The People, Process, & Progress Podcast - How to Fix a Failing Project Without Losing the Team

Episode Date: November 10, 2025

When a project starts to slip, silence is the real risk. In this episode, Kevin Pannell shares how to escalate early, run real-time retros, and rebuild the plan using the KISS method, keeping it simple and strategic.Learn how to make escalation collaborative, protect team trust, and turn failure into alignment.Based on the Progress section of The People, Process, and Progress of Project Management.

Henry Ford said, failure is simply the opportunity to begin again, this time more intelligently. Most project leaders don't fail because they didn't plan. They fail because they wait too long to admit the plan isn't working. Every one of us has been there. The team's tired. The sponsor's frustrated. And we're staring at a timeline that no longer means anything. That's when leadership matters most.

Welcome to the People Process Progress Podcast, where we talk about how to bring people together, align process, and build progress together. I'm your host, Kevin Pennell, author of The Stability Equation, and The People Process and Progress of Project Management. To connect with me and learn more, visit Peopleprocessprogress.com. If you find this episode helpful, subscribe, leave a review, and share it with others. Now let's get started. Welcome back, everybody. Now, picture this. A project that started strong, but somewhere along the way, updates started sounding fine. You know the kind of lots of words, no progress, wrist logs full of yellow boxes. that never turn green.

Everyone senses it, but no one wants to say it out loud. So this is where so many good projects go to die, right? Not in chaos, but in quiet compliance. It's not the process that's failed. It's maybe the courage or the support for folks to speak up courageously to use the process the right way. So how do we recover when we know a project's in trouble, but don't want to crush the morale or the process?

One, I've said this before, escalation is not a four-letter word, so step one is escalate early and often, but do it right. In my book, The People Process and Progress of Project Management, I wrote in the progress section about escalation is a leadership behavior, not a fire alarm, right? So it's not about panic or punishment. It's about bringing the right people into the conversation at the right time. Here's how I break it down. Start with yourself. Own what you can fix before asking anyone else to step in, ask, Have I used every tool, every resource, or conversation available to me? Then go to your team.

Talk openly about the problem. A quick huddle or daily stand-up or a quick message to somebody. Keep it collaborative. What's blocking us? How can we clear this together? Next, involve the resource managers, right? These are the people who can move time or talent, right, and approach them diplomatically. How can I get you more time?

How can we adjust to support this outcome? right if the issue crosses teams or programs move to your portfolio or program directors keep the tone pretty factual right to better support our project success i'd like to escalate this decision to the next level and then when executive decisions are required engage the leadership earlier right executives don't want surprises they want clarity options next steps bring them both the problem and your proposed solution right don't go just empty handed finally if the impact touches the organization's mission or finances. It might go all the way to the board. Right. At that level, the escalation should already be aligned with the C-suite, right? I'm not going straight to the board. That's a coordinated

effort, not a panic move. So it's you, the team, their managers, the resource managers, the directors, right, your executives, the executives of the company, the board they report to. And that happens sometimes, right? We all have somebody that we need to either report to, we'll get permission from. It could be on spend or time or strategic impact. But it should always be collaborative, when leaders use escalation as a weapon that kills the trust it's like oh you're going to tell my boss you're going to talk to this person right when it's a bridge for us teams really rally behind it and the folks you escalate to really appreciate the insight so we're going to escalate early and often the second thing we're going to do is run real-time lessons learned or retros right waterfall agile

whatever term you want to use we're going to talk about what's going on right once we open the door we need to be totally honest real-time lessons learned right so we're going to pull the team together on a call or in person, if you still do that. No slides. It's just going to be us on camera. I'm a huge advocate of being on camera, seeing people's faces, not just the static pictures. And we're going to go, what's working, what's not, and what needs to change this week. That's it, human and honest, straight up. And sometimes the best fixes come from the quietest voices, right? Maybe they've sat back and nobody's asked them. And then you ask them, right? And there's been developers or nurses or analysts that gave insights that save months of work because we gave them

a safe space to speak. It's one of those tools that really builds performance and culture and you get smarter and people feel valued at the same time. And those standups, whether it's weekly or daily, if you haven't problems like this, you should do daily until it gets better and then start cutting back. So we're going to escalate early and often. We're going to do real-time lessons learn or retros. And then we're going to rebuild this plan using the kiss method. Keep it simple. and strategic right now if you face issues and gather input it's time to rebuild so forget about whether you use an agile waterfall or something in between pull from the project management tool menu the buffet as i call it take what works toss what doesn't you might blend a backlog refinement

from agile and a risk register from waterfall or a milestone chart from a gant tool the goal isn't methodology purity it's clarity on the momentum right it's rebuilding the plan together it also rebuilds the team's belief in it. You're like, okay, this actually fits what we're really doing now that the real world has smacked us all in the face. So when people have a hand in the new map, they also are all about walking that new path together. The result is once you start leading this way, things shift really fast, right? Teams stop hiding issues, leaders start responding with support instead of surprise. That communication speeds up and the morale improves so much. And notice something else too, right? Fewer late night fire drills.

when you escalate with ownership and you rebuild with inclusion, you get ahead of the storm instead of trying to survive it. So what's a learning that I've taken away that I think you all can take away? Here it is. Escalation is communication, not confrontation, right? We're not tattling. We're teaming. Escalation, retro's rebuilds are lifelines of healthy delivery.

And it's real, right? We plan so much up front and then the rule it hits us. And to try and hold on to that is just it's just us being stubborn or saying, Well, we wrote this down earlier, so it's got to be this. Now, I get it. We're not going to waste a bunch of money or want to waste time or just let the scope grow and move and all that. We have to do that with structure, but we also have to be ready to do that because we know every project changes as soon as you kick it off, even before then. And it can show leadership isn't just about having all the answers, right?

It's about having the humility to ask the right questions and the courage to act on the answers that you get. So let's apply this together this week, right? Let's go look at something, right? I want to look at one project that feels like it's. drifting and say, okay, who needs to know about this, right? Who needs a heads up? Who do I need to engage because I need their help? Maybe as they say, it's above my pay grade, which I'll say in general, regardless of what your rank or title is, doing what's right for the right reasons isn't above anyone's pay grade. And that's essentially what this is. It's going, hey, this isn't going

well, let's fix it. But you might not have the decision-making empowerment to spend more money or stop things or that. So that's where that comes in, I would say. What decision do we need help with, right? And know it and cue it up and even have a suggestion, like, hey, we think this one's going to work the best. How can I bring that up respectfully and clearly? Just talk like adults, right?

And again, with that ownership and mindset, I've tried to help the team do this. I feel like that we have done this well. This is where our challenges are. We would really benefit from this. And it doesn't really have to be super complicated. I've done risk and vulnerability, matrices, and assessments. And sometimes that's good. and it's a good practice, but just good conversation is it, right?

Pull the team together for a quick five-minute retro, what's working, what's not. One needs to change this week. And then finish that by identifying a part of your plan that's gotten overly complicated and simplify it. Keep it simple and strategic, right? What's going to get you to done? What's going to get you to the go live and beyond to handing off to operations? That's how progress will begin again, intelligently, as Ford said in the beginning. Thank you for listening to People Process Progress Podcasts.

If today's episode helped you, share it with your team, subscribe wherever you listen, visit peopleprocessprogress.com for templates, tools, more leadership lessons. The ideas you heard today come from the progress section of the book I wrote called The People Process and Progress of Project Management, where I break down how to escalate early and often, how to run real-time retros and rebuilds and bring projects and people back on track. Remember, people first, process aligned, and progress together. Godspeed, y'all.