Be roughly right—the case for pragmatic planning in large-scale, complex software delivery

Unrealistic planning in software delivery breaks more than schedules. It eats away at trust, creates tension between teams, and leaves you carrying the stress of promises that were impossible to keep. Pragmatic planning can change that!

If you would like to

• keep the commitments you make to managers and customers
• deliver more with less without burning people out
• replace finger-pointing with clarity and shared understanding
• just have some peace of mind

you should definitely read on!

Predictability in three pragmatic shifts

Forget frameworks, acronyms, and inflated promises. This approach is deliberately low-concept and high-impact.

 1. Don’t estimate 

Focus on flow, not forecasts. Estimates often disguise wishful thinking as data. Instead of trying to guess how long everything will take, shift the focus to how work moves through the system. Track what actually happens instead of debating what might.

 2. Plan half 

Build adaptability into your plans so reality doesn’t wreck them. Whatever you think you can do, cut it in half. Uncertainty is baked into the work. The goal is not to do less work, but to leave space for the unexpected and actually finish what matters.

 3. Roadmap ≠ Release plan 

One is strategic intent, the other is operational execution. Strategy and delivery need different kinds of promises, and treating them as interchangeable is a recipe for disappointment. Keep them separate and alive.

Let's dive into them using three examples, based on organizations I've worked with in the past.

1. Stop estimating and focus on flow

Imagine a company where the roadmap was a two-lane highway, meticulously packed with 40,000 metaphorical cars (a.k.a. work items). Every inch was planned. The logic? If we fill the road to capacity, we’ll maximize our throughput!

In reality, it was a traffic jam. Flow had dropped to zero. And worse, many of the cars hadn’t even followed the planning process. They’d skipped ahead, unapproved and unacknowledged, but still on the road.

The organization refused to admit they were there. Because if they were, someone would have to take responsibility.

No one wanted to. So the traffic just stood still.

 Lesson:  Cramming more work into the system doesn’t increase output. It kills it. Flow needs space.

2. Plan for half and get more done

Elsewhere, another organization treated everything as a top priority. Literally. Priority 1. Priority 0. Even negative priorities, for those lobbying hardest. The result? A road full of emergency vehicles—sirens blaring, no one moving.

The fix: to stop pretending everything is equally urgent. Introduce predictability as a performance metric. Not speed. Not volume. Just: Did we do what we said we would do?

At first, the answer was “no.” Predictability was 0%. After a year of planning less and finishing more, it climbed to 83%. The delivery machine became reliable—and that shifted the conversation.

Because when delivery is predictable, stakeholders have to justify their priorities. And pressure is replaced with clarity.

 Lesson:  Leave space on the road. Plan fewer things. Finish them. Then—and only then—add more.

3. Separate roadmap from release plan

Quarterly planning rituals are common, so too in this organization. But too often, the beautiful dependency board created in a two-day workshop was obsolete by Monday.

They started treating the release plan as a sliding window instead, updated weekly. Visualized dependencies physically. Showed their work. Then keep showing it—across sprints, across teams, across changes.

Doing so turned the roadmap into a strategic intent heatmap:

Now: what we aim to achieve in the next two quarters.

Next: what is in the pipeline.

Later: what might happen a year or more from now.

Not everything needs a date. Outcomes, not deadlines, become the focal point.

 Lesson:  The roadmap tells you where you're going. The release plan outlines the steps you’re taking to get there. Don’t confuse the two.

What changes with pragmatic planning?

• pressure is replaced by predictability
• accountability becomes shared
• emergency-driven chaos gives way to intentional delivery
• cross-functional work stops being a blocker and starts being a feature

And most importantly: you earn trust. Because you do what you say you’re going to do. Not everything. Not always. But enough. Consistently.

Be roughly right!

That’s it. That’s the big idea. Stop trying to be perfectly wrong. Start being roughly right—with room to maneuver, room to say no, and room to deliver what matters most.

Pragmatic planning isn’t rocket science. But it does take guts, commitment, and sometimes an outside nudge. If you’re looking to kick-start your team’s journey to predictability, let’s talk.