How to ask better questions

Tell me if this has ever happened to you. You walk into a large room full of mostly strangers (it’s a party of a friend of a friend, or a networking event, or the wedding of a distant cousin), and after you’ve put your coat down and grabbed a drink and/or a snack, you end up attempting to start a conversation with one of said strangers.

If this is happening in England, after the obligatory exchange of names and maybe a comment on cocktail sausages, you find that the conversation is not getting off to a powerful start. At this point, you’ll very quickly power through the three most boring, generic conversation starters ever crafted by human society:

  • The Travel Question: Did you get here okay? [or some other question about traffic, train strikes, etc. If you’re really unlucky, your conversation partner will give you a blow by blow account, presumably because they’re so terrified of having nothing else to say.]
  • The Weather Question: Wasn’t the rain last night really terrible? [or wasn’t it hot last weekend, or did you know there's supposed to be gale force winds next week? Everyone is allowed an opinion, and no one can really agree or disagree. Safe and boring.]
  • The Work Question: What do you do for work? [the impossible question. Don’t want to bore everyone, just say something short and generic.]

What’s the problem?

The problem is not really that these questions are inherently boring. I’ve certainly managed to have interesting conversations with people about their work, and about how the chronic underinvestment in British rail infrastructure is actually partly caused by the fact that the UK was the first country in the world to build and operate national railway networks and isn’t that ironic?

I think there’s two parts to why these questions are a problem:

One, these are always always always the first three questions you ask when you’re talking to someone and you both understand that you have nothing to say to each other. As soon as you ask one of these questions, what your conversation partner hears is: “Uh oh, we’re at the start of a conversational nose dive and we’ve got about 5 minutes of go-to material before we crash and burn. One of us has to find a way out - and quickly.” 

This social signal puts an extra layer of pressure on the conversation. Now not only do I have to describe the unexpectedly light traffic on the motorway which meant I arrived a little early, I’ve also got to think of something funny, interesting, or engaging to say about it at the same time. Too much pressure, I say to myself, let’s just crash this conversation into the rocks and get it over with.

The second, and more important, problem is this: we aren’t generally good at asking good questions. It’s perfectly possible to segway from weather chat to interesting conversation, but we aren’t making it easy by asking good questions. Pulling out of the nose dive of bad conversation doesn’t have to be a matter of luck or despair. You can become the sort of person that easily crafts great questions on the fly. You can learn to recognise a great question and add it to your repertoire for future conversation-in-danger moments. That’s what I’m going to try and help you with in this essay.

How I came to love great questions

Although I am a natural introvert, I’d say that I’ve always been quite sociable and have managed to stumble through my fair share of small talk moments.

I became a real convert to the power of great questions through my work helping to co-found and grow the UK’s largest network of money coaches. Over the last 10 years I’ve seen first hand the power that a great coach has to transform lives by asking good questions.

Money is rightly one of the most sensitive areas of discussion for all of us. If you were invited to have a deep, expansive conversation with a total stranger about your attitude to money, your hopes, dreams and fears for the future and the role that money plays in your happiness and wellbeing, you’d be understandably hesitant.

And yet, that is exactly the service we’ve managed to develop. The magic of a great money coach is that they can in the space of 45 minutes ease someone into the process - from total stranger to revealing intimate feelings, worries, dreams, etc. We often hear from customers that their first conversation with a coach is the first time in their whole life they have felt really listened to and understood. It’s a truly transformative experience - and one of the most important parts of the ‘secret sauce’ is that we teach coaches how to ask great questions.

What makes a bad question?

It’s easier to understand a great question by first taking a look at common bad questions. You’ll be familiar with all of these, and probably accidentally dish them out yourself from time to time.

Closed Questions. A closed question is one that has only a one word answer, usually that is ‘yes’ or ‘no’ (but doesn’t have to be). So for example some closed questions that don’t help you have a great conversation: 

  • Do you prefer X or Y?
  • Have you been here before?
  • What’s your favourite pizza topping?

Closed questions can be okay if they are a jumping off point and you’ve got a good follow up question (more on this in a moment), but they should be used sparingly. If a conversation has lots of closed questions, you’ll end up making your partner feel more like they are taking part in an interrogation than a conversation.

Cold Start / Too Much Too Soon. Almost the opposite of the closed question problem is when you ask a question that tries to go too deep too soon, or otherwise misjudges which ‘level’ the conversation is at. 

For instance, let’s say you’ve exchanged names and established that neither of you can believe the recent weather patterns, and then they hit you with: “So what was your biggest fear growing up?”. How do you respond to that? The only way you can - by getting the hell out of there as soon as you can.

‘Why….?’. Another common mistake which you should try to avoid in the early stages of a conversation with a stranger is that you shouldn’t start your conversations with ‘Why…’. ‘Why’ questions can feel judgmental, and tend to put your conversational partner on the back foot. Compare: “Why do you work at Google?” vs “What made you want to work at Google?”. The former can be construed as having a secret agenda, a judgmental opinion coiling up and getting ready to strike. The latter is an open, curious invitation to share who you are.

So, bad questions close down the possible answers that someone can give, they rush into deep topics too quickly, and/or they end up leaving your conversation partner feeling judged (or that they’re about to be judged).

When you only have bad questions, you end up getting people wrong. As Philip Roth says in his novel American Pastoral

You might as well have the brain of a tank. You get them wrong before you meet them, while you’re anticipating meeting them; you get them wrong while you’re with them; and then you go home to tell somebody else about the meeting and you get them all wrong again. Since the same generally goes for them with you, the whole thing is really a dazzling illusion empty of all perception, an astonishing farce of misperception. 

How can we do better?

How to start asking better questions

Here’s the things that I’ve found work best as a start.

Labels.So often the reason conversations take a nose dive is because you’re not actually talking to each other, you’re just taking it in turns to say words. The first step to having better conversations is to prove that you’re actually listening to the other person and respond to what they actually said. 

The best tool to get out of this trap is given to us by expert FBI negotiators: Labels. A label is when you acknowledge what the other person has said and recognise either an emotion or deeper topic that wasn’t explicitly said out loud. All labels follow the form along these lines:

  • “It sounds like…”
  • “It seems like…”
  • “It looks like…”

Whatever your conversation partner has said, when you’re looking for a label it forces you to actually listen to what they are saying. You can pick up on whatever part of what they have said seems interesting to you, or appears to have something deeper going on, and just make the observation. So for example, suppose you have finished telling me about your job as an administrator at a local school. I’m going to be focusing on what you said, and how you said it. Any one of the labels below might be appropriate responses:

  • “That sounds like a difficult job”
  • “It sounds like you really enjoy your work”
  • “It sounds like that whole system would fall apart with you!”
  • “It sounds like you’re not sure if that’s your long term thing”

What’s magical about a good label is that it proves without a doubt that I was actually listening to what you said, and I’m inviting you to go deeper on some aspect of it. If I’ve got the label right, I’ll have picked up on something true and perhaps something you hadn’t explicitly acknowledged before. I’ll appear to be an incredibly perceptive conversationalist, and you’ll be excited to go into more detail.

If on the other hand I’ve got it wrong and misunderstood what you said, then the ‘seems like’ wording gives you a chance for you to correct me without either of us feeling awkward. Either way, you’re going to feel a little better understood, and I’ve signalled that I want to understand something about you. If we’re lucky we’ll have cracked open a topic with numerous directions from here.

Change the Frame

Another great source of good questions is to try changing the frame of the conversation. There are dozens of possible frames, so to give you an idea of what I mean, imagine you’re the school administrator again. When we get to a natural lull, I might try to change the frame in one of these ways:

  • The Time Frame: Have you always wanted to work there? Do you think you will keep doing that in the future?
  • The Best & Worst Frame: What would you say is the best thing about that job? What is the worst?
  • The Importance Frame: What’s the most important thing about that?
  • The Surprising Frame: What would you say is the most surprising thing about your job?

Just to be really clear, although the example we’re talking about here is about jobs - this same tactic can be used about almost any topic. Whether you’ve started discussing someone’s holiday to Thailand, or their love of Pokemon, or anything else. You can find an endless source of great questions by thinking about how to re-frame the same topic. Each frame gives you a perspective and has the potential to reveal something about who you’re talking to.

Ask for advice

Finally, a lot of great questions come from asking for advice. I’m a big believer in the phrase ‘advice is autobiography’. No matter what advice you get from someone, it’s always going to be a reflection of their own experiences and beliefs. Even better, people love giving other people advice, especially about topics that they feel like they are an expert in.

If you asked someone to just tell you their life story, they’d have no idea where to start, and they’ll waffle through a two minute summary. Ask them for their advice, and not only will they love you for it, but also you’ll be helping them be fantastic conversationalists by getting them to focus on the most interesting experiences / impressive challenges / learning moments / biggest successes of their life.

Again, there are lots of ways these questions can show up in practice:

  • What’s the best way to get into that [hobby / job / experience]?
  • Would you recommend someone else do the same thing?
  • What do you think stops more people from doing [x]?

Great questions are a low stakes invitation to go deeper

The reason all of these techniques work well is because a great question is a low stakes invitation to go deeper. I’m not jumping straight from “how is the weather?” to “tell me about your greatest fear?” - that’s a plunge right into the deepest stuff that’s probably not going to land well. Equally, I’m not keeping everything surface level in an attempt to avoid depth at all costs (which ends up being boring and limited conversation).

Instead, with each question I’m saying two things: 1) I’m actually listening to what you’re saying, 2) I’m interested in going deeper if you are.

Nevertheless, it’s totally up to your conversational partner how deep they want to go. When I ask how you got into being a school administrator, you can either tell me about how you needed something reliable with good working hours because you grew up in a chaotic family with no sense of security, and so you struggle to cope with a lack of order. Or, you can just tell me that you fell into it and you like that you’re helping children have a better future. Both say something interesting about you that we can use as a springboard for further conversation, but you’re setting the level of depth, and I’m just meeting you where you are.

I think this gets at the heart of why I think good questions are such a powerful and under appreciated tool.

There’s a famous metaphor used by psychologist Jonathan Haidt - that each person is like a rider on an elephant. The rider is our conscious self - rational, in control (or so they’d say), and the focus of much of the story we tell ourselves. The elephant is our much larger unconscious self - all of our emotional baggage, our drives and habits that make up much of who we are. We like to think of ourselves as just the rider, but when there is conflict between rider and elephant, we know who is winning 9 times out of 10. 

I like to think of good questions as a way of trying to understand other people’s elephants, and perhaps getting a better understanding of your own. This feeling of being understood by another person is one of the most electrifying and rewarding things you can do for another person - and it happens so rarely that people will remember how you made them feel. All of this, by just working on how to start asking better questions!

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