Measuring Success in Software Development

For a long time, I believed that a project delivered on time was a project well done. It’s a belief that’s easy to adopt in software development, where deadlines are treated as immovable objects, milestones are celebrated, and timelines are scrutinized. But the longer I’ve worked as an Engineering Manager, the more I’ve realized that hitting a deadline is just one piece of a much larger picture. True success goes far beyond the calendar.

I learned this the hard way during a particularly intense project. The team was under pressure, and the deadline was fixed. We sprinted, debugged, reviewed PRs late into the night, and, yes, we delivered on time. But as I looked around the team after that release, I saw something I didn’t expect. People weren’t celebrating. They were drained. Quiet. Some were already worrying about the next sprint. It hit me that while we had met the deadline, we had missed something more important: the health of the team, the sustainability of our efforts, and the overall quality of the solution we had delivered.

That moment changed how I think about success. I started asking myself different questions. Instead of “Did we deliver on time?” I began to ask, “Did we deliver something valuable?” and “Are we ready to sustain and support this solution after it goes live?” It wasn’t an easy shift. The world outside the team often still cared about dates and deadlines, but I realized that if I only focused on that, I would miss what really matters.

As an Engineering Manager, I began to reframe how I measured success for myself, for the team, and for our projects. I started looking beyond the sprint board and beyond the roadmap. I paid attention to the things that aren’t always easy to measure: the clarity of the problem we’re solving, the well-being of the team, and the strength of our technical foundations.

There was one project in particular where this shift made all the difference. We were tasked with delivering a new integration, and it had a hard deadline tied to a larger company initiative. The usual approach would have been to push forward at all costs. But this time, I decided to do something different. Early on, I asked the team a question that might sound simple but is deceptively powerful: “What could go wrong after we ship?”

It was quiet at first. People were so focused on "getting it done" that they hadn’t stopped to think about what comes next. But as we talked, real concerns started to surface. Someone pointed out that our automated tests weren’t as comprehensive as they should be. Another flagged a performance bottleneck that would only appear under high load. We decided to pause - not stop, just pause - and address these issues. Yes, it put pressure on the timeline, but I knew it was the right call. Because success isn’t just shipping something on time; it’s shipping something that works when people use it.

That release was one of the smoothest I’ve ever experienced. No post-release firefighting. No frantic hotfixes. And perhaps most importantly, the team didn’t feel like they had been stressed to their limits to get it done. I realized then that one of the most overlooked measures of success is how it feels to the people doing the work. If we finish every sprint exhausted, frustrated, and dreading the next one, can we really call it success?

Success in software development is more than a finish line. It’s the quality of the code, the sustainability of the pace, and the trust within the team. It’s knowing that you didn’t just meet the date - you built something with a future. I’ve started to recognize success when an engineer tells me, “I feel like I actually learned something this sprint” or when a team member says, “I feel like we had space to think this through.” Those moments matter as much as any on-time release.

This shift in perspective didn’t happen overnight. I had to have honest conversations with stakeholders and product managers. I had to explain that “done” doesn’t always mean “ready” and that slowing down early can prevent breakdowns later. But the results speak for themselves. Releases that don’t require emergency patches. Teams that aren’t burned out. Projects that don’t fall apart two months after they ship.

I still value deadlines. They keep us focused and create shared goals. But I’ve learned to treat them as targets, not as the sole measure of success. If we have to push a deadline to get it right, I’m okay with that. If we can hit the deadline but we’re compromising on quality or burning out the team, I now see that as a signal to step back and adjust.

The best teams I’ve worked with don’t just hit deadlines. They build systems that endure. They prioritize learning, technical debt, and team health right alongside timelines and deliverables. And the irony? When you focus on these deeper measures of success, you often end up meeting deadlines anyway.

Because true success isn’t about speed. It’s about strength, sustainability, and the satisfaction of knowing you didn’t just finish the race - you built something that will last.