W11 - How to Make Decisions

There are increasingly more moments for making decisions, especially longer-term ones.

There are many problems we notice, so how do we decide whether to invest and how much. Using the integration of AI and work as an example, it’s hard to make the right investment. If you don’t invest you’ll regret it—last year we found an accounting scenario but invested little, and this year we were already too slow. If you do invest it’s hard to tell whether it’s driven by FOMO. You tack on a few superficial AI features that seem cool in demos, but the real experience is underwhelming. After trying it once, you never want to open it again.

Last week I saw three decision-making models in practice that you can try applying.

The first is what many teams use in this year’s business planning: demand level, demand scope, implementation difficulty, and cost. It’s an evolution of the RICE framework; from observation I’d add that the cost element should pay more attention to opportunity cost.

The second is a decision flow I saw earlier on X, which complements single- and two-way gates. It starts by asking whether the decision is reversible, then how much time you have to decide, then how much uncertainty there is, and finally whether you’d regret not doing it in the long run.

The third is a loss–gain quadrant that Jerry used live during last week’s planning session. It’s a variant of the important-versus-urgent quadrants; the core is identifying items where acting yields large gains or not acting incurs large losses.