Making better leadership decisions sometimes comes down to one question. I learned mine decades ago in a senior leadership meeting at my PR agency.

The CEO was proposing a major restructuring. It would affect dozens of people, potentially millions of dollars in revenue, and even the entire trajectory of the agency.

She went around the table asking each leader for input.

When se got to me, I had concerns. Real concerns. But I found myself saying: “I think it could work.”

Later that day, my coach asked me what I really thought about the restructuring.

I told her the truth: I thought it was a mistake. I thought we were solving the wrong problem. I thought it would create more issues than it solved.

She asked me one question that I’ve been asking myself before every major decision since:

“What would you do if this were your company?”

And everything changed.

Why That Question Matters

Here’s what that question revealed: I had been making decisions as an employee, perhaps as a manager, but not as a leader.

As a manager, I was thinking: “Will this decision affect me negatively? Will it make my job harder? Will it create problems for my team?”

Those are legitimate concerns. But they’re not leadership questions.

As a leader, as someone who would think like an owner, I should have been asking: “Is this the right decision for the organization? Will this solve the actual problem? What are we not considering?”

The difference between those two frames is everything.

The Decision I Made Differently

After that coaching conversation, I went back to the CEO.

I told her I’d given her the wrong input in the meeting. I told her what I really thought: that the restructuring addressed symptoms, not root causes. That we’d end up in the same place in six months but with lower morale.

I told her what I would do instead if it were my company.

She listened. We had a real conversation, not a polite one. We ended up pursuing a completely different approach.

That approach worked. The original restructuring idea would have been expensive and ultimately ineffective.

But more importantly, I learned something about myself: when I stopped thinking like an employee protecting my territory and started thinking like an owner responsible for outcomes, I made better decisions.

Every time.

Where Leaders Get Stuck Making Better Leadership Decisions”

In my coaching practice, I see leaders get stuck in the same decision-making traps repeatedly.

They Let Analysis Paralysis Take Over

Some leaders have brilliant analytical minds. They can see every angle, every risk, every potential outcome.

They’re also agonizingly slow to make decisions.

The question “What would you do if this were your company and you had to make a decision by end of day?” often produces an answer in 30 seconds.

When I ask why they’ve been deliberating for weeks, the answer is usually: “Because I wanted to be absolutely certain.”

But you’re never absolutely certain. At some point, making a decision, even an imperfect one, is better than not deciding.

Delaying a decision is making a decision. It’s deciding that the status quo is acceptable.

In uncertain times, the status quo is usually not acceptable.

They Confuse Consensus With Leadership

Some leaders want everyone to agree before they make a decision.

Noble intention. Impossible standard.

On any important decision, someone will disagree. If you wait for unanimous consensus, you’ll never decide anything significant.

The question “What would you do if this were your company and you knew you couldn’t get everyone to agree?” typically produces a clear answer:

“I’d make the decision I believe is right, explain my reasoning, and move forward.”

That’s leadership.

Getting input is important. Building consensus where possible is valuable. But ultimately, leaders make decisions with imperfect information and imperfect agreement.

They Default to What’s Worked Before

“We’ve always done it this way” works for years. Until it doesn’t.

The industry changes. The marketplace changes. Client expectations shift. What worked before stops working.

The question “If you were starting this company today, with everything you know now, would you do it this way?” often produces a stunning answer:

“Absolutely not.”

Then why are you still doing it that way?

That question forces leaders to let go of “we’ve always” and start asking “what’s actually best?”

The Three Follow-Up Questions

Over the years, I’ve added three follow-up questions that make the original question even more powerful:

Question #2: “What am I optimizing for?”

This helps you see what you’re actually prioritizing, which may be different from what you say you’re prioritizing.

Are you optimizing for:

• Short-term comfort or long-term results?
• Being liked or being effective?
• Avoiding conflict or solving the actual problem?
• Protecting your position or serving the organization?

Once you name what you’re optimizing for, you can decide if that’s actually what you want to optimize for.

Question #3: “What would I tell someone else to do?”

This creates distance from your own ego and emotion.

It’s easy to rationalize your own decisions. It’s much harder to rationalize someone else’s.

If a peer leader came to you with this exact situation, what would you tell them to do?

That’s probably what you should do.

Question #4: “What does my gut say?”

I write about this in my Spin Sucks guest post about leading through uncertainty: your gut is the anatomical, biological manifestation of all your years of experience.

It warns you. It leads you.

When I look back at my career, especially on the agency side, I don’t feel my judgment was wrong. But when I made mistakes, it was because I didn’t follow my gut. My brain interceded and told me to ignore my gut.

That was always a mistake.

Trust your gut. It will always, always, always serve you well.

The Decision You’re Avoiding Right Now

There’s a decision you’re avoiding right now.

You know what it is.

It might be:

• A conversation you need to have
• A person you need to let go
• An investment you need to make
• A strategy you need to change
• A risk you need to take

You’ve been thinking about it for weeks. Maybe months.

You’ve analyzed it. You’ve gathered input. You’ve waited for the perfect moment, the perfect clarity, the perfect certainty.

Here’s the question: What would you do if this were your company?

Not if you had to protect yourself. Not if you had to please everyone. Not if you had to guarantee success.

If you owned this company and were responsible for its success, what would you do?

That’s your answer.

The hard part isn’t knowing what to do. The hard part is having the courage to do it.

I talk about what that courage looks like — and why your team needs it from you — in this short video:

Why This Question Works

This question works because it strips away all the protective thinking that keeps us stuck.

When you ask “What would I do if this were my company?” you’re asking:

• What serves the organization, not just me?
• What solves the real problem, not just the symptom?
• What’s right, not just what’s safe?

It forces you to think like a leader, not an employee.

It forces you to take ownership, not just take orders.

It forces you to be decisive, not just deliberate.

And it forces you to trust yourself, which is ultimately what leadership requires.

The Leadership You’re Called To

There’s a reason you’re in a leadership position.

Either you chose it, or you were called to it, or some combination of both.

That reason isn’t to protect yourself. It’s not to make everyone happy. It’s not to avoid mistakes.

It’s to make the decisions that need to be made, even when they’re hard. Especially when they’re hard.

And the question “What would I do if this were my company?” gives you the frame to make those decisions with clarity and courage.

I’ve been asking myself this question for twenty-five years.

It changed how I lead, how I coach, and how I approach making better leadership decisions every single day.”

And it can change how you make every decision.

Starting with the one you’re avoiding right now.

If you’re facing decisions where the right answer isn’t clear, or where you know what to do but need support in actually doing it, executive coaching provides the accountability and perspective that transforms knowing into doing. Schedule a complimentary consultation.