The good news is that conversations can be designed. Here's what I started doing to design flywheel conversations during the first round of lockdowns, when I was in a new job and trying to get to know my coworkers:
I'd reach out to someone. In my case they were new coworkers but it can also be people you already know. The point is that it doesn't need to be someone who is already your best friend.
I would ask the person if they might be up for having a conversation with me, with the sole purpose of getting to know each other better. No talk about projects or work. That could come later if needed. I'd often ask for a full hour, but less would work too.
I'd suggest that we do it virtually and without video—just a regular phone call with headset, while walking around outside. I find video calls to be very distracting, because I inevitably focus on how I look. Out walking I can let my eyes wander across the landscape and just listen.
And finally I'd suggest that we each send three questions in advance that we want to ask the other person. The questions should invite a level of vulnerability and sharing, without forcing it. By sending them in advance the respondent can decide on how much they want to open up before getting on the call. Declining to answer a question that feels too invasive is completely ok, but this has never come up for me. Everyone I've invited has been eager to share and open up. Long answers are better than short ones.
Here are some of the questions I've encountered and enjoyed:
What is something you are proud of? (accomplishment, talent, skill, relationship etc.)
If I gave you $1 billion and you had to spend them on yourself then where would you begin? (no charity, no investment, just spending)
Can you tell me about a time where you felt like you failed?
What's most exciting to you these days?
What would you do if you weren't afraid?
On the agreed upon time we both put on jackets and headsets and went out walking.
We took turns asking and answering questions. Staying on a question as long as it made sense, and not rushing to answer all three.
The interview format means that the conversation happens on different rules. Turn taking (which is notoriously more challenging on the phone than in person) becomes less of an issue. And when the other person is answering my question I can focus on listening completely to their answer without having to think about what I will say next, because I know there'll be a question for me after.
In moments it has felt daring and I felt unsure or mildly uncomfortable. But as the conversation went along, most of them ended with a kind of social euphoria that has all but replaced my previous longing for "casual conversation at the coffee machine". One time I met a person at the coffee machine whom I had only met on the phone. I had expected that this would be quite exciting, but actually I was left feeling disappointed. Why? Because the phone conversation had been so intimate that meeting in the public space at the coffee machine with other people standing around just felt limiting. Seriously, give me one good 1:1 walk and call per week and I don't need any more superficial coffee machine small talk.
If you try this, or have done something similar, I'd be curious to hear from you.
Much love
Mathias
P.s. I'm here to support you! Keep going. And reach out if you need help.
P.p.s. I'm also launching a few new online courses, all starting early January. You'll be the first to know!
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