The Wise Ask

Table of Contents

Questions Are the New Answer. Prompts Are the New Solution.

Years ago, I was doing leadership consulting for the YMCA. One of the principles they lived by was something deceptively simple:

Listen First.

Not “fix first.” Not “advise first.” Not even “lead first.”

Listen. Pause. Create space. Let people feel heard before anything else happens.

It stuck with me. Because when you really listen—without jumping in, solving, or steering the conversation, something powerful happens. In fact, a few things:

  • People tell you the truth. 
  • The real issue rises. 
  • The next step becomes more obvious.
  • People feel valued.

I’ve carried that principle with me ever since, into boardrooms, workshops, EOS sessions, and coaching calls.

But today, I believe it goes even further than just listening.

Wisdom and the Age of AI

We’ve entered a new leadership era. In a world flooded with content, opinions, strategies, and solutions…it’s not about having all the answers.

I call it The End of Answers. AI has all our answers, and already knows more than we do about every subject under the sun. 

Instead, 

It’s about knowing how to ask the right questions. 

More specifically, in this AI era, it’s also about knowing how to give the right prompts.

The best leaders aren’t always the ones with quick answers. They’re the ones who ask better questions, and draw out better thinking. Thinking from your team, your clients, and yourself. (Not to mention your technology.)

Part 1: Questions Are the New Answer

What do great leaders, coaches, advisors, and parents have in common?

They ask:

  • “What’s really going on here?”
  • “What do you want in this situation?”
  • “What does success look like?”
  • “What’s the deeper fear?”
  • “What’s your next right step?”

They don’t tell you what to think. They help you discover how to think. Because if you’ve ever tried to force advice on someone, you know this:

Telling people what to do rarely creates change. Helping them see it for themselves almost always does.

That’s why wise leaders slow down and ask. And not just for others—but for themselves too.

Self-Leadership Questions that Shift Everything:

Try these the next time you’re stuck, overwhelmed, or unsure:

  • “What’s the story I’m telling myself right now?”
  • “If I zoomed out, what would really matter?”
  • “Where am I leaking energy or attention?”
  • “What would the most empowered version of me believe in this moment?”

You’ll be shocked how much clarity comes when you stop shouting over your own inner wisdom, and start asking it better questions.

Part 2: Prompts Are the New Solution

Here’s where it gets interesting…

We’re now in the AI age. ChatGPT. Claude. Gemini. Midjourney. Jasper.

These tools aren’t just for tech nerds. They’re for every leader who wants to think better, move faster, and create more with less.

But here’s the catch: You only get great output when you give great input.

In other words: Prompts are the new skill.

If you learn how to ask a better question—whether to your team or to your AI assistant—you get better and better results.

Examples of High-Impact Prompts:

Instead of saying:

“Write a blog post for my business”

Say:

“Write a 700-word article in my voice for business owners on how to reduce burnout. Make it empathetic, story-driven, and include 3 actionable tips. End with a soft call-to-action for my leadership mastermind.”

Instead of:

“Give me marketing advice”

Say:

“Based on this offer [insert link], what are 3 pain-point-driven hooks I could use for a Meta ad campaign targeting $5M+ companies in tech or wellness industries?”

This isn’t just AI fluency—it’s leadership fluency.

The better you communicate, the better the response. The better your questions, the better your answers. And the better your prompts, the better your outcomes. 

Part 3: Mastering the Wise Ask

Whether you’re leading a company, running a team, coaching others, or guiding yourself through change…

Start practicing the Wisdom of Asking Better Questions.

  • Ask more. Tell less. 
  • Prompt better. Receive more.
  • Listen first. Speak last.

Let curiosity guide you. Let clarity rise on its own. Let people be seen, not solved.

And remember what the YMCA taught me: Listening is not a delay tactic. It’s leadership.

Final Thought: Stop Trying to Be the Answer. Be the One Who Asks the Right Question.

The world has enough noise. Enough opinions. Enough experts shouting to be heard.

What it needs—desperately—is leaders who pause, reflect, and ask good questions. (And who teach others how to do the same.)

So next time you feel pressure to have it all figured out…

Slow down. Breathe. And lead with a wise ask.

The Leader Club is hosting a leadership training and mastermind event at The AZ Biltmore November 6-7. We build on the work you’ve done installing EOS for execution and we train executives, entrepreneurs, and owners to become better leaders. 

DM us to find out more. 

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