In a recent post, I explained why we’re inherently bad at estimating, which is a major reason software projects often run late. But that doesn’t mean we can’t plan ahead for the longer term and manage expectations. Here are some techniques I’ve found effective for longer-term planning, even in the face of uncertainty:

Provide ranged forecasts 🌦, not fixed estimates

Over any reasonable period of time, providing likely delivery dates as a range rather than a fixed date is better. Doing so embraces the inherent variability and help stakeholders better appreciate uncertainty. Giving a fixed date, even when you all know it’s just an estimate, sets false expectations.

Don’t just estimate time ⏱, estimate confidence 💪

Along with estimating how long a task might take, assess how confident you are in that estimate. Is it something we’ve done before and know well? High confidence. Is it new, complex, or something we’ve never tackled before? Medium or Low confidence.Multiply time by confidence. For example, a “Small” task (e.g. 1-3 days) with “Low” confidence can be re-forecast as 1-7 days.

Longer term planning as risk management 🚨

Effective planning isn’t just about setting expectations on delivery, but managing risks over the project lifecycle. All those estimates which have come in as Large or with Medium-Low confidence? Those are your biggest risks and represent the most uncertainty. Identify risks early, identify potential mitigations, highlight those risks to stakeholders.

Account for Optimism Bias 🌈

Whilst you can’t completely mitigate against this, there are things you can do to be a bit less vulnerable. Involve the entire team in estimates, account for full end to end delivery (not just developer time) and factor in holidays, sickness and other factors that could impact delivery.Also, those ranged forecasts which provide a cumulative lowest range for all the work? Highly unlikely due to optimism bias! It’s probably best not to present the most optimistic forecast for this reason.

No silver bullet, but a better approach

These practices won’t eliminate uncertainty or guarantee perfect outcomes – there’s no silver bullet in longer term planning. However, I’ve found they help organisations plan more realistically, reducing the stress and frustration that often come with missed deadlines, and enabling more effective, adaptable strategies in the face of uncertainty.