As we near our 10-year anniversary in business, having delivered hundreds of successful products, I find myself reflecting on the life span of the client - developer relationship. Today, a business has more options than ever when selecting a development partner. If you are fortunate enough to maintain a website or application long enough, inevitably the key contributors will change. Here are a few thoughts on when to part ways.
Building software is hard. Even simple products can require months of work and tens of thousands of dollars. It’s a process filled with ambiguity, discovery, trial, and error. Every software product begins with a problem worth solving—but turning that problem into working code takes more than an understanding of a programming language. It requires alignment.
When the process goes well, it can feel effortless. The right solution seems obvious in hindsight. But getting to that solution means clearly communicating the problem, rigorously defining requirements, and iterating on possible solutions until you find the one that works. A great development partner will be just as focused on the problem as you are. They will help you refine your thinking, ask the right questions, and guide you toward solutions that are as simple as they are powerful. And when a solution proves to be a technical challenge, they should be able to explain it plainly, justify their approach, and show you why it works. If they can’t, or won’t — fire them.
Next, let’s talk about process. Software development is a collaborative effort. A competent and reliable development partner will have a well-defined process that’s inclusive, transparent, and informative. You should expect a clear project roadmap: a timeline of regular check-ins, updates, milestones, and deliverables. These aren’t just boxes to check; they’re the foundation of trust. They show that your partner is organized, professional, and accountable. If your developer’s process is vague, constantly shifting, or hidden behind jargon or a gaggle of non-technical project managers — fire them. You deserve visibility into what’s being built, how it’s being built, and what you will ultimately own once it’s done.
Speaking of deliverables; they should be clearly defined on day one. While it’s unrealistic to expect perfection (delays happen, bugs appear, priorities shift) the schedule should be maintained. And when the unexpected occurs, there should be proactive conversations and negotiated compromises. You’re not just buying time or effort, you’re paying for outcomes. Developers are doing work for hire, and that work should be owned by you from day one. You should have access to the code, documentation, and designs as they’re created, not just at the end of the project. If a developer can’t or won’t provide consistent, tangible results on schedule — fire them.
Soft skills, team fit, and culture fit can be equally valuable to the success of your project, as does the length of your working relationship. Time spent together builds context, trust, and tribal knowledge that’s hard to replace. A developer who knows your business and your product well is a valuable asset. Be weary of competitors who offer a fast, cheap, shiny new partnership at the cost of continuity. As they say, if it ain’t broke… But even great relationships have a shelf life. If your developer stops communicating, seems bored or checked out, begins missing deadlines, or can no longer articulate their contributions—it may be time to move on. Burnout is real, and even the best partners can lose steam. Don’t ignore the signs. A fresh perspective might be exactly what your project needs.
Finally, let’s talk about long-term support. All software changes. With new features, updates to dependencies, and platform changes, maintenance is inevitable. A responsible developer will talk about this from the beginning. More importantly, they’ll architect solutions that are stable and require as little maintenance as possible. But if you find yourself constantly paying for fixes, refactors, or rewrites months after launch, that’s a red flag. Your development costs should go down over time, not up. After the initial build, maintenance should be lighter, not a second full-time job. If you’ve staffed up internally to build something, remember: you don’t need to carry those costs forever. Maintenance can (and often should) be outsourced. If your team can’t transition gracefully into a lean support mode — fire them.
In summary, great developer partners bring clarity, structure, and results. They’re laser-focused on your problem, they communicate openly, they meet deadlines, and they help you own your product. Most importantly, they make smart decisions that reduce your long-term costs, not increase them. If your current partner can’t do those things, don’t be afraid to move on. Software is too expensive to get wrong, and too valuable not to get right. If these ideas resonate with you and you want to chat, Contact Us
