What is Your Career Strategy?

What is Your Career Strategy?

I’ve taken up a new habit of asking successful people I know: What is your career strategy? I ask it casually, and in person, because I want to see their body language and get a sense of just how front-of-mind their answer might be.

My discovery: when it comes to careers, most folks don’t have a true strategy. I’ve gotten a knitted brow as the immediate response, accompanied by something along the lines of, “Whatd’ya mean?” (Some keep it even simpler: “Huh?”)

The reason I’ve been asking the question is simple: I believe that if you want to increase the odds of professional success, you need a strategy. And that requires you to have a useful way of thinking about strategy.

What Is Strategy?

Strategy means different things to different people. Some define strategy as a vision or a plan. Others define it as optimizing the status quo, or perhaps following “best practices.” Still others deny that strategy is even possible, especially in times of great and rapid change.

I subscribe to the definition of strategy given by Roger Martin, one of the foremost thinkers on strategy and coauthor (with Procter & Gamble CEO A.G. Lafley) of the best-seller Playing to Win: How Strategy Really Works: “Strategy is an integrated cascade of choices that uniquely positions a player in its market to create sustainable advantage and superior value relative to the competition.” (Disclosure: I have worked with Roger helping a shared client for the past two years, and consider him a mentor.)

Before I delve into just what that “integrated cascade” is and how it can apply in the context of a career, it makes sense to unwrap the definition of strategy just a bit in terms non-business school graduates use. A few key points:

1. Career strategy matters for one simple reason: it allows you to focus your resources. The reality is that we do not have unlimited time, attention, energy, and capabilities. Few of us have the luxury of leaving our potential on the table, which will surely be the result of action absent focus.

2. Notice that the concept of planning (a to-do list of actions to be executed and timelines to be met) plays no part in this definition of strategy. We hear the phrase “strategic planning” so often that it has become synonymous with true strategy. It shouldn’t. Strategy is about choices, and choosing. In this view, strategy is not about guaranteeing success, and there is no such thing as a perfect strategy. Reason? Strategy is future-oriented, and if we know anything, it’s that the future is uncertain and we are horrible at predicting it. The best we can do is make thoughtful choices.

The future is uncertain and we are horrible at predicting it. The best we can do is make thoughtful choices.

It’s an important distinction. Making and acting on difficult choices may appear limiting, but in truth frees you to focus your resources on what matters most: winning. With a career strategy, you stop spending energy waffling and deciding and instead can spend more energy advancing your goals. What is true of companies is true of careers: you cannot become great by choosing to simply play. You must choose to win. If you are not constantly angling to win, it’s fairly certain you won’t.

This is by no means a new idea. Michael Porter told us thirty years ago in his definitive book Competitive Strategy that in order to win, you must consciously choose to do some things and not do others. We all like to keep our options open, but attempting to be the jack-of-all-trades yet master of none will limit your ability to create something of remarkable value.

3. The third idea derives from the second: like a business, a career should have a competitive dimension to it. All too often we get career advice that is one-dimensional, and that dimension is internal, e.g. “be the best you can be,” or “follow your passion.” Focusing only inwardly sounds good, but the reality is that we are the CEO of Me, Inc., and there are always others playing in our domain and competing for the same resources we need to advance. We know what happens to a company that chooses to ignore the competition…it is no different for a career.

4. Strategy should be creative and scientific. It involves generating and testing hypotheses. The set of future-oriented choices you draft are really nothing more than a set of best guesses, assumptions, tailor-made to be tested quickly in the wild and adjusted based on results, before you ever lock and load on a new path.

5 Questions for a Career Strategy

In the Roger Martin view, strategy is a thoughtful framework consisting of answers to five questions that are inseparable if you want a true strategy. We’ll use them for the purposes of our careers:

What is my winning aspiration?

A winning aspiration sets the frame for the other questions, and is a future-oriented statement that clearly spells out what winning is for you—concretely, specifically, and ambitiously. It describes the choice you make about what you exist to do and what business you’re really in. It’s not a modest statement, and it doesn’t describe playing to simply play.

Take the renowned illustrator Yuko Shimizu, whose work of which I’m a big fan. One of her illustrations, for the Sunday New York Times Business section, is above. As she revealed in an interview with Dave Benton at 99U, her winning aspiration while toiling away it her previous 11-year career in PR was to be among the most highly respected illustrators in the world. “I really wanted to make it and my name to be known.”

Where will I play?

This question teases out your playing field–specific spaces where you will and will not compete: industries, verticals, specific companies, customer segments, distribution channels, product/service, geography, stage of production…you get the picture. The heart of the five questions is the “where-to-play/how-to-win” combination, which is where I’d recommend anyone contemplating a career shift to focus their attention.

Yuko’s choice was “commercial illustration for hire,” not “fine art illustration.” She targeted advertising agencies and design firms. “[My work] is kind of specific,” she said.”So if the job doesn’t fit in the specific criteria they will call someone who does something a little more general. So it’s a decision you have to make.”

How will I win?

This is your competitive advantage, the unique value you create and deliver. You must support your where-to-play choice with a strong how-to-win choice, which will determine what you will do on your chosen playing field. The two reinforce each other to create a distinctive combination, and are especially helpful for anyone considering a career transition.
In Yuko’s case, she realized that imitating winners in her field was not a winning strategy, and that she must set her self apart with a unique and original style. As she said, “You really have to stand out to get work…I had to stop looking at other illustrators, because if you want to be like them at that point, the best you can be is second best.”

What capabilities do I need?

The choices you make in answering this question bring your where-to-play and how-to-win choices to life. Capabilities are not simply you competencies or strong suit. Competencies are ante to the game, capabilities are the specific current and future activities that, when performed well, help you win in the way you’ve chosen.

There’s a dangerous tendency to simply list your strengths as the capabilities you need. There are two problems with that approach. First, your strengths may or may not give rise to a competitive advantage. Second, they may not be relevant to those to whom you deliver value…your clients, partners, employers, etc.

For example, Yuko would not list “drawing” or “illustrating” as a capability, because, as she said in her interview, “There are a gazillion people who can draw and illustrate.” She might, however, list “self representation.” Her years as a publicist gave her winning capabilities: marketing and promoting, reaching decision-makers, and negotiating. In her words: “I tell people that I would probably make a good illustration agent, as I have the PR background.”

What management systems must I have?

Like any business, running a winning Me, Inc. requires effective systems to build, manage, and maintain your capabilities. Career management is a process, you need a reliable way to reinforce your strategic choices.

Yuko Shimizu has at least one system that does many of these things: teaching at New York’s School of Visual Arts. It’s how she stays current and relevant in the real world, and allows her to consistently generate fresh ideas. “It’s good to go to school and talk to 19-year olds and see what they have to say.”

Strategy’s Magic Question

Your new career strategy seems airtight on paper. You’ve arrived at a winning aspiration. You’ve honed in on an open and attractive segment in which to play. You’ve identified the competitive advantages that will enable you to win in your chosen spaces. You’ve got the capabilities and systems to support your choices.

But as George Patton said, no strategy survives first contact with the enemy. (Or, as Mike Tyson once quipped, “Everyone has a plan until they are punched in the face.”) Generally, that’s because multiple assumptions have been folded in to your strategy—unconscious leaps of faith you’ve made in your natural enthusiasm and optimistic outlook. Who is to say you will even live in the same city? Or maybe an unforeseen technology will be invented in the near future that renders your competitive advantage a commodity.

If not attended to, teased out, made transparent, and tested in the real world, these leaps may indeed become the very blind spots that will render your strategy a fun but ultimately academic thought exercise.

Here’s the thing: your strategy is just a collection of guesses until they’re tested. There is real power in making bold assumptions, because you can turn them into clear hypotheses, and then scientifically test them in a rapid, iterative way.

Done right, your eventual strategy will indeed survive first contact. The key lies in the approach. In my experience, simply making a list of your assumptions doesn’t work, for the simple reason that our assumptions are part of our mental models and biases—they’re so ingrained in our thinking and thus so hard to identify that it takes a tool to lend a bit of objectivity.

We naturally tend to list “known” things for sake of ease and to avoid the risk of looking uncertain. But an assumption by definition is something unknown. And that’s scary. We fear the unknown, and we are reticent to bring it up.

The best technique I’ve found to alchemically turn assumptions into gold amounts to a single but powerful question: What must be true? This, Roger Martin says, is “the most important question in strategy.”

Take a look back at your answers, and ask what must be true for those to be winning choices? You can do a bit of mad-libbing here: “For my where-to-play choice to be winning one, it must be true that______.”

By doing this, you’ll soon have a handful of “best guesses,” each of which is in reality a hypothesis, which you can now test out by getting into learning mode and experimenting.
How about you?

Got a winning strategy for your own career?

(Note: a version of this article first appeared at 99U.)

Free Change Planning Toolkit Access for All*

Wait! Before you go…

Choose how you want the latest innovation content delivered to you:

Matthew E MayMatthew E. May is the author, most recently, of Winning the Brain Game: Fixing the 7 Fatal Flaws of Thinking.

Posted in

Matthew E May




Our Annual Trends Report: Boosting the Possibilities for 2021

By Shawn Nason | February 25, 2021

  I still remember the day we got the email telling us that the in-person version of the 2021 Consumer…

Read More

Controlling the controllables

By Janet Sernack | February 22, 2021

A recent article by McKinsey and Co “COVID-19: Implications for business”  describes a paradoxical dilemma for managers: the need to process both the…

Read More

Leave a Comment