Coaching in the startup tech world has been making the news over the last few years. Turn around and almost every founder seems to have a CEO coach.
There have been best-selling books written on the topic, companies created specifically around coaching (like us), and there’s probably a Hollywood movie around the corner.
It has come to light that the most high-performing founders and CEOs, of the largest companies, all leverage coaching as part of their strategy and success.
But a lot of it is still hidden behind closed doors.
What does a coach help you with, as a founder?
How do you find one?
How much do they cost?
How do you know if they’re good?
I’m going to try and tackle some of these items given what I know about the coaching world, being both an active founder and coach to first-time founders + CEOs.
Why does a startup founder need a coach?
Lebron James reportedly spends $1.5 million on his athletic well-being and performance every year.
That number might not seem like it makes any sense, but if you consider the fact that his ability to perform at the highest level generates hundreds of millions of dollars — in salary, sponsorships, etc… $1.5 million starts to look like a bargain. He does what he needs to do to excel.
Startup founders, especially those in venture backed businesses, are in a similar situation.
The role demands high performance from you, in high pressure and high stakes situations. It also does so in tight timeframes. Like a professional athlete, having a coach on your side increases your likelihood of achieving that high performance and ultimately, improving the likelihood of you and your company’s success.
What you might not know is that the most successful founders often have a team of supporters to lean on and to push them — like other CEOs, therapists, coaches, and so on.
We’re only covering the coach part of the equation below, but the rest are equally as important.
What are the different types of coaches?
There are typically two types of executive coaches that a startup founder will run into:
- A coach who is or has been a CEO
- A coach who has only ever been a coach
There are incredible coaches from both camps and there are tradeoffs that come with both.
Coach who is or has been a CEO
- Pro:
- They’ve been in the trenches, so they can empathize with your situation much more than a person who has not founded a company.
- They might have good feedback about how to be a better CEO.
- Con:
- Because they’ve done the job, it is very easy for them to fall into “the advice trap.” a problem where someone doing active listening might fall into advice-giving that is either wrong, or inappropriate. In most situations, it’s a given that the coach probably know less about the situation than the client, which could lead to wrong advice entirely because they lack context. (Most coaches are aware of this issue.)
- Examples of coaches in this category:
- Bill Campbell (Former CEO of Intuit, coach to Steve Jobs)
- Chad Dickerson (Former CTO/CEO of Etsy)
Coach who has only ever been a coach, not a CEO
- Pro:
- They will often have a more “pure” form of coaching. Lots of active listening and mirroring — empowering them as naturally creative, resourceful and whole, capable of finding answers to their own challenges.
- The best of these will often have many CEOs that they’ve coached, so they can recognize patterns of thinking without prescribing solutions (aka, falling into the advice trap).
- The fact that they’re a professional means their training is likely more thorough, and they’re more dialed in as a coach than the CEO types. Their active listening, awareness, and presence is probably awesome if they are good at what they do.
- Con:
- They don’t know the pressure, decisions, and tradeoffs at a visceral level so it could be harder for them to empathize in a way that’s believable to you. And you may have to explain what a P&L is or something.
- Examples of coaches in this category:
- Ed Batista, Steve Schlafman and lots of others
How will you know which is the right fit for you? You’ll want to take a lot of discovery calls. And be honest with those you speak to that you’re in the exploratory phase with a few different coaches.
A few questions you’ll want to ask your potential coach:
- How many other founders have you coached that were pre/post product-market fit (or at whatever stage you are at)?
- You’ll want them to say a lot of the group that you’re in, because the challenges are distinct.
- Will you and/or have you, coached founders all the way to an IPO?
- How will you challenge me as a coach?
- What kind of clients work best for you? Which are not a match?
Discovery calls will give you an impression of what they’re like to work with. It’s a bit of a sales call, but it’s also about vibe. It’ll be a mutual decision on fit. And fit/vibe is incredibly important because you will be working with this person in a really raw way, ideally for several years.
How much does a founder coach cost?
The short answer: there are wildly differing rates.
It essentially comes down to what people are willing to pay based the value they think they’re getting. And then there’s the basic supply and demand aspect — the most sought after coaches, often have months or year long waiting lists, or they actively reject people most of the time.
Typically, the later stage businesses (series C to IPO), the more expensive it gets. Some coaches will even charge by “stage”, so you pay less at an earlier stage.
Pricing will also correlate to the number of VC backed companies that they’ve worked with and the quality of those companies. It doesn’t equate to quality of the coach, but it does correlate. As a founder, you don’t want to be the biggest fish in a coach’s pond, probably, where they’re learning to coach your level of founder from YOU.
All that being said, let’s get to some real numbers.
In 2013, I paid $300/month for my executive coach at the time, Peter Shallard.
On the far end of the price spectrum, Matt Mochary (CEO Coach to Coinbase, Opendoor, Bolt, and Clearbit and others) charges 5 figures a month and so do many others.
And then there’s a lot in between.
I used to charge my coaching clients $600 USD/hour, with bi-weekly sessions. As of this year, I’ve moved everyone to a monthly retainer.
When you’re signing up with a coach, expect to sign a 3-6 month contract, meeting every 2-4 weeks, paid monthly or quarterly. It’s not often that you see a coach charging on a session by session basis.
Okay, I’m sold. Do you have recommendations for coaches?
Referrals from people you trust are the best way to find a coach. Here are some of the best coaches I know, either personally or via referral by people I trust (personal connection or the a16z CEO list, where this was a recent topic). I hope you find the list helpful.
Directories:
- Lenny’s List of Product Coaches (some of whom also coach CEOs)
Individuals:
- Peter Shallard (I worked with personally) + CommitAction (which is more about accountability catch ups)
- Brian Wang
- Taylor Winters
- Ada Chen Rekhi
- Tim Porterhouse
- Khalid Halim
- Alexis Rask
- Cam Gregg
- Steve Schlafman
- Arielle Schnaidman
- Andy Ellwood
- Pamela Slim
- Micah Baldwin
- Ana Maria Nino-Murcia
- Robyn Ward
- Virginia Bauman
Coaching firms:
Whether you end up getting a coach or not, I hope this was helpful and illuminating as to why you might, how that would look like, and who might be a great fit for you.
As a founder, having a coach in my corner for the last 10 years has been invaluable. Maybe it’ll be a step-change function for you as well.
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