"Is it skepticism or just a no in disguise?"
We’re in the process of modernising a legacy system, and for a while, we were stuck. Every path forward turned into an all-or-nothing debate. And the last thing any of us wanted was to freeze the business while we rewrote the whole thing from scratch. So I brought in some specialists who did a review and recommended a path: build a missing capability within engineering, starting with one project. It would help us learn how to work incrementally with legacy code. The platform team would lead the first project, then we’d roll out the approach across other teams over time. I was excited. It felt like a way through. I reached out to the Team Lead whose team owns the code we were starting with. His team was already working on a high-profile project, so I knew we needed a lightweight way to keep them connected without pulling them off track. I explained the plan—expecting, maybe naively, that he’d share my excitement. Instead, he said: “What message does that send? It seems like all the exciting work will be done in the platform engineering team while my team are asked to do all the boring stuff.” I’d already tried to keep his team in the loop, we invited one of his engineers to join the platform team temporarily, to bring learning back and support the wider rollout. I explained the constraints. I explained the reasoning. He nodded. The next day, he raised the same concern again. Not with new information. Just… again. This is where it gets tricky. When someone raises a concern over and over, long after the rationale has been explained and the decision documented, it’s hard not to hear it as resistance. And when you're trying to involve people, trying to take into account the very outcome they’re worried about, it can feel personal. I want to be a leader who welcomes dissent. But I also have a job to do. There’s a line between healthy challenge and something else. And honestly, I wasn’t sure which side of the line this was. So I did what I always try to do in the messy middle: That reflection, and what I learned about the difference between skepticism and negativity, is what I’ll share in the next email. 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. |