Ask deep introspective questions at work.

At emdash, we have a no-agenda meeting every Friday where the team comes together and discusses whatever they want. One of the young ones often asks us existential questions: Do you believe in planning or going with the flow; what is true love; do you believe in god; that kinda thing.

We’re a very small firm, so we can afford to have these conversations. Also, apart from me, most of my team are freshers, so they’d like to hear from people who’ve just lived longer.

I’d understand if you’re not a fan of discussing young people’s existential problems, but within the boundaries you are comfortable with, ask deep introspective questions at work.

A few that come up often for me are:

  1. How do we decide which customer to work with?

  2. Why are you passing that lead on to another freelancer?

  3. Why are you grumpy? Why are you zen-like today?

  4. Why is X bothering you this much? It doesn’t seem like a big deal to me.

The idea here is to understand each other as individuals. To know what matters to someone and why. For instance, a customer might be okay with small delays, as long as you keep them posted — for them, communication is more important than timeliness. An employee might value recognition at the moment rather than in the form of money at the end of the year.

Having conversations beyond work, and spending time in introspection, has helped my teams work together better. It also helped build trust and faith. If your colleagues knew from early on that you have a dog and love her to bits, they won’t be taken aback when you need a day off to care for her. It also allows you to be vulnerable.

I once answered with “true love is something that lets you be who you are” in a meeting and got mocked for it. Except, it was good-hearted riffing that only made the team stronger.