Asking the Uncomfortable Questions

Asking the Uncomfortable Questions

I’m Bob Wendover. How do you deal with awkward questions and situations? That may seem like an unusual topic, but here’s my reasoning. Awkward questions and situations are generally filled with uncertainty. Your brain hates uncertainty. It starts bringing up all the thoughts of what could go wrong. “What if I say the wrong thing?” “What if I upset someone?” “What if I embarrass myself in front of my colleagues?” You know the drill. You can exhaust yourself worrying about these situations, even if they aren’t that big a deal. Have you ever had a day unravel because you began to obsess over a situation like this? I certainly have. So how do you prevent these issues from dominating your thinking and draining your energy?

Begin by putting the situation in perspective. Many times, the stress is not so much about the question or issue, but who is involved. Maybe the person you’re approaching is rather gruff. Perhaps you have crossed swords in the past. Maybe they just intimidate you because of their position, influence, or age. The people who are best at managing and overcoming feelings of burnout have learned that the best way to deal with these situations is to jump in. The first few seconds of an encounter like this is likely to be stressful. But once the conversation has begun, you’ll forget about the stress because you’ll be focusing on how the other person is reacting and what they’re saying. Remember – they are people too and may be experiencing some of the same apprehension. The vast majority of the time, the situation will be resolved and you’ll come away thinking, “That wasn’t so hard. I don’t know why I was worried about it.” Hang on to that thought for the next time a situation like this pops up.

Second, take time to prepare. Sometimes we spend so much time stressing, that we don’t get around to thinking about how to best deal with the problem. This is really a two-part issue. First, you have to put yourself in the place of the other people involved and consider how they might act and react. What might they say? How might they act? How important might this issue be to them? Is what you think the issue is the real issue? Or is there something else? What might they want to get out of the situation? Once you’ve considered all this, think about how you can best respond. The best resolution to awkward situations is for everyone to come away satisfied or at least accepting of the outcome.

Third, consider how you will approach the other person. Many times, diplomacy will save the day when asking about sensitive topics. Diplomacy tends to foster trust. If the person trusts you, they are much more likely to share what’s needed. If the person still takes offense, at least you know you’ve tried your best to approach the issue in a considerate way. Here are a few phrases I have used with good success in these situations.

“Forgive me for asking. I’d need to know . . .”

“I hope you won’t find this troubling or awkward . . .”

“Perhaps this is an uncomfortable question . . .”

“Would you mind sharing your thoughts about . . .”

“I’m not sure you’ll feel comfortable with my asking this . . .”

It takes a bit of time to feel comfortable using phrases like these. But they can be very effective at diffusing the initial impact of asking difficult questions.

Finally, accept the fact that even your best efforts can fall short. If the other person takes offense or is unhappy, one of two things is probably going on. First, they are genuinely offended for some reason you could not have known about. Second, they are taking offense because they are attempting to conceal something. In this case, a more appropriate way for them to respond to the question would have been to say, “I don’t feel comfortable sharing that.” But sometimes that doesn’t happen.

Neither of these is your responsibility, so don’t “own” them. You might think that it’s unfortunate that the person is unwilling to be forthright. But that is that’s their concern, not yours. So, once again, compartmentalize your stress, recognizing that it will only last a few seconds once you jump into the situation. And try to get in the other person’s head and prepare responses to their concerns and questions. Finally, begin with one of the diplomatic phrases I mentioned. That will take the edge off most stressful situations. Don’t let awkward situations and questions drain your energy. If you do, that will just add to your burnout.

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