A prospect reached out to me recently with a clear ask. They had a static site their team couldn’t edit, and they wanted to move to WordPress. They hadn’t exactly researched their options for a preferred CMS, it was more that WordPress was familiar to them. Something they’d used before, or seen used, and it felt like the safe and obvious choice.

I could have taken that at face value. A lot of vendors would. But before we talked about platforms or timelines, I wanted to understand what was actually going on. So I asked a simple question: what’s not working right now?

The answer had nothing to do with WordPress. Their team was completely dependent on a developer (actually, a very busy CEO) to make even basic content updates. Adding a team member to the about page, updating a service description, publishing a blog post…all of it required more and more of his time, that he simply couldn’t give. The website had become a bottleneck, and the frustration had been building for a while.

WordPress was the solution they’d arrived at because it was the one they’d heard of. And it would have solved the problem, there’s no question about that. But it wasn’t the only solution, and for their situation, it wasn’t necessarily the best one.

Once I understood what they actually needed, we could have a real conversation about what would serve them well. Not which CMS has the best brand recognition, but which one would give their team genuine autonomy over their content without creating a new set of maintenance headaches down the road.

That’s what a good first conversation should do - I never want to simply validate the solution a prospect walks in with, but understand the problem well enough to know whether that solution actually makes sense for them.

If you’re evaluating vendors for a website project, I’d pay attention to how they handle that first call. Are they asking about your business, your team, and what’s been getting in the way? Or are they only talking about what they’d build?

The best projects I’ve been part of started with someone willing to slow down and ask why before reaching for an answer.