I’m not here to pitch coaching or even to dissuade it. I’ve just seen what happens when entrepreneurs hand over their trust too quickly, and I believe a few questions up front can prevent a lot of heartache down the road. That’s the purpose of this post – not to steer you away, but to sharpen your thinking before you commit.

Somewhere along your entrepreneurial journey, you’ll likely find yourself in a conversation with a coach — or a coaching program — promising momentum, clarity, and that elusive breakthrough. And often, those promises will come from big names in the coaching world.

To be honest, I watch some of these folks with no small amount of envy. They’re polished, persuasive, and know how to speak to your ambition. With content teams, tuned-up funnels, and near-perfect delivery, they’ve mastered the art of attraction. And because I work in this space, I understand the level of skill and presentation they bring.

But here’s the thing. When it comes to coaching — your coaching — it matters who you choose and how you evaluate the offer. Stage presence may grab attention, but it’s the coaching partnership formed that determines whether your business moves forward in real, tangible ways.

So before you commit, take a few moments to ask some grounded, practical questions of them, and of yourself.

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What results have they actually helped clients achieve?
If they say they help entrepreneurs reach consistent $10K months, ask how many have done it. What kind of businesses were they running? How long did it take? What support was involved?

Will you be coached by the person you’re hiring?
Sometimes the voice that sells the program isn’t the voice you’ll hear once you’re inside. Ask how often you’ll interact directly with the coach you’re signing up with, in what ways, and who else might be guiding your journey.

What does “access” really look like?
“Lifetime access” often means digital content not live interaction. Make sure you understand what support looks like. Real-time Q&A? Personalized feedback? Or just a login and a social media group monitored by whom?

What happens if it’s not a fit?
Are there cancellation policies? Exit options? Agreements matter in coaching. They set expectations, protect time, and create shared commitment. But contracts should never be used to hold clients hostage. Coaches who value results know that trust isn’t earned by terms and conditions. It’s earned by what the work actually produces.

What’s the tone once you’re inside?
Is the relationship centered on your growth, or does the conversation shift quickly to the next offer? It’s worth noticing whether delivery is prioritized as much as enrollment.

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Before you enter any coaching relationship, ask yourself:

What do I expect to be different on the other side of this experience?

If that question is hard to answer, pause there. That clarity matters. It will become your compass.

Once you know what outcomes you’re seeking, you can go looking for someone who’s known for helping others create that. And once you find them, look again for signs of alignment — not just talk, but receipts.

Coaching, when it works, is a powerful accelerator. But finding the right coach — one who respects your journey, understands your goals, and holds themselves accountable for their results — is what makes it work.

And when that’s in place? The transformation tends to follow.

#SoarAboveAchieveBeyond