Early in my career, I made a mistake that taught me more than any project I’d built.
I built complex websites that business owners couldn’t manage. Back then, e-commerce and websites in general were just coming online. We were writing a lot of HTML and CSS by hand, and most of us copied what we could find, since why spend hours writing basic requirements when the code was available everywhere?
The sites worked. They looked good. But I’d hand them over, and the business owner was overwhelmed. They couldn’t update their own content, couldn’t manage their products, couldn’t make a simple change without calling me. Or I’d build a full Drupal site for what was really just a marketing page, when all they actually needed was clean HTML.
I was solving the wrong problems with the wrong tools. Not because I didn’t know how to build, but because I wasn’t asking the right questions first.
If I’d known then what I know now, I would have started every project the same way I do today: by listening.
My listening skills didn’t come from a course or a methodology. They came from building my own businesses over the years. As a serial entrepreneur and seasoned developer, I’ve had to wear all the hats a small business owner wears: sales, marketing, operations, support, and finance.
When a client tells me they’re overwhelmed by their website, I don’t just understand the technical problem; I understand the emotional one, too. I understand the business problem. I’ve been the person trying to update a site at midnight after a full day of actually running the business. Or quickly refreshing my outdated website, which is three or four years behind, neglecting my own business self-care just like the rest of them.
What I’m really trying to figure out for every client is how to build something that works alongside the business, not something they have to trudge after.
The only way to get there is to start by listening.
How Every Project Starts Now
Every project starts with discovery, a conversation (sometimes several) where I’m mostly listening.
I’m not listening to what they want to build. I’m listening for why.
What problem are you trying to solve? This sounds obvious, but it’s remarkable how often the stated request doesn’t match the underlying problem. “We need a new website” might actually mean “we’re not getting enough leads” or “our customers can’t find what they need.” Each of those problems has different solutions.
Who are you trying to reach? A website for enterprise clients looks and functions differently from one for consumers. Understanding the audience shapes everything from design to content to technical decisions.
What does success look like? If you don’t define this upfront, you can’t measure whether the project worked. “A website that converts better” isn’t specific enough. “20% more contact form submissions” is something we can actually track and build toward.
How Discovery Actually Works
I don’t walk into a session with a checklist of clever questions. Sessions are organic. Every business is different, and the conversation needs to go where it needs to go.
Sure, there are repeatable strategies, frameworks I’ve refined over 20+ years that I apply when they work. But the execution, the creativity, and the business needs are all different. The content is different. The message is different. The approach, right down to the site colors, is always slightly different.
What works is being able to see the prism, how a single idea refracts and spreads, ever so subtly, into something unique for each client. That only happens when I’m listening, not when I’m running through a script.
Why This Works
Here’s what I think people are actually afraid of when it comes to discovery: not the timeline, but the conversation itself. They’re not technical. They don’t know the jargon. And they’re worried they’ll sit across from a developer who talks over their head for an hour and leaves them more confused than when they started.
I am super technical. My own investors once told me I was too technical to market my own product. And they were right. So I learned how to simplify. When I can, I strip the complexity out entirely. When I can’t, because sometimes we genuinely cannot, that’s where business acumen comes in. And trust.
Because at the end of the day, that’s what it comes down to. Not frameworks, not methodologies, not a four-step discovery process. It comes down to one question: can this human deliver what I need?
That’s the real point of discovery. To show you I understand what you need, in language that actually makes sense.
The Uncomfortable Truth
Sometimes discovery reveals that what a client needs isn’t what I do. Maybe they need ongoing marketing execution more than web development. Maybe their real problem is operational, not digital. Maybe they just need someone to tell them their current site is fine and they should stop messing with it.
When that happens, I tell them. I do marketing strategy and SEO, but not ongoing marketing. If that’s what you need, I’ll point you in the right direction.
Most of the time, when things go wrong, it’s not the development. It’s that nobody asked the right questions at the start.
I’d rather lose a project than take one that won’t help. That’s not altruism, that’s just good business. Unhappy clients are way more expensive than honest conversations.
That’s what listening gets you: clarity. For both of us.
Mary Lee Weir is a web consultant and serial entrepreneur who believes the first skill in web development is knowing when not to start coding. She’s been listening to clients and building digital products for over 20 years across seven countries.
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