Strategy vs Execution

Principles for Avoiding the Failure Mode of Solving the Wrong Problems

Michael Tiffany
4 min readMay 20, 2019
Photo by James Pond on Unsplash

Strategy is direction: “Which hill are we taking?” Perfect execution to take the wrong hill is failure: a waste of human effort. But can’t we cite many examples of brilliant strategists getting beaten by waaaaay less brilliant competitors that simply execute better? What’s going on here?

The answer, I believe, is revealed by looking at how companies fail. What are people doing at failing companies differently than successful ones? In the months leading up to failure, the problem isn’t that people just “stop typing” as Paul Graham once memorably wrote. In actual fact, the period before the end is often extra intense. People are working hard to stave off failure.

The problem, by definition, is that they’re doing the wrong things. They’re not solving the problems that really need solving; they’re solving related but different ones. I believe they are doing so because of a subtle cognitive bias that Nobel laureate Daniel Kahneman wrote about: problem substitution.

It’s vanishingly rare to feel comfortable while trying to do something you do not know how to do. When faced with such a problem, Kahneman tells us that, most of the time, we unconsciously replace the problem with the closest related problem that we do know how to solve. And that is how companies fail.

Goliaths usually beat Davids

The successful leaders I know are much, much more comfortable dealing directly with problems they don’t really know how to face. The best of them do it wisely, with self-awareness. But shockingly, some of the brash, unwise ones, literally ignorant of their own limits, succeed as well. This is NOT because ignorance is good. It’s that problem substitution is so very very deadly. If you can’t take on the real problems, you will not succeed no matter how skilled you are as a manager.

Goliaths execute better than Davids. That’s because great execution requires overhead. You have to layer on a lot of work — processes, tools, oversight — to get to zero defects. You have to slow down.

Startups, in contrast, have to go fast, with cheap tools or no tools, with barely enough people to do the work, with no one left to do a lot of oversight, coaching, and mentorship. The reason your unique innovations need to be at least 10x better than anything else your customer can buy is because you are going to suck, a lot, at almost everything else, so your one big advantage has to be so extraordinarily outsized that you can build a whole company on it that can eventually afford to not be so damn sloppy.

Strategy as a failing tactic

Now let’s take a closer look at those brilliant but failing strategists. They can be divided into two camps. There are some strategies that are flawed directly because of problem substitution. In the absence of a strategy to solve The Real Problem, you get a strategy that solves for a related problem. In the end, you take the wrong hill.

But it’s the second camp that, I believe, is responsible for that ‘brilliant execution is more important than brilliant strategy’ nonsense. Strategizing is a classic work-like activity to sub in when you don’t know how to do the thing you need to do. This leads to an anti-pattern where leaders do more strategizing precisely when they’re failing to deal with the biggest problems. Have you ever seen this? I think it’s the principle anti-pattern that gives strategy a bad name.

How can we protect ourselves from this cognitive bias? It’s not enough to focus on execution. Good execution — merely good! not brilliant — requires hard work, and to work hard, your people need to understand and believe in a clearly articulated vision of where you’re all going and how you’re all going to get there. At a startup, where mistakes are inevitable and frustrations abound, any level of execution above phoning it in requires a level of motivation and dedication that is only sustainable with a brilliant strategy.

How best to aim your sights

So you’ve got to inspect your strategy for problem substitution. I offer three diagnostic techniques: look for specificity, listen to your strategy like a story, and judge the strategy on its explanatory power:

  1. A hallmark of leaders escaping-to-strategy is generality. Brilliant strategies are specific. They are specific enough to generate specific action steps.
  2. Good strategies make good stories. I have a mantra: The strategy is the story and the story is the strategy. What we tell the world about our goals and how we’re achieving them should mirror the language we use to guide ourselves. That’s a good rule that keeps life simple. It also harnesses human brains in a potent way. Business strategy is a hard and rarefied skill, but all humans are storytellers and story listeners. People can tell when a story is off. When the story is the strategy and the strategy is the story, you can use your ear for off-ness as a signal that something about your strategy isn’t right.
  3. Good strategies explain themselves. They explain why and how they solve the real problems. Bad strategies are bad explanations. That is, when accepting a bad strategy, you have to assume the leader knows something they’re not saying. Do not assume there’s an invisible reason why a strategy will work. Reject strategies that rely on assumptions you have to make.

Michael Tiffany is co-founder and President of White Ops, a cybersecurity company based in New York.

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Michael Tiffany

Michael Tiffany is co-founder, president and the least talented person at White Ops, a cybersecurity company based in New York.