What Questions Should I Ask a Web Designer?

Choosing a web designer can feel overwhelming, especially for artists, makers, and small business owners.

Most people don’t hire web designers very often. When they do, they’re usually comparing prices, looking at portfolios, and trying to make sense of a world full of technical terms they don’t use every day.

Over the years, I’ve found that people often focus on the wrong questions when they’re trying to choose a web designer. They ask about platforms, features, and pricing, and while those things matter, they’re rarely what determines whether a project actually succeeds.

The questions that matter most usually have less to do with technology and more to do with trust, communication, and whether the person you’re hiring truly understands your work.

A Good Web Designer Should Care About Your Business, Not Just Your Website

Before I started building websites, I worked 11 years as a local health inspector for my city.

A big part of that job was working with small businesses. I grew up in my family’s business, so I understood how much time, stress, money, and heart goes into trying to build something of your own. As a health inspector, I always tried to be an understanding and changes behavior through education. My favorite part of that job was helping business owners solve problems and move forward.

That’s still how I approach my work now.

I may be helping people through web design instead of inspections, but the part I care about most hasn’t changed. I’m invested in my clients’ success. I want their business to grow. I want them to feel proud of what they’re putting out into the world. And I want the website we create to actually support the bigger picture of what they’re trying to build.

That’s why I think the questions you ask a web designer matter so much.

Don’t Choose Convenience Over Connection

One of the biggest mistakes I see people make is hiring the most convenient option instead of the right one.

For artists especially, a website isn’t just a business tool. It’s often the first gallery, portfolio, or exhibition space someone encounters. It represents your work before you ever have a chance to speak with a collector, gallery owner, client, or customer.

If the designer doesn’t understand your work, your website can end up feeling generic no matter how polished it looks.

That’s one of the reasons I prefer meeting with clients in person whenever possible. Before we talk about pages, layouts, or technology, I want to understand who they are, what they’re creating, and how they want visitors to feel when they experience their work.

A website should feel like an extension of the person behind it.

The Most Important Question to Ask

If I could recommend one question for artists and small business owners to ask a web designer, it would be this:

How many artists or businesses like mine have you worked with?

If I were hiring a web designer myself, this is one of the first things I would want to know.

Not because someone needs to have worked with your exact medium to be capable, but because experience shapes understanding.

Artists communicate differently. Small business owners often have very different priorities than larger companies. Some people care most about selling online. Others care about telling their story, building trust, or creating a place that feels true to their work.

A designer who has worked with similar clients will already understand a lot of those concerns.

For me, one of my strengths is that I work in an artist community of more than 350 artists, and I’ve built websites for many of them. I’ve worked with creative people long enough to understand the way they think about presentation, process, and the emotional side of sharing their work online.

That kind of experience changes the conversation.

Ask to See Relevant Examples

A portfolio is important, but don’t just ask to see any portfolio. Ask to see work that’s relevant to what you need.

If you’re a painter, ask to see artist portfolio websites.

If you’re a photographer, ask to see how they’ve handled image-heavy sites.

If you’re a craftsperson or maker, ask how they’ve helped businesses present products, tell their story, and guide customers toward buying.

I believe in putting proof before talk.

A designer should be able to show examples of their work and explain the thinking behind them. And if they don’t have a direct example in your exact medium, they should still be able to clearly explain their process and how they would approach your project.

Ask About Their Process

One of the best things a client can ask is:

What does your process look like?

I love when clients come into a conversation with clear goals and a sense of how they want people to feel when they land on their website. Maybe they want the site to feel elegant, welcoming, modern, playful, or professional. Maybe they have content prepared, reference websites they like, or a clear understanding of what they want the site to accomplish.

That makes for a great project.

At the same time, I also think it’s important for clients to trust the person they’re hiring. The best projects are collaborative. You should absolutely have a voice in the process, but you should also feel confident that the designer knows how to guide the project forward.

A website is a creative process, and in many ways it’s not all that different from making art. There’s research, planning, refinement, and problem-solving involved. A good designer should be able to explain how they move through that process and what they need from you to make it successful.

Ask What Happens After Launch

This is one of the most overlooked questions in web design.

A lot of people think of a website as something you launch and then just wait for results to happen. But a website is only one part of a much larger marketing picture.

It still needs content.
It still needs updates.
It still needs promotion.
It still needs attention.

One of the biggest things I try to do during discovery is make sure expectations match reality. A website can absolutely help your business grow, but it isn’t a magic switch that suddenly brings in customers the moment it goes live.

Ask your designer:

• What happens after the website launches?
• Will I be able to update it myself?
• Do you offer maintenance or support?
• What should I expect if I want the site to keep growing over time?

The answers to those questions will tell you a lot about whether the designer is thinking beyond the launch date.

Ask How They Think About Results

When I look at another web designer’s work, I’m not only looking at whether it’s visually attractive.

I’m looking at how they organize information.

A good website should guide visitors through a clear journey. It should answer questions in the right order, build trust, and make it obvious what someone should do next. That might mean contacting you, booking a consultation, visiting your shop, or buying a piece of work.

There’s usually a funnel to it, even if it’s subtle.

That’s one of the things I think people often overlook when they’re hiring a designer. A website can be beautiful and still not be effective. On the other hand, I also don’t think a website should feel like a cookie-cutter sales machine.

My goal is always to create something that works and feels personal to the client. I want the site to be effective, but I also want my client to be proud to show it off.

The Right Questions Lead to the Right Fit

At the end of the day, choosing a web designer is a lot like choosing any creative collaborator.

You want someone who understands your goals.
You want someone who respects your vision.
You want someone who has experience solving problems similar to yours.
And you want someone whose process gives you confidence.

So if you’re trying to figure out what to ask a web designer, start here:

• How many artists or businesses like mine have you worked with?
• Can I see examples of websites you’ve built for people in my field?
• What does your process look like?
• What happens after the website launches?
• How do you think about turning a website into something that actually supports my business?

The best websites don’t happen because a designer knows how to write code. They happen because a designer takes the time to understand the person behind the business and builds something around their goals.

That’s the difference between hiring someone to make you a website and hiring someone who’s genuinely invested in your success.