Can You Have Too Many Business Coaches? My Experience with Business Coaching

Can you have too many business coaches? Nope—at least not for me. This year, I worked with five of them, and they moved me along faster than I’ve ever moved in business. It was like trading my roller skates for a rocket.

So, why the coaching spree? Because I was stuck and needed more than one brain to push me to the next level.

What is Business Coaching?

Business coaching is like having a GPS for your entrepreneurial journey—someone who helps you chart the course, avoid potholes, and steer clear of that “Recalculating…” voice in your head. Coaches guide, mentor, and hold you accountable.

You’ll find all kinds of business coaches: marketing gurus, financial wizards, operations masterminds, and leadership whisperers. They specialize in filling the gaps you can’t—or won’t—tackle alone. And the benefits? For me: clearer goals, stronger strategies, and the ever-terrifying but necessary accountability.

Free Business Coaching: SCORE.org

If you think good coaching has to cost an arm and a massage table, think again. Enter SCORE.org, the holy grail of free business coaching.

SCORE connects small business owners with seasoned pros who volunteer their time to help people like you and me not just survive but thrive. Their coaches helped me fine-tune marketing, master SEO, and bring structure to my chaos. Plus, they’re available in-person, via Zoom, or by email. And SCORE doesn’t care if you more than one coach at a time!

One SCORE coach, Tom, became so invested in my success he joined my wellness center as a yoga instructor. Another, Ann, gave me great ideas about marketing locally and was the perfect sounding board for me. And Danny helped get my massage business to rank #1 locally. Did I mention all this was free?

SCORE is a lifesaver for anyone on a budget—and if you are going it on your own, you have to run lean. Love me some SCORE!

Coaching Through Personal Connections

Now, about my neighbor Luke: He’s a business relationships guru who creates “value experiences.” (Whatever that means, it worked. Haha.) No, for us value experience means we make the clients feel good from the moment they arrive to the moment they leave so that they are sure to tell everyone about the great experience.

I offered Luke a massage gift certificate for his advice. He accepted. Turns out, bartering isn’t just for middle school lunch tables—it’s a great way to exchange expertise. I got Luke’s insights on creating lasting customer connections, and he got to enjoy our massage.

This experience taught me that you don’t always have to go far to find great coaching. Look around. Maybe your hairstylist has killer branding ideas, or your mechanic knows a thing or two about small business operations. Tap into your network, and don’t be afraid to swap skills. But don’t stray from the coach’s expertise.

Picking the Right Coach

Here’s the thing about having multiple coaches: it’s not a free-for-all. It’s a strategy. You need to pick the right coach for each challenge.

Take my lineup: Danny was my digital marketing coach, Ann handled traditional marketing, and Lauren optimized SEO. Each had a specific skillset I needed. If I had one generalist, at best, I probably would have ended up with mediocre results across the board. At worst, I would have been frustrated and given up on projects that I should have finished.

Before choosing a coach, figure out your pain points. Need help with finances? Find someone with P&L expertise. Struggling with leadership? Look for a coach who’s managed teams successfully. Ask questions, check references, and be clear about your goals. Make sure you click and when you do choose a coach, constantly monitor your coaching sessions to make sure the coach is giving you what you need and is still the right person for the job.

When Coaching Goes Wrong

Now, a word of caution: Even the best coaching can backfire if you don’t approach it wisely. Here are three pitfalls to dodge:

1. The Popularity Trap: Don’t pick a coach just because they’re Instagram famous or charge a lot of money. Expertise matters more than hype.
2. Coach Overload: Currently, I have 4 coaches, but I don’t meet with them at the same time. I space things out so that I can complete the task from each coach. Four at a time may be too many for you—and at some point it might be too many for me, too. But for me now it works like a charm. If you’re just starting with coaching, my advice is to start with one so that you’re not spread too thin.
3. Unclear Expectations: Always define goals, timelines, and deliverables. A confused coach-client relationship helps no one.

Get a Business Coach!

It’s not the number of coaches you have that matters. It’s having the right coach to meet your specific needs that matters—whether they’re SCORE volunteers, bartered buddies, or hired pros.

So, if you’re hesitating about getting a coach, don’t. Start with free resources like SCORE or tap into your network. Barter, research, and, most importantly, take the leap.

Because if there’s one thing I’ve learned, it’s this: great business coaching can transform you which in turn can transform your business.