When Data Migration Goes Right: A Project Manager's Dream Experience

Throughout my entire project management career, I've handled multiple data migrations across various platforms and systems. I've migrated from one website to another, from WordPress to Sitecore, from Ruby on Rails to WordPress, from one software-as-a-service system to another, and from one data repository to another. The list goes on—I've done so many data migrations that they've become a defining feature of my career.

However, I have to say that the easiest and smoothest data migration I've ever experienced in my entire professional life was at an online news publication, working with a developer named Yi. We were migrating from a very antiquated project management platform—one that had been in use for about five years—to JIRA. This wasn't a simple lift-and-shift operation. All of those projects, user stories, requirements, comments, attachments, links, images, assignees, categorizations, and dates had to be transferred to JIRA. Five years' worth of data is needed to move seamlessly to the new system.

And it was beautiful. Just beautiful.

Yi did his thing! He analyzed the existing system thoroughly, and because he was the engineer who had worked on these projects for some time, he was intimately familiar with what was embedded and linked in all those tasks and comments, which came in handy when writing the API calls. When he migrated the data from one platform to the other, it was absolutely seamless.

But we didn't just migrate the data over to this new system—we enhanced it. We had to create workflows in JIRA that the old system simply didn't have. Thankfully, the director knew exactly what he wanted and was able to articulate his vision clearly to me. This clarity made all the difference. 

Once the data was successfully migrated, I stepped in to handle the testing and workflow setup. I configured workflows that ensured only certain people could advance tickets forward or start sprints. I implemented rules that prevented issues from moving to the next status unless specific conditions were met. I added helpful pop-ups and tooltips to guide users through the process.

We also set up sophisticated automation and notification systems. For example, when an issue reached "Ready for QA" status, a notification was automatically sent to the QA team's Slack channel. When someone commented on an issue, the entire engineering team received a notification in their Slack channel. If someone was tagged in a comment, that person got tagged directly in Slack. We created workflows that only allowed forward progression, and if someone needed to move backward, they had to complete a particular field explaining why. 

We really hooked up JIRA—we made it work beautifully for our team. But that successful implementation would have never happened without Yi's spectacular technical expertise in migration and API calls.

Here's how successful it truly was: I've worked on projects where we migrated from one system to another and kept the old system running for at least a month afterward—just to make sure we had captured all the information and could clarify anything we might have missed. With this migration, we shut down the old system in just two weeks. Everything had been transferred completely, and there was no need to keep the old platform running.

Looking back, this experience reminds me why I love project management. It's not just about managing timelines and deliverables—it's about bringing together the right people with the right skills at the right time. Yi's technical brilliance, the director's clear vision, and my ability to translate requirements into functional workflows all came together perfectly. We weren't just three people doing separate jobs; we were a team that trusted each other's expertise.

This migration stands out not because it was easy—it wasn't—but because it was collaborative, well-planned, and executed with precision. It proved that data migrations don't have to be nightmares. With the right developer, clear communication, and attention to both technical and user needs, they can actually be... dare I say it... enjoyable?

That was a great migration. A truly great migration.