March 17, 2025

Want better outcomes for your team? Start by asking: "What didn't work? And what will we do about that?"

Looking back is underrated. Reflection isn't just about celebrating wins and it should never be about punishing mistakes; it's about digging deep, asking tough questions, and finding improved ways forward. You have only made a mistake if you don't learn from what happened and change as a result.

What worked? What didn't? What surprised us? What fell apart? And most importantly - what are we going to do about all that?

Early on, I learned this lesson by accident. Back at SendGrid, I was on the Developer Relations team, trying to make sure the docs were keeping up with what the business was doing. I had no formal Product Management training yet, but I had so many questions. I started showing up uninvited to the Product Planning meetings.

Eventually, I realized: success wasn't about knowing everything upfront. Instead, progress came from constant iteration - reflect, learn, adjust, repeat. That mindset helped me transition from "Docs Developer" to Developer Experience Product Manager, and eventually toward building a team-system that reinforced alignment and collaboration with company goals and progress. 

Here's what I've found over the years working with teams: 

→ Skip retrospectives to repeat mistakes.  → Ignore feedback to overlook gold.  → Ignore lessons so that nothing changes. 

Reflection is messy and sometimes very difficult, but it's powerful. It's where growth lives. Every stumble, misstep, or outright failure has something valuable hidden inside - if you're willing to take a little bit of time away from "go go go" to look and talk about it.

Missing these opportunities will actually cause more drag than the time it takes to pay attention to them.

So here's my challenge: make reflection part of your process. Ask better questions. Be brutally honest. Then take action.