Can We Have It By Christmas?

We’ve all been in that start-of-Q4 meeting. Leadership unveils an ambitious strategic initiative and asks: “Can we ship this by Christmas?” The room goes quiet. Engineers shift uncomfortably. Someone mumbles “we’ll do our best” and everyone knows that’s code for “probably not, but I don’t want to be the one who says it.”

There’s a better way to have this conversation. One that respects both the business’s needs and our team’s reality. One that replaces optimism and pressure with data and confidence levels (remember what Robert Martin said: “one of the purposes of Agile is to replace hope with data”).

Here’s what we’re NOT going to use: story points and velocity. Why? Because story points are relative estimates that drift over time as teams change, get gamed during planning, and can’t be compared across teams or even across months on the same team. Velocity is equally unreliable because it measures effort committed to, not work completed. A team can have high velocity on paper while delivering nothing to production.

What we need is something grounded in reality: how long does work actually take us, and how much work do we actually finish?

We start by measuring our historical cycle time. That’s the number of days from when work starts to when it’s done in production. We pull our last 30-50 completed items and record how long each one took. We calculate percentiles.

We might find:

• 50th percentile: 7 days
• 85th percentile: 12 days
• 95th percentile: 16 days

This tells us that half our work finishes within a week, and 85% finishes within two weeks.

Next, we count how many items we actually shipped in each of our last 10 sprints. Not started, not “almost done,” but truly shipped to production. We calculate throughput percentiles:

• 50th percentile: 4.5 items per sprint
• 85th percentile: 5.5 items per sprint

Now we run the forecast. October to Christmas gives us 6 two-week sprints. We break down the strategic objective into discrete deliverables and let’s say we count 35 items. We multiply our throughput percentiles by 6 sprints:

• At 50% confidence: 27 items completed (4.5 × 6)
• At 70% confidence: 24 items completed (4.0 × 6)

To deliver all 35 with 70% confidence: 8-9 sprints (mid-February)

When management asks if we’ll make Christmas, we tell them: “We have 35 items and 6 sprints. Based on our historical data, at 70% confidence we’ll complete 24 items. For all 35, we need until mid-February. Which 24 are absolute must-haves for December?”

We’re not saying no. We’re saying “here’s what’s probable, here’s what’s possible, and here’s the data behind both.” This approach protects our credibility because when we hit that 70% forecast, we become known as the team that actually delivers.

That’s how we build trust with management and maintain healthy relationships that don’t burn out teams. Do not overpromise and do not agree on delivering unrealistic results.

Originally posted on LinkedIn.