Before you hand over your credit card number, stop. The business coaching industry is flooded with people who will happily take your money, hand you a generic framework, and call it strategy. The problem isn’t that coaching doesn’t work, it does. The problem is that most people invest without asking the right questions first.

If you’re a service-based entrepreneur, consultant, or coach who has hit a revenue plateau, the right program and the right person could be a game-changer. The wrong one could cost you thousands of dollars and months of your time. So before you commit, here are the questions you should be asking, and honestly, the questions any reputable strategist should be asking you.

1. Do They Actually Diagnose Your Problem Or Just Sell You a Solution?

This is the biggest red flag in the industry. Most coaches lead with their program. A real strategist leads with a diagnosis.

In my work, every client conversation starts with three core areas: Pricing, Pipeline, and Sales. These are the three pillars of my Focused Visionary Framework and the reason I start there is because if your business isn’t growing, the root cause almost always lives in one of those three places. You could have a pricing problem where you’re undercharging and/or you aren’t priced in alignment with your goals and capacity. You could have a pipeline problem where you simply don’t have enough qualified leads coming in or they are they are getting stuck in your pipeline simply because there is no way for them to move through it. Or you could have a sales conversion problem where leads exist but aren’t turning into clients. These are three completely different issues that require three completely different solutions.

Anyone who jumps straight to “you need more leads” or “you need to post more content” without first looking at your data is not doing strategy. They’re doing guesswork, and likely projecting their own experience rather than addressing yours.

Ask them: “How do you figure out what’s actually holding a client’s business back before you start working together?”

2. Is Their Approach Customized or Copy-Paste?

There’s a massive difference between a program that hands you a template and one that helps you build a strategy rooted in your specific business model, your clients, and your goals. The coaching space loves to sell “proven systems” and while systems have value, a system applied blindly to your business without context can be a very costly investment with little to no return.

I tell all of my clients: “Every strategy works. But not every strategy will work for you.” Your business is not the same as someone else’s, your goals are not the same, and your capacity is completely different. Because of that, the path to your next revenue level shouldn’t look identical to everyone else in the program.

Ask them: “Can you walk me through how your approach would differ for two clients at the same revenue level but with different business models?”

3. What Does Success Actually Look Like And How Is It Measured?

Vague promises are everywhere. “Transform your business.” “Scale to six figures.” “Hit consistent five-figure months.” None of that means anything without a plan grounded in real data and facts, not emotions.

A business strategist will talk to you about your numbers – your current revenue, your conversion rates, your average client value, and what realistic growth looks like based on your capacity and the direction you’re heading and what you are trying to achieve. If they can’t speak to metrics or they pivot away from the numbers conversation, that’s a problem.

Ask them: “How do we define and track success throughout the program?”

4. What Level of Access and Support Do You Actually Get?

There’s a wide spectrum between a $97 course and a high-touch personalized strategy program, and the pricing should reflect the level of access and support you’re getting. Before investing, get crystal clear on what’s included.

• How often do you meet and what do those calls actually look like?
• Is there direct access to the strategist or are you handed off to an associate or a co-coach?
• What happens when something comes up between sessions?
• Is there any ongoing accountability built into the structure?

Inside my Focused Visionary Accelerator, clients have weekly access to me on our group Q&A calls and daily access to me in our private WhatsApp group. That’s intentional. When you invest in a strategist, you should have access to that strategist , not a assistant, not just a portal of pre-recorded videos, but the actual person you hired to help you grow your business. I never want a client to feel like they can’t reach me when something comes up.

Ask them: “Walk me through exactly what a typical month in this program looks like for a client.”

5. Do They Require a Conversation Before You Can Join?

This is a green flag, not a red one. Any program worth investing in should require some kind of conversation or application before you can sign up. Not as a sales tactic — but as a genuine filter to make sure it’s actually the right fit for where you are in your business.

A strategist who lets anyone with a credit card into their program is not protecting their clients’ results. A good coach will ask you questions, challenge you a little, and be honest with you about whether this is the right next step — or whether you need something different first.

Pay attention to the vibe. The person you meet on a sales call should be the same person you get inside the program. Just because someone is an incredible marketer doesn’t mean their personality will be a good fit for how you work and communicate. That matters just as much as the curriculum.

Ask them: “What does your intake or application process look like, and how do you decide if someone is a good fit?”

6. Are They Transparent About Pricing and References?

Two things that should never be a mystery: how much the program costs and what actual clients have to say about it.

On pricing – you shouldn’t have to get on a call or slide into someone’s DMs just to find out what a program costs. I firmly believe that people should be able to see the investment upfront and decide for themselves whether they want to pursue more information. Hiding pricing isn’t mysterious or strategic. It’s a barrier that wastes everyone’s time and signals that the value can’t speak for itself.

On references – screenshots and testimonials on a sales page are easy to curate. What’s harder to fake is a real conversation. Don’t be afraid to ask for an introduction to a current or former client so you can ask your own questions, hear about their experience firsthand, and get an honest read on what the program is actually like.

I will always happily make introductions to my clients for any prospective FVA member. That level of transparency is something I stand behind completely. Your investment deserves more than a highlight reel.

Ask them: “Can you connect me with a current or past client I can speak with directly?”

7. Can They Tell You Who This Program Is NOT For?

This one tells you everything. Any coach or strategist who says their program works for everyone is likely more interested in selling than in your results. The best programs have a specific ideal client, and the best coaches will tell you honestly if you’re not the right fit.

For example, the Focused Visionary Accelerator is not the best fit for brand new business owners. I think new entrepreneurs need time to try things on their own first – to collect data, figure out what they like and what they don’t, and start to understand how their business actually operates. FVA is the next step. It’s for service-based entrepreneurs who have been in business for a few years, have some data to work with, and are now ready to turn that data into a focused strategy to grow, scale, and plug the gaps where money is leaking.

Selectivity is a sign that a strategist takes their clients’ results seriously. If there’s no application, no conversation, and no criteria – pay attention to that.

Ask them: “Who gets the most out of this program – and who would you tell to wait before joining?”

8. What Happens After the Program Ends?

A good strategy program doesn’t just help you survive the next few months – it builds your capacity to operate at a higher level on your own. You should leave with a clear understanding of your numbers, your systems, and your decision-making process. If the program creates dependency rather than competence, that’s worth questioning.

Ask them: “What does a client look like at the end of this program – what can they do that they couldn’t do before?”

The Bottom Line

Investing in the right business strategy program can accelerate your growth in ways that going it alone never will. But the keyword is “right.” The right program is one that meets you where your business actually is, builds a strategy around your specific gaps, and gives you the tools to make smarter decisions going forward.

Ask the hard questions upfront. A strategist who is worth your investment will welcome them.

If you’re a service-based entrepreneur who has hit a revenue plateau and you’re ready to figure out whether the issue is your pricing, your pipeline, or your sales – a CEO Strategy Call is the place to start. We’ll look at your business data, identify what’s actually holding you back, and give you a clear picture of what needs to shift.