Playing To Win

Becoming a Better Strategist

Fake It Till you Make It

Roger Martin
8 min readSep 19, 2022


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Several weeks back, I wrote my Medium piece on the mindset and skills of a great strategist. I have learned by now that it is hard to tell in advance what will resonate or not, and this one resonated to an extent I didn’t predict. In doing so, it generated a host of questions and requests for more detail on how to build the requisite mindset and skills. In response, I decided to dedicate my 47th Year II Playing to Win/Practitioner Insights (PTW/PI) piece to Becoming a Better Strategist: Fake It Till You Make It. You can find the previous 99 PTW/PI here.

That means, for those of you keeping track, this is my 100th PTW/PI. I did 53 straight weeks (52 weeks plus a Year I wrap-up piece), then took three weeks off from the series, and just finished my 47th Year II piece. I never imagined I would hit triple-digits when I got started on October 5, 2020!

Background and Approach

In the aforementioned piece, I argued that to be a great strategist, you need to adopt three mindsets (strategy starts with customers; it involves operating and choosing in a complex adaptive system; and it embraces inventing the future) and possess three requisite skills (qualitative appreciation; dialogue; and juggling more balls).

There is a little bit of chicken/egg challenge here because without the requisite mindset, it isn’t obvious that a person should work on the skills, and without the requisite skills, it is a stretch to embrace the mindsets.

For that reason, I take a page out of the ‘fake it till you make it’ doctrine. While it sounds pretty frivolous, its origin stems from the thinking of one of America’s greatest philosophers, William James, who was a member of a trio American Pragmatist Philosophers (the others being Charles Sanders Peirce and John Dewey) that has been among the greatest influencers of my thinking. Way back in 1922, he wrote: “Action seems to follow feeling, but really action and feeling go together; and by regulating the action, which is under the more direct control of the will, we can indirectly regulate the feeling, which is not.”

When I am working to help people become better strategists, I don’t spend a lot of time getting them to believe that the mindsets and skills are exactly as I say and must be adopted. I just get them to practice with actions that get them more comfortable with the mindset and build the skills, per James.

The Three Mindsets

These are my recommended actions that will lead you to build the strength of your strategic mindset across the three dimensions.

Strategy Starts with Customers

Use every opportunity to talk to customers — both end-customers and channel (if your business sells through a channel). You don’t have to be at all formal or scientific about it. Make it easy to get started by doing it in a comfortable situation. If you have stores, wander a few of them talking to customers. If you are B2B, tag along with salespeople. Don’t have an agenda. Just soak in the customer thoughts, reactions, and behaviors.

I will always think fondly about my summers as a young teen working in my dad’s animal feed company. The most useful thing I could do was to accompany the truck drivers as they delivered bags of feed to farmers. I wasn’t yet big or strong enough to carry 100 lb. burlap bags of feed, but I could drag them from the interior of the box truck to the back edge so that the truck driver could stack them onto a bag cart and roll the feed bags to the location in the barn where the farmer wanted them. I got to talk to lots of farmers and developed a keen understanding of what really mattered to them.

When you get around to doing strategy, keep those customer interactions front of mind. Ask yourself: Would customers be happy that I am considering this or that decision? Or would they wonder why I am wasting my time on something that will never matter to them? Keeping customers in mind will ground your strategy work in the most effective way.

Strategy Involves Operating and Choosing in a Complex Adaptive System

This is a bit trickier because this mindset is quite abstract. Here my main goal is to help budding strategists stop beating themselves up for being unable to predict the future with as much accuracy as they think they should be able to achieve. They have all been educated to believe if they just crunch the data, they will be able to make a data-based decision about the future, and because it is data-based, it will be accurate. This is, of course, popular hogwash: complex adaptive systems don’t work that way.

So, I encourage them to see everything they do as tweaking, watching the results, tweaking, watching, tweaking, etc. That will help them internalize that their choices neither must nor can be perfect, but that is just fine.

Strategy Embraces Inventing the Future

To get strategists more comfortable with inventing the future, I encourage the practice of always reverse-engineering the status quo by asking the most important question in strategy: What Would Have to be True (WWHTBT)? Most people who follow my strategy methodology will ask WWHTBT with respect to future possibilities — and in doing so unearth the risks that they must counter in order to choose a new possibility. The downside to this otherwise helpful practice is that it can implicitly cause the user to believe future possibilities are riskier than the continuation of the status quo.

However, if you also ask WWHTBT going forward for the status quo choice to be sound, you will learn that continuing the status quo is often as risky as shifting to a different strategy possibility. In fact, when I do this with clients, after reverse-engineering it, they often eliminate the status quo because the risk of the things that would have to be true actually being true is so high that inventing the future is obviously less risky.

Hence, if you make a practice of reverse-engineering the status quo, you will provide yourself the encouragement to invent the future, even if that entails needing to make something true in the future that is not currently true. But that is the highest leverage job of the strategist — to make true something that is currently not true.

The Three Skills

These are my recommended actions that will lead you to strengthen your three key strategy skills.

Qualitative Appreciation Skills

Practice being a data omnivore. Businesspeople are taught to be the moral equivalent of a carnivore, by which the only legitimate data to consume is statistically significant quantitative data. That makes for poor strategists because you can’t invent the future by regressing data from the past; you can only extrapolate the past into the future.

The task here is a bit like following the Healthy Eating Pyramid, which is based on the notion that only by eating a balanced diet that includes fruits, vegetables, grains, fish, poultry, etc. will your nutrition contribute positively to your health. Paying attention solely to statistically significant quantitative data is the moral equivalent of eating a diet exclusively of red meat (and getting high disease) or tuna (and getting mercury poisoning).

Instead, practice seeking out and consuming all forms of data. This includes data that is qualitative in nature. It includes data from other domains than the one in which you are making decisions. And it includes quantitative data that is not statistically significant — including single occurrences. That may seem pointless but Jim March, one of the greatest management scholars of all time, begs to differ in his paper Learning from Samples of One or Fewer.

In each case, consider the data in question and practice drawing inferences from it. Keep practicing until you become a data omnivore and in strategy, you will outperform your carnivorous colleagues.

Dialogue Skills

Strategy is a team sport in which better strategic decisions arrive out of productive interpretations of diverse data and insights. Force yourself to learn how to integrate multiple views into your strategy-making by never engaging in strategy work alone. And I mean: never. That is what will get you the dialogue practice you need.

Start with people with whom you find easiest to engage in strategy dialogue, like closer colleagues or friendly customers. Then as that becomes comfortable, move out to tougher customers and colleagues with whom you don’t see eye to eye. And as you practice, focus on how you can integrate their views into your thoughts on the strategy at hand.

While doing so, practice inquiry as frequently as you engage in advocacy. Dialogue is a two-way street, otherwise it would be called ‘monologue.’ And that means asking the questions that help you ferret out insights that aren’t currently in your head. It means encouraging your dialogue partners to share rather than make them listen incessantly to your point of view.

Skill in Juggling More Balls

Not unlike the second mindset, this skill is tricky because it is an abstract idea. Great strategy comes from considering more features of the strategy landscape as you are coming up with your choices. I would argue that Steve Jobs wasn’t significantly better than his competitors at understanding the variables that his competitors were considering. Instead, his superpower was pondering the impact of variables that his competitors weren’t even thinking about. He wasn’t just thinking about how his Mp3 player worked. He was thinking about how users would want to get songs onto their Mp3 player. He wasn’t just thinking about the processing speed of his smartphone. He was thinking about how its rounded corners would feel in the user’s hand and what impact that would have.

On this front, it is difficult to know what you don’t know. So, practice going on category treasure hunts. As you are contemplating a strategy choice, write down all the features you are thinking about — e.g., customers, competitors, recent activity in the market, etc. Then seek out a diverse set of dialogue partners and don’t ask them for their answers to your strategy problem, but what categories they would make certain to consider if they were working on it. There is a very good chance you will get one or two good ideas for more balls to juggle while you consider your choice.

If you practice this repeatedly, you will get insights as to the additional categories you should keep more closely in mind every time you consider a strategy choice.

Practitioner Insights

As I have said before, I still haven’t met anyone who is a great natural strategist. The great ones are great because they have practiced so as to develop their capabilities. To the extent that I am a good strategist, it is because I have practiced for four decades.

Spend lots of time with customers, get used to continuously tweaking decisions to migrate towards perfection rather than attempting to leapfrog directly to it, reverse-engineer the status quo to embolden you in creating the future, become a data omnivore, take full advantage of the views of others, and engage in category treasure hunts.

These actions will build the mindset and skills that will make you an ever-better strategist. Don’t be discouraged or feel your current limitations are fixed. With practice, the sky is literally the limit!



Roger Martin

Professor Roger Martin is a writer, strategy advisor and in 2017 was named the #1 management thinker in world. He is also former Dean of the Rotman School.