It began as a mistake

Robin Wong
8 min readNov 21, 2020

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Fortune favours the bold, but it also favours those who can spot risks and manage them effectively. The boldest and most fortunate are great at identifying and avoiding “Leaps of faith”. Here’s how to identify your leaps of faith and make better business decisions.

Don’t believe your own hype, no matter how great you’ve been in the past.

Photo by Varvara Grabova on Unsplash

Over the course of my career, I’ve been fortunate to work with many smart and talented people on ventures that have been both bold and successful.

I’ve also embarked on several bold ventures that didn’t pay off and with the benefit of hindsight and reflection, I took some pretty massive leaps of faith on some of those failures.

Those leaps of faith led to a lot of wasted time and effort — Working in “stealth mode”, plotting late into the night about how awesome it was going to be, creating and polishing experiences packed with features that I’d convinced myself and those around me were a great idea.

But, when I eventually launched that “ground-breaking idea”, the reality was that people simply weren’t interested in what we’d had to offer.

I had jumped to a solution I had assumed was the right answer to a problem.

But the problem didn’t even exist. It was a trick of the mind.

How could I have got it so wrong?

Assume you’re wrong

To be fair to myself and anyone else who has fallen into this kind of trap, we’re the unwitting victims of how our brains have evolved. Framing situations too narrowly and Confirmation bias are part of how our brains are wired, and they are easily done unintentionally.

So to hack the problem, I stick to a principle whenever I start out on something new.

Principle #1 Always start by assuming you are wrong about everything.

So if that’s my starting point, how do I go about proving that I’m right?

The key to being right is building a foundation of verifiable facts about what happens now that can’t be disputed. Because if you’re armed with this knowledge, you can start to truly understand why something happens and this kind of insight gives you an advantage to solving a real problem.

The way to start building this foundation of facts is to obsess over the problem and not the solution.

Obsess over the problem

By obsessing over all the details of a problem or challenge, you can start to work out whether you have any evidence to back up your beliefs.

If you’ve got some reliable evidence then great. Your belief is a conclusion.

Place that conclusion into your foundation.

If you don’t have any evidence then you have an assumption on your hands, and that’s something you’re going to need to test.

If you don’t test that assumption, you’re at risk of putting a critical weakness in your foundations. One that could make it tumble down later.

Beware though, sometimes assumptions can look like facts, especially when they are opinions that come from someone who appears knowledgeable.

So here’s another principle that comes in handy.

Principle #2 Data trumps opinion

Without evidence to back them up, opinions — however well-intentioned and experienced the person offering it is — are still guesses, and not a great basis to make decisions on.

But we can’t hang around delving into every part of the problem forever, otherwise, we’ll end in up analysis paralysis.

We should always have a bias towards action so we actually get to solving the problem, so the trick is to focus on identifying the biggest and riskiest assumptions, and testing those.

Leaps of Faith

The riskiest category of assumption is what is called the Leap of faith.

Photo by Angelo Pantazis on Unsplash

It’s a kind of assumption that is so important and so foundational to your idea that if you’re wrong about it, it’s game over before you even start.

For example, diving off a rock into the sea without knowing how deep it is can be lethal.

So it’s critical we identify our leaps of faith and test them early on so we can build a solid foundation for our ideas and avoid making regrettable decisions.

To do this, we’ll need the help of as many people involved with our perceived problem or challenge as possible, as they will all have different views and experiences to draw from that we can use to build a rich model of what really happens right now. Armed with that information, we can start collecting useful clues and evidence that will give us insights that will help us make better decisions.

Building shared understanding

To help get off on the right foot, I like to use a Problem Statement to frame what I believe is happening right now and use it as a way to get the conversation going and get feedback on my own beliefs.

Problem statement example

This technique is useful because it starts to break down what everyone believes as well, and these beliefs can be grouped into themes which I can then use to build up a model of the world, which I can use as “springboards” into further questions and research activities.

The kind of questions I like to ask people after introducing a problem statement include -

  • Who is the central character or customer?
  • What are they trying to achieve?
  • What gets in their way and how can I verify this?
  • What’s the knock-on effects of the situation for others?
  • Who else is involved and how do they interact with our central character?

I like to jot these down in and start to form them into a visual story, or a Story Map, that builds a shared understanding of how a situation unfolds.

Here’s an example of a story map with all of the key ingredients for an imaginary business startup called WonderFit that supplies diagnostic tests and exercise regimes for people with Diabetes. The story covers all of the key elements including

  • A central character
  • A starting point
  • An ending with a clear outcome
  • A storyline with involving interactions with various people along the way
A story map illustration

What you’re trying to achieve with your story map is something simple enough that everyone can relate to, but not too detailed that you end up going down a rabbit hole.

By focusing the steps of the story on around 10–15 interactions that take place from start to finish, you can keep your map at a high enough level to start working out what you know to be true and what you assume to be true.

Assumption mapping

Once you have a User Story map that everyone agrees on, you can start to discuss where you think problems exist for the people involved, prompting everyone to back up their beliefs with data as they do so.

Useful questions to ask include

  • What’s the trigger point for the central character to start their journey?
  • What gets in their way?
  • Why do you think that is?
  • What takes the most time?
  • What prompts people to take a certain action?

By plotting people’s assumptions onto your collective story map, you can start to build a shared understanding of the gaps in the group’s knowledge, and you can start to help your group gain a stronger sense of perspective.

Story map with assumptions layered on top

This perspective will come in handy next when you start to prioritise your assumptions and work out which ones are your leaps of faith using an Assumptions Map.

Assumption Map

Once you’ve captured enough assumptions about what happens now, it’s essential to be clear about which of your assumptions you have evidence to back up, and what you collectively believe to be most important and foundational.

Go through each assumption one by one and split them into 2 groups.

Assumptions grouped based on evidence

The first grouping will be assumptions that someone in the group has evidence to support. This changes them into verifiable facts that can form part of your foundations.

The second group are those that have no evidence, these remain as assumptions, and are candidates for testing.

But remember, we want a bias towards action, so we want to focus on the most important of these, our leaps of faith, so the next step is to vote in your group on what’s important.

This should then allow you to move everything into one of four quadrants.

Leaps of faith on the top right

For now, we’ll ignore the bottom two quadrants, let’s focus on the important ones.

The top left quadrant should contain your evidence-based facts that you consider being important. In theory, you can start to make decisions about these, but…

That’s risky.

Because on the top right quadrant, you have important assumptions that you have no evidence for. Your Leaps of faith.

Testing, Testing

The name of the game now is to turn those assumptions into hypotheses that you can test, and see if you can move them into the top left quadrant, or uncover a new fact that might offer you insight on which to base your decisions.

But the key thing at this stage is that you’ve avoided making a mistake right at the start. You’ve avoided a Leap of faith.

Next, we’ll look at how to test hypotheses and uncover actionable insights.

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Robin Wong
Robin Wong

Written by Robin Wong

I help people turn ideas into human- and humanity-centric ventures. Global Head of Service Design at BT.

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