Asking Your Way Out of Awkward Conversations

Asking Your Way Out of Awkward Conversations

Image from pixabay by Dean Moriarty, CC0

I‘ve written before about the value and importance of asking good questions.

I described the qualities of a ‘good question’, including Warren Berger’s emphasis on:

  • Why… (eg Why Isn’t Someone Doing…),
  • What If… (eg What If We Tried Doing…), and
  • How Might… (eg How Might We Accomplish/Test/Improve…) questions.

A lot of ‘good’ questions are about eliciting imaginative and creative thinking, unearthing unique insights, or engaging people about a subject for the first time. Quite a few of them are suitable for interviewees interested in learning from their interviewee subjects (rather than unproductively confronting them to create clickbait).

My five favourite questions right now:

  • What’s Really Going On Here and Why? Is it really that simple? What are we missing and how can we find that out?
  • What Are Our Alternatives? What is the potential risk and potential benefit of each? What is the risk of not doing anything?
  • What’s Holding You Back? How might we remove those obstacles?
  • What Is Your Ikigai? ie the things that bring you joy every day. (To ask someone you are just getting to know.)

In a follow-up, I probed the types of questions that can be used to gently inquire about ideas that seem ill-founded, in a way that safely opens the conversant to different perspectives and new facts rather than putting them on the defensive. Questions like:

  • Help me understand why you think…,
  • What has led to you to conclude that…,
  • What if we instead…, or even
  • Can I tell you a story that influenced my thinking on

In a recent interview, Trevor Noah suggested this ‘final’ question to ask at the end of a fact-finding or expository interview (preferably asked in advance):

  • What do you think are the most important questions that no one in your field is asking now?

But questions aren’t just useful in ‘interview’-type situations. They can usefully be employed in almost any conversation, from the most casual to the most formal. The ‘right’ specific question in any situation is of course context-dependent, but here are a few examples of questions that might help navigate through rough spots in conversations:

  • Why do you say that? This is similar to the above ‘Help me understand’ question, and is best followed by silence, so the respondent is free to interpret the question as they choose, rather than feeling challenged by it.
  • What have you learned that has informed your perspective on this? Then you can ask where that ‘information’ came from, if it appears to be mis- or disinformation, and gently get the respondent to question their sources.
  • How are you feeling about this? Of course, this is only a suitable question if the respondent obviously feels strongly about this but is not expressing their feelings. In many cases it’s more important to understand someone’s feelings than the underlying facts. We believe what we want to believe, after all. And after asking this question, shut up and listen!
  • So what have we learned from this? 
  • So what are the next steps now? As long as you’re prepared to say what your own next steps are. And as long as you stop anyone whose answer is “Someone needs to…” or “We all need to…“.
  • What keeps you going? Gets at why the respondent is still striving to make things better despite articulated obstacles, and is not just venting.
  • How can I help? With the obvious caveats that the question must be sincere, and that it’s not currently ‘un-answerable’.
  • Why is this so hard? How can we make it easier, and/or more fun?

And of course there are lots of really bad questions, to avoid asking at all times:

  • How could you/they possibly do/say/think that?
  • Confrontational questions like Surely no one could still doubt that…?
  • Have you read…? as a conversation stopper, since the answer is usually no, and since this puts the respondent unhelpfully on the defensive, especially when the book/article cited likely disagrees with what the respondent has just asserted.
  • And even those reassurance-seeking rhetorical endings to assertions that are dishonestly phrased as questions, like  (Yes?, No?, Am I right?, and Don’t you think?)

I final thought, about a very different type of question. It’s a cliché to assert: “If you don’t ask, you’ll never know.” But it’s also a truism. Fear of getting an unwanted answer, or of appearing greedy or nosy or too aggressive, causes us, in most human cultures it seems, to wait until we’re told, or until something is offered. Such a cost! There is no magic phrasing or approach to asking for what you want, or what you want to know, safely and inoffensively. (Though damn there are a lot of people proffering dubious advice on the subject!) And the answer may well be ‘no’, or ‘I can’t tell you.’ It’s a skill you learn by trial and error. Or else you don’t learn it at all.

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