meeting with focus and energy.

Try It for Yourself

If any of these questions stirred something in you, download the Five Questions to Center Your Leadership PDF. Use it at your next offsite. Or keep it nearby for the days when things feel tangled.

Sometimes the best way forward isn’t a faster answer. It’s a better question.