Why every founder needs a coach

Imagine if your best friend or sibling told you they were going to take up golf.

You ask them how they are going to learn and they reply, "I'm just going to get out on the course and hit some balls!"

It sounds insane. What's your first thought?

"Maybe hire a coach?"

Why do people hire a golf coach? The coach won’t swing the club for them, of course. 

But they do watch and give feedback. They bring knowledge and resources, and they create accountability. In golf or tennis, it’s totally obvious to hire coaches.

But why is it not the same in business? Could there be a more challenging, complex sport than business?!

By my count, I have something like 6+ coaches right now:

1. Dave

2. A nutritionist (Laurie!)

3. A personal trainer (Rock!)

4. A physical therapist (Eric!)

5. Several tennis coaches (Dragan and Terry)

6. And, at different times, more therapist-types (Jean!)

If I want to be the best version of myself, I want to be supported by people who make me better.

From an entrepreneurship and business angle, I get the question VERY frequently so I'll answer it here.

The question is: What will a business coach do for me?

Before I jump in, I’ll give a disclaimer:

Coaches are taught to meet their client where they are, so it’s REALLY important for you to make the most out of your coach.

They will not force things on you — they are not your boss or parent.

YOU need to have a list of things you want to improve, a clear POV for where you want to go and they will support you in getting there.

With that said, here’s what you need to know about having a coach.

Let’s start there.

The best way to find a coach is to ask around from other founders you know who have very positive things to say about their coaches.

If you don’t have other founder friends with recommendations, I’d recommend finding one on The Conscious Leadership Group's website.

Just like any service provider, find three to five different coaches at different price points and meet them.

Coaches can range from $1k on the low end to $10k on the high end per month, which usually includes 2-4 sessions, offline support and, maybe, shadowing or 360 reviews.

One issue most bootstrapped founders think is, “This is my own money. Is it really worth it?”

Yes, it is — if you pick the right coach and do what I'm about to show you. Trust me. Try it for three to six months and see for yourself. Very low downside with huge upside.

Selecting a coach depends a bit on what you’re looking for. I made this 2x2 matrix when I selected a coach.

If you’re a younger founder and a first-time CEO, I suggest going a bit cheaper and more towards a business-oriented coach (they'll help you delegate, organize, think about strategy).

Or maybe, go in between, and find an experienced founder versus professional coach.

If you’re more experienced, go towards someone who is experienced, but more “spiritually-focused” (meaning they’ll help you grow yourself, face your demons, etc. versus giving you business advice).

My coach, Dave Kashen, started me between spirituality and biz. He taught me a ton about running meetings, feedback, etc. He even ran Ampush’s offsites to help my team.

Over time, we shifted right on this matrix toward more spiritual growth and less business help.

He started companies before becoming a coach, and that experience was important to me.

Critically, the x-factor of CHEMISTRY is super, super important.

Do you like this person? Do they fit your style? Do you see yourself being vulnerable with them?

That is very important. If they look right on paper, but you don't feel the chemistry, don't force it. Keep looking.

Ok, so you selected a coach.

I’ve found at least four major things:

Coaches act as a mirror to you to help you build self-awareness.

When I first started coaching, Dave was like, “You use the words ‘should,’ ‘must’ and ‘need’ a lot… Do those feel like energizing/inspiring words to you?”

I had never noticed that. It was a small change, but it changed my communication with my team and my wife!

"Should" was replaced with "like to.” Example: “I’d like to beat this year's revenue target” is so much more inspiring than “I should beat this year's revenue target.”

That’s a tiny example, but a coach will notice and share back patterns across how you work with people, what you stress about, etc. They are an amazing resource.

As a founder/CEO (especially bootstrapped), there really isn’t anyone in your life to help you with your to-dos. If you’re like me, you have a million things either in your head or on random lists that you want to do.

Some dates, maybe. But they never get done. At the end of most coaching sessions, you will say “I want to do X, Y and Z.” Then your coach will say, “OK, great. By when?”

Then they’ll write it down and help hold you to it.

A good coach has lots of clients, sees a lot of things and reads a lot.

They are usually personal growth-focused themselves, so they bring a TON of frameworks, examples and dot connections.

It’s hugely valuable to grow as a leader. I’d guess close to HALF of what I share came from Dave’s teachings.

They are the only person in your life you can share ANYTHING with, and there are no judgments: co-founder issues, family issues, personal stuff… Whatever.

Sometimes it's just great to have a place to share those things.

They are, typically, amazing listeners and question-askers, and that is so valuable when processing the insane journey of building a company.

One FAQ I often get is what’s the difference between a therapist and a coach?

My understanding is that therapy tends to be more backward-looking with a focus on understanding. Coaching is forward-looking with a focus on action.

That brings up a potential fifth thing: A vision enabler.

Coaches often start with, “So, what is your dream for one year from now?” And they really help you do all the things to accomplish that vision.

OK, so we know how to select a coach and what a coach does. HOW do you get the most out of your experience?

This is the one I see many people get wrong. They walk into a coaching session, don’t have much to ask or share and then feel like there isn’t much value to coaching.

As I said above, coaches are taught to MEET you where you are and SUPPORT you.

So if you don’t have items you want to work on or goals to achieve, the coach isn’t going to tell you what to do. THEY ARE NOT AN ADVISOR.

So come prepared with a few items, have a vision for yourself and drive the sessions YOURSELF.

My early focuses were on being a better leader and having less emotional ups and downs.

Another classic mistake. You pay someone a ton of money and then you hold back 50% of your truth, your thoughts, etc because you’re afraid they’ll judge you.

Then, you get little value. Of course, it takes time to build trust with someone, but push yourself to share as much as you can and get 20% out of your comfort zone.

If not, it's like going to a golf pro and being like, “Sorry, I don’t want to swing in front of you.” They just can’t help.

I mean this in multiple ways. Do it for AT LEAST six months. Pay upfront if you don’t like the meter running. Don’t reschedule. This is your time to invest in you.

And talk to your coach between sessions — communicate with them, explain the business and bring them along. Make them part of your workflow.

This relates to committing, and it shows up in two primary forms:

• Read the books, videos etc that your coach suggests. If you don’t educate yourself, you won’t actually internalize how this works

• When you say you will do something, do it. Tough conversations, waking up at a certain time, no longer criticizing your team — whatever it is. Do the work.

Like with weightlifting, if you don’t keep ticking up on the amount of weight and reps, you won’t grow.

What that means is, as you accomplish your first few goals, take on bigger and different challenges. Push yourself and your coach to help you get to the next level.

So there you have it: a practical guide to using coaches.

If you’ve had a coach, tell me something I missed and I’ll share it with the whole community.

Have a great week everyone!

jesse