Stop Asking the Wrong Questions: What Really Matters When Choosing a Coach

Introduction

When you’re looking for a coach—whether for business, leadership, or personal growth—it’s easy to ask the questions everyone else asks.

• “Have you worked in my industry?”

• “Have you built a business like mine?”

• “How much money have you made?”

Those might feel like the right questions. But they rarely lead to the best coaching relationship—or the best results.

Why? Because those questions focus on similarity, not skill. On surface-level credentials, not transformation. And in the coaching world, that’s a dangerous trap.

Let’s dig into what you should be asking if you’re serious about growth.

The Common (But Misleading) Questions

Most people approach hiring a coach like hiring a contractor: they want someone who’s “done it before.” But coaching isn’t about doing the work for you—it’s about helping you think and act at a higher level.

Here are the questions I hear all the time:

• “Have you worked in my exact industry?”
  This assumes industry experience is more important than strategic thinking or people development. It’s not. Industry experience CAN BE important when it comes to finding a mentor, but even then, it is incomplete information at best.

• “Have you built and sold a business like mine?”
  While success leaves clues, this doesn’t tell you anything about the coach’s ability to help others succeed. And many people claiming to have built and sold their home service business were simply part of a company that had an exit. They weren't the owner or CEO.

• “How much money have you made?”
  This often measures charisma or marketing—not coaching effectiveness. There are broke geniuses and rich charlatans.

These questions are built around credibility theater, not coaching substance.

Ask These Instead: Questions That Actually Predict Growth

If you want to get real ROI from your coaching investment, here’s what to ask:

1. “How do you approach coaching clients?”

You’re looking for a system. Structure. A clear method—not just someone who “wings it.”

2. “How do you hold clients accountable?”

The best coaches don’t just give ideas—they help you follow through. Ask how they support implementation and execution. And ask how they handle it when a client doesn't follow through (this will tell you a lot!).

3. “Can you share some transformations your clients have had?”

Look for changes in thinking, systems, confidence, and results—not just revenue wins. True coaching unlocks people.

4. “How do you tailor your coaching for different personalities?”

A great coach doesn’t coach everyone the same way. Emotional intelligence, adaptability, and deep listening matter.

5. “How are you continuing to grow as a coach?”

Coaches who aren’t actively learning usually plateau—and so do their clients. You want someone who sharpens their own saw. Do they work with a coach?

The Power of True Coaching

Think about this: The best athletes in the world still hire coaches.
Their coaches aren’t better at the sport. They’re better at developing the player.

Tim Grover didn’t become irreplaceable as a coach because he was better than Jordan or Kobe—he did it because he knew how to bring out their best.

That’s the role of a real coach: to help you become someone who performs at a higher level—consistently.

Coaching isn’t about transferring knowledge. It’s about engineering transformation.

This isn't to say training, mentoring and consulting don't all add value. They each serve a very clear and distinct purpose. But when you want a coach for your home service business, you want someone who can help you transfer knowledge to wisdom to performance to results.

Make the Shift

If you’ve been evaluating coaches by their resume, pause and reconsider.
What really matters is:

• Can they help you see what you can’t see?

• Can they challenge your thinking in a way that leads to change?

• Can they help you stay consistent, focused, and in motion?

That’s what moves the needle. That’s what builds the business and life you actually want.

Ready to See What Great Coaching Can Do?

If you’re serious about leveling up, I offer a complimentary strategy session where we’ll identify hidden profit, uncover execution gaps, and build a plan to grow—faster and with less stress.

Schedule a free Discovery Call here.

Let’s stop asking the wrong questions—and start building real momentum.