Improvement, Planning and Repeatability

Improvement is an interesting word, especially when the change we are talking about takes time. Because improvement is not just something we measure. It is something people should feel. Not just understood, but experienced, a sense that something is moving in the right direction.

There will always be naysayers, people who prefer to complain rather than contribute to progress. And every change, no matter how well intended, comes with its own casualties. We all have our thresholds, speeds, and levels of comfort when it comes to adapting to change. It takes a toll on all of us. But we all learn.

For those familiar with scaling Agile, The PI Planning is a crucial event where teams come together to plan the next 10–12 weeks. But PI Planning is not just something we attend. It is something we prepare for.

Over the last two years in our journey, one thing has become very clear to me. Most of the success or failure of PI Planning is decided before we even enter the room. Yet, we often treat those 2–3 days as the main event, when in reality they are only a reflection of everything that happened in the weeks leading up to it.

Being part of an Agile organization, the ask is simple, not just to show up to plan, but to show up ready to plan. And that raises an uncomfortable but necessary question: how ready are we, really?

If we are in Product, do we walk in with clarity of the problem, or just a list of features or stories? If we are in Architecture, are we bringing forward unknowns early, or discovering them during the session? If we are in Engineering, does our engagement begin before the event, or only when planning starts? And if we are in Leadership, are we creating a space for honesty, or simply pushing for commitment?

PI Planning can sometimes feel like filling capacity, but at its best, it is about building a shared understanding. If we are doing quarterly planning like this, it is worth pausing and asking ourselves, do we really know why this matters? Do we understand what good looks like? Have we engaged with the teams we depend on? Are we discovering risks early, or performing alignment too late?

The 2–3 days of PI Planning will always reflect the 6 weeks before it. And if we want a different outcome, the work has to start much earlier.

Somewhere in those long hours, across time zones and roles, what stands out for me is not the plan we build, but the commitment so many people bring to it. The patience to listen, the willingness to question, and the effort to align. These rarely get called out, but your team is what make all of this work.

I always do a self-reflection before any retrospective, and the question I get stuck with is, “Can we repeat what went well?” This time, I think I had a clear answer. Because improvement is not what we achieve once — it is what we can consistently repeat.