Why does planning fall over?
In our experience of working with software development teams, we often see clients struggle when using traditional project management techniques to predict delivery timelines. These methods tend to rely on upfront planning – assuming that scope, timelines, and priorities will remain stable throughout a project, and that it is even possible to know these things before they start. They might also rely on managing people as resources and plan in a granular way. But in the real world of software, the best plans allow for change and learning, creating the conditions for resilience. Requirements evolve as knowledge grows, priorities shift, technical challenges emerge, and people get sick, making those early projections less and less useful as the project progresses. We work with teams who feel pressure to stick to outdated schedules, only to burn out or deliver something that no longer aligns with stakeholder needs. It’s not a failure of the team, or any individual – it’s a system failure, a mismatch between the approach and the nature of the work.
What could make it better?
What we find more effective with clients is creating space for agile forecasting techniques. These provide a more flexible way to plan that work with the evolving nature of modern work. Instead of trying to lock everything in upfront, these practices draw from actual team performance, using data like velocity or throughput, to estimate future delivery. This shift allows teams to respond to change without sacrificing transparency or accountability.
We often help teams to implement lightweight forecasting models that evolve as the work progresses, offering stakeholders regular updates and the ability to adjust based on real progress. It’s not about being vague or non-committal – it’s about being honest and practical in a dynamic environment. Clients appreciate this approach because it builds trust and improves communication while still keeping delivery goals in sight.
Where to start?
If you’re thinking about introducing agile forecasting to your organisation, here are three steps we typically recommend to clients. First, begin tracking your team’s delivery consistently. Even a simple log of completed work per iteration provides a valuable baseline for future forecasts. Second, treat forecasts as living documents – something you revisit and update regularly rather than a static plan. This allows you to respond quickly when things change, which they inevitably will. And third, make forecasting a shared responsibility. Bring the team into the process so the estimates are grounded in their experience, not imposed from above. When teams feel ownership over the forecast, they’re more likely to meet it, and to raise concerns early when things start to shift.
This collaborative, data-informed approach helps create a culture of predictability without sacrificing agility.
How to start?
We encourage incremental change, and building knowledge and awareness into the teams this helps build psychological safety for teams and stakeholders. It also takes people on the journey and makes the change belong to people instead of it being something that is done to them, this helps it become more long-lived, valuable, and sustainable. If you would like to talk to us about how to go about this, please get in touch. We are always happy to help people navigate this complex journey of organisational change and for more information on forecasting without Estimation, read our article on #NoEstimates.
Founder, Exec & Transformation Coach