Four Project Management Lessons from March Madness

As I write this, we’re in the midst of another March Madness college basketball tournament season. Last-second game-winning shots, upsets, Cinderellas, and busted brackets abound. If you’re going to win your office pool, it’ll take a combination of skill and luck. Once the dust clears and the nets have been cut down, here are four lessons we can take away from the excitement of the tourney and apply to project management and planning.

1. Upsets Are Going to Happen

If there’s one rule to live by when filling out your bracket or planning a development project, it’s that upsets are going to happen. No March Madness ever concludes with all of the higher seeds winning all of their games, and no project concludes without its share of surprises.

The key insight here is that this isn’t a bug in the system—it’s a feature! Upsets and Cinderella stories are part of what makes the college basketball tournament so captivating. Likewise, a project that goes exactly according to plan is probably a project that either hasn’t truly been completed, or wasn’t a project worth doing in the first place. Sometimes a surprise upset isn’t what you were rooting for, but unlike a fixed bracket, a disrupted project plan gives you the opportunity to make adjustments.

I find this mindset extremely useful when confronted with unexpected complications. It can be easy to get frustrated by the unforeseen. However, when I can frame a hiccup in a project as something to embrace, cheer, and learn from, I find my ability to get to good solutions and keep the project on track greatly improves.

2. Some Upsets Are Easier to Predict than Others

Since the men’s tournament expanded to 64 teams in 1985, 5-seeds playing against 12-seeds in the first round have only a 90-50 record. It’s practically common knowledge that you should pick at least one 12-seed to upset a 5-seed in every tournament. You may not always predict the correct 12-5 upset, but just being on the lookout for it gives you an edge when filling out your bracket.

While upsets are bound to happen, that doesn’t mean you have to be caught completely off guard when they occur in development projects. You’re probably going to have some scope creep. You’re going to discover that some fundamental assumption you made about the project is not quite so simple or even achievable. You’re going to spin your wheels waiting for the client to provide a crucial piece of hardware or documentation. You’re going to run into a snag when it comes time to actually deploy the project.

Hopefully, over the course of a project, you won’t have to face all of these upsets, but you should be on the lookout for them from the tipoff, and you should try to prepare for the ones you expect are most likely. At Atomic Object, we make great use of risk-tracking spreadsheets to keep a clear and up-to-date picture of the most likely “upsets” to completing the planned scope of work on time.

3. A 1-Seed Will Probably Win It All

Despite all this upset talk, the truth is that higher-seeded teams are ranked that way for a reason. Until last year, in 135 attempts, no 16-seed had ever beaten a 1-seed in the first round of the men’s tournament, and 1-seeds have won 20 of 34 possible championships. The only time a 16-seed accomplished the first-round upset in the women’s tournament was a total fluke, when the top-seeded team (Stanford) lost two of its top players to ACL injuries right before the tournament. Since their expansion to 64 teams in 1994, women’s 1-seeds are 19-25 as national champions.

Just because we know some unexpected things will happen during a development project doesn’t mean we should throw out all of our plans and preparation. I can trust my intuition to estimate the difficulty of common tasks, and I can trust my colleagues to ask important questions and find the answers we need. Our combined experience allows us to choose the best tools for any given job, and established practices like TDD and Agile provide some predictability to any work we do.

Every project comes with its own unique set of challenges, but I believe every project has the same factors for success. Whenever we deliver a successful project for a client, it happens despite the upsets we encountered along the way. Our Atomic principles like Owning It and Sharing the Pain are our 1-seeds, and we don’t take them for granted.

4. No One Picks a Perfect Bracket

The exact odds of correctly picking all 63 games of a March Madness bracket are disputed, but they are probably on the order of one in 2.4 trillion. Warren Buffet has famously offered his employees $1 million a year for life just for perfectly predicting only the first two rounds of the tournament–something not a single one of the 17.3 million brackets on ESPN managed to achieve in 2018. To win your office pool, you don’t need to pick a perfect bracket. You just have to pick the most correct bracket.

This is undoubtedly the most important lesson for project management. No amount of planning will ever achieve perfection, and too much time spent planning will actually hinder your ability to get meaningful work completed. Fortunately, unlike a bracket, a project can be changed. It’s not about how rigidly you stick to your initial predictions, but how flexible you can be when the requirements change.

I never go into a project expecting failure, but I also never go in expecting everything to go exactly as I and our clients envision. The best outlook we can take is to hope for something interesting, fun, and memorable. Every once in a while, something new and special happens, something we haven’t seen before. A 16-seed beats a 1-seed, we broaden our horizons of what’s possible, and we take these lessons to the next project.

Just because your bracket is busted doesn’t mean you can’t still enjoy the tournament, root for the underdogs, and appreciate when the confetti drops on whichever team is ultimately victorious.