Why You Should Ask Strangers Personal Questions


Something very weird happened on Tuesday night.

Or, if not weird, then… alchemical might be the word. I had actually fully intended to write a blog about something else – some straight up networking advice (like I gave you here and here). But I’m still reeling from that evening and feel like I have to tell you about it.

It started innocently enough:

Sat on folding chairs in the bar’s big, back room, we – the hundred-or-so-strong audience of True Stories Told Live, the show I run and host in Toronto – had already enjoyed two tellers that were funny and sweet.

It was our second birthday, so I made the audience all blow up balloons

Connie Tsang had described her first job in TV, when she was a painfully shy twenty year old – a cautionary tale about the pitfalls (pun intented) of buying your smart office wear second-hand from the Goodwill. Then we’d rolled around at Chris Graham‘s attempts to save a stranger from a terrible first date by teaching him some etiquette (it did not end well). For anyone new to the show, this seemed to be what the event is all about: warm, funny, light stories.

My introductions and segues between the acts were the kind of silly fun you’d expect if you’ve seen my videos. I brought on the musician – we have one every time, who tells a story about a song, then plays it.

Tall and grinning with a guitar slung around his neck, he told us warm, sweet stories of playing bass in a pirate-themed band for waist-high audiences made up of kids. We caught each other’s eyes and giggled. 

But then, something happened.

Before any of us had quite realised, the story had slowed down, shifted and moved into the darkest of places. We stopped giggling. We stopped looking at anyone other than him.

We were no longer an audience in the big, back room of a Toronto bar. We were now in the basement of this guy’s house, seven years ago. Ghosts, sitting next to him on the bed. Watching him dissolve into psychosis and self-harm. Unable to look away and powerless to help.

In the two years-worth of shows we’ve had, I’d never seen this. Over a hundred people, spread about the room, silent. SILENT. I can’t say for sure how long; five minutes? Ten? Time stopped; everything stopped. We must all have been breathing – no one passed out – but you couldn’t be sure from listening.

“And then,” he said. Huge gaps between his sentences. “Two words came to mind. Granville Bridge.” We knew he was talking about jumping off it. “Because, anything else means you don’t love the world enough. And I can tell you quite honestly, I’ve never been remotely as terrified as right then.”


He continued, the story moved on both from that episode and eventually –guitar we all breathed out – to his recovery. He was fine, is fine, and the story wrapped up with his song: a re-writing of the pirate’s search, with the treasure being inside of him, and us, all along. He gave us a line to sing. One of our characteristics as Torontonians is that we tend to be rather shy of audience interaction. But needing a release from that tension, we belted it out.

He finished and we cheered, roared our appreciation. And relief.

The thing is, that wasn’t the story he’d intended to tell. Not even slightly. It was all my fault.


Before every True Stories Told Live show, I meet up with each of the storytellers. We go through the story and shape it together. Sometimes, they (like our musician here) have never told a story onstage before, so there are certain rules of storytelling they may not know.

Like: always tell things in the chronological order that they happened to you at the time; or: don’t say your age and the date this happened – then you’ll lose your audience to math, as they stop listening to you and try and work out how old you are now.

But sometimes, it’s about excavation. People begin telling me their story and, through digging around, something in my bones tells me that the one they’d planned on isn’t their story – that there’s another beneath it, that needs to come out.

I’ve had a storyteller come to me with a fun anecdote about childhood mischief, and leave with an intense coming of age move to Hong Kong, that affected her relationship with her dad and her entire career. Often people bring me sprawling epics of an entire summer, and leave with the detailed events of just one afternoon.

If you’re interested in the mechanics, here’s how it works:

We meet, preferably in person but sometimes over the phone or skype.

I say,
“Tell me the story as much as possible as if we’re just sitting here. I’m going to ask you a million questions. We’re going to go down avenues you would never go down on stage. You’ll get frustrated because it might feel like I’m obstructing you from getting to the point, but just trust me. If there’s anything you don’t want to talk about, you can say, ‘I don’t want to talk about that’ – or maybe, ‘I’ll tell you, bhands tableut I wouldn’t say this on stage’”.

It usually takes about two hours, and i LOVE it. Here’s why:

(1) I get to satisfy a huge part of me – without getting into trouble

I am wildly curious. Wildly. Because of this, I tend to ask people I’ve just met a lot of questions. I’ve also learned, over the years, to ask quite personal ones.

This is disarming, so what used to happen was:

I’d ask loads of really personal questions, and this new friend would tell me lots of really personal answers.

Then, in the days before I’d had five years of therapy around boundaries, I’d suddenly feel the (very human) urge to reciprocate, and respond with loads of personal details about myself.

Then, because that’s a pretty intense experience and it was out of the ordinary for them, the other person would often (reasonably) think, “Oh my goodness! Marsha and I just had A Moment! We have this Special Connection!”

Whereas it was kind of a daily occurance for me. I’d done the same thing with the taxi driver on the way there.

And that could cause problems.

Doing the story coaching: I get to ask people all these REALLY personal questions.
They don’t expect me to give anything away about myself, because the whole reason we’re there is them and their story. Because we’re in this professional container, they don’t see it as a meaningful relationship changer – it’s just part of the process.

I get all the kick of having that intense conversation, without any of the previous repercussions.

(2) I get to feel like an insider

They leave with a beautifully constructed ten minute story – that everyone at the show will enjoy – but I get to hear the Director’s Cut.
I really think that one of the best things you can do to engage peoplIMG_4134e is make them feel part of a special secret club that no one else is part of – and when that storyteller is onstage, I get that delightful feeling of being aware of all the context around what everyone else is hearing. 


(3) I go through what they went through

Because I’m getting the full version of the story, because the two- (and sometimes, three- and four-) hour process is so intense, I get to feel like I actually did spend time in all these different worlds. In the way that you do with an excellent book, or a dream you can fully remember.

In the last few months, via the story coaching, I have: been in a massive earthquake in Chile; transported an unruly cat across the atlantic, flying first class; been robbed by disarmingly polite (but pretty scary) rebelling soldiers in Congo; spent a summer tree-planting in British Columbia; been haunted at dinner by the ghosts of an 18th Century sex worker and her secret love; had an affair, in Edinburgh, with a man twice my age who was always covered in purple glitter; and, of course, been in our musicians basement, slowly coming to the conclusion that everything is connected, and that understanding this made me a god.

It’s not just escapism; I’m left with all the tastes, smells, sounds and – most powerfully – emotions that they experienced.

(4) I know that soon, the best of this will be passed on to everyone at True Stories Told Live

An audience has a substantially less attention span than one person. They don’t get to interject with questions, and they don’t have the focused eye contact. Plus, you never know if they need a wee.

But this is counterbalanced by the sorcery of what happens when you tell a story to a crowd of people. There’s something chemical about it – maybe the neurons and protons of over a hundred heads, each constructing their own internal movie of how it looked happened, each having their own blend of emotional reaction.

(5) The storyteller feels incredible

Once onstage – I often say that telling a story onstage is like opening your soul; or sometimes like time travel – you get to re-experience what happens.

But they also feel wonderful straight after the story-coaching experience. Because, when else do you have one person sit and spend upwards of two hours asking you intensely about your experiences? With no interjections of their own similar ones, no switching of topics to something not directly related to you – and no weirdness that the conversation is so one-sided? Never, I’d guess.

What would I like you to take away from this?


Ask better questions.

As I’ve said before, I hate making small talk as much as the next person. My trick is just not to do it.

Stop making small-talk. Ask better questions


Actually – small caveat: you tend to need one small talk question to enter a conversation, just so that the person you’re asking understands that you have good judgement. But then, you can usually launch pretty quickly into more personal, more interesting questions.

The key is to be respectful.

Always, always tag your probing questions with, “If you don’t mind me asking…”. And if you sense they do mind: quickly ask something gentler, then behave as if nothing unusual has happened.

Remember: people will always follow your physical cues. If you pretend this is the most normal thing in the world and nothing weird just happened – even if you’re internally shrinking with regret – then they will quickly assume that everything is fine and you’ll both soon forget it ever happened.
I truly believe that people love answering these kind of questions – as long as they’re being asked respectfully, and by someone who is focused, holding good eye contact, and being very present. (more tips in those links)

If you have a story you’re dying to tell but no clue as to how to shrink it from the two hour version to a compelling ten minutes – or three minutes, or one and a half – I’d love to help you out. You can find out more, by looking HERE.


Over to you

What was the last intense conversation you had with someone you’d recently met? How did it make you feel – in the moment and afterwards?

I’d love to know that – or just your thoughts on any of this stuff – in the comments below.

Thanks so much for reading! If you know anyone who’s as obsessed with storytelling as I am – or who wishes they could have more fulfilling conversations with aquaintances and strangers – they and I would both love it if you shared this article, using one of the round buttons below.

You rule!

xx (Yes Yes) Marsha

PS need help with a story yourself? Look here.

PPS Want to see that story in full? Here you go. Please note that we didn’t have audience microphones, so you can’t hear quite how loudly they were singing (and laughing in the funny bits). But trust me that they were:


Photo credits: Symic and Stuart Chalmers via Compfight cc, and me (Marsha).


  • Caroline

    Reply Reply February 27, 2015

    Well that’s a great story in itself! Thank you Marsha! But I want to know more – what happened in the room afterwards? Did someone have to follow this amazing tale? Can we have the next chapter please?

    • Marsha (Yes Yes Marsha)

      Marsha Shandur

      Reply Reply February 27, 2015

      Caroline! So in fact, there *is* a video, recorded but not yet edited. The moment it is, I’ll stick it up and let you know! So glad you enjoyed it.

  • Becky

    Reply Reply March 1, 2015

    In a world where so many people crave connection, this is a beautiful thing you’re doing. <3

    • Marsha (Yes Yes Marsha)

      Marsha Shandur

      Reply Reply March 3, 2015

      Aw, thanks Becky. I do think that the reason this storytelling scene is exploding is because it touches something primal within us. x

  • Charmaine

    Reply Reply March 19, 2015

    I was there for that show and you couldn’t have described it more perfectly! That is exactly how we I felt! It was an incredible moment! And you’re absolutely right – you feel like you’re going through the moments with him. My girlfriends and I have been coming to your shows for the last few months and we love them. We’ll be there this Tuesday :)

    • Marsha (Yes Yes Marsha)

      Marsha Shandur

      Reply Reply March 19, 2015

      Aw, thanks Charmaine, what a lovely thing to say!

      See you on Tuesday – come and say hello if you get the chance :)

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