Ask Questions That a CEO Squirm

Mark Evans
1 min readDec 18, 2023

When I was a reporter, I loved asking CEOs questions that made them squirm.

They were uncomfortable questions that challenged their “media training.”

I don’t get to do that much as a marketing consultant.

And it certainly doesn’t happen over Zoom, which is more about talking than having a conversation.

At an in-person strategic planning session this week, I leaned into reporter mode with the CEO. It was fantastic!

It was an opportunity to ask difficult questions about things that needed answers.

It was the right forum because we were together. We could see each other’s body language.

I could read the room and determine how to ask the questions, when to press for more information and when to back off or change directions.

It’s hard to do that over Zoom or the phone. There’s a lack of intimacy and connection.

Tough questions are tough to ask. But there’s a time and place for them.

Good corporate leaders create a culture and opportunities to ask questions that put them on the spot.

The best CEOs want the tough questions and answer them with forthrightness, candour, and honesty.

It’s your job as an employee (or consultant) to ask them.

If you’re a SaaS CEO looking to refresh your marketing, check out my 90-day sprint — strategy and tactical execution done well and quickly.



Mark Evans

A fractional CMO for B2B SaaS looking to attract & engage better prospects. I focus on positioning, planning, and content-driven marketing.