In September 2019 I shared a thought in a tweet, and it was seen by over 100,000 people. Mind = 🤯

The tweet?

I formerly did a podcast episode about spending big money on coaches, where I talked through why I think coaching is a secret weapon. But I need to expand upon it.

To me, the hardest thing about business is figuring out who to listen to. There is SO much advice out there that it’s hard to cut through the noise.

So, I’ve created a rubric for myself to figure out if I should listen to someone:

  1. Have they done it before?
  2. Have they published about it online so that others can interact with their ideas, and thus the writer gets clearer in their thinking?
  3. Do I like them as a person and want a similar life to what they have?

If someone has two but not all three, I deprioritize listening to them. Simply put, listen to those with the experience, the humility to be wrong, and who have done it all in service of living the life that you want to live also.

Let’s look at all three.


I stated this as “Have they done it before?”, but let’s get a bit clearer on what I mean by “it”.

By “it” I mean two things:

  1. Have they built the kind of business you are building? and
  2. Do they have experience coaching others?

Why do I look for both.

On the “built the kind of business you are building” side, I do this because I want someone who has seen the roadmap and can expedite my learnings while helping me avoid the pitfalls they went through. While every business is different, every business model has challenges that you can learn from. I want to expedite that learning as much as possible.

And on the “experience coaching others” side, I firmly believe that coaching/consulting are learned skills. Being strategic and helping the coached see their blind spots and being proactive in overcoming those and teaching the strategies is something that a seasoned coach can do. While a less experienced coach may have just as many learnings, they likely will not be as effective in communicating those learnings.

They should have a prove-able track record of growing a business like yours.

Clarity of thinking

Something I value immensely is clarity of thinking and having thoughts and beliefs honed in public view. Some of this probably comes out of my two years spent at a commune in Switzerland where every idea was on the table and yours were challenged daily.

There’s nothing like daily debate and challenging to really refine your beliefs and change your mind on areas you’ve stubbornly held onto or didn’t know you held at all.

Something important to me, as a content creator before I am anything else, is seeing that they have published about their area of expertise online so that others can interact with their ideas.

Take Chris Lema for example. On he’s published HUNDREDS of posts about WordPress, which let me know that he is one of the most qualified people to help me grow a business based on WordPress. He’s also built and sold multiple marketplaces and other businesses, which means he understands the unique challenges that marketplaces have.

But without publishing and speaking like he has, he wouldn’t have the clarity that comes from teaching publicly..

Direction in life

Finally, one that I’ve added in over the last few years is whether I like the coach as a person and then I ask myself if I want a similar life to what they have.

There are a lot of successful people out there, and a lot of ways to become and remain successful. There are a lot of ways to live your life as well, but not all of them are for you.

For me, the things I look for are:

  1. Is the person well thought of by others?
  2. Are they family-oriented and understand the challenges that come from being a parent as well as an entrepreneur?
  3. Are they consistently striving to get better?
  4. Do they have a coach as well?

Life and business are dynamic, so it’s important to not just look at their specific experience but also to see what direction they are going on their journey.

I was recently reading Trillion Dollar Coach (Amazon link) about legendary Silicon Valley business coach Bill Campbell. What amazed me about Bill was not just that he had so much experience, but also that he kept learning and kept pushing himself as he pushed those he coached.

And his coaching roster was incredible. Pretty much any household name Silicon Valley entrepreneur leaned on Bill when they had issues – Steve Jobs, the Google founders, Zuckerberg, the Microsoft guys.

And the crazy thing is, they kept leaning on him as their businesses changed throughout the years because he kept investing in himself, in his own learning, and taking what he was learning from his own experience and mentors and then teaching it to others.

THAT is the kind of coach you want.

When to look for a business coach

The next question I get when talking about having a coach (or two, as in my case) is “when should I look for a business coach?”

Since a coach is someone you pay (different from a mentor whose time is given freely and sporadically), the first barrier is that you are able to afford to pay someone to coach you.

Essentially, you are paying them for their knowledge. They’re not giving you deliverables, they’re probably not reaching out to their network for you (though they may make intros if needed), and you are fully responsible for learning and taking action to see the results.

Thus, there are a few things you need in place:

  1. Enough revenue to afford to pay them. Most coaches start at $1,500-$2,500 per month and go up from there.
  2. A growing business that is becoming more than you can handle, and you need someone to point the way for you.
  3. A strong work ethic to put their teachings to work for your business.

Without all of these three, you’ll end up wasting a lot of time and money. And then, you’ll say “coaching didn’t work for me.”

That’s the worst thing that could happen, because then you’ll close yourself off to working with brilliant people.

Basically what I’m saying here is that you need to be the kind of client that a coach wants to invest themselves in. Coaches charge for coaching because you’re much more likely to take their advice to heart and put it into action when you’re paying them for it.

But coaches usually are not in it for the money. Sure the money is nice, but ultimately they want to have impact. And if they’re not changing your business, they shouldn’t want to keep working with you.

Where to find a coach

Now you might be asking “Ok that’s great John, but where do I find a coach like this? There are so many garbage coaches online!”

You’d be right that there are a lot of garbage coaches out there online hawking their wares after shifting from being an SEO guru to a Facebook ads guru to a crypto day trader.

Steer entirely clear of anyone advertising their coaching services to you who has not earned your attention outside of those ads.

Instead, when looking for a business coach you should find one in your own network or just outside your network and thus known well by someone within your network.

Talk with colleagues

Talk to your friends/colleagues in a similar position and ask them who they work with. Expect that most will not have a coach, but those who do will be glad to tell you and maybe even make a referral.

Ask those you already listen to

If you already have people you listen to online who have built the kind of business you’re building, consider reaching out to them and asking if they currently offer coaching services or know of anyone who is that they could refer you to.

Don’t forget the point made at the top about the person you hire having experience with coaching already. This is why you ask if they currently offering 1:1 coaching services. If they come back and say they were thinking about it, then ask for a referral. My advice is to not be their first coaching client.

What kind of coach are they?

In sports, every team has a head coach and then specialist coaches. In football you have your head coach, your quarterback coach, your offensive coach, your defensive coach, your special teams coach, etc.

I finally understood the importance of this when I listened to Noah Kagan’s podcast episode on coaches, which I highly recommend.

In business, you can have multiple coaches too. I like to talk about levels of relationship in business (peers, coaches, and mentors) but had never really considered levels of coaches.

Types of coaches you can have in business are:

  1. Executive coach – helping you get better at being a leader
  2. Product/marketing coach – strategic and tactical advice to directly move metrics
  3. Finance coach
  4. etc

I currently have the first two, and then have others I can tap into for other areas like specific paid acquisition strategies or financial modeling.

Consider building out your coaching bench, but definitely find someone who specializes in the area in which you have the biggest need.

By the way, a great executive coach can help you find other coaches as well for specific areas where they are not the best.

Agree to an initial engagement

Much like hiring a marketing firm, you need to know the terms before you agree and sign.

Unlike hiring a marketing firm, there are no deliverables. Instead, because it is likely a strategy engagement you need to understand:

  1. How the engagement begins (how they get to know your business, if they don’t already)
  2. How they go about helping you stay focused on what matters in your business
  3. The cadence of meetings

If they’re a new coach, I recommend agreeing to a three or six month initial engagement, to make sure that you’re getting value from it (remember, you can afford it and are an action taker before you sign up). Then it goes month to month rolling indefinitely.

What other questions do you have about hiring a business or executive coach?

Update: Ramit Sethi published a post about this just before I finished mine, so I recommend you read that too.