Dig in and Deliver: Project Management for the Long Haul

Advice for project managers ushering complex web initiatives toward delivery

The city of Boston is well acquainted with complex mega-projects prone to stretching out beyond budget and anticipated timeline. The Big Dig—with its string of delays and mishaps—is just the most famous example of these, but there are plenty of others as well. A historic city, Boston has been outgrowing its horse-and-carriage infrastructure for some time now.

At an even faster rate, companies are having to launch large scale digital initiatives to keep up with our highly evolving, post-pandemic future. The need to innovate is dire, and the timelines are aggressive. Such large-scale change requires a coming-together of many stakeholders and team members to bring innovation to life, and at the center of it all is the project manager.

Balancing the needs of a complex project is all about perspective.

For project managers trying to usher these complex web initiatives toward delivery, challenges can easily outnumber successes. Every day, we’re met with familiar questions and roadblocks: how to prevent cave-ins before they occur, where to move a crucial waterline, which stakeholders needs to be kept happy, who can help keep on top of environmental standards.

At some midway point, when everyone is wondering where we began and what the payoff will be, the project manager needs to really shine. When the dig seems too big, here are some things to remember.

Grinding out the Vision

When delivering any large-scale project it’s necessary to maintain the vision, but making the vision become real can be a grind. It’s not just about remembering the sparkles of the early designs and UX magic. Things will get muddy. Designs may become outdated as scope warps various unknowns into unfortunate or unexpected knowns. Flexibility is a necessary quality for any project manager hoping to adapt to continual adjustments independent of milestones.

Along the way, the project manager should also hone her personal vision for managing similar projects: What worked and what didn’t? Looking back, what would you change in Month One of requirements gathering given what you know in Month 22? The early missteps and successes may be hard to weed out, but they will be important to consider and review in retrospectives even as the team approaches release. The biggest win is sometimes learning how to improve your long-term vision for managing that next delivery.

Mapping Windows, Doors, and Exits

Project management is not all Gantt charts and high-level milestones. It’s also sometimes important to roll up the sleeves and track those finer details. The project manager should have some sense of which details to fix and when to ensure the team doesn’t get buried as release approaches.

Broken windows theory says that an unattended repair will give the appearance that no one cares and no one is in charge, thus inviting even more shattered glass. Applied to the digital space, these “broken windows” become bugs and tech debt that inevitably amass as new features get built. When allowed to pile up, addressing all the broken windows becomes a seemingly insurmountable task, leaving partners and stakeholders uneasy.

Maintaining priority is crucial. If certain rooms of your house can’t be entered and the space can’t be enjoyed, the crack in one upstairs window isn’t going to be the thing that puts your timeline back on track or generates morale for the team. Carefully planned, regular sprints can help everyone align on the priorities. This way, developers know when to work on fixing a few windows and when to focus on building out the next room. You know the value of fixing a key bug, but there’s nothing more exciting than demonstrating that must-have feature.

Archiving Expectations

Managing expectations is the number one way to keep stakeholders happy. But how should the project manager handle expectations over a number of years, amid multiple team changes and shifting priorities, added scope and competing timelines? To start, documentation should be kept updated meticulously. In particular, requirements documents should be a fixture throughout the project, so when questions arise they can be answered in context of the original vision. Over time, not everyone on the team will remember that vision or have access to the original specs.

A project manager should be the archivist, the memory keeper. That mentality should carry across requirements and tickets and requests for new or backlogged scope. If there is a business analyst involved, even better—but the project manager should still know a project’s artifacts and documents inside and out, even if not always creating them. This archival skill serves not only stakeholders but also internal team members, some of whom may run into bouts of product amnesia as timelines extend.

Keeping the Team Together

Always remember that the team is the project. They are the day-to-day, and that’s a good thing. We may be building software, but we’re people in the end and that’s the beauty of it. No one likes when meetings stack up on the calendar, but for the project manager each call is also a chance to build upon, repair, or revisit a relationship.

A project manager should also play a role in keeping spirits high as one developer fixes the same window he already fixed three times before, and another deals with a risky but important ask you can’t let slide. It’s not just about telling jokes at the start of stand up or turning on your camera when you look like hell to remind everyone that we’re all human here. As project manager, your best day may be the result of someone else’s best day, and that shouldn’t be forgotten.

The project manager might not design that original vision or code those cutting-edge features, but she plays an important role in keeping the path clear and the team together until the final product emerges. Delivery is always an easy cause for celebration, but along the way, hard-fought wins should be tallied up and counted in the moment.

Balancing the needs of a complex project is all about perspective. Fifteen years after its 2007 completion, Bostonians still love to take cracks at the Big Dig. But despite the years of turmoil and uncertainty, the project has by now seen many of its original goals realized. This isn’t to say we need to uphold the Big Dig as the shining beacon of megaproject success, but it’s a lesson on perspective.

An ambitious vision for technical innovation will always encounter formidable obstacles—if it doesn’t, maybe the vision isn’t as ambitious as it needs to be to keep up with the demands of our swift-moving digital lives. Luckily, there’s never a need to wait 10-15 years to dig up the takeaways of delivering complex projects in the digital space. By the time the high-fives go around, the next big thing is already likely in the works.