Everyone has had a “worst project ever”. Mine has been recent and is still ongoing. I don’t mean it’s the worst because the work is bad or the client is bad, quite the opposite with this one. Our team has created amazing work and everyone really cares about this project. The client is fantastic and smart, willing to think outside the box when it comes to design and to take our input. When it finally completes, it will be a great piece of work out there in the world.

But that’s the problem, when it finally completes.


What Your Worst Project Ever Can Teach You About Digital Project Management

It’s easy to blame others when things don’t go as planned but project managers need to be bigger than that. If it didn’t go according to plan, it means your plan didn’t work. Why not? Where were you? Why weren’t you paying attention? Or if you were paying attention, why did you miss the clear red flags that things were going awry and your plan was not working? How come you didn’t fix it?

The questions go on and on. The answer is that nobody’s perfect. Even the most ironclad project plan can fall apart for a number of reasons. And the most conscientious project manager can lose track of the situation, not knowing how to fix it from foreseeable doom.

I mean, we’re talking about websites here, not nuclear weapons, so the fate of humanity is not at stake here. But your client’s money, expectations, and most importantly, trust are at stake. That’s big stuff.

So instead of shrugging off your “worst project ever” as a one-off or fluke occurrence, examine it after the fact and try to find some lessons in it. It’s often our worst moments that teach us how to be our best.

Oh snap, that’s some straight up wisdom comin’ at you.

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Here’s what I learned from my worst project ever.

It Is My Fault

Humans don’t like to admit when we make mistakes, especially big ones. We may think our mistakes only contributed a small amount to the failure of a project and that most of the fault lies with the people who are actually doing the project work, but that’s just not true. When the projects falls apart because different parties don’t know what the other one is doing, or aren’t aligned toward the same goals, then yes, it is all your fault.

In my case, I took a few days to really let this sink in. At first I didn’t think I was solely responsible and parts of my brain are still protesting that I’m not. But at the end of the day, a project manager’s job is to get the damn project done, on time and on budget. Did I? No, I didn’t. Therefore, my fault.

Don’t Repeat History

Once I realized it was my fault, I wanted to make sure to avoid this in the future ever again. I spent a week thinking about it, writing down mistakes I had made — specific things — and what I could do differently next time in a similar situation. I would think of different things and write them down as they popped into my head during that week. I ended up with a list of about 10 major mistakes, and how to hopefully avoid them next time.

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Having this reflective period was crucial to helping me think of a solution-oriented approach instead of just wallowing in failure. I love having this list to learn from.

Have the Tough Feedback Conversation

I can’t stress this enough. Have tough conversations, especially with your clients. Be honest. I struggle with this still, as I think you’d agree when I say that most people don’t like confrontation or having to deliver bad news. It’s just not fun. But, it’s important. Your client pays for your existence and they deserve to know everything that’s going on, and how you’re going to solve it/fix it/deal with it. Your candor will build trust over time, and you might just need to rely on a bit of that later on when you say, “Trust me, I’m handling it.” You want them to believe that you are. So always be honest, admit your mistakes, and think of your client as your boss.

At the end of my worst project ever, I invited my client to meet with me to ask them about their experience.

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It was a bit unpleasant, hearing some negative things about myself, but it was all constructive and focused on positive learning for the future. I really appreciated my client taking the time to tell me what they thought, even if it may have stung a little. Ultimately, I’ll be better for it.

Focus on Solutions

Okay, you fucked up. But how are you going to fix it? While delivering bad news to your client is something that needs to be said instead of buried, you also need to come to them with solutions on the table. Not just say, “Hey, well, everything’s going to shit. Just wanted to let you know. Okay, bye.” That ain’t gonna fly. A better tactic is to say, “Hey, everything’s going to shit, but here’s how we can fix it. I need you to (A) and I’ll (B) and that will alleviate the problem of (C).”

Much better, huh?

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So get out there, digital project managers, and keep learnin’.


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