10 Ways to Help People Say Uncomfortable Things

Are you struggling to foster open, frank, candid communication among your teammates? Do uncomfortable conversations happen behind the scenes or not at all? Have passive-aggressive conflict styles stuck you with the same unresolved issues month after month? It might be time to focus on making it easier for people to say uncomfortable things.

There’s no surefire way to get someone to say something that feels risky. The right prompt depends on whether sharing their message might reflect poorly on them, spark conflict and friction with other team members, slow things down, or create uncertainty in some other way.

Here’s a list you can draw from that covers the landscape. Using any of these approaches can make it feel less daunting for people to express to you an unpopular or uncomfortable point of view.

Ask for disagreement. Let’s start with a simple question: just ask for it. Tell the person that you need someone to present other sides of the argument. Try, “I’d like to hear dissenting perspectives now so I can bake them into my plan,” or “I really value it when you’re transparent with me.”Request that they share a different perspective. It can be helpful to name your biases and encourage people with different perspectives to share them. “I’m not a salesperson, so my perspective is biased. Could you share how this looks from the sales perspective?”Express the value you get from the person’s candor. People might remain silent because they believe speaking up could do more harm than good. You can counteract that by being explicit about the importance of their input. “I know it’s hard for me to hear, but when you help me spot the flaws in my plan, I get to a much better outcome.”Find a private spot to ask for contentious input before a meeting. If you have a meeting where you’re worried the stakes will be too high for people to air their grievances, ask for input in a safer environment. “We’re doing talent calibration tomorrow, and I need candid feedback on Anders. Could we grab a couple of minutes in private so I can get your thoughts?Frame disagreement as helping to reduce implementation risk. You can make it more likely that someone will share an uncomfortable message if you position it as helping you for later. “It’s tempting to push this through, but I need your thoughts on how this might go wrong during implementation.”Thank people (publicly and privately) who disagree with you. If you want more people to share uncomfortable messages, reward them for it. “In yesterday’s meeting, Fran’s feedback about how my delegation wasn’t clear enough really made me think. Fran, I’m grateful to you for sharing that.”Explain your reactions. If you have a strong (or even a subtle but clear) adverse reaction to someone raising a contentious issue, take a moment to explain it so that it becomes less aversive. “I’m reacting because I’m worried about how I’m going to communicate that to the team, but I’m very grateful for you pointing it out.”Leave silence. Do you know what stops someone from saying something uncomfortable? When they can’t get a word in edgewise. Sometimes, you need to let the silence drag on for longer than seems normal. The person might start to find the silence more uncomfortable than saying what needs to be said.Encourage hypotheticals. People don’t have to admit to having contrary thoughts. It can be valuable if they just imagine what contrary thoughts might be out there. Encourage them to share by asking, “Hypothetically, if someone were to complain about this, what would they be worried about?”Ask broad questions that allow people to share their values. The right question allows the person to paint your blank canvas with the most personal answers. Try questions like, “What is this about for you?” “What’s at stake here?” “What would be an unacceptable outcome?”

In Conclusion

Beyond all the specific words, the vital thing to realize is how you engage with difficult conversations (and with colleagues in general) affects how comfortably your teammates share contentious messages with you. If they’ve seen you start yelling at someone, don’t expect them to step up to be the next in line for a dressing down. If you’ve gossiped with them and violated someone else’s trust, they probably won’t be willing to risk sharing their discrete message with you.

That doesn’t mean you have to be perfect. If you do get angry at one person, make sure your apology is public so others know you were in the wrong. If you need to sleep on an uncomfortable message before seeing its value, return to the topic when you’re ready to acknowledge the person’s contribution. Mistakes can be remedied well and are just as important as getting things right the first time.

Additional Resources

If Your Team Agrees on Everything, Working Together is Pointless

The Art of the Difficult Conversation

How to deal with passive-aggressive people

 

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