inquiry – Sasha Dichter's Blog

Do I want to be a superhero or drive a firetruck?

Do I want to be a teacher, a doctor, a lawyer or a veterinarian?

Do I want to be a salesperson, an entrepreneur, an investment banker or a professor?

Goldman or Morgan? TFA or Robin Hood? Charter school or public school? Facebook or Google?

…

Until, eventually:

What kinds of problems do I want to solve?

How much direction do I need?

And how much do I want those around me to need?

What kind of approval do I seek?

Do I like creating new things or polishing others’ great ideas?

Do I work best with people who are highly structured or more free form?

Do I thrive or crack under pressure?

Do I want a workspace that is quiet or loud? Open or closed?

What happens when I’m in the spotlight? What should?

How do I manage my time to be most effective?

How hard can I work in a sustained way?

Am I a starter or a finisher?

Do I process information best alone or in groups? In conversation or in writing?

How important is culture to me? Values?

What does leadership mean to me?

How do I make others shine?

We’re generally really good at and comfortable with talking about “what:” what we’re proposing, what the big vision is, what the plan looks like. We’re eager to spend our time constructing the argument, perfecting the slides, and standing up and making our big pitch.

“We want to do this and this and then this.”

But “why” often stumps us. We treat “why” like it’s some sort of attack. “Why” makes us feel defensive.

“Why” can sound to us like someone is tearing down the “what,” just without doing it directly.

Here’s a suggestion. Hear “why” for what it is: a chance to dig into the assumptions, the core issues, the strategic opportunity. “Why” means: I share your goal of getting to the bottom of this one, let’s figure it out together by getting to the core issues.

More often than not, when someone asks “why” they really mean just that.

Why?