As I boarded the 30-seater plane in subzero temperatures headed for Sydney, Nova Scotia, I developed butterflies in my stomach. Not because I was afraid of flying but because I was scheduled to deliver a full-day workshop on Running Lean to a room full of biotech researchers the next day.

What could I, a software entrepreneur, have to teach these researchers? Software and deep science are worlds apart.

The reason I found myself on that plane was that I had just published my first book of the same title, and when the opportunity to branch out to a wider audience presented itself, I had intellectually jumped on it. Now I wasn’t so sure.

The next day, I decided to focus on just surviving until the first break, then checking in with the organizers to re-assess if/how to carry forward.

I delivered my usual 3-step overview of the Running Lean process:

1. Document your Plan A using a Lean Canvas

2. Identify what’s riskiest, not what’s easiest

3. Systematically test your plan using small and fast experiments

I followed with a few rapid-fire case studies and then called a break.

During the break, several researchers approached me to share how excited they were to see such a simple (and scientific) approach to starting a business — one that matched their worldview perfectly.

We continued with the workshop. The researchers captured their big ideas on a Lean Canvas, and I found myself still able to advise them on risks, experiments, and validation strategy — despite knowing how their solution worked.

Emboldened by this experience, I sought out many more uncomfortable situations where I put myself in domains outside my immediate expertise. I was similarly able to steer and deliver numerous transformative aha moments to attendees by taking a principles-driven versus tactics-driven approach.

This led to my first epiphany:

While tactics show you how, principles tell you why.
Tactics are specific, principles are universal.

A couple of months later, I was delivering another full-day workshop at a well-known startup accelerator. The organizers had inserted a speed-mentoring session during lunch where teams sought advice from a dozen seasoned entrepreneurs and domain experts.

When we resumed the workshop, I asked the teams about the advice they had received. While they were all appreciative, most were paralyzed by what to do next. They all had filled up several pages of very tactical how-to advice from their sessions. Their problem now was prioritizing which advice to follow — especially since much of the advice they had received directly contradicted each other. Who should they follow? Who had the biggest exit or the entrepreneur that made the most sense?

When pressed to choose, I found that the founders often cherry-picked the advice that was easiest to implement and aligned with their way of thinking. The problem with that is what’s riskiest usually isn’t what’s easiest. Choosing to tackle what’s easiest (versus riskiest) wastes needless time, money, and effort on the wrong actions at the wrong time.

I witnessed this same adviser paradox play out at several other accelerators after that. Of course, none of these advisers were intentionally trying to confuse or mislead these founders. They were all well-intentioned experts taking time out of their busy schedules to help these startups.

Yet, they were causing more harm than good.

This led to my next epiphany:

Early-stage uncertainty + Conflicting advice = Aimless wandering

Following the rollout of my book, I started delivering more regular workshops, which put me in positions where I got to see and advise many more teams. It didn’t take long for a common pattern to emerge.

Immediately after teams would present their ideas captured on a Lean Canvas to me, they would ask me what I thought of their idea. While I understood why they were asking, I found that question amusing. If I could tell good ideas from bad ideas just by reviewing a Lean Canvas, I wouldn’t be advising them but running my crystal ball VC firm.

I told them that it wasn’t my job to tell them if their idea was good or bad because nobody can see through the fog of uncertainty that clouds the early stages of an idea. What I could show them instead were fast(er) ways to test whether their idea was good or bad by helping them focus on the right risks and ignoring the rest.

That’s also when I realized that advising and coaching are two very different things. I had arrived at another epiphany:

At the earliest stages of a product, entrepreneurs need coaches not advisers.

I define an advisor as anyone with an impressive enough track record, like a seasoned entrepreneur or a domain expert. A coach, on the other hand, is someone trained to steer a team through the entrepreneurial journey and hold them externally accountable. They do this by constantly optimizing for right action, right time.

To be fair, there is a place for advisers at the early stage — to help startups tactically implement the right action once they’ve been identified, but not before. An analogy here might help.

Think of coaches as primary care physicians (doctors) and advisers as specialists. When you have bad headaches, you don’t schedule an appointment with a neurosurgeon. You start with your primary care physician. They diagnose you and, if warranted, refer you to a specialist.

This same approach works well during the early stages of a product. Instead of pairing teams with dozens of advisers, I find it much more effective to assign teams to a dedicated coach whose job it is to help the team first systematically identify right action, right time, and, if warranted, refer them to an adviser.

This not only drives more focus and accountability but also leads to more repeatable and scalable outcomes.

As I began to coach even more teams, I started developing patterns, diagnostics, and tools to help increase my efficiency and reach. I began to wonder if these coaching meta-skills could be taught to others and started running Coaching Lean workshops.

In the next section, I’ll outline seven key meta-skills we teach.