Why I Always Start Conversations With These Key Words

William Rudd
4 min readFeb 5, 2021

The easy route to fantastic conversations with new people

“Great Conversations, Any Location” : Photo by Start Digital on Unsplash

Have you ever walked away from a conversation and thought ‘I’ve learnt nothing from that’? Do you detest ‘small talk’ or dread meeting new people?

We’ve all had the same unsatisfying exchanges:

  • What’s your Name? Steve
  • What do you do? Finance
  • Where are you from? London

These are closed questions that can usually be answered in one word, with a high chance that you won’t find anything in common to build on. It can also make them feel like they are being interviewed so they may start to get defensive! Apart from the occasional unique answer, this seldom inspires great conversation.

‘What do you do?’ has issues in that a significant proportion of people don’t enjoy their job and may feel that it is not a relevant proxy for their identity. They may tell you slightly reluctantly and not give you enough in their answer to keep the conversation moving.

‘Where are you from?’ is equally complex: a lot of people have been formed by multiple places, so will always feel conflicted about the question. They will usually dismiss it by saying one of the places that they are from. They may feel resentful if you dig as it is something they repeat often and far more complex than a two minute answer. Again, unlikely to make the conversation fly.

When the first answer is not what was expected based on the colour of your skin or the sound of your voice, it leads to an inadvisable follow-on question for a multicultural world: “Where are you really from?” This is a common occurrence for White people from Africa as well as with Black or Asian-looking people from Europe.

“What’s Your Story?”

I’ve been lucky to meet a lot of very diverse people, having lived in many different places across three continents. I’ve always tried to make the most of these meetings, usually by asking more surprising and open questions right from the start.

“What’s Your Story?” works fantastically in my experience.

  • It is still unusual enough to make people pause and actually think before answering.
  • It gives them the power and the opportunity to shape their own narrative.

This is excellent on many levels.

It stops people jumping to conclusions based on the fact that they are meeting a Banker from London called Steve. This is especially good for people whose job or home town is frequently stereotyped — believe me, they’ve heard your next response a hundred times.

‘What’s Your Story’ allows Steve to tell his own story about how he has three siblings & a beautiful wife, is enjoying an evening away from his young but noisy kid & loves to do triathlons when he gets the time.

This gives you a large supply of more universal future questions and potential for a far deeper relationship than you would have had with ‘Steve from London’.

Some people are a bit taken aback by the question; they can feel pressure to give you a good answer and it may take them a little while. This is good. While they think, I try to be quiet but attentive. I’ve said my piece, now my aim is to help them feel calm.

Usually, this calmness works very well & you get some interesting responses from these more introverted people.

If they clarify what story you mean (‘In life? Or right now?’), which is a common response from those who haven’t been faced with this question before - you can give them an easy route: “just tell me about you”.

So far, you’ve already learnt that they are less gregarious & spontaneous — which is more than you would have learnt from quick answers to closed questions. After they tell you about themselves, it’s often good to build rapport with a self effacing: “sorry for putting you on the spot with difficult questions!”

I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.’ (Maya Angelou) / Carl Buehner

Is this the magic bullet? I have to put a caveat in… It doesn’t always work. I once ended up in a bar with Leigh Halfpenny, the legendary Welsh professional Rugby player, so I thought I’d try it out. A few drinks down, I walked over and, mangling it slightly, said: “Leigh, tell me a story?”


Was the rapid & heartfelt response I received. I respect him completely for it. “What’s your story?” probably works less well with celebrities. Their story is on their official Social Media page; leave them in peace when they are out with their friends!

Famous people aside, I have found that ‘What’s your story’ works exceptionally well, but it’s just the start. If your aim is to build good relationships, please make sure you actively listen to the answer!

I always aim to walk away from a conversation having learnt something, because you never know what hidden talents & perspectives a person may have. This could be groundbreaking scientific information about the next Tesla-challenging Electric Car, or as mundane as their favourite colour is Purple. Either way, your genuine curiosity will shine through, people won’t forget & they will look forward to seeing you again!

“What’s your story?” works for me, please let me know your experiences?



William Rudd

Lived in Kenya, UK, & now Singapore. Love meeting people, reading, & playing sport. Enjoy everything from Entrepreneurship to Education to Ecology.