"When a check-in feels like a challenge"
A while back, I noticed someone on the team had gone unusually quiet. No commits, no Slack chatter, nothing in the backlog. I checked calendars, not on leave. I hoped I’d just missed something. But I hadn’t. So I messaged their Team Lead and asked if everything was okay. The reply came back fast and sharp: Ouch, that hurt. I hadn’t drawn a conclusion. I wasn’t accusing anyone. I just didn’t want to overlook someone who might be stuck, struggling, or quietly disengaging. But in that moment, my question landed like a challenge, not a check-in. Here’s the thing I’ve come to understand: even if my intent is care, my position gives it weight. I hold power, whether I’m using it or not. My curiosity isn’t always neutral, especially to someone who might feel like they’re being judged. It wasn’t risky for me to ask the question. But I still felt trepidation, because I knew it had the potential to upset someone I trusted and respected. And yet, not asking would have felt worse. Because sometimes people do need help, and they’re not going to raise their hand. So I ask. But I try to do it better now, with clearer intent, softer language, and more context. I try to make it feel like a hand extended, not a spotlight turned on. Until next time, ✉️ Enjoying The Messy Middle? If someone sent this email your way and you’d like to get it direct, you can sign up here. |