I build websites for a living, so writing a piece telling you how to grill people like me is mildly uncomfortable. But I have seen too many small business owners get burned by web designers who either disappeared, charged for every comma change, or locked the client into a platform they did not understand. So here are the questions I would want anyone to ask me, and that you should ask any web designer before you sign anything.
If a designer dodges these, that is the answer. Pick someone who answers them straight.
"Who owns the code and the assets after launch?"
This is the single most important question, and most people never ask it. The right answer is: you do. You should leave the engagement with full ownership of the codebase, the design files, the domain, the hosting account, and any login that touches your business. If a designer says "we own the code and we host it for you," that is a leash. The moment you stop paying their monthly fee, your site goes dark, and you cannot take your business elsewhere without rebuilding from scratch.
This shows up most often with template based builders. The designer slaps together a site on a closed platform, and three years later when you want to move, you find out you cannot. Get the ownership question answered in writing before you pay a deposit.
"What platform are you putting me on, and why?"
There is no single right answer to this, but there is a wrong answer: "whatever I always use." A good designer picks the platform based on your business, not on what they happen to know. A restaurant with a menu that changes weekly needs a different setup than a law firm that updates the site twice a year. A brand that runs paid ads at scale needs different speed and analytics than a local plumber.
Ask why they are recommending what they are recommending. Listen for whether they talk about your needs or about their workflow. If they only talk about their workflow, that is a flag.
"How do edits work after launch, and how am I billed?"
Some designers build the site, hand it off, and you can make edits yourself with a simple visual editor. Some build the site in a way that requires them for any change, then charge an hourly rate every time you need a phone number updated. Both are legitimate models. You just need to know which one you are buying.
Ask: "If I want to change a headline on the homepage three months after launch, what is the process?" If the answer involves a ticket, a queue, and a minimum charge, factor that into the total cost of ownership.
"What is the plan for site speed and SEO from day one?"
Site speed and SEO are not features you bolt on at the end. They are decisions baked into how the site is built. Image handling, code bloat, mobile load time, structured data, sitemap, meta tags, all of that is either done right from the start or expensive to fix later.
A good designer will talk fluently about Core Web Vitals, mobile performance, and what they do during the build to keep the site fast. A weak designer will say "yeah we'll add SEO" and not have a real answer for what that means.
"Can I see three examples of sites you built more than a year ago?"
Anyone can show you a site they launched last month. Look at sites that have been live for over a year. Are they still up? Are they still fast? Is the design still holding up? Did the business grow on top of it, or did they ditch the site after eight months?
Longevity is a better quality signal than portfolio polish. A pretty site that the business owner abandoned six months in is not a success story.
"Will you build for conversion or for your portfolio?"
This one is uncomfortable to ask but worth it. Some designers build sites that look incredible in a portfolio screenshot and convert terribly. Big hero images, slow scroll animations, beautiful typography, but no clear call to action, no phone number above the fold, no obvious next step for a visitor.
Your site has a job. Usually that job is to turn visitors into leads or customers. Ask the designer to walk you through how they think about conversion, where buttons go, what they put above the fold, what they cut to keep the page focused. If they talk about awards and aesthetic without mentioning conversion, you are buying a portfolio piece, not a business asset.
"What happens if you get hit by a bus?"
Phrase it more politely if you want. The point is: what is your continuity plan? If the designer is a solo operator and gets sick, takes a long vacation, or just stops responding, what happens to your site? Do you have access to everything? Is there documentation? Can another developer pick it up without re engineering it from scratch?
A serious designer has thought about this and has an answer. A casual one will hand wave.
"How do you handle the boring stuff?"
Backups. Security updates. Domain renewal reminders. SSL certificate expiration. Spam filtering on contact forms. These are the unsexy operational details that determine whether your site keeps working in year two and year three. Ask specifically how each of these is handled, and whether it is included or extra. The answers will tell you a lot about whether the designer is thinking about your business long term or just about shipping a launch.
"Can I see a contract before I commit?"
Read it. Look for the scope, the change request process, the payment schedule, the ownership clause, the termination terms, and what happens if the project stalls on either side. A good contract protects both of you. A vague contract protects nobody.
If a designer pressures you to skip this step or "just sign the proposal," walk away.
A note on the answers you want
You are not looking for perfect answers. You are looking for honest, specific ones. A designer who says "we use this platform because it fits 80% of our clients, but for your case I think we should look at this other option, here is why" is more trustworthy than one who has a polished answer to every question on the first try.
If you want to put me through this list myself, that is fair. We offer a free discovery call where I expect to be grilled. Bring the questions, bring your skepticism, and we will see if we are a fit. If we are not, I will probably know someone who is.