Tip
Bret Taylor talks about getting advice: “Don’t just ask what to do but why. Be an obnoxious two-year-old kid, why? Why? Why? Really try to understand the framework that someone is using to give you advice. The interesting thing about advice is people are often extrapolating from relatively few experiences. So they will say, never do this or always do that. And it’s because they had one experience where something backfired… It’s a useful anecdote, but if you don’t ask why and understand they had one experience and here’s what happened, it can come across as a rule when in fact, it’s [limited] data.”
Turns out giving advice about AI strategy works the same way.
Your board advisor tells you “never deploy AI agents without human review loops—it’s too risky.” Sounds definitive. But when you ask why, you learn they saw ONE company get burned when an agent hallucinated pricing information and caused customer churn. That’s real data, but it’s one data point from a specific context (unvalidated evals, no guardrails, consumer fintech).
Younger managers hear “never” and treat it as gospel—they don’t have enough context to question categorical advice. You’ve been on the other side. You’ve GIVEN advice that sounded definitive but was really extrapolated from two experiences. You know the difference between “I saw this fail once and here’s why” versus “this is a universal principle.”
That recognition—that most advice, even from smart people, is pattern matching on limited samples—lets you dig deeper. Ask why. Understand the context. Extract the framework, not the rule. Then apply YOUR pattern recognition from dozens of technology transitions to evaluate whether it applies to your situation.
This is the meta-skill of experienced leaders: you’ve given enough advice to know how provisional most advice actually is. You can extract signal from experienced people without treating their n=1 or n=2 as universal law.
Context
Bret Taylor is co-founder/CEO of Sierra, former co-CEO of Salesforce, chairman of OpenAI board, and created Google Maps and the “like” button at FriendFeed. His insight about advice comes from both seeking it (hundreds of decisions across multiple companies) and giving it (as board member, advisor, and executive).
The framework: most advice is extrapolated from a handful of experiences, so understanding the “why” lets you extract the principle while recognizing the limitations. For experienced leaders, this works both ways—you know how to receive advice skeptically AND you recognize when YOUR advice is being overgeneralized.