Dreadful questions

Kathryn Crawford Saxer Career Transition

The room was full of software engineers and technologists. I was on stage to talk about confidence and impostor syndrome (both very coachable, by the way).

Those engineers were looking at me skeptically. They were ready to eat me alive.

“Bring it on,” I thought to myself. I flipped to the first slide of my presentation, projected in large, bold font on the screen behind me:

Who am I and how do I have credibility to coach executives in industries I know nothing about?

That would qualify as something I call a Dreadful Question. Much of the coaching I do in my office is helping my clients get out in front of Dreadful Questions.

Dreadful Questions are the questions you know you are going to get in that networking conversation, in that business meeting, at that dinner party, on that soccer sideline. Dreadful Questions are the questions that make you stumble, questions that put you on the defensive, questions that poke at your soft spots.

Dreadful Questions are the questions you’re hoping they don’t ask.

I knew those skeptical engineers were questioning my credibility. I knew they couldn’t care less about my credentials. So I put that Dreadful Question in big, bold words on the screen behind me and told them a true story about something I cared about:

“In my family — I have two teenagers and a good husband — I’m the one who knows knots,” I began.

I could feel the energy in the room immediately shift. Those engineers weren’t expecting me to talk about knots. Knots are interesting. Much more interesting than an MBA (which I have).

“If something needs to be tied or untangled, I’m the go-to,” I continued. “Kite strings, tent stakes, boot laces, clotheslines — I’m in charge of the tying and untying.”

Those engineers might not relate to a so-called executive coach, but they can relate to the responsibility of tying a good knot.

I took them on a metaphorical leap:

“And that might be a useful metaphor to describe my coaching process,” I said. “I have the ability to tease out the tangle. I ask useful questions that can loosen up a seemingly impossible situation.”

I could see the skeptical expressions begin to warm. I could almost hear them thinking, “Hmm … that could be useful.”

And I grounded the metaphor in real experience:

“This ability is informed by my years working in an environment much like this one; by my years raising children while working in an environment like this one; by my education and training; and, profoundly, by my work as an journalist.”

By the end of this random story about knot tying, I have those doubtful engineers on my side, smiling and laughing along with me. This was no disingenuous elevator pitch: I told a true story about something I cared about. I owned the Dreadful.


It’s not enough to have a good story — and it takes time to come up with that good story, by the way. You need to write it out and practice it. I tell my clients to memorize their Dreadfuls to a Happy-Birthday-song level, a concept borrowed with great appreciation from the blog Wait But Why.

All of which is a lot of work. I practiced my knot tying story on the dog, on my eye-rolling teenagers, on the plants in my living room. I got it to Happy-Birthday-song memorized so I seemed confident and credible as I stood up on that stage in front of those skeptical engineers.

And, as a result, that Dreadful Question projected on the screen behind me wasn’t dreadful at all.

Bring it on.

First published in The Seattle Times. Read my archive of Seattle Times Explore columns.