From Execution to Leadership: Lessons from a Project Fixer

By Bhavana Tadiboina| #CoffeeandProjectManagement Series

"Project management should not be an entry-level job.”

That’s how Benjamin Chan kicked off our conversation—and from that moment on, I knew we were diving deep. Ben isn’t your average PM. He’s the person companies call when their projects are failing and they need someone who can steer the ship through a storm. But what makes him so good at what he does isn’t just technical knowledge—it’s how he thinks, communicates, and leads.

Benjamin Chan

The Gap Between School and Reality

If you’ve studied project management, chances are you’ve seen the clean models: charters, timelines, Gantt charts. Ben? He calls that “utopia.”In the real world, projects start without charters. Team members resist Agile. People don’t follow the plan.And the biggest trap new PMs fall into? “Why isn’t everyone just doing what they’re supposed to?”

Ben’s advice: Don’t chase the perfect process. Learn to lead through the mess.

The Myth of the Lone Project Manager

New PMs often feel like they have to prove themselves alone.

But Ben’s take is clear: Project success is never a one-person show.

You’re not meant to be the hero. You’re the orchestrator.Use your executive sponsor. Rally your team. Make sure the why of the project is loud and clear. And if you're not getting buy-in? That's a signal—not a failure.

Fixing Failing Projects: It’s Not About Hustle

Ben has rescued his fair share of struggling projects. But he doesn’t come in with a cape—he comes in with calm. When things go wrong, most junior PMs push harder. Longer hours. More meetings. More pressure.But Ben says the opposite often works better: “Sometimes the bravest thing you can do is pause.”

Slow down, reassess, replan. Then move with purpose.

From Tactical PM to Strategic Leader

The real turning point in any PM’s career?Shifting from “Am I delivering the tasks?” to “Are we delivering value?”

Strategic PMs zoom out. They watch for external risks—organizational changes, regulations, and shifting priorities. They don’t just do the work. They question it. They’re not afraid to say,

“Should we even be doing this anymore?”

Final Thought: It’s Not About Doing More—It’s About Thinking Differently

Ben’s energy is calm, clear, and confident. You won’t hear him rattle off buzzwords. You’ll hear him talk about curiosity, resilience, and the importance of learning fast. The best project managers? They’re thoughtful communicators. Strategic thinkers. And they’re not afraid to question the system they’re working in.

I left this conversation not just with insights—but with a new perspective. And if you’re on the journey from student to project leader, Ben’s words are ones to keep close.

Follow the #CoffeeAndProjectManagement series as I interview 100 project managers to uncover what the textbooks never taught us.

☕✨What part of Ben’s story resonated with you most? Let me know in the comments!