Why “What keeps you up at night?” Is a Bad Question and What Communicators Can Do about It

Full moon photo by Gregory H. Revera. Image courtesy of Wikimedia Commons.

I don’t know about you, but whenever I’m at an employee meeting where the CEO is speaking, I always cringe when a staff member raises his or her hand and asks, “What keeps you up at night?”

You might not care what I think, but would it make a difference if you knew the CEO considers it lazy and cliché?

Perhaps that’s why this question never stumps CEOs. They hear it all the time, from employees, from reporters and shareholders. It’s so ubiquitous that the communications person supporting the CEO (cringing at the front of the room) always prepares an answer to this question.

So, I was thrilled when a friend, who co-wrote the excellent book Power Questions: Build Relationships, Win New Business, and Influence Others, dedicated an entire chapter to the CEO’s view of “What keeps you up at night?” (Note: This is an unpaid endorsement of the book, which I received as a free copy to review.)

The authors talk to the chief executive of North American operations for a multinational corporation about the problem: “It’s a terrible question,” he says. “Overused. Clichéd. Stale. And worst of all, lazy…They thought that by posing that question I would – as if by magic – immediately volunteer to tell them all about my toughest issues.”

And, really, what employees asking this question want to know is: Are there going to be layoffs? And, specifically: Am I going to lose my job?

The executive is clear that no smart CEO would divulge something like that, or be involved so directly in day-to-day issues management. CEOs, he explains, are “focused on growth and innovation, not operational problems.”

Laying the Cliché to Rest

Okay, it’s a bad question, but employees probably aren’t going to stop asking it, so now what?

As the communicator, you could recommend the CEO turn the tables. Instead of responding with a standard talking point, have the CEO ask the employee what keeps him up at night. (Gently and kindly. The CEO doesn’t need to be Mike Wallace here.)

The employee will be so stunned, he’ll probably give the CEO a raw, but honest answer. Your job is to make sure the CEO responds to the answer.

How do you manage that without being a mind-reader? How do you know what an employee might ask?

Solicit employee questions before the meeting – if you already do this, but have a tendency to weed out the negative ones before you show them to the CEO, make sure you review all of them. If people are angry or upset, prepare the CEO to address such issues with concrete solutions.

Talk with functional communicators – these folks are closer to the day-to-day operational issues in each department. They should know what’s causing concern among employees in the business units they support, whether it’s that new initiative in Manufacturing or cutbacks in perks for Sales or rumors of layoffs among Administrative staff. If there’s a major issue brewing, work with the comms person to get the senior leader in charge to the employee meeting – prepped with talking points – to address the problem head-on. The CEO can introduce the leader and she or he can take it from there.

Look at what employees are saying on social media – study conversations about your company in the social channels and on industry forums. Has the tone changed? Is something particularly concerning employees?

Find out what customers care about – check in with Customer Service to see if there are any concerns that are having an impact further up the supply chain.

Address market and competitive issues – these frequently drive internal efforts at efficiency and product development, so make sure the CEO has talking points on external drivers of change in your organization.

It takes a bit more prep time, but changing the dynamics of a dull, heard-it-all-before employee meeting enables more helpful information to reach employees and creates greater transparency and respect between employees and the CEO.