Let’s start embracing the idea of asking questions at work

Asking Better Questions At Work

Here’s a cool article from Harvard Business Review about how companies value curiosity in their employees, but nonetheless stifle it. The idea of a company talking out of both sides of its mouth shouldn’t surprise anyone — for example, leaders always claim they “want people who can operate in times of uncertainty,” but then they mostly chase the same old, tired, safe, revenue-producing ideas they always have. So wait … why did you need someone who does well with uncertainty?

Here’s an insane section from the beginning of the Harvard article that should make you a little worried about humanity:

And yet, as we grow older, curiosity tends to be wrung out of us. Parents, schools, and workplaces impose rules and discourage risk. Rather than provoking with inquiry, they insist on correct answers. A child asks 300 questions a day. By middle school, the number is down to practically none. By adulthood, our disposition toward questioning can range from the timid to the hostile.

This last sentence is important to reflect on: oftentimes at a job, if you ask questions about specific things — especially about things that are near and dear to the executives or top dogs — the responses can legitimately be hostile. But wait … aren’t questions a good thing?

They should be, yes.

Let’s talk about questions for a second

If you can ask good, powerful questions — not just small talk bullshit — that’s a tremendous life/social advantage. Here’s the problem with questions at work, though: they are oftentimes accusatory. When you ask accusatory questions — “Why did this happen in this way?” — your only real goal is painting someone into a corner or getting them back on their heels so that you can show your hierarchal flex or “own” a situation. It’s useless.

If you want a really fun game to play at work, whenever your manager is going accusatory on you? Just say something totally logical (“That is entirely my fault, yes”) or propose an action plan to fix the situation in the future. Most managers look stunned when you do this. They just wanted to yell. They didn’t want things to actually come from it. 

We’re screwed on both sides of the question equation, by the way: some studies indicate that only 3 in 10 salespeople are ready for a buyer’s questions. If your base job is to sell someone something based off questions and concerns they might have about that thing, and only 30 percent of people are even ready for those questions? That’s bad.

Here’s the game that’s afoot here: it’s just like that pull-quote above. When you’re a young kid, everything needs to be explored and asked about. Obviously that’s going to happen less — you know, at some point you’ll know what a toaster is — as you get older, but being curious should be viewed as a good thing.

We should look at employees like that and say “Wow, my man over there is trying to learn more about the business and the model and the processes we have.” Instead, we get our backs up and go nuts. Why?

Why don’t companies like questions?

Here’s what Harvard says:

Common stumbling blocks cited (across industries) were a top-down approach to decision-making, limited time for creative thinking, a preference for safe ideas over new ones, and fear of standing out from the pack.

Yes, yes, yes, and yes. You can trace all those things back to one central concept: no one ever wants to be viewed as incompetent or phony. When people ask questions — especially at work, which is just a fraught exercise in relationships most of the time anyway — that gets other people nervous. Why is he/she asking this? What is their end game? Are they sneaking around to something? 

It’s a shame that’s how most companies and executives react, but it’s also pretty logical. People are all about protecting their perch or their scratch; questions can kind of mess that up. Remember: in most workplaces, good ideas are seen as a threat — as opposed to something that can be embraced and even make more money.

Is there a way to ask questions at work ‘the right way?’

Honestly, probably not really — and it totally depends on your chain of command and how comfortable they are with new concepts or ideas opposite their own.

Here’s what Harvard lists:

  • Reward questioning positively (most managers would have no clue how to do this)
  • Emphasize observation (it’s hard, because most workplaces are ‘heads-down’ cultures)
  • Seek different perspectives (stop meeting with just your team/silo, in other words)

Here’s what Lifehacker says about becoming amazingly good at asking questions:

  • Don’t ask yes/no questions
  • Dig deeper
  • Understand the power of silence
  • Don’t interrupt

I’m terrible at the last one, but I think I’m OK at the first three. Here’s what I would add: every human being on the planet ultimately wants to talk about their stuff and their goals and their objectives and their life. So if you can phrase questions in a way that will allow the responder to tell a story about themselves, that’s going to work better. That’s what people want to do. That’s especially what anyone who became an executive at a company will want to do. That’s the same reason why ‘networking’ really has absolutely nothing to do with discussing yourself and your accomplishments.

Here’s another good piece of advice: don’t initiate assumptions or try to show your intelligence when asking questions. That’s not the point. Also, if you’re trying to show intelligence up a chain (to someone higher than you), it will last about 11 seconds before you get smacked back into your place.

Here’s a great sequence from Inc about asking questions at work that made me LOL:

So it starts with the leader and flows downward to create a culture of inquiry, where people feel they can ask questions without necessarily knowing the answer. It drives me crazy when bosses say, “If you are going to bring a problem to me, you’d better have solutions.” Great questions don’t get answered in 10 minutes. They may take six months. You want people to bring you those great questions, and maybe the whole company ends up working on them.

If you bring a problem up in here, you best have solutions, boy!

That’s like every boss I’ve ever had/known or my friends have had/known. It’s so dumb. You don’t solve a problem in 10 minutes (although most middle managers assume you can, if it’s hair-on-fire time). You solve it by good, deliberate questions.

And of course, there’s always this gold standard:

If you really want to do better with questions at work, you need to honestly start with why. It’s so simple, but so many people miss the boat completely on it. Why would you ever do something — anything in your life, really — if you didn’t know why you were doing it? Yet businesses chase so many deliverables and targets daily without any real understanding of why they’re doing it (aside for, you’d hope, “to make money”).

“Ted, why are you snorting that drug?”

“I have no idea why!”

That conversation would never happen. But organizations operate like that all the time.

Bottom line is this: we need to reward, instead of punish, people that are curious and want to grow/learn. We’re not there yet at many companies and with many leadership teams.


Ted Bauer


  1. You do open up a whole big world with this post and it is wonderful. Asking questions at work can actually be frightening. The idea of messing with the status quo is still very much out there in the corporate world. Going to watch the TedX clip you recommend. Thanks for sharing.

  2. Questions can be threatening, take time to answer and/or solve, and really mess with the “can’t stop now!” mentality that drives us everyday. It’s all the more reason to purposefully bring them into our meetings and everyday work. I especially enjoyed the second TEDx clip.
    Thanks for your honest, entertaining writing.

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