I have been coaching entrepreneurs for about 10 years now. Before that I was making theatre performances. These two big streams of life have informed my practice as a coach for entrepreneurs. I have been asked to analyse what I do, so here it is.

COACHING JOBS TO BE DONE

Establish trust. If the team does not trust the coach, they will not authentically collaborate.

Make things. Run experiments. Do stuff. Stop people talking all day long.

Activate emotional labour. Get teams frickin’ loving what they do and passionate about their work.

Smash through crap (excuses, fear, permission, expectations) and be there on the other side to help them land.

Unblocking traction.

Be the unspoken voice. “Give me your pitch and I’ll tell you what the investor is privately thinking (instead of listening to you) at the end of each component.”

PREPARATION

Here’s how I train.

I work a lot with founders. I spend time listening to them. I do that a lot. No secret sauce there but this is, in the end, the most important work out for a startup coach.

I devour stuff that teaches me new ways of thinking. I read. I read books about music, acting, programming, business, science. I read the newspaper every day so that the work I do has a relevancy. I speak with weird people.

More importantly, I let my mind make connections between unrelated things. “What if…” is my favourite start to a sentence. My theatre background taught me a lot about this.

“What if you were stuck to that chair while you say that?”

“What if we try that in complete darkness?”

“What if each section of the soundtrack was inspired by the Periodic Table? Number of atoms = number of notes that can be used?”

The context forces creativity. Applying this to venture building…

“What if carparks full of electric cars became power stations?”

“What if we try that experiment again but in Jakarta?”

“What if we design the UX for this finance app so that a 6 year old knows what to do?”

I call this X-Learning. It is why my notebooks are full of exploding mind maps rather than neat notes (which I wish I could take). Make surprising connections and get the brain ready to do it on the fly when I coach.

MINDSET

Here’s my mindset when I am in a coaching session.

I listen more than I talk. When I am listening, I show that I am listening.

I tell stories about things I have experienced and then try not to follow up with “So what you need to do is…” because that simplifies the learning. I let the founder make their own connection where I can. Connect it to their own work and problems.

I empathise with them. It is hard being a founder. It is hard learning new habits such as Startup Science. Know when to stop. When to push.

I believe that DONE is better than PERFECT. If I have shared a new skill and it is not perfectly executed that is fine.

I like to see creative sparks. Even if it is not immediately clear why this is valuable. Try the opposite. What is an image that communicates what you are thinking? What is your soundtrack?

I balance the scales of brutal (and often vulnerable) honesty and hope. There is no value for anyone in not saying things because it might be hurtful but we must always end the conversation with hope.

I smile a lot. No one wants to talk to a flat or serious stare. No one wants to feel judged.

Even though much of our work is focused on discovery of a customer <> problem fit I find that imagining the solution can be a great unblocker. Founders can get stuck in a loop failing to find something valuable. Asking them to describe (or build) a solution and then reverse engineering the problem/customer can release the creative juices. Also, when describing a business to other people, a thousand words can be replaced by showing them.

I have hypotheses and state them as clearly as possible. “This is what I think is true”. This puts a clarity stake in the ground that activity can follow from. I work hard to not present a hypothesis as a truth.

I will do work with someone I am coaching. I avoid lecturing and then asking them to show me their work. I’d rather do it together. Like a team.

I am not their manager. I am not in charge. I am not the decision maker. They are.

I am comfortable with founders receiving conflicting feedback, as long as they don’t spend ages then discussing the merits of both directions, as long as they don’t get cross as though there was some universal truth, as long as they are willing to test both. Always happy to help.

NEW TEAM ORIENTATION & SCOPING

The job of the first meeting is to establish velocity and trust. If we don’t leave the first meeting with them in place, we probably won’t get them.

In the first meeting I want to know where the team sits on these two spectrums. Knower <> Learner. Doer <> Talker.

Establish a common framework such as the lean canvas for us all to describe what we are doing in a consistent way.

FRAMING BAD NEWS

Bad news is the secret weapon of an entrepreneur. It is our ‘selfish gene’ – it is natural selection for ideas. An experiment fails. A co-founder leaves. An investor pulls out. It makes us stronger. We adapt.

Be there for them.

Don’t leave the conversation without a list of next steps.

WORDS AND PHRASES

What if…

How will you test that?

What did you learn?

Did anything surprise you?

What does it remind you of?

Can it be bigger?

Can it be smaller?

What could you do in 3 hours?

Who can help you?

How can I help you?

What is your #nofail goal?

Would you take out a mortgage on your house and put $50K into this idea right now? What do you need to find out before you do?

OPENING AND CLOSING THINKING/ACTION

Start a new canvas with a single cell completed.

Show. Do. Demo.

Patterns. We have a few. E.g. Standup: What did you learn, what do you intend to learn what’s blocking you? E.g. Lessons Learned: What surprised you, what do you need to find out, what changed?