The Aventura boutique owner had already interviewed four freelancers and one small agency. All of them said they could build her site. Three of them had beautiful portfolios. Two of them had reasonable prices. She still could not tell them apart. She emailed us for a second opinion, not to hire us, just to help her interview the others.
We sent her the eight questions in this post. Two days later she called back to say the answers had eliminated three of the five candidates. One of the remaining two withdrew after seeing the specificity of what she was asking. She signed with the fifth, launched a beautiful site three months later, and has not needed a rebuild since.
This is the interview script we use ourselves when we help Miami clients evaluate designers, whether those clients end up hiring us or someone else. Eight questions. The right answers are less important than the pattern the answers reveal. If you want to run this on our team too, our about page has the context you need for question one, and our portfolio has the receipts for the rest.
A note on scope. This is written for Miami businesses hiring a designer for a project between $3,000 and $25,000. Below that, you are usually in template territory and some of these questions do not apply. Above that, you should be evaluating agencies, not individual designers. Use different criteria.
Question 1: Show Me Three Sites Like Mine
Not "show me your best work." Show me three sites for businesses like mine. Same industry, same size, same complexity.
A designer who has built three sites like yours knows the specific pitfalls of your business type. They know what content is missing that customers ask for. They know which platforms handle your specific needs. They know which integrations are common and which are rare.
A designer whose portfolio is beautiful but full of unrelated work will learn on your project. That is fine if the price reflects it. It usually does not.
The right answer names three specific projects, sends the links, and explains what worked and what did not. The wrong answer is vague, defensive, or generalizes ("we have worked with businesses of all kinds").
Question 2: Who Does the Actual Work
If you are hiring an individual designer, this question is straightforward. Is the person I am talking to the one who will design and build my site? Some solo designers subcontract without saying so. If you find out three weeks in, you have a problem.
If you are hiring a small agency, this question is harder. Is the senior person I met with the one doing the work, or will a junior designer or contractor do the work with senior review? Both are defensible. Neither is wrong. But you should know.
The right answer names people. "I will design and build the site personally." Or "our senior designer will do the design, and our junior developer will do the build with my review." The wrong answer stays vague. "Our team handles everything."
Question 3: What Is Your Process, Week by Week
An honest designer can walk you through the timeline in specifics. Week 1: discovery and content audit. Week 2: sitemap and wireframes. Week 3: design of home and one interior page. Week 4: revision and remaining page designs. And so on.
A designer without a process will improvise. Improvisation on a paid project usually means scope creep, missed deadlines, and change orders.
The right answer sounds structured. The wrong answer sounds free-form.
For projects under $10,000, expect a 6 to 10 week timeline. For projects above, 10 to 16 weeks is normal.
Question 4: What Do You Need From Me, and When
Half of every website project depends on the client delivering content, feedback, and approvals on time. Designers who do not name what they need from you either do not know or are not going to hold you accountable, which means the project will drift.
The right answer sounds like a shared responsibility list. "By end of week 1, I need your content brief and any brand assets. By end of week 3, I need your feedback on the wireframes. By end of week 6, I need all page copy finalized." Specific, dated, mutual.
The wrong answer treats the process as one-directional. "Just give me feedback when I share the designs."
If the designer does not have a client-side deliverable list, ask them to write one before you sign. Their willingness to do so tells you a lot.
Question 5: What Platform Will You Build On, and Why for My Business
A good designer has opinions about platform. They also explain the reasoning in a way that applies to your specific business, not just their preferred stack.
WordPress for a content-heavy site with regular updates and a marketing team that will use it. Webflow for a design-driven marketing site with a small team. Shopify for ecommerce. Custom Nuxt or Next for premium builds or complex integrations. Squarespace for solo operators.
The right answer explains the trade-offs and why one is the right fit for your business. The wrong answer defaults to the designer's preferred platform without discussing your specific needs.
A designer who says "I build on Webflow" without asking what your business needs is a designer who will build on Webflow whether Webflow is the right choice or not. That is fine if Webflow happens to be right for you. It is expensive if it is not.
Question 6: Show Me a Contract or Statement of Work
Ask to see a sample contract or statement of work from a recent project. Not because you need to review the legal terms deeply, but because the shape of the document tells you how organized the designer's practice is.
A one-page contract on a $12,000 project signals scope trouble ahead. A five-page detailed SOW with milestones, deliverables, and specific payment triggers signals a designer who has done this before and knows what to protect.
Payment structure matters too. Standard is 30 to 50 percent deposit with milestone payments and a final payment at launch. Watch for designers asking for 100 percent upfront (a red flag) or offering to work on trust without a contract (a different kind of red flag).
The right answer is willingness to share a redacted example and walk you through it. The wrong answer is opacity.
Question 7: What Happens If This Does Not Work Out
Every project can fail. Personalities clash. Business needs change. Timelines slip. A designer who has thought through failure modes is a designer who will handle problems well when they arise.
Ask specifically: What happens if I need to end the engagement early? What happens if I am unhappy with the design direction? What happens if you miss a deadline?
The right answer is direct. "You can terminate with 14 days notice and I will hand off everything I have produced. You pay for work completed but not the balance of the project." Or, "if the design direction is not right after two rounds, we will do a reset call and try a third approach at no extra cost."
The wrong answer avoids the question or gets defensive. Designers who cannot talk about failure modes usually have not planned for them.
Question 8: What Do You Wish Your Last Client Had Asked You
This is the cheat code question. A confident, experienced designer will have a thoughtful answer. Something like: "I wish they had asked me for a written content plan before signing, so we could have scoped the copywriting properly." Or, "I wish they had asked what my hourly rate was for revisions after the included rounds, so we could have avoided the friction at the end."
The right answer teaches you something useful about the project ahead. The wrong answer is silence or a generic non-answer. Designers who cannot reflect on past projects will not learn from them.
For extra insight, follow up: "How did that project turn out, and would you work with that client again?" The answer to those two questions tells you more about the designer's practice than three references ever will.
The Freelancer vs Agency Question
Many Miami small businesses debate whether to hire a freelancer or a small agency. The honest answer depends on the project.
Freelancers are usually the right choice for straightforward marketing sites, tight budgets, and business owners who like working directly with the maker. Communication is faster. Costs are usually lower. Risk is that the person can get sick, get busy with other clients, or move on mid-project.
Small agencies are usually the right choice for complex builds, businesses that need multiple specialists (design, development, copywriting, SEO), and clients who want continuity after launch. Costs are higher. Communication has more layers. Continuity and specialization are better.
Both can produce excellent work. Both can produce poor work. The eight questions above apply to either.
If you want to see how these questions play out in practice, our portfolio has examples of the kinds of projects we take on and how they came together.
Red Flags Any of These Questions Might Surface
Six warning signs worth taking seriously.
The designer cannot name three past projects like yours or send links.
The designer speaks about "the team" but cannot name individuals.
The process is described in generalities without weeks or deliverables.
The client-side deliverable list is missing or hand-waved.
The platform choice is presented without reasoning specific to your business.
The contract is one page or verbal only.
None of these are automatic disqualifiers. Any two of them together is enough to walk. Three is a certainty. If a designer sends three of these signals, the project will have problems, and you will pay for them.
The good news: designers who have real practices will pass all eight questions comfortably. Use the interview to find them. Our website design service explains how we would answer these ourselves.
The One Thing to Do Tomorrow
Send the eight questions to every designer you are currently considering. Ask for written answers within 48 hours. The response speed alone will filter half the field. The response quality will filter most of the rest.
When you are ready to bring the questions to us, start a project with us and we will answer each one on the first call, share three references within 24 hours, and tell you honestly whether we are the right designer for your project.
