Most difficult conversations ebb and flow between good progress and difficult moments, those times it’s a challenge to access our best selves and skills. Here are five common difficult moments and five powerful questions to help you through them.
Scenario 1: They are defensive or uncommunicative.
It’s tempting to plunge ahead, hoping they’ll come around. If they’re truly defensive or withdrawn, they may only be half listening or not listening at all. At some point, you risk your own frustration increasing if they don’t start to “meet you halfway” as a conversation partner. Instead of plunging ahead, try this question:
How can I help make this a conversation you want to have with me? Don’t be deterred if their first response is “Nothing.” That’s a defensive response. Try waiting in silence. Or try this follow-up: Ok, nothing would make you want to have this conversation with me. But if something could, what would it be? It’s surprising how often patient silence or an inviting follow-up engages a reticent conversation partner.
If you’re going to use this question, it’s essential that you not defend against their answer. If, for example, they reply, “You stop attacking me,” it’s not helpful for you to answer with, “I wasn’t!” When you do that, you prove to them that they were right to withdraw from the conversation. A response that helps build engagement might be, “I want to understand that more. What did I say that sounded attacking?”
Scenario 2: They’re unloading a lot and you’re feeling overwhelmed.
It’s natural for people to unload when they feel someone is finally listening. It’s as though a spigot turns on and sometimes they can’t turn it back off. It can be a lot to absorb. When you fear you’re losing track of important points they’re making, or you’re just feeling deluged by the amount of air time they’re taking, try this question:
What is the most important thing you want me to understand? A question like this helps them refocus and “chunk down” the conversation into bite-sized bits you can digest.
Scenario 3: You’re trying to listen but feeling defensive.
It’s very difficult to listen deeply when the things they’re saying feel unfair, unjust, or untenable. Yet healthy personal and professional relationships need the opportunity to air concerns and grievances without those frustrations getting shut down. When you want to demonstrate your ability to consider feedback even when it’s difficult to hear, try this question:
How has this been affecting you? This is another refocusing and redirecting question. It invites them to direct their attention away from criticisms that increase defensiveness and toward a useful reflection about the impact on them. Separating intention and impact can transform a difficult moment into a problem-solving one.
Scenario 4: They fire off a dead-end statement.
Dead-end statements are reactive responses, often issued when the speaker feels defensive, attacked, or backed into a corner. They often start with “Fine!” like these: “Fine, I’ll move out!” or “Fine, I’ll never ask you for help again” or “Fine! I’ll just do it all myself.” To keep the conversation going when it sounds like they’re unilaterally ending it or lashing out unreasonably, try this question:
That’s an option we can consider. How can we figure out a less extreme solution? A response like this acknowledges their dead-end reaction without pushing back against it or caving to it. And “How can” questions engage people’s problem-solving abilities without first requiring them to say yes or no.
Scenario 5: You want to suspend the conversation for now but they want to keep going.
Continuing a conversation when you’re emotionally hijacked increases the odds it’s going to veer off course. It’s very difficult to reason someone back into reasonableness once they’ve lost their composure or feel emotionally overwhelmed. If you’re aware that you’re getting swamped, but they don’t see it or are hell bent on plunging ahead, try this question:
How can we make sure we can both continue to bring our best thinking to this problem? This one is best prefaced by the observation that you’re getting overwhelmed by the conversation and need some relief. The question itself leaves open the possibility that you may be able to stay in the conversation if something changes about the way it’s going. And the possibility that a break or a rescheduling is a viable — and possibly very smart — option.
