Blog Series: Making Software Work for Growing Businesses
Why Your Last Software Project Failed (and How to Avoid It Next Time)
If you’re running a mid-sized business, chances are you’ve had at least one bad experience with a software project. Maybe you hired an offshore team that promised the world and delivered… crickets. Maybe you had developers who just ghosted you when things got hard. Or maybe you went live with something that looked good on the surface but crumbled the first time your team tried to actually use it.
Sound familiar? You’re not alone.
I hear this story again and again from business owners:
- “We spent six months waiting for updates, only to find out nothing worked.”
- “They kept telling me it was almost done, but every week there was another excuse. That turned into 4 years, $500k spent, and still nothing useable.”
- “We finally launched, and it broke on day one. Not to mention it was expensive to run.”
The truth is, most software project failures don’t happen because of bad code. They happen because of bad management, bad communication, and mis-alignment.
3 Big Reasons Projects Go Off the Rails
- You Didn’t Have Visibility
Outsourced or offshore teams sometimes work in a black box. You send requirements, they disappear for weeks, and then suddenly drop something in your lap. No feedback loops, no check-ins, no way to course-correct.
How to fix it: Routine demos. At least once a week, you should see the actual software working, not just status updates. If they can’t show you progress, that’s a red flag. Ideally, you can “touch” the working software yourself.
- The Team Overpromised and Underdelivered
It’s tempting to believe the cheapest bid or the fastest timeline. But the problem you’re trying to solve is rarely that simple and neither is the software that solves it. If someone says they can build your entire platform in a month for $10k, you’re setting yourself up for disappointment.
How to fix it: You have a BIG vision. But you’re more likely to achieve it by identifying the small problems in the workflow, solving and paying for those as you go. That way, you’re getting value immediately. Iterate towards your vision.
- Nobody Owned the Outcome
When you hire a team, you assume they’re invested in your success. But sometimes they’re just cranking out tickets without understanding your business. That’s when you end up with features that “work” technically but fail in the real world.
How to fix it: Make sure your partner isn’t just writing code. They should be asking questions about your business. If they’re not curious, they’re not going to deliver value, because that’s not their focus.
What to Do Differently Next Time
- Insist on transparency — weekly demos, daily check-ins, clear ownership.
- Validate before you commit — start small, prove the team can deliver, then expand.
- Find a partner who cares about your business — not just the code.
Good software isn’t just about technology. It’s about trust, communication, and alignment.
If you’ve had a project fail in the past, you don’t have to repeat that mistake. I put together a Software Project Kickoff Checklist with the exact questions you should ask any development partner before you start.