What questions should I ask?

You might be asking the wrong questions

In my newsletters, I’m aggregating all the advice I can find about how to talk to people across the political divide. My sources include from experts in hostage negotiation, communication specialists, psychologists, cult experts, anthropologists, historians, and political scientists. As I’ve been collecting thoughts from experts in a variety of fields, all the advice seems to coalesce around the same ideas — the process of asking questions, listening, agreeing with what you can, and then figuring out how to respond. Those steps are useful in building bridges.

So, we need to start by asking questions. Often, we make assumptions and never ask.

But sometimes, the questions we ask can also be a problem. Leading questions, biased questions, and questions that create a dichotomy can all make things worse. Yes or no questions don’t help either; they lead to dead ends. Questions that attempt to force people to agree with you by setting up an extreme scenario can end badly and hurt you. (I heard one story about a young woman — call her Brooke — who told a very emotional story about a hurtful conversation she’d had with her aunt. In that conversation, Brooke’s aunt had “chosen” to vote for a rapist over a baby killer. The situation Brooke described sounded so unrealistic that I wondered whether she might have set up the entire scenario by asking a question with an extreme scenario and pushing her to aunt to make a choice.) Don’t ask questions that back people into a corner.


Ask questions that lead to understanding, not more argument.

In his book, “Think Again”, psychologist and author Adam Grant suggests an all-purpose open-ended starter question. “I’m really curious to understand more about what you think about (issue). Can you explain it to me?”

For this to work, you have to really be curious. That’s not something you can fake. And if you’ve already been in a contentious debate with the person, it might not work.

As I’ve been suggesting this process to people, I’ve heard skepticism. That skepticism is based on their experience, and perhaps it’s because they’ve been asking the wrong type of questions or even that the person they’re talking to feels like that they’ve been attacked. If that is the case, they might need to do something to clean the slate. That might be an apology, which might be necessary if you want it to be believed that you’re going to do something differently. The apology might be something like this: “I know we’ve had conversations before where I haven’t listened very well. I’m trying to turn over a new leaf. Will you give me another chance?” That’s important if your goal is building the relationship back.

And I’ve heard people saying that, when they try to ask questions, all they get back is a slogan with no discussion, which doesn’t move the conversation further. They need more guidance on questions. So, here are some more suggestions from various sources.

Adam Grant reports that asking, “How would what you propose work? Can you give me details?” has been shown to really get people to think and talk.

And here are some suggestions of questions adapted from Essential Partners, an organization whose slogan is “Build a community strengthened by differences, connected by trust”:

·       “What would the future be like if what you suggest happened? If that happened, what would that mean for you personally?”

·       “What are your hopes about this issue? Your fears? Your concerns? Your unmet needs?”

·       “If you were president, what would you do?” Or “If you were a Black person, what would you do?” Or fill in the blank. And then follow up, with probing questions, “What would happen if you did that? How would that work? Would there be problems? How would you deal with those?”

·       “When did you begin to understand that people like you are viewed in a particular way? How does that fit with how you understand people like you? What would you like to not hear again about people like you?”

·       “When did you first start to believe that? Was it said by someone you trust? What makes you trust that person?”

·       “Can you tell me the advantages and disadvantages of what you propose?”

Essential Partners has a training program if you’re interested. You can get more details here: https://whatisessential.org/

And if you uncover fears in this process, here are some questions I ‘ve come up with:

“How long have you been afraid of that? Are these fears recent or longstanding? Are there certain things that make you more afraid? How would that happen?”

Psychology tells us that exploring fears often makes people less afraid because fears are often not closely tied to reality. I know this has worked for me when I try it about my fears.

Plus, each situation might require special questions, as I talk about in my newsletter on cults. Click here for more.

I hope this helps you be more specific about how to start the process to mend those fractured relationships in your life. The next step is listening, which can be found here.