Questions to Ask Any Career or Business Coach

Before I hire any coach, I want to know six things. Not their story. Not their aesthetics. Six specific things that tell me whether this person has built anything real, whether the method actually exists, and whether I can trust the results they’re promising. I’ve written them down here because I think every woman considering coaching should have them.

I came to coaching with healthy skepticism.

Not because I was cynical about the idea of it. I believed in the concept. What I was skeptical about was the market, which at the time looked like a lot of people with a logo and a Canva template and a very compelling story about transformation. Or ‘life coaches’ trying to be all things to all people.

But I also realized that when I was building my first business I felt very alone and lost. I had initially hired a coach through a very well-known self-development company that offered coaching as one of the upsells to their live events. She was one of dozens of coaches farmed out but our sessions quickly devolved into her woo-woo energy practices. (I have great respect for the woo – but ethereal energy work was not what I needed when starting my first business).

I didn’t have anyone checking my thinking. Nobody asking the hard questions. Nobody keeping me accountable. Nobody whose job it was to look at my plan with a second set of eyes and tell me where the gaps were. I had friends, kind people, people who wanted me to succeed. But wanting someone to succeed and being equipped to help them isn’t the same thing.

That first company collapsed one month before we would have launched. The manufacturing deal fell through, and I was devastated at the time. Later, much later, I understood how much that collapse saved me.

What I didn’t understand until I became a coach myself was how differently that story might have unfolded with the right person in my corner. 

So yes, I believe in coaching. And no, I don’t believe in all coaches. Here’s how I’d separate them.

First: Do you have a specific and structured methodology that you follow?

If the answer is vague, I’m out. 

If it’s “we coach you on what you bring to the table”, I’m out.

“We do deep transformational work” is not a method. “We help you become your best self” is a brand line, not a framework. I want to know that you’re guiding me to a specific outcome, with a specific approach and you have a methodology that is proven to work in a structured way.

If a coach doesn’t have an architecture to their program , one of two things is true: either they haven’t coached enough people to know what works, or their thinking isn’t structured in a way that is teachable and coachable. Neither is acceptable.

The method doesn’t have to be complicated. But it has to exist, and it needs to work.

Second: Has this person actually done the thing they’re coaching?

Not as a hobby. Not on the side while a partner’s income covers the household. Not with significant financial backing from another source.

Under real pressure. The kind where the business had to work because there was no fallback.

This matters because the experience of building something when your financial security depends on it is categorically different from the experience of building something when it doesn’t. The decisions feel different. The fear is different. The discipline it requires is different.

I’m not saying someone has to have failed at something to be a credible coach. I’m saying the experience of genuine consequence teaches things that a comfortable side project does not. I want to know they’ve been where I’m going, with real stakes.

Third: Do they teach both strategy AND mindset?

One without the other is half a program.

Strategy without mindset: you’ll get a beautiful business plan and stall on execution when the fear hits. And it will hit. There is not a woman building a business who doesn’t encounter a moment where the fear is bigger than the strategy. If your coach has no tools for that moment, the strategy is useless.

Mindset without strategy: you’ll feel very clear and confident and have no idea how to build a business model that actually works. Belief is not a business plan.

I spent years watching women in this market get sold one half of the equation. The strategy programs that treated mindset blocks as personal problems the client should sort out on her own. The mindset programs that treated “you can do it” as sufficient preparation for building a real business.

The programs that work address both, in a specific sequence, because they’re not separate. They’re intertwined.

Fourth: Are there reviews on platforms they can’t delete or control?

Testimonials on a website are selected by the business. Of course they are. I do this too. We all choose the quotes that represent the best outcomes.

That’s not the problem. The problem is when testimonials on a website are the only evidence.

I want to see reviews on third-party platforms where the business doesn’t control what stays up. Trustpilot. Google. Somewhere with verified purchasers leaving unfiltered feedback. Not because I expect perfection, but because a track record you can’t curate tells me something real about the experience of being a client.

Her Big Leap has 30 five-star reviews on Trustpilot. I put that out there not as a brag, but because it’s the kind of evidence I personally require before trusting anyone with this kind of money and this kind of decision.

Ask the coach where their unmoderated reviews live. If they don’t have a good answer, that’s your answer.

Fifth: Do they turn people away, and can they tell me why they’d turn ME away?

Programs that take everyone are not selective. Selectivity is not a marketing tactic. It’s a sign that the coach has been honest about who the program works for and who it doesn’t.

I want to know: who is this NOT for? What disqualifies someone?

And then I want to ask: given what you know about me, would you turn me away? What would you look for? A coach who can answer that question honestly, without flinching, without pivoting to all the reasons you’d be a great fit, is a coach who is actually thinking about your outcome rather than your enrollment.

If the answer to “who would you turn away” is vague or nonexistent, either the program hasn’t been thoughtful enough to define that, or the coach isn’t willing to turn anyone away. Either way, it tells me the enrollment conversation is more sales than fit.

Sixth: Does the program define what success means to me, or does it assume everyone wants the same thing?

This one is personal.

My life and level of success changed the minute I got clear on what I wanted my life to look like and started building a business to support that life. Because a business built based on market opportunities instead of real alignment, even a wildly successful one, is still wrong, and will likely burn you out just like corporate did.

I spent years building a career that looked right and felt wrong. I was not going to do that again with a business.

The Life Design phase we run at the start of Her Big Leap exists because of that. It’s not optional. It’s not a mindset warm-up. It’s the foundation, because if you don’t know what you’re building toward, you’ll optimize for the wrong things and hit the goal and wonder why you’re still not satisfied.

If a program doesn’t ask you who you want to be and how you want to live before it asks you what your business model is, I’d wonder whose definition of success you’re being built toward.

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I apply every single one of these questions to Her Big Leap. We have a proven methodology based on business strategy and psychology. I built my business under real financial pressure, after a layoff, as a sole breadwinner. We teach strategy and mindset together, because we’ve seen what happens when programs skip one of them. We have unmoderated third-party reviews. We turn people away, specifically, with real criteria. And we start every engagement with what the client wants her life to look like.

You should hold us to this list. If we don’t pass it when you apply it, don’t enroll.

That’s not false modesty. That’s just the standard I’d hold anyone to if I were sitting where you’re sitting.

Sarah Janzen is the founder of Her Big Leap, a program that has helped hundreds of corporate women across North America and Europe build thriving businesses on their own terms. She does all of it while raising two boys, which is the best proof she knows that “waiting for the right time” was never the strategy.