Why does everyone want to do strategy?

Conversation with Shreyas, Evan, Karan

Why does everyone want to do strategy? What’s really behind execution problems? How is everyone so confident in this meeting? And is “finding purpose” overrated?

These were a few of the topics covered in a conversation with Shreyas, Evan and Karan. I learned a lot from them, and want to share the highlights with you. 

Strategy as intelligence?

How strategic are you? Most people will say they’re above average or maybe even exceptional. But, by definition, most people cannot be above average.

Part of the allure of strategy is that it’s seen as a proxy for intelligence. It’s why so many people want to “do strategy”. It feels like the pinnacle of important work.

Here’s the problem: strategy is intricately tied to something else — execution:

Every PM wants to do strategy

The best strategies are right-sized for what can be executed given the team, capital and timeline you’re working with. They don’t exist in a vacuum.

Is it possible to weigh strategy on its own merits? Maybe. You can aim for quality execution. If it doesn’t work, you’ll know the strategy needs to be changed.

Quality execution means built to spec, (mostly) on time and within budget. But quality execution isn’t just about paying attention to pixels.

Execution is pixels and people

Execution problems are often rooted in how we work with each other:

  • Does Bob get the point of the project? 
  • Is Harry the right person to carry out X?
  • Is it in Lucy’s interest to do Y?

This gets especially difficult on: 

  1. Big, growing teams
  2. New teams

The bigger the team, the more people don’t know each other and don’t have shared context. This is why pulling additional people onto a delayed project rarely makes it go faster. The extra firepower comes at the cost of more actions to synchronize.

New teams also have it rough. It takes time to develop trust and effective communication. Even if the team is full of A-players, it takes a while to synchronize and hit their stride. 

I’ve found that small, consistent teams tend to win the race. Create long-term games between people who know each other well.

Small, consistent teams win the race

A mindset shift is also useful. Here’s a great analogy from Shreyas:

• Thought: This person is very different from me
• Reaction 1: This must be a bug! Why are they not more like me?
• Reaction 2: This is a feature! I can learn from them

Working with others is a slog until you replace reaction 1 with reaction 2. Evan frames it as taking a thought and moving it to a different part of the brain.

In short, being a “strategic” thinker is not just about understanding customers and the market, but also about the people on your team. To make a single shot, there are many hoops to line up. It takes more than one brilliant mind.

Confidence theater

Confidence theater: fake it till you make it
Source: Dilbert.com

Have you noticed how confident people are, especially in high-stakes meetings?

I first observed this in consulting: my presentations would go a lot better when I spoke with more confidence and conviction. Same went for pitching product ideas.

Confidence inspires confidence. Conviction inspires action. 

But the danger of confidence theater is that it’s easy to get high on your own supply. When you have to be certain to be taken seriously, you convince yourself that you are certain even if there are many unknowables.

When supreme confidence takes over, play devil’s advocate: 

  • Let’s assume this went wrong. What happened? 
  • What don’t we know? What can’t we know? De-risk the first, test the second
  • What are the biggest risks? 

It’s also worth tracking the life of an idea from conception to launch. What were you confident about that was not true? Looking back uncovers blind spots.

Meaning > purpose

Have you found your “purpose”? My search for purpose sent me from job to job, only to be met with crushing disappointment.

The problem was that I never defined the scope of “purpose”. By default, I assumed it had to mean world-changing, preferably universe-altering. This is a fool’s errand:

  1. If you don’t enjoy the process of making a “dent on the universe”, you’ll be miserable even if you succeed — and isn’t the point of working hard to feel good?
  2. The things you do enjoy probably don’t ladder up to a “dent on the universe”, at least not right away

Instead of searching for a grand “purpose”, start by taking note of “meaning”. Meaning is local: do you find what you do meaningful? Are you having fun?

Purpose is usually revised history. It doesn’t emerge on day 1, it’s more of a day 100 or day 1000 phenomenon. Everything big and purposeful once started as small and meaningful.


  1. Great strategic thinking comes down to understanding people: what customers need and what teams can do
  2. Confidence theater leads to a false sense of certainty; counteract by playing devil’s advocate
  3. “Purpose” is lofty and overrated; start by taking note of “meaning”

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