I Don’t Know about CEO Coaches. But We All Could Use CEO Trainers.

warriorOnce you’ve been venture backed, if not before, you’ll hear a lot about CEO Coaches.  The classic example is Bill Campbell, CEO coach to Steve Jobs, Google, Mark Pincus, and other leaders in between.  VCs generally have great networks of ex-CEOs and want to help, and plug you in with a CEO coach.

The problem is, at least for me, is the CEO Coach Just Doesn’t Work until you are reasonably big, and have a fully built out team, processes, and infrastructure.  Say $20m-30m+ ARR, maybe higher.  Why?  Because the CEO Coach who Has Retired from Billion Dollar Tech Company always wants to just talk about Strategy.  Not the nitty-gritty of how your business is really run.  The CEO Coach doesn’t get his/her hands dirty.  And if you are struggling to get to $2m or $4m in ARR — you know, strategy is super important and all, but you really don’t have the people, or the luxury, of spending leisurely time with The Coach on Strategy, where the Coach really has no idea how the exact drama and details of your space work.

Personally, I couldn’t find a way to benefit from CEO Coaches.  Instead, I used a network of seasoned advisors for tactical advice, which works great and everyone needs.  But you only use advisors for point solutions and one-off advice.

But now I see I was wrong-ish.  Because what I really needed, as soon as we had just the earliest  traction — and what I see many of my peer and friend founders and CEOs needing — is something in-between: a CEO Trainer.  A position more proactively involved than an advisor, but less at 20,000 feet than a CEO Coach.

OK, what is a CEO Trainer, and What Does He or She Do?

Just what a truly great trainer does for a professional athlete (or highly motivated weekend warrior).  Pushes you to your 100% max.  Pushes you to do what you know you already need to do, but are just struggling to get done, too tired to do.  Shows you where you are really doing well, and calls you out when you slip.  No pain, no gain.

Your CEO Trainer doesn’t need to have been the CEO of Intuit or Apple or whatever.  But he/she needs to have had (x) a decent success — a level or three above you, (y) in a similar domain, and (z) have successfully experienced everything you are going through in the next 12-24 months.  So if you’re doing $1-$2m in ARR, your CEO Trainer should have done at least $10m in their SaaS company.  If you are doing $10m, they should have done at least $40m.  If you are doing $20-$30m+ ARR, they should have IPO’d.  Also, your trainer needs to only work for you, not your board.  Be carefull if he/she is a close friend of your VCs.  In fact, find another trainer in that case.

Then, here’s some thoughts on what your CEO Trainer can do:

  • Pushes You To Make the Hard Hires.  We all get tired, and either take too long to make a key hire, or settle.  Your trainer won’t let you do either.  He/she will interview your top candidates, and push you to get them made.  
  • Pushes You To See Your Company’s Strengths – And Double Down on Them.  Most founders are pretty self-critical.  We know when things are going OK, but it can be hard to see when we’re really doing better than one might expect.  Your CEO trainer has the experience to push you here, and will get you to double-down earlier, which is key in SaaS.
  • Pushes You to Mix It Up.  We can all get a bit stale, getting comfortable doing what works, what we know.  Your trainer (ok, now taking the trainer metaphor too far) knows to mix it up.  Try experimenting in an adjacent vertical, or going a little more up-market, or down-market … even if it didn’t work before.
  • Pushes You to Spend More Where It’s Accretive.  As founders, we can often be cheap.  Generally good, but sometimes we miss the forest for the trees.  The CEO Trainer can push you to make investments that will pay themselves back, even if over a longer timeframe.
  • Spots Issues and Flags.  And presents them to you, non-judgmentally, to improve.

How Often Do You Meet with Your CEO Trainer?  My guess is, in a formal structure as often as you have board meetings.  You can use the board deck to get him/her up to speed in between meetings.  And then just do an open and deep, and probably unscripted, dive when you meet.  Tell him/her what’s on your mind.  And Your CEO Coach will already have 10 or 20 questions and ideas from the Board pack alone.

I can tell you, if I’d had a great CEO trainer, I would have done even better, in both my start-ups.  Someone that knew enough about how similar SaaS businesses worked to tell me when to push harder in sales, for example.  When to make changes, and when to push me to make them earlier and more decisively.  In the tougher times, someone to tell me to get up off the floor, that we had great customers, a strong product, and good traction — and kick me in the arse the right way.

I know we’ve done the trainer metaphor to death, but it’s the same thing in sports and start-ups.  Very few can get to peak performance without a trainer.  You can push yourself hard without a trainer — but not to max productivity.

And in fact, looking back, twice I did have a CEO trainer, but only for temporary periods, and not by design as a trainer.  But when I had them, I made more progress, more quickly.

P.S.  I think this holds for all founders and VPs as well, not just CEOs.  If they are lucky though, the CEO will act as their trainer.  If they are lucky, and the CEO has the skills.

7 comments

  1. sutoiku

    Excellent article! I could not agree more.

  2. Sounds great, when do you begin your next career as a CEO Trainer to other entrepreneurs, “young jasons”?

  3. Will you be my trainer Jason? Seriously. And thanks for coming by the other day :)

  4. Pingback: Imagine a World With Unlimited Capital, and See Where It Takes You « saastr

  5. Great post Jason. I completely agree with you. I got one of these after about six months in the job, and it’s been incredibly helpful. Biggest benefit: stay focused on the few things that really matter, and spend the majority of your time thinking about and doing those things.

    We have a structured process where we meet quarterly to review results, objectives, constraints, and talent on a quarterly basis, with hour long phone calls in between.

    I can’t imagine what founder or startup CEO wouldn’t benefit from this process.

  6. This is great to hear you used a Trainer, not just a Coach. Too rare I think. Great confirmation here.

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