Why stakeholders care about When
"When will it be done?"
It's a simple question to ask. It's hard to answer.
What is "it"? What is "done"?
We've learned that relying on estimate-driven Gantt charts is a losing game. Estimates rot. Priorities change. Even if we could predict the upcoming year's delivery in detail, we’re likely to change our minds.
Most of our industry has adopted the notion of feedback-driven, iterative software development. We want that flexibility. Even dinosaur banks no longer design their entire solution upfront and turn that into a rigid WBS.
We're agile. We're flexible. We're optimized for discovery and can pivot at the drop of a hat.
Yet, we've neglected the When question. Or better: we refuse to answer it.
Story Points were invented for the sole purpose of avoiding the When question.
Product Managers will prioritize and play Now-Next-Later. What they won't do, is give you a timeline.
When someone inevitably asks "When?" a collective sigh goes through the agile software development community. Not again!
When is hard to answer. Yet, it's the number one question our stakeholders care about.
Why is that?
Let's start by stating the less-than-obvious. With the exception of certain sales-related promises, stakeholders don't really care whether a feature is delivered in June or in August. The delivery date isn't the point of the When question. More often than not, stakeholders want a timeline to calculate progress and Return On Investment.
Building software is expensive, and stakeholders know this better than anyone. A feature isn't a cost; It's an investment. We allocate money today so we can hopefully reap the benefits in the future. But investments are risky, and we want to limit the exposure. That's why a Return On Investment typically has a timeframe attached to it. If we invest €1000 and think we can get €1100 out of it, is that a good investment? The answer depends on the timeframe. 10% in a month is a great investment. 10% in 30 years is not. That last ROI is too low for such a long risk exposure.
Product managers and agile software developers talk a lot about "business value". Story Points aren't days, they're value. Our teams don't build features; they deliver value. Yet we seem to ignore that value is tied to an Iron Triangle. Those features only deliver their value if they can do so within a time and budget. Time still is money. The longer it takes us to reap those benefits, the higher the risk and the lower the value.
When we refuse to provide a delivery date, it seems like we're designing smokescreens to avoid answering our stakeholders’ favorite question. We are actively denying them the tools to calculate the ROI.
When stakeholders see their expensive teams burn through cash but can't see when they can expect to see the results, they get scared. They have no way of tracking progress or assessing whether they are still on track. They see teams churn out product increments but aren't sure these are moving the needle toward what matters. It's like throwing money into a wishing well, hoping something good will come out. As they run out of cash, fear, anxiety, and low trust start to build. And when stakeholders don't trust their teams, bad things happen.
That's why timelines matter so much. They build trust by giving stakeholders the tools to calculate progress and ROI.
And here's the crazy thing: it doesn't matter that the roadmap changes every month. Stakeholders love reprioritizing if there's a chance for better investments. They want change if the value turns out to be less than projected.
The timeline isn't supposed to be fixed.
Nobody expects that.
Nobody even wants that.
But what we need to avoid is that feeling of constantly being behind schedule with no end in sight.
I truly believe business value is the ideal currency for software products. It is the common language we should be speaking throughout the company. But then we need to accept value is tied to time/money.
Once we start seeing a timeline as a tool for building mutual trust rather than a crazy one-sided commitment, powerful things happen.