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Story and task estimates can be a struggle. Sometimes, teams even forgo estimates completely when they find them challenging or don’t see the value. But when teams skip this step, they also forgo all the benefits these estimates offer!

(And it goes beyond just committing to deadlines 🙂)

Even rough estimates can help teams plan workload

One of the primary reasons I see a team skip estimating is because “no one is good at estimates.” Whether implicitly or explicitly, the team thinks: “If the estimates are always wrong, why estimate at all?”

This is fundamentally flawed because estimating is a skill like anything else. With practice, everyone can get better. But this reasoning also assumes we want estimates to be correct predictions of how long something will take. While that would be wonderful in a perfect world, that’s not where an estimate offers value.

Estimates are valuable in their relative size. As a team practices estimating, they learn which stories or tasks are bigger and by (roughly) how much. This makes it easier to plan a sustainable workload.

Rather than always committing the team to seven tickets without a clear indication of their size, the team can choose to commit to roughly the same workload week over week — regardless of how many tickets that is. Some weeks it could be seven, others it could be 13.

When a team can gauge roughly how much work they have planned, they can also account for time off or other priorities such as hiring activities, on-call rotations or team building.

A sustainable workload is one of the primary ways to mitigate burnout and attrition.

A tool for psychological safety

Another reason teams skip estimating is because estimates have been used punitively in the past. If a team was punished when they didn’t meet an estimate, then it makes perfect sense why they no longer use them. This scenario points to a much larger top-down culture problem within the organization.

Estimates are educated guesses that set realistic expectations. Estimates are not predictions or promises.

When estimates are punitive, it’s up to organizational leadership to step back and reevaluate how they use estimates. Often, this is where my team steps in. External consultants are uniquely poised to have hard conversations. We educate higher-ups on how to use the information estimates provide to reset their expectations.

Fear- and shame-based tactics are extrinsic motivators with a short shelf life. They also do a lot of damage to your team’s mental and emotional health. Punishing a team that exceeds its estimates will not lead to leadership’s desired outcomes, because a team needs to feel psychologically safe to explore and innovate.

Treating estimates as communication tools rather than hard deadlines creates a safe space for the team to creatively problem-solve.

An important step for a collaborative culture

Finally, estimates can serve as a tool for knowing when to ask for help. But I see many teams miss out on this value.

In team cultures that celebrate “rockstar programmers” or individual achievements, using estimates in this way can be scary. In individualistic team cultures, asking for help is discouraged or tolerated at best. In a collaborative culture, estimates act as a guidepost to let a team member know they might be rabbit-holing and should ask for help.

Creating estimates as a team means agreeing on the amount of effort a task or story is expected to take. This spreads the responsibility if something takes longer than anticipated. If a team member picks up a one-point story and gets stuck, they have a shared expectation of how much time they should spend investigating and troubleshooting. So, if your team assumes a one-point story is roughly one day of work, the assignee can reach out for help after a few hours if they haven’t made progress.

Changing organizational culture is a slow process, but estimating as a team is one strategy to start building a collaborative environment.

Even when it’s messy — don’t skip the estimate

Team estimates are valuable software development tools. They help teams plan sustainable workloads, create space for problem-solving and provide guidance for asking for help. Teams shouldn’t abandon estimating — and miss out on all the benefits it can provide — just because it’s hard.

Estimates provide tremendous value, and with a little practice, we can all start to take advantage of that value. To help you get started, check out my recent post about the art — and science — of crafting an estimate.

In Mercedes' approach to software delivery and technical leadership, she learns everything she can about her client's and her team's goals to make an actionable plan to achieve success. She views her clients as partners and brings a unique blend of technical expertise, non-technical language, and empathetic insight to her work.

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