The questions you should be asking before you buy website design

You’re not supposed to know what questions to ask. That’s the whole problem.

You’re sitting in front of a web company’s sales page, or on a Zoom, or standing in your own shop while someone explains your web design problems what they can do for your business — and you’re trying to figure out whether any of it is real. Whether the thing they’re describing is worth the money. Whether the version of themselves they’re showing you right now is the version you’ll get six months from now.

And you don’t have the vocabulary to check.

That’s not a failure on your part. We can only be so good at so many things, and we can only understand at a deep level what questions to ask about the things we’re good at. These things are inherent in the human condition, and that’s fine. The information gap doesn’t come from laziness or carelessness — it comes from the fact that web design buying triggers real fears in people who are experts at running their own businesses and not at evaluating someone else’s.

This post is the framework. Not a list of clever questions to memorize — a way of thinking about the buying process that makes the right questions obvious once you’re in the room.

The First Question to Ask Before Buying Web Design — and Why It Changes Everything

If you’re coaching a business owner through the web design buying process, the first question you tell them to ask is this: what does it look like us working together? That questions alone can stop you from overthinking how you should hire a web designer.

Not “what do you charge.” Not “can I see your portfolio.” Not “how long does it take.”

What does it look like?

Briefly outline the sales process, the build process, the launch process, and the customer service process. That alone will tell you so much. You’ll be able to clearly see if that’s how you want to work. You’ll find things you don’t like — and even with us, we’re not a fit for everybody — but you’ll know before you sign instead of finding out after.

Most people skip this question because it feels too broad. It’s not. It’s the most diagnostic question you can ask, because it forces the company to describe reality instead of selling a feeling. A company that can walk you through each phase clearly has done the work. A company that redirects you to the portfolio or the pricing page hasn’t thought about the experience beyond getting you to say yes.

The difference between a company that can answer this question and one that can’t is the difference between a company that has a Yeetish philosophy and a company that has a pitch.

The Questions Before Buying Web Design That Make Bad Companies Squirm

Once you’ve asked the big-picture question, get specific. There are a handful of follow-ups that honest companies answer without blinking — and dishonest companies treat like a cross-examination.

Detail exactly what I’m paying for. What is this line item $50 charge and what do I get for it? Do I have a contract? Can I take my website with me if I leave?

Ask us any of these questions and it’ll be very clear that we’re indifferent to the answer. We’re not trying to trick you in any way or hide anything. The answers are on the website, in the pricing, on the first phone call. There’s nothing to protect because there’s nothing hidden.

But that’s not universal. Some companies build their entire model around the assumption that you won’t ask. The line items stay vague because vague line items are profitable. The contract stays buried because the contract is the product — not the website. The portability question never comes up because they’re counting on you not knowing that portability is a thing you should want.

These aren’t trick questions. They’re the baseline. A company that squirms when you ask what you’re paying for is a company that knows the answer won’t help them close the deal. That tells you everything about what the relationship will look like once the deal is closed.

The Contract Trap Nobody Mentions Until It’s Too Late

Contracts are a big one. Especially now — everyone’s so used to that terms of service popup where you just check the box. Download an app, agree to the update, click through to the next screen. No one reads that stuff, and the companies know that. They throw all kinds of things in there because they’ve learned that the checkbox is basically a blank signature.

The reality is some of these companies go door to door to businesses and a lot of people aren’t tech-savvy. The sales rep says “okay, we’re all set — sign here.” Never mentions the one-year contract. That’s pretty common in sales, unfortunately. It’s not like every sales rep does it, but it does happen often enough that you need to assume it’s possible every time you sit down with someone new.

You’ve got to ask when you enter any relationship: is there a contract at all? If I decide to give you appropriate notice and leave, is there a penalty?

You’ve got to ask that in anything you do these days, because full disclosure and ethics just isn’t ingrained in people like it used to be. That’s not cynicism. That’s pattern recognition from decades of watching how business relationships go wrong — and the contract is where they go wrong most quietly. By the time you realize you’re locked in, the company has already stopped trying to earn your business. They don’t have to. The contract earns it for them.

When a business website fails, it’s rarely because the design was bad on day one. It’s because the incentive to keep improving it disappeared the moment the signature dried.

Why You Don’t Know What to Ask — and Why That’s Normal

The information gap comes from life.

We can only be so good at so many things. You’re an expert in your business. You understand your customers, your margins, your competitive landscape — the things that matter to your daily operation. Web design is not one of those things, and it shouldn’t have to be. The fact that you don’t know what heading hierarchy means or what a CDN does or why your hosting matters for page speed doesn’t say anything about your intelligence. It says you’ve been busy running a business.

But the reality is that almost everybody knows somebody that’s good at this stuff. A friend who works in tech, a cousin who built their own site, a business contact who’s been through the process and came out the other side with opinions. Find that person.

Bring an advocate. Do these meetings with that advocate — someone who understands the questions to ask, who can validate what the web company is telling you, who can sit on the Zoom and listen for the things you wouldn’t catch on your own. We encourage it. A client who brings someone who can push back on us is a client who’s going to trust the relationship more once they see we don’t flinch.

Not everyone has that person, and not everyone feels comfortable asking. That’s fine too. But if you do know someone willing to hop on a call with you, use them. As much as we’d like to take entire market share, that’s just not going to happen. You’ll be in situations with a different company’s sales rep who may or may not give you the opportunity to ask all the right questions and protect yourself. The advocate is your insurance policy for those conversations.

Three Proposals on the Table and You Can’t Think Straight

Here’s what happens more often than people admit: you got one proposal and it was overwhelming. So you thought, if I get more, the answers will come to me. Now you have three, and you’re more confused than when you started.

That’s not a you problem. That’s a confusing web design proposals problem.

Most web design proposals are written to impress, not to inform. They’re full of language designed to make the company sound capable without telling you what you’re getting. Stack three of those on top of each other and the only thing that’s clear is how different the prices are — which is the worst possible way to make this decision, because the cheapest option and the best option are almost never the same thing.

You need to find a trusted advisor and have them sift through it. Obviously, you can reach out to us and we’ll analyze all three and give you a fourth. And if someone is legitimately better than us — better pricing, better deliverables, clearly knows what they’re doing — then obviously we’re not going to say go with us. That’s not how we operate.

The real question, once you’ve got comparable options in front of you, is simpler than you think: who do you like better?

If they’re $10 different but you love one company’s personality, what they stand for, how they communicate — that’s worth more than the $10. If they’re $100 cheaper but you think the more expensive option will work better with you long-term, that relationship is a more valuable thing than just cheaper. Because cheaper gets you exactly what that is. It doesn’t necessarily get you better.

The affordable option isn’t always the cheapest one. It’s the one where the price makes sense relative to what you’re getting and who you’re getting it from.

What This Checklist Won’t Do

It won’t guarantee anything.

Some people will answer every question on this list cleanly, look you in the eye, and still break those answers six months later. Salespeople under pressure do things that calm circumstances don’t produce. Someone who believes the promise they’re making in the moment may not think too hard about whether the company behind them can keep it.

But the questions make the lies harder. They create a record — in your memory, in their words. Most companies won’t manufacture answers to a list this specific and then plan to contradict them later. The ones who would are rare, and the more questions you ask, the more obvious they become.

This isn’t about becoming a web design expert before you hire one. It’s about walking into the room with a framework that forces honesty to the surface — so you can see it when it’s there and feel the absence when it isn’t.

If you want to go through this list with someone who won’t flinch at a single question on it — we’re right here.