Social skills challenge · Challenge
Take a work chat past small talk
Have one conversation with a colleague today that goes past logistics and weather — ask what they're working on and what's annoying about it, or what they're looking forward to.
Why this works
Work friendships form in the two-minute gaps between meetings, and 'what's annoying about it' is a magic question — everyone has an answer and it's more honest than 'how's it going'.
How to do it
- 1
Use a natural gap: before the meeting starts, at the coffee machine, in the last two minutes of a call.
- 2
Ask the magic question: "What are you working on at the moment — and what's the annoying part?"
- 3
Match their honesty with one line of your own: "Same — mine's the deployment pipeline this week."
- 4
Let it end when the meeting starts or the coffee's done. Two real minutes beat twenty polite ones.
If your brain is fighting you
If it feels intrusive, remember that almost everyone at work is quietly starving for a conversation that isn't logistics. You're not prying — 'what's annoying about it' invites exactly as much honesty as they want to give. Remote? The same question works as a Slack message, and a two-minute voice call after standup counts fully.
Felt easy? Level up
Follow up on the answer days later: "Did the pipeline thing get sorted?" Remembering is what turns colleagues into work friends.
Go deeper
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More challenges at this level
- Make the call you've been avoidingThat phone call you've been putting off — appointment, question, awkward follow-up — make it today. Write your opening sentence down first if it helps, then dial.
- Talk to one strangerHave one conversation with a stranger today that goes past the greeting — aim for two minutes. Comment on the shared situation, ask a question, see where it goes.
- Only ask follow-up questionsIn one conversation today, don't change the subject once. Every question you ask must dig into something the other person just said.