This was recently a topic of discussion I had along with other engineering leads. I reflected back on my own experience because I remember how early in my career, software estimation would cause stress, anxiety, and worry. I knew how to do the work, but the uncertainty tied to this was a challenge.

The truth is that software estimation is hard, often imprecise, and sometimes wildly off. And yet, it’s a necessary part of planning. Whether it’s for sprint planning, stakeholder alignment, or setting expectations, engineers are constantly asked to estimate the level of effort for a task. But here’s the truth: estimates are guesses, not guarantees.

Why Estimates Go Wrong

• Software is complex and unpredictable.
• Hidden requirements or edge cases emerge mid-task.
• “Simple” can hide lots of integration or testing effort.
• Context switching, meetings, and interruptions aren’t always factored in.

Rather than trying to eliminate uncertainty (hate to break it to you, you can’t), we can aim to make reasonable guesses and reduce stress while doing it.

6 Tips for Producing Software Estimates And Keeping Your Sanity

1. Break It Down

Don’t estimate the whole feature-estimate the steps. Smaller tasks are easier to understand, and errors in estimation compound less dramatically.

2. Use Ranges, Not Absolutes

Instead of saying “this will take 3 days,” say “2 - 5 days.” This gives room for surprises and sets more realistic expectations.

And if someone says, “I don’t like ranges. Give me one number”, tell them the high range number. Observe their reaction carefully. Is that the reaction of someone who wanted the truth or someone who wanted delusion?

3. Base It on Past Work

Use historical data when possible. “Last time we built something like this, it took X.” Past work is often your best calibration tool.

4. Add Buffers Intentionally

Instead of inflating estimates randomly, be clear about known unknowns and add time accordingly. Say, “this is 1 day of work, plus a half day of buffer for testing and reviews.”

5. Talk About Confidence

Include a confidence rating with your estimate. “I’m 80% sure this will take 2 days” vs “I have no idea, but my best guess is 4 - 5 days” helps your team or PM weigh risk better.

6. Split Research From Implementation

If you get something out of left-field where you have little experience and no way to provide a number, you can make the first task “research what it would take”. Take as much time as you need to begin to undertstand the problem.

Make the second step to meet with your stakeholder, share your findings, and inform them you have a better idea and provide a guess if that makes sense. Usually, the research part helps uncover what needs to be done. You can iterate here or start on implementation if you have condfidence to go forward. Sometimes, the only way to know is to do and experience it.

Let Go of Perfection

Estimates are not promises. The goal isn’t to be perfect, it’s to provide a reasonable forecast that enables planning, without burning out the team.

Talk openly about uncertainty, improve your estimates over time, and give yourself permission to be wrong. Estimating well is a skill. Give it time, and give yourself grace.

• software development