Asking for advice doesn’t work

You need to make a decision and you’re stuck. You don’t have the experience to confidently choose a path. What do you do?

The natural thing to do is to “ask for advice”. You find someone with more experience, someone who really should know, and ask for a direct recommendation about what to do. This expert will almost certainly be happy to “tell you what to do” and you’ll be relieved to listen. After all, they should know and you’re stuck! But this type of advice fails almost every time for a simple reason: you can not execute a strategy you don’t understand, no matter how perfect or brilliant that strategy is.

Getting the right answer isn’t enough because there are too many little details that go into actually acting on a decision to try to use someone else’s plan. This is the same reason why managers delegate decision making to the person responsible for delivering the result of the decision and why intervening in those decisions should be done only when you’re certain the decision is catastrophically bad.

Advice that works: clarifying your own thinking #

Fortunately, there is one type of advice that works: advice that clarifies your own thinking.

The way to get this kind of advice is to ask people to listen to your thought process and provide feedback. What you want from them is just 3 things:

• Get them to describe what they think you’re asking in their own words (“so it sounds like the problem you’re trying to solve is….”)
• Challenge or validate “core” assumptions you’re making (“are you sure X isn’t an option?”)
• Explain how they think about the problem (“the first thing that I would think about is……”)

This keeps you squarely in a world you fully understand rather than attempting to transport your advisor into that world so you can get a recommendation. Challenging and validating your core assumptions allows your advisor to make sure the basic building blocks of your thinking are right without giving you a direct answer on what to do.

You may end up with an alternative way of thinking about the problem that is radically different from what you came in with and that’s totally fine! A brand new way of looking at a problem works because it allows you time and space to figure out how it fits into what you already know. A concrete suggestion will always lack this context.

The downside to this is that you’ll end up ignoring a lot of good advice the first time you could have applied it. You’ll get a lot of real or imagined “I told you so"s from advisors and friends when you realize later their advice was good. This happens to me almost every day. Don’t worry about this! The process of realizing the advice was good is a process of understanding that will pay off in the future because now you have a strategy going forward you can actually use. It’s easy to look back and think "damn, should have taken that advice”, but it’s not true.