I had lunch with a colleague this week during which we talked about her near-term plans and long-term aspirations over a bowl of bi bim bap. She reflected on options ranging from graduate school to life-long ambitions, from alternative career paths to renegotiating her relationship with her childhood pastimes. At the end of the discussion, as I munched on the leftover bowls of banchan, she paused, reflected for a moment, and remarked: “You ask really good questions.”
I? Ask good questions? That’s interesting, because I wasn’t trying to ask good questions.
There was a time when I tried to ask good questions. In fact, I’ve wanted to ask good questions most of my life. As far back as elementary school, I sought to ask the interesting, non-obvious question to the teacher, less because I wanted to know the answer and more because I hoped to signal just how advanced my comprehension was. “I understand graphing real and imaginary numbers on a two-by-two, but what if you add a third dimension?” I delighted in stumping the teacher and didn’t mind taking the class completely off-track.
This inclination continued in the working world. Asking the right “high-gain question” was celebrated as a great skill. If someone was evaluating many options, I might say “It seems like there are really two approaches here: A or B. Which seems most useful?” Similarly, if someone was trying to understand a situation, I might say “In my experience, it is always a matter of X or Y. Which is at stake?” My questions were crawling with clever frameworks and embedded advice. Intentionally or incidentally, I casually showcased how brilliant I could be while simultaneously seeming helpful. While my questions presumed to help the other person find their direction, let’s be honest: they were all about me.
As I’ve started to work on my ego (only partially successful to date), I’ve tried to shift to asking questions in the service of the other instead of for my own benefit. This has prompted me to realize two things:
The smarter you try to be, the less useful you become, and
The most powerful questions are the most simple.
Everyone has heard the perennial advice to “ask open-ended questions.” Beyond this, I propose adding the guidance: “ask simple questions.” It’s not about providing a maze of options, a clever trade-off, or a new framing. It’s not about leading people in the direction that you see unfolding. And it’s certainly not about receiving recognition for your endlessly clever perspective.
Instead, it’s about reducing to the simplest question in service of the individual:
“What do you want?”
“What’s important about that?”
“How do you feel?”
Though I can’t always get out of my own way, I am always most useful to others when I’m not trying to be clever. In other words, keep it simple, smarty.
So, what now?