4 Tips for Asking Better Questions

In many ways, the people you learn from today will determine the potential of your growth tomorrow.

So, how do you learn as much as possible from your leaders and mentors? 

It usually comes down to asking the right questions. 

In this post, I outline four tips for asking great questions when meeting with a leader you admire. 

1. Start with intentionality.

Before you meet with a leader, you need a clear idea of what you want to learn from them. 

What do you admire about them? It could be how they prioritize their time, how they manage resources, what they value, or some other important area. 

Whatever it is, you should be able to finish this statement: “This time will be successful if I learn ______.”

If you go into a meeting without a clear plan, that leader will pick up on it immediately and might think you’re wasting their time.

2. Focus on “how” and “why” questions.

Knowing what a great leader does is not enough; work to understand how and why they do it. 

Ask questions that help you discover principles instead of just practices.

Don’t just ask about their strategy; ask why they chose it. Don’t just ask about their values; ask how they came up with them. 

Usually, you can’t copy what someone does precisely, but you can learn how they think and the principles behind what they do.

3. Ask about who or what influences them.

You want to ask questions that uncover what ideas they’re interested in, what books they’re reading, and what podcasts they’re listening to.

Finding the source of who or what shapes a leader you admire can open windows of learning opportunities for you. 

Asking questions like “Who is the author you’ve learned the most from?” or “What podcast has challenged you to grow the most?” are always great questions to ask.

It’s also helpful to ask what a leader is listening to and reading right now. Good leaders are growing leaders, so they probably have a current resource to recommend. 

4. Try to find the story behind their story.

You want to ask questions that help you uncover what’s in a leader’s heart, not just their head. 

What makes a person great usually isn’t head knowledge. It’s often something deeper. 

Unfortunately, most people never get to this level of conversation. 

One way to do this is to ask, “Hey, there’s something special about you. Can you tell me the part of your story that most people don’t know about?”

When you dig deeper, you’ll often find a well of untapped wisdom. I call this "taking the levels down." 

When you take the levels down, you want to find the story behind their story. 

You also want to look for the areas where they think differently than you. When you find a place you disagree, that’s likely an area where you can grow. 

The point at which you push back the hardest is often where you have the most to learn. 

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