Playing To Win

Your Personal Playing to Win Strategy

How to Make Strategy Choices to Accelerate Your Career

Roger Martin
7 min readMay 24, 2021


Copyright: Roger L. Martin, 2021

I get many questions about the breadth of Playing to Win’s applicability. Does it work for start-ups? Does it work for non-profits? Does it work for functions? (Yes, yes, and yes) But only once have I been asked about Playing to Win for an individual, an insightful question with a broadly applicable answer. So, I decided to dedicate my 34th Playing to Win/Practitioner Insights (PTW/PI) to Your Personal Playing to Win Strategy. (Links for the rest of the PTW/PI series can be found here.)

The Fallacies about the Modern Job

There have been vast changes in the structure of work over the past century. A century ago, nearly 90% of jobs were of a routine nature involving very little room for independent decision-making. These were jobs mainly in the manufacturing and resource sectors — working in a factory or a mine, performing the identical set of clearly prescribed tasks each day. This kind of job hasn’t gone away, although now it is much more likely to be in a service operation — like retailing, health care or fulfillment/customer service. The striking growth has been in jobs requiring a high-degree of independent judgment and decision-making, what my colleague Richard Florida and I term creativity-intensive jobs. They have tripled to almost 40% of jobs and rising. These include professional jobs (lawyers, doctors, accountants, etc.), educational jobs (teachers, scientists, professors), artistic jobs, and all managerial jobs, among others.

For better and worse, many features of job structuring have been maintained from that earlier world. From the world of routine jobs has come full-time jobs with descriptions that primarily detail the activities the incumbent engages in on a consistent basis — largely as if the incumbent held down the door-handle station on the auto assembly line or was a pick-axe wielder in a coal mine.

This produces two consistent anachronisms for the modern creativity-intensive job. If you read any modern job description, it will specify lots of things the incumbent rarely if ever does. And it treats the job as if you do the same elements of the job all the time. Both are holdovers from a time where both of those features were accurate. They aren’t anymore — especially in the business realm. In the modern business world, the incumbent engages in a set of projects that come and go and change constantly. And this is the case especially as you advance in your career.

Your Personal Playing to Win Strategy

Because the modern creativity-intensive job description is more of a catch-all housing for a portfolio of potential projects, there is great scope for strategy choice about how you perform your job. (I will return to argue that it isn’t choiceless for routine-intensive jobs, but I don’t want to overstate the more challenging environment in those jobs.)

Whether you are a lower-level Brand Manager or a higher-level VP-Marketing, there will be lots of things in your job description that you do occasionally or not at all. It might say “design advertising,” which you may well do once a year or “oversee product launches,” which you may do once every few years. I often argue that if you were rigorously audited on whether you do on a regular basis all the things in your job description, you would be fired! As a result, there is enormous room within the vast expanses of your job description to make Where-to-Play (WTP) choices. You could focus on some things within the array more than other things.

Your first reaction might be to think it your boss’s job to define your WTP. And technically it is. But in my experience, most bosses are distracted by the various facets of their own job and/or not very good at defining your WTP. They will give you projects, but not think systematically about your whole job. Think of your boss as you would a distribution channel, laying between you and the end-customer. If you pay attention only to the distribution channel, it may lead you astray. If you ignore the distribution channel and pay attention only to the end-customer, the distribution channel may block your access to the end-customers (or the moral equivalent in this case: fire you). Your WTP strategy choice task is to determine how to best apportion your resources to help your boss serve your joint customers the best you can. That is a big and important choice. For example, it is to spend disproportionately on understanding existing customers or on finding new customer segments or supporting the sales force, or supporting the R&D efforts on your product line, etc.

But it is not an independent choice. It must be tied to your How-to-Win (HTW) choice. You need to think about how across the various potential value adding WTPs that you will be able to produce the highest level of value given your particular set of Capabilities. You will naturally be better at some tasks than others and part of your strategy choice is how to select a HTW that is nicely matched to your potential WTP.

But as with all strategy, the WTP/HTW combination doesn’t have to be restricted only to one possible with current Capabilities. It can necessitate that you to build the necessary Capabilities to Win where you have chosen to Play. And that takes Management System choices that guide you in building the Capabilities that enable you to Win where you want to play. That might be a personal Management System that ensures you are out with customers enough, taking finance classes, spending time with mentors, building a network, and so on. Those won’t necessarily happen without a Management System for doing so.

The final check across the boxes of the Strategy Choice Cascade is the Winning Aspiration. Does this set of WTP/HTW/Capabilities/Management Systems choices produce an outcome that is exciting and motivational for you? If it doesn’t, it is time to rework the set of choices. If it does, then that is your personal Playing to Win strategy.

What about those holding the routine-intensive jobs? To be sure, it is tougher to fashion a personal PTW strategy. I wish that 100% of jobs currently involved a high level of independent judgment and decision-making as a matter of course. But it is going to take a long while to get from 40% of jobs to anywhere near 100%. However, I would still argue that thinking about WTP/HTW in important. There is still a range of optionality across which you can figure out where to spend time versus not.

I will always remember a story my father, who picked peaches as a summer job growing up, told me about the farmer who hired him as one of the handful of other teenagers to pick peaches at his peach farm during the picking season. Prior to the first day, the farmer gathered the boys around and gave them a choice: “The picking day is eight hours. All the other farms around pick from 9 am to 5 pm because the pickers can sleep in and by 9 am the morning dew has dried so that you don’t get your pants soaked. However, I find that the heat by 2 pm is brutal and you are already tired, so the picking isn’t either enjoyable or productive. So, I start at 6 am. The bad news is you have to get up really early and the dew is still heavy from 6 am to nearly 9 am. But you are done by 2 pm, in time for a nice swim. I won’t impose. I will leave you to vote on which to do starting tomorrow am.” My dad and his cohort chose the early start — a great WTP/HTW choice for a very routine job. Strategy is choice and there are always better ones and worse ones.

Practitioner Insights

I suspect the response from some readers will be: “Isn’t this pretty calculating and even bordering on conniving? Shouldn’t you just do your job?” As I have pointed out previously in this series, every organization has a strategy — even if that happens to be an organization of one. It is what you do, not what you say. Your strategy is the choices that you are making. So, you have a strategy for your job. The only choice is whether to make the choices consciously and thoughtfully or let them happen implicitly and incrementally. And if it seems I am framing this as an obvious choice, I am.

It is important that the PTW choices be led by your Winning Aspiration. Never lose sight of that. The only good WTP/HTW choice is one that is consistent with your Winning Aspiration. Just as every corporation needs to define its Winning Aspiration for itself, yours isn’t defined by someone else but by you. That is why it isn’t conniving. It is aspirational. You need to think carefully about the WTP/HTW choices that will best fulfill your Winning Aspiration and will guide you in choosing the Capabilities in which you invest through both formal education and practical experience, and the Management System choices that will help keep your capability-building on track.

Others may be asking: “How can I know that my personal WTP/HTW is correct?” You can’t. No strategy can ever be certainly correct, whether for a person or a business. It is always a judgment call that has two main purposes. First, it is to shorten your odds of success. Careful thinking on strategy can increase the probability of success and clip off the tail of avoidable catastrophes (like this one!) Second, it is to enable speedy course correction. I argue that when choosing strategy, the most important question is What Would Have to be True. An important use of WWHTBT is that after you have decided on your strategy, you can post your WWHTBT in front of you at your desk and check it every morning. If the important things that would have to be true for your personal strategy to succeed aren’t looking particularly true, then you have an early warning that it is time to course correct and think ahead about your next set of strategy choices.



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.