Stumbling into chaos

Problem

"I joined a startup some years ago as a new director of engineering. My plan was to spend the first few weeks getting to know people, the product, and the culture. Once I'd gotten established myself, I'd start to look for opportunities to help out. Unfortunately, things weren't going to play out that way...

Right before I'd joined, the team had done a re-org and re-oriented the product roadmap. Much of the team was confused as to their new roles and structure and had an aggressive plan to launch their initial product in the coming months. The team began to look to me for guidance, so I had to jump in on day one."

Actions Taken

"First order of business was to understand why the new structure had been put in place, so I wasn't stepping on toes. To do this, I met with our CTO and the other engineering leads and asked a lot of questions. Once I started to understand why, I needed to get people working on things. Bored engineers can be a dangerous thing.

To do this, I worked with the product managers for each of the teams, and explained that we needed some work short-term to help them. I knew that they had just experienced a bit of a reset of the product roadmap and were overloaded, but I urged them to focus on what pieces we had high certainty that we would need, so we could get the engineers to start designing these.

Next, I needed to give the engineers some structure to hold on to. Much of the feedback I'd received in the first few days from my team was concern about not knowing what they were supposed to be doing. To help align the engineering and product teams and create some feeling of consistency. To start small, we added weekly planning meetings for each of our product teams, in addition to our daily standups. These meetings were a chance for engineers and product to sit down face-to-face and discuss what they'd be working on the next week. This created strong incentive for the product team to be ready for the coming week and created accountability for the engineering team to meet their commitments each week.

Once we'd established some sense of order over the first month or two, we then had the foundation to start working on adding nuance to the teams and process. Using retros and feedback from 1:1s and other sources, we took these initial short-term fixes and tailored them to our needs."

Lessons Learned

• "The best laid plans often go awry, and we have to adapt to the reality in front of us, not what we hoped reality would be."
• "When long term roadmap plans change, look for short-term engineering work to give the product team time to plan."
• "Creating a predictable process cadence for a team can help create a sense of stability when things are otherwise uncertain."