Structuring a Growth Coach Arrangement (if you do; which you probably shouldn’t)

Business and Coaching

Startups that build tools for startups. Something has always felt wrong about that, to me. I know it’s a real market, but it just seems so ironic. 

Business coaching seems the same way. “Hi, I’m a business coach. My business is to coach your business. Without the skin in the game that you have. And the boring work. And the long hours. And the times you can’t make payroll.” 

Again, I know that’s oversimplified, not entirely accurate, and mean. And hypocritical. 

But I feel like all of us trying to build businesses really need help from people who are willing to jump in the boat and row along with us; the kind of people who are willing for at least some of the reward to be that we reach our reward.

After all, that’s what is so satisfying about coaching: it’s not collecting a paycheck, but seeing your client defeat Darth Vader in the way that only they can.

First off, I’m a fan of business coaching; but not a big fan of paying for it

I’ve received quite a bit of coaching in my life and business. My debate coach and trumpet teacher both taught me life in the context of the skill I was learning, and invested in me personally. 

I also am currently coached, in non-official (unpaid) coaching relationships, by…

  • a TED-talk giver/professor/savant who does what I hope to someday
  • a retired Army Colonel and director of a major national nonprofit
  • two close friends in similar businesses

I also say that coaching is one of my superpowers, because I’ve done it for 15 years mostly as a volunteer and coached some of the country’s top speakers and debaters. The most rewarding experience of my life was starting and coaching the Vector VA speech and debate club as my volunteer side project for several years. 

I’ve studied coaching. I’ve coached coaching and won awards for it. I’d love to break down for you what I think makes a great coach. 

I’ve built a software company around coaching, working with professional athletes and coaches. 

But I just can’t stand business coaching

Because it feels like entering the darkest parts of the world of multi-level marketers, realtors, lawyers, “networkers,” and other quick-buck wannabes. (Again, not everyone in those spaces are dark! And my heart goes out to everyone struggling to make it who thinks those are their best choices!) 

My best coaches have all been involved in some aspect of my life or industry or work—none of them were hired “as a coach.” Some were hired as a teacher (such as a professor or my trumpet teacher) but ended up being a coach instead. 

And I’ve spoken with several self-acclaimed business coaches, who (in my opinion) tend to dish advice before they even know the resources available to the person facing a challenge. Great coaching should feel like a removal of weight, not an adding of things to do. 

So I’m just plain skeptical, if not cynical, of the entire “business coaching” world.

Why Choose a Growth Coach?

Not everyone should. First-time founders and new executives ought to consider it most strongly. 

Please note that getting a growth coach and hiring a growth coach are two different things in my mind. You can likely achieve much of the growth coaching you need from your network and team, as long as you open yourself to their guidance.

Choose a growth coach if you need help staying true to a growth mindset. It’s different from building an immediately viable business. Some of the mindsets you may have to overcome, especially as a first-time founder or executive, are these three anti-growth mindsets:


  • Technical Mindset—you have the “but this is a great product!” bias, which may lead you to over-engineer before cash-based feedback loops that will teach you everything. Each dollar you spend will be wildly inefficient after a certain point, and you need to see that you really can do more with less.
  • Sales Mindset—you think “sales solves all problems,” which may lead to hooking some whales that hurt you more than they help you to establish a valuation, true north, and successive fundraises. Big clients that cost a lot to support and aren’t 100% on model, and aren’t your sole focus for repeatability, will likely set you back on your growth potential as a company.
  • Scaling Mindset—you ask everyone “but how will that scale?” before product-market fit is humming. Don’t succumb to the temptation to build systems and processes 14 times before product market fit—let the fires burn, treat the reference customers with white gloves, and try weird stuff until a model, process, and system pops out as the solution to real problems (not expected problems). 


What’s self-deceptive is that each of these mindsets are powerful under the orchestration of a great growth leader, but they must live within the guardrails of your growth strategy. 

A growth coach is going to help you focus on these things instead:


  • Target market penetration – sticking with it until you get “there”
  • Milestones for growth
  • Spending appropriately to your stage
  • Avoiding fatal distractions and false positives


If you feel comfortable with those topics, you probably don’t need a growth coach. If you’re worried about succumbing to mindset biases, then you probably do.

How to Structure Paid Business Coaching

Distinguish advice from coaching

Steer clear of business coaches who charge per hour to give you advice

That’s not a coach. That’s a teacher. If I need an expert, I’m fine paying $500/hr for the best person in the world to rapidly unblock me on where I’m stuck. 

But I don’t want to enter an ongoing $500/hour weekly relationship with that same expert. Being an expert doesn’t make a great coach. Being a great questioner helps you get all you need from a great expert. 

I guess what I’m saying is that coaching is more of something you do, and less of someone you are. Meaning it’s available right inside your organization already, or from friends and mentors, or from all kinds of people who have walked the road before and are willing to walk with you for a bit. 

Get skin in the game

Someone who meets with you weekly and you pay them has exactly zero skin in the game. They need to care about your results: because they’re listing you as a marquee example of their services, because they have a piece of the upside, or some creative reason beyond merely another few hundred bucks because they met you again. 

Establish a rhythm

Coaching works when it’s uncomfortable. It’s a trust-based relationship focused largely on blinders that are holding you back. Since you don’t see past your own blinders, by definition, you need to commit to regularity with the coach so that they can. Don’t just wait until you’re on fire to find a coach—that’s usually when you need advice instead. 

Share a language

There are dozens of leadership and management models and frameworks. What helps the most is when the whole team is speaking the same language. If one team speaks Leadership and Self-Deception trust language and the other speaks Five Dysfunctions of a Team trust language, you could find it challenging to be on the same page. 

Both are some of my favorites, but I’ve found over and over again that just ONE person in an organization finding salvation doesn’t spread anything until others pick up the language. Conversely, it matters less which model is selected than that a model is selected. 

So think through how you’ll be sharing what you learn and developing a shared language inside your team. That could mean training sessions, videos, memos, whiteboards, conversations, or even t-shirts and offsites. 


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