Think Like a Top CEO: 10 Questions for Critical Thinking

What separates top CEOs from everyone else isn’t luck or genius. It’s how they think.
They ask sharper questions, see what others miss, and make choices that move their companies forward when others get stuck.

If you want to lead better, make smarter calls, or just approach problems like a strategist, these 10 questions will help. They’re not complicated, but they’ll change the way you see your business and your team.

1. Who on my team would I rehire in a heartbeat?

Every team has a few people who make everything better. They bring energy, ideas, and reliability. You don’t have to push them; they push themselves.

Now imagine starting your team from scratch. Who would you bring back without a second thought?

Those are your core players, your A-team. Spend most of your time helping them grow. Recognize their effort. Give them the tools and freedom to thrive.

And if there are people you hesitate about… that’s a signal. Maybe they need clearer direction. Maybe their role doesn’t fit. Or maybe it’s time to part ways.

Strong teams are built by choice, not by chance.

2. If we could only keep 20% of what we’re doing, what would stay?

Most businesses try to do too much. A dozen projects, half-baked goals, endless “priorities.” The result? Nothing stands out.

This question forces you to focus. If you had to keep only the top 20% of your work, what truly matters?

Which projects actually move the business forward? Which ones bring in revenue, build trust, or strengthen your brand?

Everything else might be noise.

Top leaders are ruthless about focus. They know that saying “no” is often more powerful than saying “yes.” When your team works on fewer things that matter more, the results multiply.

3. What are we pretending not to know?

Every company has truths nobody wants to say out loud. Maybe a product isn’t working. Maybe a leader’s behavior is hurting morale. Or maybe a strategy is clearly off-track.

But people stay silent because it’s uncomfortable.

Top CEOs face those truths head-on. They don’t wait for problems to explode; they bring them up early.

You can start by asking your team privately, “What’s one thing we’re ignoring right now?” or by letting people give anonymous feedback.

It’s better to be slightly uncomfortable now than completely blindsided later. Honesty isn’t risky—denial is.

4. What behaviors do we reward that don’t match our values?

Culture isn’t your company slogan. It’s what you reward and what you tolerate.

If you say you value teamwork but celebrate individual wins, you’re sending mixed messages.
If you claim to care about balance but only praise people who work nights and weekends, you’re building burnout, not culture.

Look at your last few promotions or bonuses. Were they given to people who truly represent your values? Or just to the ones who hit short-term numbers?

The behaviors you celebrate shape who stays and who leaves. Great leaders make sure their reward system matches the culture they talk about.

5. If our biggest competitor had our resources, what would they do?

This question makes you see your company from the outside.

Imagine your fiercest competitor had your talent, your budget, and your technology. What would they build first? What would they fix?

That’s often where your blind spots are.

Competitors tend to be more daring because they’re hungry to win. But why wait for someone else to do what you could do right now?

Sometimes the best way to innovate is to think like your rival and then beat them to it.

6. What skills will matter most in 3 years that we don’t have today?

The world changes fast. Skills that made your company great yesterday might be useless tomorrow.

Top CEOs are always looking ahead. They ask what skills their people will need to stay ahead of the curve, not just this year, but a few years from now.

Is it data literacy? AI? Creative problem-solving? Emotional intelligence?

Look at where your industry is heading and start preparing now. Train your team. Encourage curiosity. Let people grow beyond their current roles.

The best companies don’t just hire talent; they build it.

7. What would happen if employees owned half the company?

Imagine if everyone on your team acted like a true owner.

Would they make smarter decisions? Waste less time? Care more about the results? Probably yes.

Ownership changes everything. People work differently when they feel trusted and responsible for outcomes.

You don’t need to literally give away 50% of the company. You just need to build a culture where people feel like their voice and effort matter.

Share results openly. Ask for input before making big decisions. Celebrate wins as a team.

When employees think like owners, motivation and trust go through the roof.

8. Which customers would we stop working with if we could?

Not every customer is a good fit. Some drain your energy, argue over every detail, or don’t respect your team’s time.

Bad-fit clients can actually hurt your business more than they help.

Top CEOs know this and aren’t afraid to “fire” customers who don’t align with their values or goals.

By doing so, you make space for better clients, the kind who value your work, pay fairly, and help your team grow.

You don’t have to please everyone. Focus on serving the right people incredibly well instead.

9. What decision did I take too long to make — or avoid completely?

We’ve all been there. Staring at a decision, hoping more time will magically make it easier. But usually, it just makes things worse.

Think about the last big choice you delayed. Maybe it was hiring someone new. Maybe it was ending a project that wasn’t working. Maybe it was giving feedback you knew needed to be said.

What happened because you waited?

Top leaders reflect on these moments. They don’t beat themselves up — they learn. They ask,

“What stopped me?” and “What will I do differently next time?”

Good judgment doesn’t come from being perfect. It comes from learning fast and moving forward with courage.

10. Am I the bottleneck in any big decision?

This one stings. But it’s worth asking.

Sometimes leaders become the very thing slowing progress. Maybe everyone’s waiting for your approval. Maybe you hold too much control out of habit.

Ask your team honestly: “Am I blocking anything?” You might be surprised by what you hear.

Great CEOs delegate authority, not just tasks. They trust people to make decisions and own the results.

When you remove yourself as a bottleneck, your team moves faster, and your company grows stronger.

What It Really Means to Think Like a CEO

These ten questions aren’t tricks; they’re habits. They push you to see things clearly, challenge assumptions, and focus on what matters most.

You don’t have to be a CEO to use them. You just have to be curious and brave enough to ask tough questions.

Try this: Pick one question each week. Reflect on it. Talk about it with your team. Write down what you discover.

Soon, you’ll start noticing patterns, things you’ve been ignoring, areas that need focus, and decisions that suddenly feel obvious.

Thinking like a CEO isn’t about being the smartest person in the room. It’s about being the most aware.

The leaders who ask better questions always find better answers.

Final Thought

Learning to think like a CEO doesn’t happen overnight. It’s a mindset built one question at a time.

Ask honestly. Listen carefully. Act decisively.

When you do, you’ll stop just running your business and start leading it.

FAQs

1. Why are these questions so important for leaders?

Because they reveal blind spots, highlight priorities, and help you focus on what actually drives results.

2. Can small business owners use this, too?

Absolutely. These questions are just as powerful for a five-person team as they are for a global company.

3. How often should I go through them?

At least once a quarter. Some, like team performance and culture, are worth revisiting every month.

4. How do I make my team open up when discussing these questions?

Create a safe space. Let people share ideas or concerns without fear. Sometimes, anonymous feedback helps too.

5. What’s the biggest mindset shift I need to think like a CEO?

Stop reacting. Start reflecting. Don’t chase everything. Focus on what matters and trust your people to rise with you.

How to Think Like a Top CEO: 10 Questions to Sharpen Your Critical Thinking