I'm trying to figure out when it's better to talk and when it's better to write. In most situations the ideal is probably a bit of both, but sometimes one approach seems much better than the other.

You should always talk if you want to build relationships. When you're onboarding a new hire, documentation is good for knowledge transfer but bad for building camaraderie, which is more important early on. These should probably be 1-1 conversations to allow for depth and whimsy - group activities like icebreakers or playing games don't feel effective. To build a meaningful connection, I think you either need to have a truthful conversation about your worries, values, and aspirations, or you need to talk while collectively suffering in pursuit of a common goal (e.g. sprinting to make a deadline).

A common situation where people talk is in a meeting. If you're having a group meeting to come up with a plan (e.g. figuring out PMF, building a roadmap), I think it's useful to assume that the meeting won't be effective. The main reason why may be that a good plan requires critiquing and integrating many ideas raised during the course of conversation, but the pace of a group discussion tends to overwhelm working memory. Then you end up with a plan based on the ideas you can remember, which is a subset of the ideas that are important (at worst there is no intersection).

In the case of creating a plan, writing seems more effective than talking for several reasons:

1. You take your ideas out of working memory so you're less likely to miss important but unmemorable ideas. You're sampling from the entire space instead of a subset.
2. Hand-waving, unclear thinking, unfounded assumptions, and unknown unknowns are easier to identify by eye than by ear (probably related to working memory).
3. You get rid of noisy influences like how happy, confident, or shy a person seemed while conveying their ideas, and focus on their content.
4. People can read faster or slower depending on their familiarity with the context. Someone more familiar can skip the background and focus on action items, whereas someone less familiar can dig in to the context. Everyone's attention can be optimally placed. In contrast, when someone is talking, everyone has to process it at the same rate - the familiar person tunes out while the unfamiliar person struggles to keep up.
5. A written document is a snapshot of background, reasoning, and conclusions you can review in the future or share with people who weren't there (e.g. VCs). A 6-pager is the best example of this.

I think this suggests that you should write instead of talk when the quality of the result depends on the amount of correct information you have (about the state of the world), and the sources of that information likely contain a lot of noise (e.g. discussions with various people).

If you're trying to get at the truth of something, it's still helpful to start by talking to others (and build meaningful relationships in the process), but you should always end by writing things down and wrestling with each point yourself.

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