I want to share this as a personal lesson to remember. I was leading a project for a regional roll-out of a digital operations platform meant to standardize how thousands of field employees processed transactions. The kind of project where hundreds of small moving pieces have to come together for the system to actually work in production.
One of those pieces involved a vendor contracted to handle API integrations with a legacy ERP systems. Their job was simple on paper: create connectors so that the new cloud platform could talk to the 15-year-old finance and inventory software still running in the background.
I’ve been told and taught the way I should manage this new project is to monitor, document areas that need to be discussed at the end of the project whether mild or critical at post mortem Halfway through the project, I noticed a missed deliverable in a test environment. It was brushed off by both my team and the vendor as a two-week delay. And to be fair, it was fixed quickly. But the deeper I looked, the more I realized the “slip” wasn’t the timeline, it was our blind spot.
The problem:
The vendor was optimizing for their contract terms, not for the success of the program. They were paid per API delivered, not per successful integration tested under real-world conditions. Internally, my team was reporting progress based on green checkmarks in Jira, not whether those integrations actually worked end-to-end.
The dashboards looked fine. Status meetings sounded fine. But when I pushed into a live test scenario, the data wasn’t syncing properly. If I hadn’t poked at that one slip, we might have gone live with integrations that broke under scale and crippling finance reconciliations, slowing order fulfillment, and frustrating end users across multiple regions. As a vendor, this could be great. Very lucrative in fact if our agreement had limits to what constitutes a warranty.
My concern:
This isn’t about one vendor or one missed deliverable. It’s about how operations are often designed to measure output, not outcomes; how our very large company has always operated. The long-term risk is cultural: when executives accept dashboard optics as truth, they create organizations where bad data hides in plain sight.
That’s not just a project management issue. When I took this job, I thought the problems I walked into was due to past operations team but instead it’s more of “we do things the way we’ve always done it”. Now I understand why we have ongoing matters. So far from my observation in 2 years it’s due to:
Misaligned incentives with vendors who deliver “checkmarks” but not business value.
Fragile systems that collapse at scale because they were never tested under real-world stress.
Leadership blind spots where teams don’t escalate problems because they don’t want to be the ones holding the red flag.
Somewhere in the future or with other projects, these cracks could become chasms. Do I put my head down and then we write off the project?
Why I quit
November 27, 2023