The Worst Project I’ve Ever Worked On (and What It Taught Me)

Every seasoned project manager has a “war story” – a project so chaotic, stressful, or mismanaged that it becomes a cornerstone of their learning journey.

This is mine.

It’s one of those stories that, in hindsight, feels obvious – like all the warning signs were there, but at the time, I couldn’t see the wood for the trees.

The project seemed straightforward enough: a rebrand and e-commerce website for a new retail business with substantial investment. It had all the makings of a high-profile, exciting project. Yet, as you’ll see, things unravelled in ways that taught me invaluable lessons about expectation management, scoping, budgeting, and teamwork.

This is the story of how it all went wrong – and the lessons that came with it.

Setting the scene

I joined the project after the pitch was won and the kickoff completed. The agency I worked for had already agreed on a price and timeline. Everyone was excited – it was a shiny project, something to show off.
The branding team smashed it. They came back with a gorgeous visual identity that the client loved. All smiles, all good.

But when it came time to scope out the website build, that’s when the red flags started popping up like weeds.

The client had a wishlist as long as your arm, and we’d never sat down to properly define what the site was supposed to be. No detailed scope, no real plan – just a vague idea of “an e-commerce website.”

Oh, and the best part? We’d already agreed on a price and timeline.

Great. 😅

The downward spiral

So, we’re building the site. The front end looks great, but we hit a snag: the platform we’d planned to use isn’t going to cut it.

Enter Magento.

The problem? We didn’t have anyone in-house with Magento experience, so we outsourced the development to a specialist agency. On paper, this seemed like a smart move.

In practice, it was a disaster.

The outsourced team couldn’t keep up. Deadlines slipped. We couldn’t show the client anything beyond a few front-end templates, and they started getting twitchy. Our leadership team, desperate to keep them happy, kept making promises. Big promises.

Before long, we weren’t just building an e-commerce website. We were building an ERP system. Stock management, warehouse tracking – the kind of functionality Magento wasn’t designed for.

When things got really bad

Then it got worse.

The outsourced agency missed another deadline. The client was frustrated. The leadership team was panicking. And me? I was spending my life travelling, ping-ponging between the client and the supplier, trying to keep the plates spinning.

Finally, we managed to get the supplier to present their progress to the client. It did not go well. The client was unimpressed, and for good reason.

The following Monday, the supplier declared bankruptcy.

Gone. Just like that.

We were left with nothing – no code, no progress, no budget, and a furious client.

The reset

At this point, I was ready to call it. I suggested to the leadership team that we give the client a full refund.

Shock, horror – that was not going to happen. Instead, we brought in an experienced Magento developer and took the project back in-house.

This was the start of a project reset. We sat down with the client, owned up to what had gone wrong, and promised to do better.

To their credit, they stuck with us.

The final stretch

Things improved. The developer we brought in was a godsend. The team pulled together, and we started making real progress.

But the client wasn’t the same. Their investors were breathing down their necks. Their marketing team kept throwing in last-minute ideas. And our leadership, still in people-pleasing mode, kept saying yes.

We delivered most of what was promised – around 85%. But by the end, the client had lost faith. They moved the project to another agency, and we were left licking our wounds.

The fallout was significant. Internally, morale was destroyed, and leadership decided to abandon web development entirely, pivoting the agency towards content marketing.

For everyone involved, the experience was exhausting, stressful, and unsatisfying.

Lessons learned

Looking back, this project was a masterclass in what not to do. Here are the key takeaways:

1. Define the scope – early and clearly
   It’s tempting to dive into an exciting project, but without a clearly defined scope, you’re building on quicksand. Vague ideas and undefined deliverables will spiral out of control.

2. Expectation management is crucial
   If things are going wrong, say so. Transparency isn’t just good for the client – it’s good for you. It stops problems from snowballing.

3. Don’t outsource what you can’t control
   Outsourcing can work, but it introduces risks, especially if you don’t have direct control. When outsourcing, choose reliable partners and maintain close oversight.

4. Budget discipline is non-negotiable
   The budget isn’t some awkward elephant in the room. Track spending closely, flag overruns early, and make budget discussions a regular part of client communication.

5. Don’t let shiny objects distract you
   Leadership’s focus shifted to other priorities mid-project, which compounded the chaos. Stay committed to finishing what you start before chasing the next big thing. Not every project is worth your sanity.

6. Team morale matters
   Stress and poor communication can destroy a team. Protect your team by setting realistic expectations and advocating for their well-being.

Final thoughts

Projects like this one are painful, but they’re also invaluable. Mistakes are powerful teachers, and I’ve carried the lessons from this experience into every project I’ve managed since.

If there’s one thing I’d encourage others to do, it’s to reflect on your own “worst project.” Be honest about what went wrong, share your insights, and use the experience to grow.

As the saying goes: you either win, or you learn.

And sometimes, the lessons are worth the cost.

This was a painful project. But pain teaches you things.
If there’s one thing I’d encourage others to do, it’s to reflect on your own “worst project.” Be honest, take stock, and learn everything you can. Because when the dust settles, you’ll be a better project manager for it.

As for this project? It’s my go-to story when people ask me about my worst. The agency, the client, and the supplier – none of them exist anymore.

Maybe that says it all.