Lessons from Leading 5,000+ Meetings


The Project Operator

Lessons from Leading 5,000+ Meetings

891 words

I’ve led more than 5,000 meetings. That’s not a brag, hell, far from it — it’s context, and a sad reality. As project managers, especially those with engineering backgrounds, meetings consume more of our time than almost any other activity. Yet most meetings range from forgettable, to useless, to downright painful.

In my early career, I genuinely believed that a crisp, clear agenda would make any meeting effective. Engineers love structure, and it felt natural to think that a good agenda will guarantee a productive meeting. But after years and literally thousands of meetings, it became obvious that a good agenda was a good start — but absolutely not a everything.

Years ago, I took over a large infrastructure project—a messy, sprawling, complex, nightmare of a job. We were months behind schedule, morale was in the gutter, and the entire team was clearly frustrated. It was, simply put, a shitty situation.

To address it, I set up another “status update” meeting. I did everything right on paper: clear agenda, detailed slides, precise talking points. But the minute we started, I knew something was off. Nobody was really talking. They weren’t debating; they weren’t engaging; they were silent. And silence, in project management, usually means trouble—issues were being buried, not openly addressed.

That meeting taught me a crucial lesson. The problem wasn’t my agenda—it was the lack of trust and openness. People weren’t speaking up because they didn’t feel safe to be honest.

Since then, I’ve significantly changed my approach. Here’s what I’ve learned that really matters:

1. Start with a Clear Agenda, But Don’t Overestimate It

An agenda is non-negotiable, but it’s not magic. It lays out what you need to accomplish, but it doesn’t guarantee meaningful conversation or honesty. Think of your agenda as the entry fee—it gets you in the door, but it doesn’t mean you're gonna enjoy the event.

A clear agenda doesn't need to be excessive. Always start with introductions to make sure everyone knows who everyone else is in the meeting. Then 4-6 topics that you need to discuss (additional sub-points are acceptable), and close it with a summary.

2. Say the Uncomfortable Things Out Loud

If you’re thinking it, others probably are too. Be the first to name the elephant in the room. Say clearly, “We’re in a shitty situation,” if that’s what it is. This directness may surprise people, but it creates immediate honesty. It breaks down barriers and opens genuine dialogue.

Don't hesitate to swear a little (within reason, and stay neutral and non-offensive, obviously) - it'll break the ice, make people smile and help them open up a little.

3. Be Firm, but Always Human

Accountability matters. Clearly state what needs to happen and when. But also acknowledge that people face pressures outside the meeting room. If someone struggles, don’t attack—ask how you can help. Being firm doesn’t mean you can’t be understanding.

Always remember people have lives, and they will have issues in their personal or professional lives that they are dealing with everyday, and often you, and your meeting, are the lowest level on their list of priorities.

4. Always Open with Small Talk (and Mean It)

Meetings back-to-back can exhaust and frustrate everyone. I start each meeting with simple small talk for a couple of minutes — asking about weekend plans or commenting on the weather. It seems trivial, but it genuinely helps people reset and remember that we’re humans first and coworkers second. If you can get people to smile during the opening, it'll leave that feeling throughout the meeting, and comfortable people will speak up and raise issues that they might otherwise not.

5. Open the door to raise issues not raised before

Before closing, always ask, “Is there anything we haven’t talked about that’s going to bite us later?” It’s uncomfortable, but essential. Engineers especially understand how unmentioned problems quickly become major issues. This question gives everyone permission—and responsibility—to speak up.

6. Close Firmly and Clearly, but Casually

I wrap meetings up with, “Throwing it open to the group—does anyone have anything else to raise? Going once, going twice, aaaaaaand sold. Have a great Tuesday.” This clearly signals the end, inviting any final comments without dragging things out.

So, in conclusion:

Great meetings aren’t about perfect agendas or precise PowerPoints. They’re about honesty, openness, and the ability to face tough conversations directly. And if you can help people feel good in a tough meeting, you're on your best way to mastering the art of leading meetings. And mastering that art, will be a huge part of really catapulting you into becoming the best leader you can be.

Your weekly actionable Tip:

Before your next meeting, spend five minutes thinking about:

  • One or two specific outcomes you absolutely must achieve.
  • The emotional state you want participants to leave with (clear, relieved, informed, empowered).
  • Who will attend you next meeting and how you can make them feel good (or what to ask them for small talk).

Keep these in front of you during the meeting, and use them to steer conversations, particularly when things start drifting.

Andy Barbirato

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The Project Operator

I'm helping engineers become highly effective project managers. I write about hard and soft skills for engineering project managers and the mindset shift required to transition from successful engineer to successful project manager.

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