Today I sat down with Jennifer Houle for a live conversation about what happens inside teams when leadership is new, unclear or under pressure. You can watch the full recording above.
Jen writes Uncompliant, where she covers what’s broken in HR and what we can do about it.
The conversation grew out of two pieces we have published together on The Art of Asking Questions. The first, Lean In, tells the story of a team handed a tight deadline and a single vague instruction: “if we all lean in, this should come together.” Nobody asks what that means, and one person (our protagonist, Rahul) ends up absorbing all the ambiguity alone. The second, 5 Practical Ways to Navigate the Peer-to-Manager Shift, follows Rahul after he’s promoted to team lead, and explores his changing relationship with the people he used to work with and now needs to manage.
We got into the kind of stuff that doesn’t usually make it into leadership advice: why people absorb ambiguity alone instead of raising it, what it actually feels like to give tough feedback to someone who used to be your peer, and the particular loneliness of realising your informal thinking partners are now the people you’re supposed to have answers for.
Now, looking at these articles together, there’s a thread we keep coming back to. And that’s the fact that they both end without a neat resolution. The first story ends with Rahul sitting in silence over a cooling coffee. The peer-to-manager piece ends with him looking at his old desk, now occupied by someone else, wondering when the promotion started to feel less like a step up and more like a step away.
We were deliberate about that. These situations rarely resolve cleanly - they just become the thing you carry into the next one.
If you have missed the articles, take a look below:
Thank you for watching, and see you next time!
