How To Make Friends with Uber Drivers Part 1

Oliver Rutherford
3 min readNov 5, 2020

Art art of opening a conversation

From uber.com

Last year, I moved to the US for work and in the space of 6 months found myself taking over 700 Ubers to transport between meetings.

That’s a lot of Ubers 🤭

Each ride was around 10–12 minutes long, and it quickly occurred to me that the Uber drivers were sick and tired of hearing the same opening questions:

“So… how long have you been doing Uber?”

“What do you like about doing Uber?”

😱😱😱

So I started experimenting with new ‘openers’ to figure out how I could build a meaningful connection with my drivers in 11 minutes, and sow the seeds for a friendship.

At first I played it safe:

“So… do you do Uber full-time or part-time?”

““I see you also have a Lyft sign… do you prefer Uber or Lyft?”

But I could tell they’d been asked these questions thousands of times and they would naturally not be inclined to go ‘off-script’.

How could I build a meaningful connection with someone if I was asking them questions that encouraged them to be ‘on-script’?

Then I went to the other extreme:

“Isn’t life beautiful?”

“What’a lie that you’re telling yourself right now?”

About half of the drivers reacted well to this and we instantly killed the small-talk BS, but the other half looked at me like I was insane 🤣🤣🤣

The response I got after I asked some overly deep questions

So I thought: what’s an opening question that would enable the drivers to take the conversation to whatever level they wanted? If they were feeling deep chats, they could take it there, but if they wanted to keep it simple/not talk to me, they were empowered to do that too?

What’s on your mind these days?

That became my go-to question

10% answered with “nothing”, with no “and you?”.

Hint taken, thank you, I’ll just pop my headphones in, then 😎

Most answered with something like

“Ah, well, I’m just trying to juggle driving with my normal job as a realtor and my wife and I are expecting a baby so it’s all a bit exciting and scary, how about you?”

Amazing. So much to dig into there!

About 20% went straight for the really deep stuff and some are still my friends to this day. In fact, for my birthday party that year, almost 20 people who showed up were Uber/Lyft drivers 🎉

Morale of the story?

  1. Everyone has a story. Be curious.
  2. Ask questions that give the other person agency to take it to the level of brevity/depth they want.

What are some things you’ve learnt about conversations recently?

Are there better ways to open conversations that lower the barriers to entry whilst enabling the skipping of ‘on-script’ small-talk?

Curious to hear your thoughts!

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Oliver Rutherford

CEO @ UniRise, Co-Founder @ Polymatic, Co-Host of High Performance 4 Lazy People Podcast