The Two Worst Questions at Work

Some questions put everyone to sleep; others make people sweat. Both are dangerous.

1) Sleepy Questions

TV host, David Letterman was interviewing Larry David, the star of "Curb Your Enthusiasm."

Letterman: "What was the name of the Woody Allen film you were in?"

Questions like this steal time—and deliver no value. Also, they lack zest.

On the other hand, it's a perfect question if you're trying desperately to make chit-chat with someone who's not responsive, because maybe, for example, he or she is in a coma.

Larry David refused to answer: "That's really none of your business, Dave."

If you watch the interview, it's a nice comic moment. Larry David acts offended by a question that's too bland to offend (except for Letterman's apparent lack of prep).

David Lees | Digital Vision | Getty Images

Sleepy Questions seem safe—that's what makes them so risky.

They sap the energy right out of a room.

As Larry David tells Letterman: "Dave, I don't really think you're bringing out my best self."

2) Sweaty Questions

Consider Warren Buffet's recent problems.

One of his top execs urged Buffet to acquire a company. The exec also mentioned that he held stock.

Buffet didn't ask:

a) How much stock do you own? (Answer: $10 million.)

b) When did you buy it? (Answer: a few weeks ago.)

Result? The press attacked; the SEC considered investigating; the exec resigned.

Sweaty questions are tough to ask.

But sometimes, the biggest risk is not asking. For example:

"Where, exactly, will I be working?"

Roy Cohen, career coach & author, "The Wall Street Professional's Survival Guide" had a client who never asked that during her interview, even though she knew there were space constraints.

She ended up working at a conference table with several other managers, all of them angry about sharing a tiny space and a single phone.

She left the company a few months later.

Then there's the money question.

Business coach, Laura Rose used to be a Software Manager. She suspected pay inequity, even though her boss had just given her a top performance rating, and a top raise.

"How do you like your raise?" the boss asked. She expressed appreciation.

But then she asked, "Could you check whether my base salary is in line with other managers at my level?"

Laura's manager did check, found a gap, and committed to closing it. Laura stayed 10 years.

Tip: Watch your questions. Playing it safe may be dangerous.

Consultant, author, speaker, and founder of express potential® (, Paul Hellman has worked with CEOs, executives, and managers at leading companies for over 25 years to improve performance and productivity at work. His latest book is “Naked at Work: How to Stay Sane When Your Job Drives You Crazy,” and his columns have appeared in the Wall Street Journal, New York Times, Washington Post and other leading papers.

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