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Second-Order Thinking: How to See the Consequences Before You Create Them

7 min readOct 5, 2026

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A few years ago, one of my managers came to me with a situation.

One of his team members, Matthew — a senior engineer, was frustrated for lack of growth and was thinking about leaving. The manager saw Matthew as a high performer, and didn’t want to risk losing him, so he wanted to promote him.

It seemed like a simple fix, and I approved it.

But the “fix” didn’t last long.

A few weeks later, two other engineers on the same team came to the manager asking for a promotion. One of them had actually been doing the next level work for longer than Matthew, and was resentful for not being picked for the promotion.

Within a month, the team had three people who felt that they deserved a promotion, and the manager was spending 90% of his 1:1s negotiating instead of actually coaching them.

The manager had made a reasonable call that seemed right in the moment, and let’s face it — we all do this from time to time. But he didn’t realize the cascading impact of that.

In this post, we will discuss Second-Order Thinking, which is a powerful model that can help you avoid such situations. Here’s what we will cover:

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Experienced technology leader by day and passionate storyteller by night. I write about leadership, engineering and life in general.

The Good Boss
The Good Boss

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The Good Boss is the platform where experienced and budding leaders come together to collaborate, share experiences and best practices in leadership