Apparently, I Ask Good Questions
- Apr 2
- 4 min read
When being terrible at small talk finally ends up being helpful...
I am absolutely horrible at small talk / meeting new people / walking into rooms of people I don’t know. Any of the above really. I can do it, but it sucks the energy from me and if I don’t have someone else in the conversation that can help it flow you can best believe I will be filling that awkward silence with inane chat about the weather. Ugh.
I was told recently though that I ask good questions and I hadn’t really ever considered this to be a skill that I possessed. Obviously, my first instinct was to reflect the compliment and the attention. Then I moved to interrogating the comment - Was it genuine? Were they trying to check I had done the work myself?
It had been a set of submitted questions before a Q&A type thing and actually what I realised was, I’m just better and writing my thoughts that I am speaking them at the time. It allows me to bypass the boring questions and get to the bits I really want to know. Which then made me think…

So what actually makes a good question?
I’ve been thinking about this since the comment landed and I think, for me at least, it comes down to one thing: the willingness to go underneath the obvious.
A written format absolutely helps give me the time and space to voice that question under the question. When I was submitting questions ahead of a Q&A rather than firing them off in real time, I had the opportunity to ask what I actually wanted to know. It allowed time for the list of predictable questions to fall away and I re-ordered what I actually want to know to the top. It’s less a skill and more just... how my brain is wired.
The thing is though, the questions (for me at least) don’t stop forming in real life even if I don’t feel like I can’t ask them. If I’m in conversation and the moment passes, or it doesn’t feel like the right time or I just don’t know that person well enough, my brain will start up a parallel conversation anyway. The only way I can describe it is like a kind of tandem conversation where I am turning over what’s being said, tossing around what I think is driving it, what the person actually means underneath what they’re telling me. Do you ever do this?
The playground problem
I am genuinely, comically bad at small talk though and thinking about it now, I think it is probably the tandem conversations going on in my mind over shyness.Picking up the kids after school is a prime example. How was your day? Oh it’s so cold today isn’t it? The silent conversational death spiral afterwards because you either don’t know them well enough or you know you don’t have time to get into anything before hungry tied kids come running at you.
Uuuuuggghh.
It’s not even because I don’t care either, it’s quite the opposite. Give me a wine and a chat over a few hours and I am in it. I want to dig into what is going on and really find out about who they are, what makes them tick. I have realised over time that I just need depth to engage properly - that surface level chat feels like speaking an entirely different language and I am no pro. I run out very quickly of questions to keep things light and breezy. And now I am writing about it and thinking it through, I think it’s more of my core than I realise.
As an aside - Pub quiz teams: I am not your woman. You can give me a hard pass on having me in your team and I won’t be offended. I'm a percolator, a discussionist, not a rapid recall merchant and I will be of no use to you. I want to dig into how that fact came about, who decided it mattered, what it connects to... by which point someone else has already buzzed in and we've lost the point. I’ll stick to getting the round in instead!

The UX connection
I am learning that good UX research is built on asking the question underneath the question too. Less “do you like this?” and more “walk me through what you were trying to do”. We are taught to avoid “what do you want?” and dig into “what were you expecting to happen?” instead.I’ve been doing this instinctively my entire life. I just didn’t know there was a framework for it until now. What I need to work on now though is surfacing these brain wanderings more often.
My challenge is getting those questions out of my head, from the tandem conversation I am having with myself, and into the real life chat so I can get the answers I am already asking. Removing the guess work and gathering the evidence to back up my assumptions. I wonder, what would happen if I did just ask the question in real time and see what happens? What if the parents in the playground actually want (or need?!) to dig in right there and then?
The one I can’t answer…
I think this is probably something lots of people wonder too: how do people actually experience me? Have you ever thought this? I would absolutely love to jump into someone’s head and see through their eyes how I am experienced out in the wild! I spend so much time observing others and considering their drivers. I would LOVE to know how others actually see me. Probably wouldn’t enjoy the answers mind…
Maybe the best questions are the ones that don’t have any clean answer yet.Maybe good questions are actually the ones that lead to more questions?And maybe, just maybe, being terrible at small talk and brilliant at depth aren’t two separate things. Maybe they are part of the same wiring, just present like that in different contexts.
Tell me, what is one question you have thought about, want the answer to, but maybe not asked yet?



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