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Coaching Versus Advising

👋 Hi there - I’m Ash. I share battle-tested recipes, strategies, and how-tos for systematically building repeatable and scalable business models delivered to your inbox every week.

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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.

Meta-skill #1: Coaches focus on asking the right questions versus being right.

The true job of a startup is finding a working business model before running out of resources. The key to doing this effectively is correctly diagnosing the riskiest assumptions in a business model.

Too many people (and advisers) simply guess. Sure, our judgment improves with experience, but educated guessing is still guessing, and there’s too much at stake when we simply guess.

Incorrect prioritization of risk is one of the top killers of startups.

The best way to uncover what’s riskiest is to discover it. You do this by asking the right questions to uncover the root causes of problems holding the business model back versus prematurely doling out prescriptive solutions or tactics.

Problems, not solutions, create spaces for innovation.

Meta-skill #2: Coaches use standard tools to baseline teams.

Sticking with the general practitioner analogy, imagine seeing ten doctors about your headaches and getting ten completely different prescriptions. Which would you follow?

The good news is that, barring complicated cases, most doctors generally arrive at the same diagnosis after running a few standard tests. Coaching should be held to the same bar.

While every startup is different in its way, when viewed at a meta-level, they all share the same goal: To build a repeatable and scalable business model. All business models have customers, all customers have problems, etc.

It is, therefore, possible to devise a set of standard diagnostics to baseline teams and systematically identify what’s riskiest in the business model. As I outlined above, this is the single most important step in keeping the startup focused on right action, right time.

In the Continuous Innovation Framework, we use three standard tools to baseline a startup:

  1. A Lean Canvas to describe the overall business model story,
  2. A Customer Factory to measure key metrics, and
  3. A Customer Forces model for understanding customer behavior.

I’ll cover these models and diagnostics in future posts.

Meta-skill #3: Coaches study validation patterns.

In addition to standard diagnostics, a coach uses a pattern language to navigate extreme uncertainty.

When a grandmaster looks at a chess board, they don’t see individual chess pieces but patterns. Similarly, when an experienced coach looks at a Lean Canvas, they don’t see individual assumptions but business model patterns.

Patterns help codify what’s worked before.

Patterns are heavily used in chess, architecture, design, science, and software. The same is true with entrepreneurship.

Meta-skill #4: Coaches use the Socratic Method to discover how teams think.

The biggest challenge with getting teams to follow through on advice often requires getting them to overcome their own biases. This requires one or more mindset changes.

The problem here is that mindset change is immune to lecturing. If you simply ask teams to do something they don’t want to do, like talking to customers or selling before building, they ignore you.

You can lead a horse to water, but you can’t make it drink.

The first step to causing a mindset change is first understanding the team’s or founder’s current mindset. Next, you have to trigger them to want to change by breaking their old way and making a case for a better new way. This requires further discovery and using different tactics based on what you find.

Meta-skill #5: Coaches design for behavior change.

Depending on the team’s coachability and receptivity to change, it is sometimes possible to trigger them to adopt a new way simply through conversation. More often, though, you need to design for behavior change using something I call the Judo strategy.

In Judo, when faced with a larger opponent charging at you, you don’t stand your ground and try to block them but instead, aim to get them off balance.

Similarly, when faced with a ZEBRA team that fails to see why they need to change their validation strategy, it is often more effective not to slow them down but to instead make them go faster.

ZEBRA: Zero evidence but really arrogant.

The key to making this work is designing an experiment that aligns with something the team wants, like fundraising, versus something you think they need, like interviewing customers. If/when the experiment fails, it creates a trigger for mindset change.

I’ll share examples of specific scenarios and experiments in a future post.

Meta-skill #6: Coaches are evidence-driven.

While tempting to rely on your experience and instincts to prescribe experiments, a coach must stay humble and recognize that what may have worked last year may not work today.

Rather than prematurely jumping to prescriptive experiments (tactics), it is best to adopt a lean DIET approach.

lean DIET: Discovery - Insights - Experiments - Traction

In other words, problem discovery is often the best first course of action to identify root causes and true risks, not rushing to test hypotheses. Remember that hypothesis is just a fancy word for guessing.

Meta-skill #7: Coaches invest in team learning.

Even in cases when the problem and solution are obvious to you, a coach should strive to help the teams derive the solution on their own, either through analysis or experiment. This helps instill critical thinking and problem-solving skills — which are key to developing a learning mindset.

Your job is to teach your teams how to fish, not fish for them. Sure, it will sometimes be necessary to demonstrate how to perform a certain skill, but more often, it will be far more effective to have your teams perform the skill to the best of their ability. Then coach them on how to do it better.


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