I spent an afternoon recently with someone who didn't ask me a single question the whole time we were together. It was a very odd experience, and it made me think a lot about how important good questions are in building relationships. And what gets signalled - and what the effect can be - when we don't ask them.
For context, this was someone I hadn't seen for a long time. We'd kept tabs on each other's lives via social media, and our winding career paths had recently taken us in a similar direction, which was the main reason we'd finally made the effort to meet up. It was a nice afternoon. But as I came away, a few things dawned on me:
- Firstly, I was absolutely exhausted. I'd had to work really hard to keep the conversation going, continuously finding things to say with no help, and no jumping-off points from her side.
- Secondly, I had no idea where her real interests lay. She'd responded to my questions, but because she hadn't asked me anything in return, everything I volunteered felt like a shot in the dark. I was constantly trying to gauge her level of interest in what I was saying.
- Thirdly, I couldn't help feeling as though she was just tolerating me being there. Surely, my logic went, if she wanted me there - if she was interested in me - she would have asked a few questions to keep the conversation going? I know now that she really enjoyed our time together, as she followed up very enthusiastically afterwards and was keen to meet again. But in the moment, her lack of questions made me question myself.
I truly believe that curiosity is one of the most important qualities to bring if what we want is to strengthen and deepen our relationships over time. But I also know from experience that it's something many people struggle with.
So let's talk about it.
Why Do Good Questions Matter So Much?
When I recently ran a session on asking good questions with members of The Friendshift Circle, we started our conversation by talking about why questions matter so much. Here's what we agreed:
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Questions help us get to know people, and to find out what we have in common.
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Questions can help us get beyond surface-level chit-chat to have deeper and more meaningful conversations.
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Questions can help us clarify and understand another person's perspective.
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Questions show you're interested in what the other person is saying, which makes them feel valued. Every time you ask a question, you're indicating that you want to know more about them, which shows them you genuinely want to be there.
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Questions help you to find out where someone else is 'at' and give permission for people to open up.
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Questions also play a far simpler role - they keep conversations moving and prevent awkward silences.
What Happens When We Don't Ask Questions
Flip all of this around, and you can start to see what happens when questions are missing from a conversation. If we're on the receiving end, we feel like our conversational partner isn't interested in us. That we're talking at rather than talking with. We feel it. We come away feeling drained, unsure, and questioning whether the other person actually wanted to spend time with us at all.
If we're the one who isn't asking questions, the conversation can feel awkward, unsatisfying, unfocused.
Why We Sometimes Find It Hard to Ask Good Questions
So if questions are so important, why do so many of us struggle with them? In talking to hundreds of people about exactly this, here are the most common reasons I hear for avoiding asking questions:
- We don't want to intrude. We worry about being too personal, too nosy, or stepping over a boundary we can't quite see.
- Our minds go blank. We know we should ask something, but in the moment, we can't think of a single thing to say.
- We're worried about speaking up. Especially in groups, we worry our question will sound stupid or we'll interrupt the flow.
- We're too busy thinking about what to say next. Our attention is on ourselves - what we'll contribute, how we'll look - rather than on the other person.
- We feel stupid. We don't know enough about the topic to know what to ask.
All of these are completely understandable. But if we want to unlock the benefits of asking questions, we have to find a way past these blockers.
How to ask questions to show curiosity and interest
Here are a few ideas:
- Use broad openers to kick off the conversation. "How was your weekend?" "What's been taking up most of your time lately?" "What are your holiday plans for this year?" These questions are open-ended enough to let someone take the conversation in whatever direction feels most natural to them.
- Use open-ended questions to explore topics more deeply. "How are you finding learning to drive?" "What's been the most challenging part so far?" These questions invite someone to expand on their experience and give you insight into how they're feeling about it.
- Ask what happened next. Help them finish the story. "What happened after your teacher told you that you were going too fast?" People love telling stories, and you're giving them permission to take you along for the ride.
- Ask how they felt about what happened. "How did you feel when your teacher told you that you were driving too fast?" This is where conversations move from surface-level to meaningful. You're not just asking for facts; you're asking for their internal experience.
- Notice what lights them up. Pay attention to where they smile, where they speed up, where their energy shifts. Then ask about that. "You sound really excited about the idea of being able to drive. What are you hoping you'll be able to do once you've passed your test?" When someone lights up about something, lean in.
- Use either/or questions to test theories. "Do you think they cut in front of you because they felt annoyed, or just because they weren't paying attention?" These questions show you're thinking deeply about what they've said and invite them to think about it too.
- Use yes/no questions sparingly - and strategically. Yes/no questions are useful for checking you've understood something or gathering context. "Which company are you using for your driving lessons?" "Are you learning in a manual?" "How long have you been having lessons?" These questions help you understand the situation better so you can ask more interesting follow-up questions. But if all your questions can be answered with yes, no, or a single fact, the conversation will feel like an interrogation.
- Ask about what you're naturally interested in. "Are many people your age learning to drive at the moment? I feel like fewer people are learning these days." Don't force interest where it doesn't exist, but when something genuinely piques your curiosity, ask about it. Your authentic interest will come through.
- Bring someone in on advice or knowledge. "Do you know if the old race track is still there? It used to be brilliant for practising turns without an instructor." This shifts the dynamic slightly - you're not just asking questions, you're collaborating, sharing, creating reciprocity.
- Use what/where/when/how/why/who questions. These starter questions are your friends. They're open-ended, they invite detail, and they keep conversations flowing.
- Respond well to what's being said. This is absolutely crucial. Questions are only half the equation. The other half is how you respond. So nod, smile, raise your eyebrows to show surprise. Mouth "wow!" or "no!" Add your own observations to show understanding and empathy: "I wonder if..." or "That must have been so..." remember that your non-verbal responses matter just as much as the questions you ask. They show you're engaged, present, and genuinely interested in what you're hearing.
How to put this into practice
Asking good questions is a skill we can all get better at. But it's okay not to be brilliant at it straight away! Learning new skills takes time, and it's fine to start small as you put the ideas above into practice. Try one of the ideas above at a time until it feels natural and normal, before you move onto the next one. Write lists of practice questions and memorise 3-4 before you go into a social situation. After you've spent time around other people, reflect on what went well, write yourself notes on what you will do differently next time - then do it. Get feedback from trusted people in your life when you can. Practice, and treat the whole experience as a learning process in which you'll sometimes get it right and sometimes not - and get okay with it not always going completely how you'd hoped it would. Be kind to yourself as you learn, and keep going. Things will change, your conversations will become more energised and meaningful, people around you will feel valued and seen by you, and you will start to open the door to more meaningful connections.
Would you like to join conversations like these? The Friendshift Circle is a learning community where thoughtful, independent adults come together to build meaningful friendships and practise the skills that matter most - including asking brilliant questions.
