Avoiding the Potholes: Leadership Lessons in City Project Management

If only I could have seen some of the project management breakdowns I've had coming at me when in the planning stages of a project. I could have avoided a slew of much bigger back slides further down the line. That hindsight is telling, and it's something most project managers in city government can relate to. Whether it’s a new parks initiative, a road improvement contract, or a downtown revitalization project, the early decisions - or indecisions - often set the tone for the entire effort.

Leadership in this space isn’t just about hitting deadlines or staying within budget. It’s about anticipating roadblocks, managing competing interests, and knowing when to lean into collaboration over control. A good leader in city projects understands not just the technical workflow, but the human dynamics that drive it. This includes internal staff, elected officials, contractors, consultants, and of course, the public. Having the right leadership lens can mean the difference between a project that drags for years and one that actually makes it to ribbon-cutting day.

Common Breakdowns and How to Steer Around Them

One of the most common issues I’ve seen is unclear project ownership. It’s easy to assume that assigning a project manager solves this, but if that person doesn't have decision-making authority or is buried under multiple responsibilities, accountability slips through the cracks. In one city project involving a stormwater infrastructure upgrade, responsibilities were split between engineering, public works, and planning departments. No one had the full picture, and as a result, permits were delayed, community outreach was half-baked, and the project fell six months behind schedule.

Another pitfall is underestimating the value of front-end engagement. I’ve witnessed projects that skipped early conversations with stakeholders to "save time," only to face public backlash or council resistance later. It’s far more efficient to build those conversations into your timeline from the start. According to the American Planning Association, early engagement can significantly reduce rework and opposition during implementation phases¹.

Lessons Learned from the Field

One project that taught me a lot was a community center renovation. We had a solid contractor and a strong internal team. But we underestimated the coordination needed between the city’s IT department and the design team. The result? A beautiful new facility with no functioning Wi-Fi for three weeks. Small detail, big headache. It taught me that every department impacted by a project should have a seat at the table early on - not just when their part of the work is scheduled.

Another example involved a traffic signal upgrade at a major intersection. Seemed straightforward at first. But we didn’t factor in that the utility company needed a six-week lead time to relocate a pole. That one oversight delayed the project substantially and led to overtime costs for city crews. Since then, I’ve used pre-construction checklists that include all external dependencies. Turns out, a simple checklist can save thousands and prevent a lot of frustration.

Actionable Tips for Leading City Projects Effectively

Based on both successes and a few stumbles, here are some practical strategies that can help keep projects on track and leadership focused:

• Clarify Roles Early: Ensure everyone knows who owns what. Use RACI charts (Responsible, Accountable, Consulted, Informed) to eliminate ambiguity.

• Engage Stakeholders Upfront: Include internal departments, elected officials, and the community early. Their input can prevent rework later.

• Use a Formal Kickoff Meeting: Set the tone, expectations, and communication structure from the beginning. This is your chance to align everyone.

• Create a Risk Register: Identify potential risks at the start and assign someone to monitor each one. This helps keep surprises to a minimum.

• Document Decisions: Use a decision log to track key choices and why they were made. This is helpful when projects drag on or staff turnover occurs.

• Don’t Skip Post-Mortems: After project completion, hold a lessons-learned session. Capture what worked and what didn’t for future reference.

These aren’t just theoretical tools. They’ve been tested in the trenches and can be implemented without needing major new systems or expensive software. It’s more about discipline and habit than technology.

Building a Leadership Mindset That Anticipates, Not Reacts

Strong leadership in city project management involves shifting from reactive to proactive thinking. This means not just solving problems as they arise, but setting up systems and culture where fewer problems occur in the first place. Leaders who foster open communication, encourage cross-department collaboration, and consistently reflect on past projects tend to lead more resilient teams.

A leadership mindset also includes a willingness to admit when something isn’t working. One of the best project managers I’ve worked with would routinely pause mid-project and ask, “What are we missing?” That simple question often revealed overlooked details or upcoming risks. Encouraging that kind of honest assessment within your teams builds trust and improves project outcomes over time².

Conclusion: Leadership as a Daily Practice

Leadership in city project management isn’t a title or a role. It’s a daily practice. It’s showing up with clarity, asking good questions, and being willing to make tough calls. It’s also knowing when to listen more than talk. If you can build habits that emphasize planning, communication, and accountability, you’ll not only avoid the big breakdowns - you’ll build a team and a process that can handle unexpected challenges with confidence.

And if you’re ever unsure whether you’ve covered all your bases, just ask yourself: “If this goes sideways, what will I wish I had done differently?” That one question has saved me more than once.

Bibliography

1. American Planning Association. “Public Participation in Planning.” 2021. https://www.planning.org/publications/document/9213878/.

2. Project Management Institute. “Pulse of the Profession 2023.” 2023. https://www.pmi.org/learning/library/pulse-of-the-profession-2023-13334.