Counting Calculi

The Strategy Trap

The complexity yet ease of strategy is the real cause of analysis paralysis.

by Kevin McLaughlin

“Strategy is great, but boat speed is better.”

The above quote is a one of my father’s favorite dadisms. As someone who sailed in multiple Olympic trials, he would know. What he means is that all the analysis and discussions of “points of attack” will come to nothing if your boat isn’t actually in the water picking up speed.

Anybody who’s ever sat in a company’s all-day strategy session meeting knows what this means. Sometimes these strategy sessions remind me of the medieval Scholastics who would argue about how many angels could dance on the head of a pin. These discussions can be fun and engaging, but at the end, you often leave feeling like you’ve wasted hours in useless babble. Typically people attribute this over-strategizing to indecision, hence the term “analysis paralysis”. But I think something other than indecision is actually at work in our predilection for strategy. And it comes from the two distinct scales we’re referencing when talking about difficulty, namely easy-to-hard and simple-to-complex. Let’s examine these scales and why they lead us into too much talking and take us away from actual doing.

Let’s start by looking at the first scale, easy-to-hard. This is what people most often mean when they talk about difficulty and what we intuitively think of. It is the level of energy required to perform a task. It ranges from sitting on the couch in an air-conditioned room at the easy end to digging ditches in the hot sun at the hard end. It doesn’t just have to be physical effort though. It can also be mental effort. Think about the difference between watching TV and reading a book. Watching House of Card on Netflix takes almost no energy, but plowing through Adam Smith’s The Wealth of Nations will leave you drained. 1

The second scale of difficulty ranges from simple-to-complex. Simplicity and complexity are distinct from ease and hardship. Digging ditches is very hard, but it is not complex. 2 Complexity, by contrast, requires understanding the inter-dependencies of disparate elements - as the word’s Latin roots, com (meaning “together”) and plex (meaning “woven”), nicely indicate. As college students whose parents make their living with manual labor doubtlessly hear regularly, being a student is a comparatively easy life. But juggling four classes, switching between differential equations and Shakespeare, and even navigating the college social scene is very complex.

To understand what these two scales have to do with excessive strategizing let’s plot them in a two by two table.

The Difficulty Spectrum

Simple Complex
Easy • watching TV
• casually chatting with friends
• strategy
• planning
Hard • cold calls
• sales meetings
• voter registration
• coding
• composing music

The table lets us see the full spectrum of what we mean when we talk about difficulty. Some things can be easy and simple like watching TV. Almost nobody gets paid to do these things because everyone just does them naturally. On the other end of the spectrum, things can be both complex and hard, like coding. 3 You might think that the most difficult tasks on the spectrum would be what organizations shy away from the most. But not so. Tasks that are hard and complex are often very enjoyable, as someone who's experienced the unalloyed joy of coding can tell you. 4">flow.)

The tasks organizations shy away from the most, as far as I can see, are the hard but simple tasks. I realized this when trying to recruit volunteers for a political organization to register voters. All of these volunteers had signed up on our website knowing in advance that the only thing we did was voter registration. These volunteers were happy to take time out of their day and drive through downtown Austin traffic to meet me for coffee. But when we met, they usually wanted to discuss strategy. They always had suggestions on how should the organization could register more voters. Or even more broadly, how the Democratic Party should develop a rural outreach strategy.

These conversations were always enjoyable, and I really do appreciate the thought that these volunteers put into their civic duty. But inevitably the people who wanted to talk about strategy the most never actually showed up to register voters. Why? Registering voters is exhausting. You stand outside and ask everyone passing you by if they’re registered to vote. Most people ignore you. You’ll likely register less than 10% of people you talk to. But it’s probably the single most effective thing you can do for politics as a volunteer.

Strategy, 5 like discussing how the Democratic party can reach rural voters or why Hillary Clinton should have spent more time in Wisconsin is much more fun. The only energy it requires is enough to maintain a conversation while comfortably sitting in a coffee shop. It also does absolutely nothing if you’re a low-level volunteer.

Companies do the same thing. Employees of companies naturally don’t want to do the simple and hard tasks like cold calling or taking sales meetings because, like voter registration, it takes energy to talk to strangers about something they don’t often want to be talking about.

So how can organizations mitigate our almost insatiable tendency to talk about strategy or other complex, yet easy tasks? How do we actually pick up boat speed? New techniques that programming teams have created like Agile development are in part designed to do this. Agile schedules strategy sessions at preset times and tries to limit the amount of time spent in these meetings. This at least seems like a solid first step. If you’re not meeting, it’s much harder to discuss strategy.

Companies can also require strategies to be formalized in six-page prose summaries like those required by Amazon. Requiring fully flushed out strategy essays not only leads to more careful thinking about strategy but also makes strategy sessions more effortful, ie harder, because writing in prose takes time and concentration 6. People will then naturally want to do it less.

Limiting meetings and requiring effortful results are good techniques to try. Ultimately it will come down to building company cultures that recognize the strategy trap and emphasize the simple yet hard things that all companies must do to be successful. That will likely be hard, but worth it.


1. Trust me. ^

2. Most physical activity seems to be like this. ^

3. Things in this quadrant tend to be the domain of experts who’ve acquired specific skills after long years of practice. Think about physics and musical composition. ^

4. These are the tasks that most naturally lead to a state of ^

5. For thoughts on what strategy is and why it’s important, despite this post, see Sir Lawrence Freedman’s Strategy: A History. ^

6. The same cannot be said of powerpoint presentations. ^