If you’ve ever searched for a business coach, you already know how this goes.
You type a simple phrase into Google and suddenly it feels like you’ve raised your hand and shouted, “Please sell me something.”
Now you’re staring at business coaches, mindset coaches, life coaches, strategists, consultants, programs promising six figures in 90 days, and at least one offer that costs more than you spent starting your business.
And that’s just Google.
If you’re on social media at all, it’s louder. Ads. Webinars. Challenges. Masterminds. Courses you sort of remember buying. Free trainings you meant to watch and never did.
Most service-based business owners I talk to aren’t new. They’ve already spent money trying to fix things. Sometimes a little. Sometimes a lot. And they’re still asking the same question:
How do I choose the right kind of help so I don’t waste any more money?
That’s the part nobody puts on their sales page.
So how do you find one that actually works for you?
The Murky World of Business Coaching
Here’s the uncomfortable truth: the online business world has incredibly low barriers to entry. Anyone can call themselves a business coach. Some are genuinely excellent. Some are just very confident. And those are not the same thing.
I learned this the hard way.
When I started my business in 2008, I didn’t hire a coach. I hired experts. Different ones. For different things. All very good at what they did.
I just hired them in the wrong order.
Within my first two years, I spent over $23,000 trying to “do it right.” Gorgeous website. Professional video. Smart people. Terrible sequence. The copy didn’t land. The messaging wasn’t clear. And no one stopped me to ask if the foundation made sense before building on top of it.
I wrote about that experience in detail in another post because it shaped everything I do now.
👉READ: The $23,000 Mistake That Cost Me Years (and How to Avoid It)
Looking back, the right kind of help could have made launching my business faster, less stressful, and far less expensive.
That experience is also why I have very strong opinions about how to choose help.
Here are the questions I wish I’d known to ask back then.
Is This Person Actually Experienced With Your Kind of Business?
For me, the work I do is very specific.
I work with service-based business owners—coaches, creators, and entrepreneurs—who are building an online business and want clarity around their messaging, visibility, offers, and how all of it works together. People who want to attract the right clients, grow an email list, and stop throwing money at random tactics.
That focus fits my experience and the work I’ve been doing since 2008.
It also means there are clear situations where I’m not the right fit:
- I don’t work with product-based businesses
- I don’t work with venture-backed startups or companies raising capital
- I don’t work with brick-and-mortar or local service businesses that aren’t building an online audience
That clarity matters.
Because hiring someone who doesn’t understand how your business actually grows is one of the fastest ways to waste time, money, and momentum. The right support should match the business you’re building—not the one someone else assumes you have.
Do They Walk the Walk?
Be cautious of the “visibility expert” with no visibility.
Or the business coach preaching momentum while quietly spinning their wheels.
This isn’t about perfection. It’s about congruence.
Before you hire anyone, spend ten minutes doing light recon. Skim their website. Scroll their content. Read a blog post or two. You’re not looking for polish. You’re looking for evidence that they actually live inside the world they’re advising you on.
- Are they actively running a business?
- Making decisions in real time?
- Dealing with the same trade-offs, constraints, and complexity you are?
For me, this shows up in something I talk about openly with clients: my business “superpowers.”
On a good day, I’m operating in my top strengths about 60–70% of the time. Not 100%. And that’s intentional. I know where I’m strong, where I’m not, and where I need systems or support instead of pretending I can do everything well.
I also don’t outsource blindly. I’ve done most roles in my business at least once so I know what good actually looks like before handing it off. That’s not martyrdom. That’s how you make smart decisions instead of expensive ones.
If someone claims they’ve cracked the code and live in constant alignment, I’d question that. Real businesses are built by people who know their strengths, acknowledge their limits, and design around both.
That’s walking the walk.
Do You Like Them Enough to Be Honest When Things Get Uncomfortable?
This one matters more than you realize.
Any decent business coach or strategist should offer some kind of check-me-out conversation before you ever commit to working together. Not a pitch. A real, two-way conversation.
Because if you’ve already spent money you regret, questioned your judgment, or feel embarrassed about where you’re stuck, you’re going to need to be honest about that. And you should be able to do that without being talked into something.
When I work with someone privately, we start with a quick call. It’s designed to see if we’re actually a fit. You get to ask questions. I’ll ask some too. We talk about what you’ve tried, what hasn’t worked, and where things feel confusing.
Some of these calls turn into ‘done with you’ coaching. Many don’t. That’s intentional.
If it’s not the right fit, I’ll say so. Because working together only works when it works for both of us.
This is also why clients sometimes joke and call me a business therapist. Not because I’m here to talk about feelings (and what’s going on in your head), but sometimes life is, well, life.
If the idea of having an honest, grounded conversation about your business feels relieving instead of stressful, that’s usually a good sign you’re talking to the right person.
Do They Offer Value For Your Situation?
Here’s a simple gut check.
You should be able to understand what you’re paying for, what’s supposed to change, and why one level of support might make more sense for you than another. If that’s not clear, you’re being asked to trust instead of decide.
That’s why I don’t offer one vague “everything” program. Not everyone needs the same level of support, and pretending they do is how people waste money.
I believe in clear options with clear outcomes, so you can quickly see what fits your situation and your budget without guessing.
That’s how I’ve structured my work.
- Visibility BreakthroughEver wish you could have someone just look at your business and tell you how to fix it? Think of the Visibility Breakthrough like a skilled mechanic taking a look under the hood of your business. This is your chance to get my focused attention on your visibility strategy and pinpoint exactly what’s not running smoothly.
- Business Clarity Session
Getting 1:1 support can mean the difference between staying stuck and having the breakthrough you deserve. If you are anything like my other clients, you’ll be surprised how much we can accomplish together quickly with a single session.
- Private, done-with-you coaching
For business owners who are tired of duct-taping strategies together and want customized guidance, strategic clarity, and hands-on support to move forward without second-guessing every step.
Prices are listed. Outcomes are clear.
You get to decide what makes sense for your business, without awkward sales calls or guessing games.
Do You Actually Like Them?
This one might just be me.
But if I’m going to work with someone for months—talking through their business, their decisions, and the things they keep circling but not fixing—it matters that we can be human with each other. Including laughing. Especially laughing.
Because business is already hard enough without pretending everything has to be serious all the time. That’s how I work, and it shows up everywhere else I show up
Your Connecting Advantage is about building a personal brand and strategically networking in a way that actually creates opportunities. Bob Burg, co-author of The Go-Giver, was generous enough to endorse it and call me the greatest networker in the world, which still makes me shake my head—but the point is, this is work I’ve lived, not theory I teach.
Just Another Leap is the mindset side. A smart, unfiltered, no-fluff roadmap for high-achievers, overthinkers, and anyone whose brain won’t shut up long enough to move forward. If you’ve tried to out-journal your doubt, out-hustle your burnout, or out-positivity your procrastination and still feel stuck, this isn’t about trying harder. It’s about understanding what your brain is actually doing—and how to stop it from running the show.
And The Midlife Leap on Substack is where my alter ego lives. Midlife, unfiltered. Brain-based clarity. Sweary self-care. Zero bullshit about balance. It’s where I work things out in real time, not polished, not performative—just honest thinking about what’s next.
All of that reflects how I work with clients.
Strategic. Direct. Practical. And human.
Because if you don’t feel comfortable being yourself with the person you hire, the work slows down—and no strategy fixes that.
