How to set reasonable deadlines and get the team excited about them

Problem

"A few years ago, I took over leading an engineering team that was pretty loose in their process of setting sprint goals and project milestones, and of respecting them. The problem was that the rest of the company depended on their deadlines, and our product team wanted a predictable timeframe."

Actions taken

"In order to solve this problem, I worked directly with the product team to gather a very clear, prioritized backlog of what they were expecting. Then, with my team, we did high-level technical research and added rough estimates (aka 't-shirt sizes') for the items on the backlog. From there we mapped out week-by-week who was going to work on what, on a resource planning spreadsheet that was made visible to everyone. When projects were within a few weeks of kicking off, the engineers working on the given project planned out and committed to a series of deadlines and a launch date, and this was tracked in the same planning spreadsheet. When planning milestones, we include some buffer time, in order to anticipate potential complications and bug fixes that may need to be handled. Clearly, planning the allocation of engineering time and having a set of intermediate milestones helped to not overburden engineers, and held tech leads accountable for the dates they had committed to. We also switched to weekly sprints and a lightweight weekly sprint planning session. Every week, in addition to reviewing individual tasks for the week, each of my tech leads checked in on their milestones with me and the rest of my team and we made updates if needed."

Lessons learned

"I would definitely recommend having a transparent planning process within your team, with product management, and with the rest of your organization. Engineering team deliverables are often the heart of the whole company. Having committed milestones and launch dates that are driven by the team, and not by someone external, enforces accountability and makes engineers feel empowered about having control over their work and scheduling, which tends to produce the most fulfilled and passionate teams. Equally as important, it earns trust with the rest of the organization, as they always know what the engineering team is up to and what tradeoffs would need to be made to slot in a new request or investigate a random issue."