Project Management Best Practices: Estimating Work and Tracking Progress

Karl Wiegers


In part one and part two of this series, adapted from my book Practical Project Initiation, I’ve described fifteen practices the project manager can apply to lay the foundation for a successful project, plan the project, and estimate the work to be done. In this final article I share two additional estimation practices, three good practices for tracking your progress throughout the project, and one practice for learning how to execute your future projects more successfully.

Estimating the Work (continued)

Practice #16: Use estimation tools. Many commercial tools are available to help project managers estimate entire projects. Based on equations derived from large databases of actual project experience, these tools can give you a spectrum of possible schedule and staff allocation options. They’ll also help you avoid the “impossible region,” combinations of product size, effort, and schedule where no known project has been successful. The tools incorporate a number of “cost drivers” you can adjust to make the tool more accurately model your project, based on the technologies used, the team’s experience, and other factors. You can compare the estimates from the tools with the bottom-up estimates generated from a work breakdown structure. Reconcile any major disconnects so you can generate the most realistic overall estimate.

Practice #17: Plan contingency buffers. Projects never go precisely as planned. The prudent project manager incorporates budget and schedule contingency buffers at the end of phases, dependent task sequences, or iterations to accommodate the unforeseen. Use your project risk analysis to estimate the possible schedule impact if several of the risks materialize, then build that projected risk exposure into your schedule as a contingency buffer. An even more sophisticated approach is critical chain analysis, a technique that pools the uncertainties in estimates and risks into a rational overall contingency buffer. Chapter 10 of Practical Project Initiation is all about contingency buffers.

Your manager or customer might view these contingency buffers as padding, rather than as the sensible acknowledgment of reality that they are. To help persuade skeptics, point to unpleasant surprises on previous projects as a rationale for your foresight. If a manager elects to discard contingency buffers, he has tacitly absorbed all the risks that fed into the buffer and assumed that all estimates are perfect, no scope growth will occur, and no unexpected events will take place. Sound realistic to you? Of course not. I’d rather see us deal with reality—however unattractive—than to live in Fantasyland.

Tracking Your Progress

Practice #18: Record actuals and estimates. Unless you record the actual effort or time spent on each project task and compare them to the estimates, your estimates will forever remain guesses. Someone once asked me where to get historical data to improve her ability to estimate future work. My answer was, “If you write down what actually happened today, that becomes historical data tomorrow.” It’s really not more complicated than that. Each individual can begin recording estimates and actuals, and the project manager should track these important data items on a project task or milestone basis. In addition to effort and schedule, you could estimate and track the size of the product, in terms of requirements, user stories, lines of code, function points, GUI screens, or other units that make sense for your project.

Practice #19: Count tasks as complete only when they’re one hundred percent complete. We give ourselves a lot of partial credit for tasks we’ve begun but not yet fully completed: “I thought about the algorithm for that module in the shower this morning, and the algorithm is the hard part, so I’m probably about sixty percent done.” It’s difficult to accurately assess what fraction of a sizable task has actually been finished at a given moment.

One benefit of using inch-pebbles (see Practice #6 in Part 2 of this series) for task planning is that you can break a large activity into a number of small tasks (inch-pebbles) and classify each small task as either done or not done—nothing in between. Project status tracking is then based on the fraction of the tasks that are completed and their size, not the percentage completion of each task. If someone asks you whether a specific task is complete and your reply is, “It’s all done except…,” then it’s not done! Don’t let people “round up” their task completion status. Instead, use explicit criteria to determine whether an activity truly is completed.

Practice #20: Track project status openly and honestly. An old riddle asks, “How does a software project become six months late?” The rueful answer is, “One day at a time.” The painful problems arise when the project manager doesn’t know just how far behind (or, occasionally, ahead) of plan the project really is. Surprise, surprise, surprise.

If you’re the PM, create a climate in which team members feel it is safe for them to report project status accurately. Run the project from a foundation of accurate, data-based facts, rather than from the misleading optimism that can arise from the fear of reporting bad news. Use project status information and metrics data to take corrective actions when necessary and to celebrate when you can. You can only manage a project effectively when you really know what’s done and what isn’t, what tasks are falling behind their estimates and why, and what problems, issues, and risks remain to be tackled.

The five major areas of software measurement are size, effort, time, quality, and status. It’s a good idea to define a few metrics in each of these categories. Instilling a measurement culture into an organization is not trivial. Some people resent having to collect data about the work they do, often because they’re afraid of how managers might use the measurements. The cardinal rule of software metrics is that management must never use the data collected to either reward or punish the individuals who did the work. The first time you do this will be the last time you can count on getting accurate data from the team members.

Learning for the Future

Practice #21: Conduct project retrospectives. Retrospectives (also called postmortems and post-project reviews) provide an opportunity for the team to reflect on how the last project, phase, or iteration went and to capture lessons learned that will help enhance your future performance. During such a review, identify the things that went well, so you can create an environment that enables you to repeat those success contributors. Also look for things that didn’t go so well, so you can change your approaches and prevent those problems in the future. In addition, think of events that surprised you. These might be risk factors to look for on the next project. Finally, ask yourself what you still don’t understand about the project, so you can try to learn how to execute future work better.

It’s important to conduct retrospectives in a constructive and honest atmosphere. Don’t make them an opportunity to assign blame for previous problems. Chapter 15 of Practical Project Initiation describes the project retrospective process and provides a worksheet to help you plan your next retrospective. It’s a good idea to capture the lessons learned from each retrospective exploration and share them with the entire team and organization. This is a way to help all team members, present and future, benefit from your experience.

The twenty-one project management best practices I’ve described in this series of articles won’t guarantee your project a great outcome. They will, however, help you get a solid handle on your project and ensure that you’re doing all you can to make it succeed in an unpredictable world.

Also read Project Management Best Practices, Part 1
Also read Project Management Best Practices, Part 2

Jama Software has partnered with Karl Wiegers to share licensed content from his books and articles on our web site via a series of blog posts, whitepapers and webinars.  Karl Wiegers is an independent consultant and not an employee of Jama.  He can be reached at  Enjoy these free requirements management resources.

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