How To: Point Out Problems and Not Sound Like a Jerk

Someone asked me an interesting question after a large group event the other day. I attended a meeting talking about the roll-out of a revamped leadership development program at my workplace. As you’d imagine, I’m very interested in the subject, and on this occasion I was more informed than most people since I’ve been working a side project related to the program over the last few months.

At the end of the meeting, during the Q&A, I stood up and asked a pretty pointed question (cuz I ain’t afraid). The presenter gave a… less than satisfactory answer, so I asked a quick followup, which was dodged with artful verbal dexterity. It was frustrating, but I knew I’d keep working on the project with my sub-team and hopefully be able to help out in that way. Didn’t think much more of it.

When the presentation dismissed a few minutes later, a gentleman I’ve never met before approached me. He asked me something really interesting:

How did you learn to ask critical questions like that without sounding like you’re baring your teeth?


In other words, he wanted to know how I was able to be critical of something without sounding like a critic. Or one more way of putting it, how to criticize an idea without sounding like a jerk.

Guess I hadn’t really thought about it specifically before. In an uncharacteristic moment, I fumbled around and gave him exactly the kind of half-answers he was ultimately complaining about. He asked me if I had taken classes or practiced in front of a mirror or joined a speaking club or read books about it. Unfortunately, in the moment he asked, I hadn’t formulated anything solid. Even though I didn’t have a good answer for him then, and even though he’ll probably never see this post, I thought it would be a good thing to post for the rest of us. Down to business: how do you ask pointed questions without being too edgy?

  1. Don’t aim for destruction. I think many peoples’ default mode when asking tough questions is to shame the recipient so they look like they’ve “won” the exchange. In this case, I did disagree with the presenter, but I also understood that she was most likely just like me, trying to do the best job she could. She didn’t want me to fail, and I didn’t want her to. When you adopt a team spirit and keep your perspective on the best answer for everybody and not just your ego, you’ll talk differently than if you see it as a word contest or debate.
  2. Avoid indictment. The presenter may have been the leader of the program, and yes, she had some stake in both the successes and failures of it. But had I been out to incriminate her for her failures, the question would not have been nearly as effective as it apparently was. One of the classic rules of criticism in Carnegie’s classic How to Win Friends and Influence People is to let people save face when being critiqued. Even better, avoid making them feel defensive by avoiding the word “you” entirely. You points a finger. It puts people on the spot. If you want to be effective, you need to challenge without overtly blaming. Focus on the situation at hand, not the people involved.
  3. Know the difference between passion and emotion. Passion makes for a great argument. When you care about the subject, you’re going to speak much more genuinely and say more important things. Passion makes people want to listen. But when you get emotional and let the issue shake you instead of facing the issue with confident concern, you’ll be less influential.

It’s all in the approach. You don’t necessarily have to be a wordsmith to bring up the big questions. Truthfully, a short, poignant question can be even more impactful than one drawn out and eloquently stated.

Be familiar with your own style. Be aware of your personal tendencies. Look for opportunities to use and develop many different approaches. And always keep in mind the tips above. Now go out there and ask away!