What Should I Ask a Web Designer Before Hiring Them?
A guide for established founders with discerning taste but a website that doesn’t match up.
You've been in business long enough to know the difference between a website that exists and a website that works. You probably have one from a few years back — built by a freelancer or small studio, uploaded with your photos and copy, launched with a ribbon-cutting moment that felt exciting at the time. And then... it just sat there.
Maybe it's on a platform you never figured out how to update. Maybe it looks like dozens of other sites in your industry. Maybe it draws traffic but not the right clients — or no traffic at all.
If that sounds familiar, you're not alone. Most founders who come to us have been through at least one website that underdelivered. And in almost every case, the problem started before the project did — in the questions that never got asked.
Here's what to ask before you hire anyone.
1. What platform do you recommend — and why?
This sounds like a technical question. It's actually a strategic one.
The platform your site lives on shapes everything: how easy it is for your team to update, how well it performs, how much design flexibility your designer has, and how the site grows with your business.
We've inherited sites built on ShowIt — a visually beautiful platform that doesn't have a native blog, which is a significant gap for any business investing in content. We've worked with founders whose WordPress sites became unmanageable after years of posting every project as a new entry, until the content was sprawling and inconsistent. We've also seen Webflow sites that looked stunning at launch but became messy over time because the firm didn't have in-house design expertise to maintain them.
A good designer won't push you toward the platform they know best. They'll ask about your team's technical comfort level, your content plans, and your long-term goals — then make a recommendation that fits you.
Red flag: "We build everything on [platform]." Full stop. Green flag: "Here's what I'd recommend based on how you'll actually use this."
2. What's the best way to display our content to drive conversions?
Most web designers think about aesthetics. Fewer think about what happens after someone lands on your page.
Conversion rate optimization — the practice of designing sites that turn visitors into inquiries — is a distinct skill set. It involves understanding how people move through a site, where they drop off, what makes them trust you enough to reach out, and how to remove friction between interest and action.
Ask your designer what they know about it. Ask them to walk you through how they've structured a site to move someone from curiosity to contact. If they look at you blankly, that's information.
3. What will you need from us before we start — and what happens if we don't have it?
Projects usually stall because of asset gaps, not design problems.
Before a single page gets built, you should know: Does the designer need finalized copy? Existing brand guidelines? Professional photography or video? And critically — what happens if you don't have those things? Does the project pause? Do they have partners they bring in? Will they write placeholder copy that ends up living on your site for two years?
Get this in writing before you sign anything.
The questions that matter here:
What do you need from us to get started?
How quickly do we need to turn around feedback at each stage?
Who on our end needs to be involved in approvals?
What project management tools do you use?
A well-run studio will have clear answers to all of these. A designer who wings it operationally will wing it creatively too.
4. What platform will we use to manage the project?
This one reveals a lot about how a studio operates.
A studio that uses structured project management — we use Asana — has thought through workflow, accountability, and communication. You'll know what's happening, when to expect things, and where to give feedback. A studio that manages everything through email threads and Slack DMs is a sign of what's to come when something goes sideways.
5. What's included in the maintenance plan after launch?
Your site is not a finished product the day it goes live. It needs updates, security patches, occasional content changes, and someone to call when something breaks.
Ask specifically: What's covered in your maintenance plan? What's billed additionally? What's your typical response time? What's my responsibility versus yours?
The handoff is where a lot of founders get surprised. A great designer sets you up for independence. A mediocre one leaves you dependent on them for everything — or leaves you stranded entirely.
6. Can you walk me through a case study — not just show me the work?
Pretty portfolios are table stakes. What you actually want to understand is how a studio thinks.
Ask them to walk you through a project: What was the strategic problem? What decisions did they make and why? What did they learn? What would they do differently?
When you're looking at their portfolio yourself, go beyond the screenshots:
Check the live sites. Experience them the way a real visitor would. Does the site feel considered? Does the user experience hold up?
Look for micro-interactions. Subtle animations, hover states, scroll effects — these signal a studio that designs beyond templates.
Look for range. If every site in their portfolio looks the same, they have a style. That's not always a bad thing, but it's worth knowing whether their aesthetic will actually serve your brand.
Read the case studies. Impact matters. A studio that can articulate outcomes — not just deliverables — is thinking about your business, not just your website.
7. What do you know about our industry?
You don't need a designer who only works with firms like yours. But you do need one who understands how your clients make decisions, what builds trust in your world, and what a high-end digital presence looks and feels like at your level.
For our clients in interior design, landscape architecture, and professional services, this matters enormously. The buying psychology is different. The visual expectations are different. The way trust gets built is different.
A designer who has done the work to understand your world will ask different questions, make different recommendations, and catch things a generalist would miss.
8. What do you know about site speed, accessibility, and AI optimization?
These are the questions most designers can't answer well — which is exactly why you should ask them.
Site speed affects both user experience and search ranking. A beautiful site that loads slowly is a beautiful site that no one sees.
Accessibility means your site can be used by people with visual, motor, or cognitive differences. Beyond being the right thing to do, it's increasingly a legal and reputational consideration.
AI optimization is newer territory — but it matters. As more people use AI tools to research and make decisions, the way your content is structured affects whether your firm shows up in those answers.
A designer who can speak to all three is thinking about your site's performance, not just its appearance.
9. Pay attention to what they ask you
Here's something most hiring checklists miss: the best signal isn't in a designer's answers. It's in their questions.
A studio that asks about your goals, your target audience, your brand positioning, your current messaging, and how your existing site is or isn't serving you — before they've shown you a single design — is signaling that they understand what a website is actually for.
It's not a brochure. It's a strategic asset. And the designers who treat it that way will ask you to think about it that way too.
At Ethos, every project begins with a Brand Blueprint — a focused strategic engagement before anything visual is touched. We look at where you're positioned in your market, what's working and what isn't, and how your digital presence can be elevated to reflect the level you're operating at. It's how we make sure the website we build is doing real work for your business, not just looking good.
The designers who skip this step aren't wrong — they're just not building what you actually need.
10. How will this site hold up in two years?
This is the question almost no one asks. It's the one that matters most.
The founders who come to us after a disappointing website experience almost always describe the same thing: it looked fine at launch, and then gradually stopped feeling like them. The platform became a limitation. The design felt dated. The content outgrew the structure.
A great web studio thinks about longevity. They build sites that can grow with your business, on platforms your team can actually use, with content structures that stay organized as you scale. They hand you something you own — not something you're dependent on them to maintain.
Craftsmanship in web design isn't just about what a site looks like on launch day. It's about whether it still serves you well years from now.
The shift worth making
Most founders approach hiring a web designer the way they'd hire a contractor: get quotes, check portfolios, pick someone whose work looks good at a price that feels reasonable.
But a website is not a renovation. It's a strategic communication platform. The firm behind it should understand your brand, your audience, your market position, and your goals — not just your color palette.
The questions above are designed to help you tell the difference between a designer who executes and a studio that thinks. One builds you a website. The other builds you a digital presence.
If you're at the point where your current site no longer reflects the level you're operating at, that's not a design problem. It's a strategy problem — and it's exactly where we start.
