Damien asked for help resolving some delivery issues with their fledgling SAAS product. He was dreading the next planning meeting and couldn’t see a way forward. As the technical team lead, Damien was good at maintaining a calm demeanour and warm smile, but behind that, he was anxious and feeling overwhelmed, unsure how to turn around the time-consuming discussions and poor team dynamics that characterised planning.
Damien confessed he was seriously thinking about moving on.
We talked through what was happening - planning took an entire day to step through the tickets, discussing each one as they went, and on one occasion it spilled over to the following day. A few individuals dominated the discussions and some developers told him it was a waste of their time. Damien was overwhelmed at having so many developers and was finding he barely ever had time to plan for planning meetings, the irony of which wasn’t lost.
It wasn’t always like this.
The largely remote team used to enjoy meeting up in person and planning as a team. Everything had been going well until the commercial success of their fledgling SAAS product and an influx of investment put growth on the agenda. Growth had been rapid, and one of the VCs dropped in an agile coach to help scale engineering capacity. However, Damien struggled to keep up with his own technical work whilst managing the much bigger team, and the recent departure of the agile coach was the final straw.
Damien needed good technical support so he could focus on leadership responsibilities. We agreed to give it three months, and then reassess.
I started running the planning meetings, ensuring sufficient tickets were well defined ahead of time. Damien’s anxiety reduced immediately. I also transitioned much of the ‘on the day’ planning to regular refinement sessions ahead of time, attended by only those who needed to be there.
The refinement sessions ran twice weekly, 90 minutes each. I invited only the developers working on upcoming features, the product owner, and occasionally a designer. We’d work through 5-8 tickets per session, clarifying requirements, identifying technical dependencies, and surfacing questions before planning.
This meant planning meetings became decision-making sessions, not discovery sessions. Developers arrived already understanding the work. We could focus on commitment and capacity, not debating what tickets meant. The quiet developers who rarely spoke in large planning sessions contributed actively in smaller refinement groups.
Damien could finally see what good planning looked like - short, focused, with decisions made quickly because the groundwork was already done.
The transformation was stark. Planning went from 8 hours (sometimes 16) to under 3. More importantly, sprint completion improved - developers weren’t blocked by ambiguous requirements mid-sprint. Team morale recovered. The developers who’d complained about wasted time started volunteering for refinement sessions.
Damien’s anxiety reduced further, and he started enjoying his work once again. Planning meetings became about 2-3 hours, no one was bored or frustrated, and everyone enjoyed a good team lunch afterwards.
I eventually hired my own replacement and said goodbye to Damien, confident the new approach was bedded in and would continue working.