Hiring a web designer is a significant investment. The wrong choice means wasted money, months of frustration, and a website that doesn’t work for your business. The right choice means a partner who makes your life easier and delivers real results.
These 25 questions help you evaluate any web designer or agency before you commit. I’ve included what good answers sound like, red flags to watch for, and at the end, how I personally answer each question.
TL;DR: The 5 Most Critical Questions
If you’re short on time, these five questions will tell you the most:
- Can I see examples of sites you’ve built for businesses like mine?
- What’s included in your price and what costs extra?
- Who owns the website when it’s done?
- What happens if I need changes after launch?
- How will we communicate during the project?
A designer who answers these clearly and confidently is probably a good choice. Vague or defensive answers are red flags.
Section 1: Experience & Fit
1. Can I see examples of websites you’ve built for businesses like mine?
Why it matters: Past work predicts future results. A designer experienced in your industry understands your customers.
Good answer: They show relevant examples with specific details about the project.
Red flag: “We can do any industry” without relevant examples, or a portfolio that looks nothing like what you want.
2. How long have you been designing websites?
Why it matters: Experience matters, but it’s not everything. Quality of work matters more than years in business.
Good answer: Clear answer with context about their background and how they got into web design.
Red flag: Vague about experience or defensive when asked.
3. Do you work solo or with a team?
Why it matters: Both models work. But you should know who’s actually doing the work.
Good answer: Clear explanation of who does what. If it’s a solo operation, they’re upfront about it. If it’s a team, they explain who handles design, development, and content.
Red flag: Vague about who does the work, or implying they’re bigger than they are.
4. What size businesses do you typically work with?
Why it matters: A designer used to enterprise clients might overcomplicate a simple small business site. One focused on small business will understand your constraints.
Good answer: Clearly describes their typical client and why that’s a good fit for you.
Red flag: They work with “everyone” (probably not great at anything), or their typical client is very different from you.
5. Can I talk to a few of your past clients?
Why it matters: References reveal the real working experience.
Good answer: “Absolutely, I’ll send you a few contacts who can speak to their experience.”
Red flag: Hesitation, excuses, or “our clients are too busy.”
Section 2: Process & Communication
6. What’s your process from start to finish?
Why it matters: A clear process means fewer surprises and better results.
Good answer: They walk you through defined phases: discovery, design, development, review, launch. Each phase has clear deliverables.
Red flag: “We just start building” or no clear process.
7. How long will the project take?
Why it matters: You need to plan around the timeline.
Good answer: A realistic range based on project scope. “For a site like yours, typically 1-3 weeks from kickoff to launch, depending on how quickly you can provide content and feedback.” Modern tools have made development faster — the bottleneck is usually your availability for decisions and content.
Red flag: No timeline at all, or timelines that don’t account for your input. Fast is fine if they can explain their process; vague is a problem.
8. How will we communicate during the project?
Why it matters: Communication breakdowns cause most project problems.
Good answer: Clear expectations for how often you’ll connect, what tools you’ll use, and how quickly they respond to questions.
Red flag: “Just email whenever” with no structured check-ins.
9. How many rounds of revisions are included?
Why it matters: You need to know what happens if you don’t like something.
Good answer: Clear revision policy. “Two rounds of design revisions are included. Additional rounds are [price].”
Red flag: Unlimited revisions (often means they don’t care about quality) or zero revisions (inflexible).
10. What do you need from me, and when?
Why it matters: Most project delays happen because the client wasn’t ready with content, feedback, or decisions.
Good answer: Clear list of what they need (content, images, logo, access credentials, feedback) with realistic timelines for when they need it.
Red flag: “We’ll figure it out as we go” or no mention of your responsibilities.
Section 3: Technical & Deliverables
11. What platform will my website be built on?
Why it matters: The platform affects what you can do later, how easy it is to update, and whether you’re locked in.
Good answer: Clear explanation of the platform, why it’s right for your needs, and what the tradeoffs are.
Common options:
- WordPress — Most flexible, but requires maintenance
- Squarespace/Wix — Easy to update, but less flexible
- Shopify — Best for e-commerce
- Custom/Static — Fastest and most secure, but harder to update yourself
Red flag: Proprietary platform you’ve never heard of (lock-in risk), or platform choice without explanation.
12. Will I be able to update the website myself?
Why it matters: You shouldn’t need a developer for every small text change.
Good answer: “Yes, I’ll set it up so you can easily update [specific things] yourself, and I’ll train you on how to do it.”
Red flag: “You’ll need to come back to us for changes” (dependency) or “It’s too technical for non-developers” (bad platform choice).
13. Who owns the website when it’s done?
Why it matters: You’re paying for it — you should own it.
Good answer: “You own everything — the design, the code, the content. I’ll transfer all credentials to you.”
Red flag: “We retain ownership,” “It’s hosted on our proprietary system,” or vague answers.
14. Will my site be mobile-responsive?
Why it matters: Over 60% of local searches happen on mobile. A site that doesn’t work on phones is broken.
Good answer: “Of course — we design mobile-first.” They should show mobile versions in their portfolio.
Red flag: This should be a given in 2026. If they hesitate or charge extra for mobile, walk away.
15. What about website security and backups?
Why it matters: Websites get hacked. Data gets lost. You need protection.
Good answer: “SSL is standard, we set up automated backups, and [if WordPress] we keep core, themes, and plugins updated.”
Red flag: “That’s your responsibility” with no guidance.
Section 4: Pricing & Terms
16. What’s included in your price?
Why it matters: “Website for $2,000” could mean wildly different things.
Good answer: Clear itemization: number of pages, design revisions, content writing (or not), SEO setup, training, post-launch support period.
Red flag: Vague quotes with no breakdown, or “we’ll figure out scope as we go.”
17. What’s NOT included that I might expect to be?
Why it matters: The best designers proactively tell you what’s extra.
Good answer: “Content writing, stock photos, ongoing hosting, and extensive SEO are not included but can be added.”
Red flag: Discovering extras after you’ve signed.
18. Are there ongoing costs?
Why it matters: Some designers charge monthly fees forever.
Good answer: Transparent breakdown of what’s recurring: “Hosting is $X/month, maintenance is $Y/month if you want it, but there’s no required ongoing fee from us.”
Red flag: Required monthly fees without clear explanation of what they cover, or fees tied to a proprietary system you can’t leave.
19. What’s your payment structure?
Why it matters: Payment terms should be fair to both parties.
Good answer: “50% upfront, 50% at launch” or “1/3 upfront, 1/3 at design approval, 1/3 at launch.”
Red flag: 100% upfront (too risky for you), or 100% at end (too risky for them — suggests desperation).
20. What happens if the project goes over budget?
Why it matters: Scope creep happens. You need to know how it’s handled.
Good answer: “If you request changes beyond the original scope, I’ll let you know the additional cost before doing the work.”
Red flag: No change order process, or “we just bill hourly for overages” without caps.
Section 5: After the Project
21. What happens if something breaks after launch?
Why it matters: Things break. You need support.
Good answer: Clear post-launch support policy. “30 days of bug fixes are included. After that, support is [hourly rate or maintenance plan].”
Red flag: “Our job ends at launch” or no clear answer.
22. Do you offer ongoing maintenance?
Why it matters: WordPress sites especially need regular updates. But maintenance should be optional, not mandatory.
Good answer: “I offer maintenance plans at $X/month that include [specific things]. It’s optional, but recommended if you don’t want to manage updates yourself.”
Red flag: Required maintenance with no clear scope, or no maintenance option at all.
23. What if I need changes in 6 months?
Why it matters: Your business will evolve. Your website should too.
Good answer: “Reach out anytime. I bill [hourly rate] for additional work, or we can discuss a retainer if you have ongoing needs.”
Red flag: “You’d have to hire us for a new project” (inflexible) or no path forward.
24. Will you help me with hosting and domain setup?
Why it matters: Technical setup can be confusing.
Good answer: “I’ll set up or transfer your hosting and domain as part of the project” or “I’ll guide you through it and make sure everything is in your name.”
Red flag: “That’s your problem” or hosting/domain in their name (lock-in risk).
25. What if I want to switch to a different designer later?
Why it matters: You shouldn’t be trapped.
Good answer: “No problem. You own everything. I’ll make sure you have all credentials and files, and any standard designer could take over.”
Red flag: “That’s not really possible with our system” (massive red flag — they’re locking you in).
Red Flags Summary
Run away if you see these:
| Red Flag | Why It’s Bad |
|---|---|
| Proprietary platform you can’t leave | You’re locked in forever |
| Won’t provide references | Hiding bad experiences |
| 100% payment upfront | No leverage if they don’t deliver |
| No clear process | Project will be chaotic |
| Website ownership unclear | You might not own what you paid for |
| Guarantees that sound too good | ”Page 1 in 30 days” is a lie |
| Mandatory expensive monthly fees | You’re renting, not buying |
| Can’t explain in plain English | Either they don’t know, or they’re hiding something |
Green Flags Summary
Signs you’ve found a good partner:
| Green Flag | What It Means |
|---|---|
| Clear portfolio with relevant examples | They know your type of project |
| Transparent pricing with itemization | No hidden costs |
| Written contract with clear terms | Professional, protects both parties |
| Process they can walk you through | They’ve done this before |
| References they offer proactively | Confident in their reputation |
| Answers questions directly | Nothing to hide |
| Asks good questions about your business | They care about outcomes, not just outputs |
| Tells you when you’re wrong | Partner, not yes-person |
How I Answer These Questions
Since I’m asking you to evaluate designers on these criteria, here’s how I’d answer each:
| Question | My Answer |
|---|---|
| Examples for my industry? | I show relevant work. If I haven’t done your exact industry, I explain the transferable skills. |
| How long in business? | Building websites since 2009. Full-time independent since 2018. |
| Solo or team? | Solo. You work directly with me — no handoffs. |
| Typical client size? | Local businesses and small teams, typically 1-50 employees. |
| References? | Happy to provide. I’ll connect you with past clients. |
| Process? | Discovery → Design → Build → Review → Launch → Support. Each phase has clear milestones. |
| Timeline? | Typically 4-6 weeks for most local business sites. |
| Communication? | Weekly check-ins, email/text for questions, response within 1 business day. |
| Revisions? | Two rounds included. Additional rounds billed at hourly rate. |
| What I need from you? | Content (or I can write it), logo, photos, feedback at defined checkpoints. |
| Platform? | Depends on your needs. Usually Astro or WordPress, explained in plain English. |
| Can you update it? | Yes — I train you on anything you need to manage. |
| Who owns it? | You own everything. Code, design, content, domain, hosting. |
| Mobile-responsive? | Always. I design mobile-first. |
| Security/backups? | SSL standard, automated backups, security monitoring if WordPress. |
| What’s included? | Itemized in every proposal. No surprises. |
| What’s extra? | Content writing (unless included), stock photos, ongoing SEO. All clear upfront. |
| Ongoing costs? | Hosting ($10-50/month depending on setup). Maintenance optional. |
| Payment structure? | 50% upfront, 50% at launch. |
| Over budget? | I’ll tell you before doing work outside scope, with a clear quote. |
| If something breaks? | 30 days post-launch support included. After that, hourly or maintenance plan. |
| Ongoing maintenance? | Optional plans available. Not required. |
| Changes in 6 months? | Email me. I bill hourly for small changes, or we scope larger updates. |
| Hosting/domain help? | Yes — either I set it up in your name or guide you through it. |
| Switch to someone else? | No problem. You get everything. Any competent designer could take over. |
Frequently Asked Questions
How many designers should I talk to?
At least 2-3 to compare. More than 5 becomes diminishing returns.
Should I go with the cheapest option?
Rarely. The cheapest option often means hidden costs, poor quality, or a designer who can’t sustain their business. Middle of the range is usually safest.
What if they don’t have experience in my industry?
Industry experience helps but isn’t essential. Look for experience with similar types of sites (service businesses, local focus, lead generation) rather than the exact industry.
Is a contract necessary?
Absolutely. A clear contract protects both parties. No contract = no hire.
Should I pay for a “discovery” or “strategy” phase first?
It’s reasonable for a designer to charge for initial strategy work, especially for complex projects. But they should be able to give you a rough estimate before any paid work.
What This Means for Your Business
Hiring the right web designer isn’t just about getting a nice website. It’s about finding a partner who understands your business, respects your time and money, and delivers something that actually generates results.
The questions in this guide help you separate professionals from amateurs, and good fits from bad fits. Take the time to ask them. Your future self will thank you.
Whether you’re a boutique in Boston, a contractor in Cleveland, or a clinic here in Springfield, Oregon — the right designer is out there. These questions will help you find them.
Next Steps
Use this guide to evaluate designers you’re considering. Print it out, take notes, compare answers.
If you want to know how I’d answer all of these in detail, let’s have a conversation. I’m happy to explain my approach and help you figure out if we’d be a good fit — or point you toward someone else if we’re not.
Continue Reading
50+ Content Ideas for Service Businesses
Stuck on what to post? Here are 50+ content ideas for local service businesses, organized by type and platform.
8 min Local BusinessDIY Website vs Hiring a Pro: An Honest Comparison
Should you build your own website or hire a professional? Honest breakdown of costs, time, results, and when each option makes sense.
11 min Local BusinessDo I Need a New Website? How to Know When It's Time
Honest assessment of whether your website needs a refresh, redesign, or complete rebuild. Decision framework for business owners.
10 min