5 Critical Lessons This Business Owner Learned While Launching a Tech Project

Everything Brian B. Simmons knows about software development he learned the hard way.

Simmons (R), with his brothers and business partners, Kevin (L) and Todd (M). (Courtesy askalender.com)

Brian B. Simmons had sunk 18 months and more money than he’d care to admit into the development of AskALender.com before realizing he had a problem. He’d overseen the building of the website for his mortgage originators magazine, Scotsman Guide, but this was different. This was a software project — a tool for helping consumers search for and secure loans — and he knows nothing about software. He knows business. He knows loans.

When he called in a consultant firm to look at the work his team had done, the news was even worse than he’d expected. None of the code was usable. He was going to have start over completely. “I’m the perfect case study of wasting money,” he says now with a sheepish grin. This story has a happy ending, though. Within nine months of starting over — this time with a stronger team and a new perspective on development projects — he had the site up and running.

Now, eight months later, he’s willing to reflect back on what he learned, in the hopes of helping other business leaders avoid some of the same pitfalls.

Don’t fall prey to the full-stack developer myth.
If you’re trying to navigate a major software product without a technical background, it can be all too tempting to enlist a so-called full-stack developer to handle all phases of the project. Simmons entrusted the development of AskALender.com to the same team that built a website for his company’s editorial product without fully grasping how different the two projects were. And, well, the rest is history. So for his second crack at the project, Simmons was determined to hire a team of developers, each with their own unique skills.

Hire an ego-less engineering lead.
“People in leadership positions tend to hire people who are less competent than them,” Simmons says. “It’s human nature.” And their goal, typically, is self-preservation. Instead, you want an engineering lead who has a breadth of skills but won’t feel threatened by team members who, individually, are stronger in certain areas. “I don’t need my lead to be an expert in UX. That’s what the UX designer is for,” Simmons says. “I need my lead to lead.”

Create a culture where people feel safe asking questions.
If there’s one thing that drives Simmons crazy, it’s when a developer hits a wall but, instead of asking for help, wastes hours (or days) trying to solve the problem on their own. That’s why he’s a big proponent of implementing a daily stand-up, in which each development team member reports in on what he or she is doing — and has an opportunity to enlist others in cracking tough nuts. But that only works if your developers are confident that they won’t look weak by asking for help.

Trust but verify.
Constantly hovering over your development team’s shoulders and asking to see their progress will make it impossible to build trust. But that doesn’t mean you’re not entitled to get access to the code if you need to. “Someone who’s doing their work the wrong way will protest,” Simmons says. “Someone who’s doing their work the right way might feel a little insulted, but they’re more likely to be open to it.” Remember: This is your project. And so is the code — even if you weren’t the one to write it.

Launch isn’t the end. It’s the beginning.
Within two days of launching AskALender.com, Simmons was getting feedback from his customers — that parts of the site weren’t working. “No matter how good your developers are,” he says, “there’s always going to be something you have to fix later.” In fact, he learned the hard way that incorporating user testing early in the development phase will save you a lot of headaches later on. “Sometimes you just get too close to a project,” Simmons says. “Getting that third party involved will make it so much easier to find problems that you just can’t see.”


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