TBM 329: Deep vs. Broad Context Traps

A quick holiday season post.

I have been thinking a lot recently about the value (and risks) of deep vs. broad contextual exposure. Two risks come to mind:

Deep (but Narrow) Contextual Experience

People with deep expertise in a narrow context often overestimate how applicable their experience is to similar-looking contexts. For example, someone who has only worked in venture-backed startups might overlook how those environments uniquely shape their understanding of what works—and why it works. 'All you need is A+ players willing to fully commit,' they explain, while leaving out the access to funding, the tolerance for rapid turnover, and the high-stakes incentives that drive that level of commitment. Put them in a different context, and the playbook doesn't work for reasons they can't immediately identify (and often misattribute).

Shallow (but Broad) Contextual Experience

Meanwhile, people with broader (but shallower) experiences frequently fall into the trap of believing they've discovered 'first principles' that apply everywhere. They observe similar patterns across contexts and convince themselves that the same underlying mechanism is at play. But often, that isn't the case—it looks the same, but the environment uniquely shapes those outcomes.

Take the example of a consultant who sees the trust death spiral (where declining trust leads to escalating dysfunction) in every organization they encounter. Their confidence in recognizing the pattern can become their Achilles' heel, preventing them from understanding the organization's unique context and helping. You can label the pattern but can't do much to help.

A Bit of Both

We all probably experience a bit of both. We're all a bit t-shaped, m-shaped, or comb-shaped: a mix of deep experiences and broad experiences. In a sense, they are two sides of the same coin. Both represent a drive to explain what we see and experience and then use that to navigate different situations. We will also undoubtedly have to work with people who are a bit of both and must work with the good parts (the deep experience and/or broad view) and the challenging parts.

Questions/Exercises

Some quick exercises to counter these tendencies:

1. Pay close attention to when your pattern-sensing radar goes off and you start congratulating yourself for seeing something you've seen before. Why? This is often a signal that you might be overgeneralizing.

2. Write down where you've worked and for how long, compare those contexts, and ask yourself, "Where did I form my foundational beliefs about how things work, and do they still hold here?"

3. Do a quick inventory of your "justs" (e.g., "to succeed, you just need trust"). Ask yourself: Where did I form that belief? How might it manifest differently in other contexts?

4. Write down some "first principles" you believe apply everywhere (e.g., "transparency builds trust"). Then, ask: What factors must be paired with these principles to make them work in different contexts?

5. Think back to a company you worked at that was successful. Reflect on the factors you usually attribute to its success, then run a thought experiment: What other factors—environmental, structural, or even luck—might reasonably explain part of that success?

6. Ask yourself, "Do the things I try work because I make them work in a given context or because they are inherently the right thing to do everywhere?"

7. Ask yourself, "Do I keep arriving at the same diagnosis because it's genuinely helping or because it's the pattern I'm most comfortable recognizing? What might I be missing about this specific context?"