The Dark Side of Strategy

Matthew E. May
4 min readJun 21, 2019

Can You Separate Strategy From the Strategist? The Unfortunate Answer.

There’s a meme that’s been floating around for some time: “Culture eats strategy for lunch.” As with most memes, it’s rather silly. But what makes anything comical is the presence of some kernel of truth.

To set strategy against culture is obviously nonsensical: Culture at its root is the product of choices that have been made by those with the power to shape how the organization is run; and if we know anything, it’s that strategy is about choosing to do some things, and not do others. In reality strategy and culture share a meal.

But I believe the kernel of reality within the meme is that there is in fact a dark side to strategy, an unfortunate truth, and it is this: strategy all too often follows the strategist. In other words, a strategy and its creator are all too easily separated.

Recently I had the chance to chat with my friend and mentor Roger Martin (coauthor of Playing to Win: How Strategy Really Works) on this very topic. Roger and I share a passion for tennis, and one of the biggest tennis tournaments of the year — the Miami Open — was in its final weekend, with the potential for an all-Canadian men’s final. Now, most people know Roger is Canadian, but not everyone knows how involved he has been in setting the direction of professional tennis development in Canada. (Here’s an article on how his Playing to Win strategic choice framework influenced Canadian tennis.)

A Canadian woman had just won the title of another huge tournament — Indian Wells. It occurred to me that the strategy he had put in motion years earlier was now hitting Main Street. So I sent him a quick note:

“Roger, looks like the Canadian tennis strategy is paying dividends….here’s to hoping for an all-Canadian Miami men’s final!”

Roger: “Hey Matt. Great to hear from you. Indeed it has been a great time for Tennis Canada. With Bianca [Andreescu] at Indian Wells and Shapo [Denis Shapovalov] and Felix [Auger Aliassime] in Miami.”

Then the other shoe dropped.

“But don’t get too used to it,” he continued. “These are the final three players that were produced in the system governed by the strategy that four of us put in place in 2005 and enforced ruthlessly for nine years (nine because it was the time of three consecutive chairs, each of whom was part of the gang of four). After I stepped down as chair (third of the three), management and the board went Bolshy and watered down the precision and force of the strategy. After Milos/Vasek/Eugenie [Milos Raonic, Vasek Pospisil, Eugenie Bouchard] and those three, we have almost nothing behind. The only Canadian over 12 with a chance for you to hear about them is Leylah Fernandez — and she is only 9th in ITF as a 16 year old. And you know that on the girls side, that isn’t good enough to be a likely top 50 player at your professional peak.

“Strategy matters my friend. And Bianca, Shapo and Felix know that!”

That saddened me, and I told Roger so: “Sad to hear…and the lesson keeps banging me on the head about strategy, and the unfortunate truth that it seems to travel with the strategist. New regime, needing to put their fingerprint on things, so easily toss out the former strategy in the face of undeniable success.”

His next comment gets to the heart of the matter:

“You have put your finger on my biggest angst right about now. I helped create and then enforce a strategy for The Monitor Group that was far, far, far from the norm. I was the only one in the company that fought to make sure that we didn’t go-to-market in industry specialist groups — because the only way to become a good strategist is to work across industries — and to not use case interviews in recruiting, because they get you the wrong people, not the right ones. Both choices kept us distinct and we were flying high as of August 31, 1998 when I left [to become Dean of U. Toronto’s Rotman School]. Within a month of my departure, Monitor had industry practices and case interviews. Monitor now had to compete head to head with bigger firms — with no distinctiveness. And it was sold out of bankruptcy in 2013.”

He went on:

“I was the co-creator and enforcer of the Tennis Canada strategy. And it has been watered down. And as Dean, I was the creator and enforcer of the Rotman School strategy — which was unique from everybody else and made us the School that everyone identified as having moved up the most between 1998–2013. Since I stepped down, every plank of uniqueness has been destroyed. Basically my life’s work has been to lead really boldly and (thankfully) successfully only to have everything I built torn down. It is a sad realization.”

Wow. Just wow. I felt the full weight of his sorrow. I didn’t know quite what to say, but I knew I couldn’t let the dark side of strategy win.

“It’s the gravitational pull of mediocrity,” I said. “Just know there’s a reason you’re the best strategist on the planet.”

Call it what you will — ego, vanity, narcissism — but when a winning and uniquely defensible strategy is abandoned in favor of something clearly inferior and obviously mediocre simply because the strategic creator has left the building, don’t blame culture, blame the dark side of human nature.



Matthew E. May

Senior GTM strategy advisor at Insight Partners. Co-author, What a Unicorn Knows: How Leading Entrepreneurs Use Lean Principles to Drive Sustainable Growth.