My work here is wrapped around the idea of “Striving Strategically”. Put simply, this title is a two-word reduction of the broader axiom “Work smarter not harder”. But deeper still, the origins stem from a quote by the philosopher Kwame Anthony Appiah, by way of Graham Duncan:

“In life the challenge is not so much to figure out how best to play the game; the challenge is to figure out what game you’re playing.”

And this week’s book compels me to add another line. Appiah is right: the challenge is to figure out what game you’re playing and, in addition, what it means to win it. Because true to our book’s title, the challenge is to adopt the mentality that we are Playing to Win.

Playing to Win is co-written by the former CEO of Proctor and Gamble and the Dean of the Rotman School of Management at the University of Toronto. It is a very accessible introduction to strategy and is a great precursor to the best book in the category, Richard Rumelt’s Good Strategy, Bad Strategy. I say precursor because this week’s book really does lay a beautiful foundation with their framework of “cascading choices” that we’ll study. Then there is the clarity of language. These guys talk the brass tacks, starting with an opening salvo that hits me pretty hard. It reads as follows:

“What matters is winning. Great organizations choose to win rather than simply play.”

Win what? Well, that depends. No organization can really choose to defeat Apple or Amazon. Not tomorrow, anyway, and certainly not with the initial strategy they devise. In either case, it really hits me hard to read the sentence “What matters is winning.”

How many of us work in organizations that are truly focused on “winning” anything?

Consider the ending phrase of the quote: “… simply play”. The vast majority of organizations seem to adopt this approach—sometimes deliberately, often subconsciously. They are spectacularly mediocre groups that are, at best, “just fine” or “not bad”. They roll along on the momentum of one or two big products or clients and keep to the standard more-of-the-same growth opportunities.

I’ve worked in those places. The experience is like playing soccer on a field with no goals. It gets pretty boring pretty fast.

We are prone to “simply play” in most arenas. We have to. I see no need to be THE BEST when it comes to washing dishes or writing emails. This is where we find an intersection between the line from our book and the message from philosopher Appiah. Great organizations “choose to win”. But they don’t try to win at everything.

They might not even try to win the whole market! Companies like Basecamp and Zappos want to win in many pursuits, be it workplace culture or customer service. But they aren’t trying to become a monopoly. There are countless ways we can define excellence and endgame.

The point is that there is a choice that beckons us in the work we do. The choice is “I can’t be the best at everything but I can be the best at this.” Whatever this is, the pursuit of winning at that particular game is what makes the journey the reward—regardless of whether or not you actually do “win”.

This is easily understood in sports. People give their time and money and energy to chase $20 trophies. They call it fun. I think we know why.

Nothing enlivens the conventional workplace like having a genuine pursuit for everyone to work towards together. It could be a meaningless trophy to others but it’s powerful trophy to them. This is the stuff of Charles Schwab’s “Big Number 6” and Tobias Lutke’s great line “Everyone wants to be on an epic journey with their friends.”

The pursuit of winning captures that. All it takes a few clear, difficult choices.

Because beyond the slot machine, winning doesn’t happen by mistake. So we must choose the game, choose to win, and play accordingly. This week’s book will help. Not just in business, either. Nor in mere competition. We’ll broaden the ideas because Strategy (with a capital S) applies to everything.

Image provided by David Luders