Hello! I’m sliding into your inbox with a bit of a different newsletter this morning, and for good reason.
As many of you know, my educational background isn't in computer science; I'm actually a trained therapist. (The connection back to software engineering started when I was 11, but that's a story for another day.) Part of my training as a therapist means I've learned to help individuals confront some of the most challenging conversations they need to have with others but continue to put off.
I think the reason these conversations get delayed isn't really about the content. Most managers I talk to know what they need to say. They can articulate the issue clearly. They could write the talking points in ten minutes.
What they don't know is how to open it without triggering defensiveness, how to handle it if the person pushes back or gets emotional or goes quiet, and how to end it with a real next step instead of a vague "let's check in again soon." The gap isn't knowledge of the problem. It's a plan for the conversation itself.
And without that plan, most of us do what's natural: we wait. We hope the situation resolves on its own. We drop hints. We give feedback so softened it doesn't register as feedback. We tell ourselves we're being patient, when what we're actually doing is letting the problem get harder.
That’s why I'm running a workshop on May 16 called Navigate Tough Conversations at Work. It's a three-hour working session, not a lecture. You bring a real conversation you've been avoiding — underperformance, misalignment, direct feedback — and we work through it together. You leave with:
A clear goal for the conversation (what actually needs to change)
A structured way to open it without triggering defensiveness
A plan for handling pushback, emotion, or silence
A framework you can reuse the next time one of these shows up
It combines the leadership side of my work with my training as a therapist, which is a lens I don't bring to the newsletter often but is genuinely useful here. The goal is that you leave ready to have the conversation, not just informed about it.
I’ll be taking the next two weeks off writing while I’m on vacation, but I’ll be back in your inbox in mid-May!
Kelly