Why and How

Your boss suggests something that you don’t understand, what is your first instinct.

Ask Why?

The classic question that gets to the root of the issue. You want to understand why are we doing this and not that. Of the million different options, we can choose, why this one?

It feels like a straightforward question, the problem is that it is a very challenging question. Why basically asks the other person to justify themselves.

No one has ever asked why when someone says do you want some ice cream. You understand the why, you never ask why. You might ask what flavour, but never why.

If your boss is insecure or unconfident then they will find this question very intimidating even if it is asked with the utmost sincerity. If your boss thinks that you should just follow their orders because they are in charge then this will be taken as an act of insubordination.

How

Former FBI hostage negotiator Chris Voss suggests asking how questions. How questions don’t come off as confrontational. They are asking for help to understand.

Yale researchers found that asking someone to explain how something worked changed their perception of how well they understood what they were talking about.

Timing

Why questions are value questions. You are really asking them to explain to me why this is important. No one really changes their values. In Jay Heinrichs book Thanks For Arguing he suggests we argue in time.

When we argue in the past, we are arguing about blame. This is your fault, your decisions did this. No one wants to admit fault.

When we argue in the present we are arguing about values. This thing is better than that thing. What I like is better than what you like. Values are hard to change.

When we argue in the future we are arguing about outcomes. Shall we do X or Y? This is where you can get everyone on the same page and where Heinrichs suggests you want to have your arguments.

Arguing about outcomes then gives you the chance to get the other side to explain how their idea will work, not why it will work.

Resist the temptation to ask why, in a perfect world, they would have the answer. We don’t live in a perfect world and they usually don’t have an answer why, so focus on asking how.