A perfectly framed question

I once worked for a CEO who could make me sweat simply by asking me a question. His reputation was legendary. Leaders would be presenting to the executive team, and he could stop them in their tracks and reduce them to a damp, limp shell of a person by identifying the smallest crack in their thinking and asking them about it, head on.

Preparing for a meeting with him would totally unhinge me. I’d spend my nights thinking about every possible question he’d ask, and mentally run through my answers. And it was never enough. He always found an angle I hadn’t prepared for.

Then one day, as I was reapplying deodorant after a particularly tough meeting, it occurred to me that he wasn’t doing this to be a jerk (though, in retrospect, I think he could have used a little coaching on the tone and delivery). He was doing it because it was his job to make sure we had thought of every possible angle before committing the resources of the company to a particular course of action. And so was born my obsession with becoming a great question-asker.

Actually, I probably can trace this genesis to several months earlier in my tenure in that role. I had just been promoted to Director, which at many organizations is a big professional hurdle to clear. At my company, it came with a significant jump in both responsibility and compensation. This meant that I was participating in discussions I previously had no exposure to, including financial performance and enterprise strategy. And while I was sitting at the table, I was terrified of opening my mouth because I was worried I’d sound like an idiot. (See also: imposter syndrome symptoms.)

After one of these meetings, a woman in our C-suite pulled me aside and said, “you know, Jen, we didn’t promote you to director just for you to sit silently in meetings.”

Gulp. I explained to her that I wanted to participate, but felt like I didn’t know enough yet to contribute directly. “What if I ask a question that everyone knows the answers to, and I’m exposed to be under-qualified to be at the table?”

She made me, on the spot, list the questions I might have asked in our meeting. And this woman – 20 years my senior with multiple graduate degrees – told me that even SHE didn’t know the answers to some of the things I was asking. But she wished someone would have asked them.

So I started asking questions in meetings.

Go back to that slide on the Q4 campaign performance. Help me to see what you think are the 2 most important take aways from that work?… Can you say more about the projected revenue miss? I’d like some more context about the contributing factors you mentioned… I noticed that you didn’t cover X campaign in your report this month. Is there anything we need to know about the status of that work to make the decision on next month’s activities?

And you know what happened? People would come up to me after meetings, and tell me that they were so glad I asked a particular question – they had no clue what the speaker was trying to say but were afraid to ask the question themselves.

I was and continue to be mindful of the tone in which I ask these questions, because I know first hand what it feels like to be in the spotlight. As often than not, speakers are grateful for the questions because although they intend to cover all their angles, they forget things sometimes and your questions are all they need to prompt their memory.

Much has been said about the way that language affects the perception of women’s competence – we’re not supposed to ask for help or apologize in our business discourse. But asking for help in understanding can sometimes be about asking for it for everyone in the room. And if done right can actually elevate your perceived competence because just like the CEO above, you’re asking it to make sure the best possible decisions are going to get made. And that makes you invaluable to an organization.

Jen S.

Jen Swanson (@jgswanson) a digitally curious designer of experiences, a mom, a wife, a reader, a gardener, a cook, and a little bit of a bad-ass. Professionally speaking, of course.

2 Responses

  1. megan flynn says:

    But how to frame it not to put people on the spot – I spend so much time thinking of the right way to frame things, and often it feels watered down – AND – that men don’t have to think about that quite so much . . . . Love this. really well written!

    • Jen S. says:

      I just try to use as much non-verbal support as I can for the person, to show it’s not a gotcha – I really want to know the answer. And I give people an out when it’s clear they can’t answer in the moment, asking them just to follow up with the group after the meeting with more info. Not that it isn’t sometimes uncomfortable, though, you’re right.

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