You’ve got calls scheduled. The portfolios all look nice. Everyone says the right things. Now you need questions that cut through the sales pitch and reveal whether an agency will actually deliver or just sell well.
This guide gives you specific questions to ask a web design agency, explains what good answers sound like, and flags the responses that should make you walk away. Whether you’re vetting a full-service agency or figuring out what questions to ask a website developer for a smaller project, the principles are the same. Use this whether you’re talking to us or our competitors.
Before you ask anything: are you talking to the right type of vendor?
The questions you ask depend on who you’re talking to. A $5,000 freelancer project and a $75,000 agency engagement are different animals entirely.
Freelancers ($3K-$15K typical)
Best for: Simple sites, tight budgets, straightforward execution. You’ll manage the project yourself and provide direction. They execute your vision.
Questions focus on: Technical skills, availability, communication style, portfolio relevance.
Boutique agencies ($25K-$100K typical)
Best for: Strategic work where you need partners to challenge your assumptions and bring expertise you don’t have. They’ll guide the process and push back when you’re wrong.
Questions focus on: Strategic thinking, process methodology, team structure, how decisions get made.
Enterprise agencies ($100K+ typical)
Best for: Complex organizations with multiple stakeholders, compliance requirements, and integration challenges. They have deep benches and formal processes.
Questions focus on: Account management, escalation paths, enterprise experience, risk mitigation.
If you’re reading this, you’re probably in boutique agency territory. That’s where the questions get interesting, because you’re not just buying execution. You’re buying judgment.
The questions most people ask (and why they’re incomplete)
Most prospects ask some version of these:
- How much does it cost?
- How long will it take?
- Can you show me your portfolio?
- What CMS do you use?
These questions aren’t wrong. They’re just incomplete. They tell you whether an agency can do the work. They don’t tell you whether the agency will do the work well, whether they’ll understand your business, or whether they’ll challenge you when your assumptions are wrong.
The better question behind each of these:
Instead of “How much?” ask: “What determines whether this costs $30K or $80K? What would make it cost more after we start?”
Instead of “How long?” ask: “What’s realistic for a project like this, and what typically causes timeline slippage?”
Instead of “Show me your portfolio” ask: “Walk me through why you made specific decisions on this project. What did you learn in discovery that shaped the outcome?”
Instead of “What CMS?” ask: “How do you decide which platform fits a client’s situation? What factors would change your recommendation?”
Generic answers to the first set are easy. Thoughtful answers to the second set require actual expertise and experience. That’s the difference you’re testing for.
Questions that reveal strategic thinking
Once you’ve confirmed you’re talking to the right type of vendor, these are the questions for your early conversations.
“What will your discovery process actually look like for us?”
Every agency claims to be research-driven. Few actually are. This question forces specifics.
What you want to hear: concrete deliverables (“We’ll produce a competitive analysis, customer research synthesis, and positioning framework”), real time investment (“Discovery takes 4-6 weeks and involves interviews with your team, customers, and stakeholders”), and who actually participates (“Our strategist, designer, and developer all join discovery calls. Everyone working on your project gets firsthand access to research.”)
What should concern you: “We do a kickoff call and then get started on design.”
Or: “We’ll send over a questionnaire to gather your requirements.” Or vague references to “reviewing your existing site and competitors.”
Agencies that shortcut discovery are guessing. They’re gambling your budget on their intuition rather than your customer’s reality.
“What did your web designer learn from your last client’s discovery?”
This is an integration test. In siloed agencies, designers work from filtered briefs. They never see customer research or competitive analysis directly. The strategist does discovery, writes a brief, hands it off, and the designer executes from secondhand information.
In integrated teams, every specialist consumes the same research. Your designer can explain customer insights because they actually heard the interviews. Your developer understands business goals because they participated in strategic conversations.
A good answer sounds like: “They learned that our client’s customers valued speed over comprehensiveness, which completely changed the homepage approach.”
Or: “Our designers sit in on customer interviews. On that project, the designer caught a pattern in how users described their problems that became the headline.”
If they look confused by this question, you’re looking at coordination theater, not integration. Same goes for answers like “Our designers focus on design. The strategy team handles discovery.”
“What would make you recommend we NOT do this project right now?”
You’re testing for owner-to-owner honesty versus sales-first thinking.
Good agencies will name specific situations: “If you’re six months from a major product launch that might change your positioning, we should wait.”
Or: “If you don’t have someone internally who can own this project and make decisions, we’ll both be frustrated.”
Or: “If your business model is still in flux, a premium website is premature. Start leaner until you’ve validated.”
Watch out for: “We can handle any situation.” “We’re flexible and can adapt to whatever you need.” Or an immediate pivot to reassurance without actually answering.
The best agencies occasionally talk themselves out of projects. If every prospect conversation ends with “let’s do this,” they’re optimizing for closing deals, not for client outcomes.
Questions that reveal process quality
“Walk me through what happens between contract signing and seeing the first design.”
This tells you how much upfront work they do before making things.
You want to hear about phases and time: “After kickoff, we spend 4-6 weeks in discovery before any design work begins.” You want specifics on research activities: stakeholder interviews, customer research, competitive analysis, content audit. You want decision points: “You’ll see our strategic recommendations and approve direction before we move to design.”
Be wary of: “We’ll have something to show you within a couple weeks.” Or: “We start with mood boards and style tiles to get alignment on aesthetics.” Or vague references to “understanding your brand” without explaining what that actually means.
Agencies that jump straight to design are usually guessing. They’re excited to make things before they understand what to make.
“What does revision actually mean in your process?”
Revision practices are where scope creep lives. Get specific. Ask: What counts as a revision round versus a change order? How many rounds are included? What happens if you want to change something after approval? How do they handle feedback that contradicts earlier approved direction?
Clear answers look like: “A revision round is a consolidated set of feedback on a presented design. New feature requests or significant scope changes are change orders.”
And: “We do 2-3 revision rounds per major deliverable. If we need more, we’ll discuss why and what it means for timeline and budget.”
Vague answers like “we revise until you’re happy” or talk of “reasonable revisions” should raise flags. “Unlimited revisions” sounds generous. In practice, it usually means the agency has padded their pricing or will push back hard when you actually need changes.
“What types of change orders happen most often, and why?”
This catches agencies off guard because they’re not eager to discuss scope creep. But the honest answer tells you a lot.
Thoughtful answers identify patterns: “The most common change orders are content-related. Clients realize during the project that their content needs more work than expected.”
They explain root causes: “Timeline extensions usually happen when client feedback takes longer than planned or when decision-makers aren’t available.” And they show learning: “We front-load discovery to catch these issues before we’re deep into design, which is cheaper than changing things later.”
Answers like “we rarely have change orders because we’re thorough upfront” should make you skeptical. Every agency has projects that go over budget or timeline. The question is whether they understand why and have systems to prevent it.
Questions that reveal who actually does the work
“Who will I be working with day-to-day, and who will I see in the pitch?”
The senior team often disappears after the contract is signed. Junior staff does the actual work while you get access to leaders only when problems arise.
What you want: “Everyone in this meeting will be working on your project directly.” Clear ownership: “Your primary contact will be [name], who leads projects from discovery through launch.” Senior involvement that’s specific: “I personally review all strategic recommendations before they’re presented.”
Warning signs: “Our team will be assigned once we kick off.” Vague descriptions of “handoff processes.” Account manager as primary contact with “access to specialists as needed.”
If the people selling you are different from the people doing the work, you’re at risk of buying one thing and experiencing another.
“What’s your team turnover rate?”
High turnover means institutional knowledge disappears. The person who understood your project leaves. Their replacement starts from scratch.
Look for specifics: “We’ve had the same core team for 5+ years.” Or honest transparency: “We lost a developer last year. Here’s how we handled the transition for affected clients.”
Deflection or discomfort here is telling. “We have a strong team” without data is a non-answer. Agencies don’t like this question. Ask it anyway.
Questions that reveal whether they’ll actually understand your business
“Have you ever recommended a client NOT rebuild their website?”
This tests for solution bias. Agencies that only sell websites will always recommend websites, even when a landing page refresh or conversion optimization would deliver better ROI.
You want to hear yes, with specifics: “Last quarter, we recommended a prospect hold off on a redesign and invest in fixing their lead nurturing first. The website wasn’t their problem.” Or: “We sometimes recommend phased approaches where we fix the highest-impact pages first and revisit a full redesign later.”
If they can’t cite cases where they didn’t sell their main service, or if they immediately pivot to explaining why a redesign IS the right call for you, that’s solution bias in action. They’ll fit your problem to their solution rather than recommend what actually works.
“What questions will you ask me before making recommendations?”
This tells you whether they lead with curiosity or assumptions.
Good agencies ask business questions first: “We need to understand your revenue model, customer acquisition costs, competitive position, and growth goals before we can recommend anything.” They get specific to your situation. They talk about validation: “We’ll interview your sales team, review your analytics, and talk to some customers before we start making recommendations.”
If their first questions are about design preferences and visual examples, or if they start with “based on your industry, we typically recommend…” they’re pattern-matching, not thinking.
The best agencies ask uncomfortable questions. They challenge your assumptions about what you need. They want to understand your business, not just execute your brief.
A note on “industry specialists”
Be careful with agencies that position themselves as “the healthcare agency” or “the SaaS experts” or whatever vertical matches your business. This sounds like a selling point. Often it’s the opposite.
Industry specialization frequently means the agency has a playbook they’re going to run regardless of your specific situation. They’ve built templates they know “work” in your space, so they can move fast.
The problem: your business isn’t generic. You have specific customers with specific problems and a specific competitive position. An agency that assumes they know your market because they built a site for your competitor is the same agency that will give you something that looks like your competitor’s site.
What you actually want is an agency that’s expert at extraction and translation. They know how to learn a business quickly, pull out what makes it distinct, and translate that into web strategy. That skill transfers across industries. A playbook doesn’t.
When an agency leads with industry experience, ask: “What did you learn about our specific market that surprised you?” If they can’t point to genuine learning, they’re planning to apply a template.
“Is there anything in our RFP you’d do differently if we didn’t specify it? Why?”
If you’ve provided a detailed brief or RFP, this reveals whether they’ll bring perspective or just execute what you’ve requested.
Good agencies push back: “You’ve specified X, but in our experience, Y typically works better because…” Or they ask before answering: “Before we’d recommend changes, we’d want to understand why you specified X. There might be context we’re missing.”
“Your RFP looks comprehensive. We can execute this exactly as specified” with no pushback or alternative perspectives is a warning sign. You’re paying for expertise. If they agree with everything, you’re either a genius or they’re just trying to close the deal.
Questions about past project reality
If those early conversations go well and you’re narrowing to a shortlist, the questions shift. Now you’re vetting their actual track record.
“For your last five or six projects: What was the original timeline, and where did you actually end up?”
Past performance predicts future performance. Get specific.
Honest answers sound like: “About 60% delivered on the original timeline. The others extended 2-4 weeks, typically because of client feedback delays or content not being ready.”
They show learning: “We’ve gotten better at timeline estimation. Our recent projects are more predictable than older ones.”
“We always deliver on time” is either a lie or timelines padded so much that “on time” has lost meaning. No agency delivers 100% of projects on the original timeline.
If they try the cherry-pick defense (“Well, every project is different so we can’t really compare”), push back. Patterns exist. You’re looking for the pattern, not a specific number. An agency that can’t identify patterns in their own project history isn’t paying attention.
“Same question for budget: What was original versus actual?”
Budget overages reveal process issues. Understand why they happen.
Honest answers: “Most projects land within 10% of original estimate. About 20% have change orders that add 15-30%.” With explanation: “Budget increases typically come from scope additions the client requests, not from us underestimating the original work.” And prevention: “We’ve implemented checkpoint reviews to catch scope creep early.”
“We stay within budget” without data, or blaming clients exclusively for all past overages, tells you they haven’t done the introspection.
“How many of those clients would you be comfortable giving me their phone number?”
References are easy to cherry-pick. This question tests confidence in overall client relationships, not just showcase projects.
High confidence looks like: “I’d be comfortable with 8 out of 10. Happy to provide contacts for any you’d like to speak with.”
Even better: “Let me give you a mix. One that went perfectly, one that had challenges we worked through, and one long-term relationship.”
Hesitation, or only offering 2-3 handpicked references, or “we can provide references after we’re further along in the process” are all telling.
“Can we speak with a client whose project went wrong?”
This one surprises agencies. It also reveals the most.
Willingness to connect you is a good sign: “Yes. I can connect you with a client where we had timeline issues and how we resolved them.”
Ownership is even better: “We had a project last year that didn’t go smoothly. We learned X and changed Y. Happy to discuss what happened.”
“All our projects go well” is a lie. Every agency has difficult projects. The question is whether they learn from them and maintain relationships through challenges.
Questions about what you’ll actually own
When you’re close to signing, shift attention to contracts, ownership, and what happens if the relationship ends.
“Who owns the code if we part ways?”
This should be clear and unambiguous.
You want: “You own all code and assets. If we part ways, everything is yours.”
And: “Upon final payment, we transfer all files, credentials, and documentation. You can work with anyone afterward.”
And: “We’ll set up hosting and accounts in your name. You’re never locked to us.”
Any hesitation, conditions, or ownership tied to ongoing relationship is a red flag. You shouldn’t be held hostage to a vendor relationship.
“What happens to my website if your company closes tomorrow?”
This tests for documentation and client independence.
Good answers: “You have all credentials, files, and documentation. Nothing depends on our company existing.”
And: “Everything is in your name: domain, hosting, accounts. You’d just need to find a new partner for ongoing work.”
And: “We deliver documentation that any competent developer could pick up.”
“That won’t happen” is not an answer. Dependencies on proprietary systems should concern you.
“What does your SOW actually guarantee versus exclude?”
Contracts matter. Understand what you’re signing.
Ask specifically: What defines “completion” of each deliverable? What happens if you request changes after a phase is “approved”? What’s the change order process and threshold? What’s included in “support” post-launch and for how long? What’s the liability cap and do they carry E&O insurance?
Good answers are specific: “Design approval means signoff on layout, structure, and visual direction. Copy changes after approval are revisions. Layout changes are change orders.”
And: “Post-launch support includes bug fixes for 30 days. Feature additions or content changes are billable.”
“We can discuss contract details later” or resistance to explaining terms means they’re either disorganized or hoping you won’t read carefully.
Contract details that separate serious agencies from the rest
A few specific things to ask about or look for:
E&O (Errors and Omissions) insurance. This protects you if the agency makes a mistake that costs you money. Serious agencies carry it. Many small shops don’t. Asking about E&O insurance is a quick filter for professionalism.
Warranty period. What happens if something breaks after launch? Industry standard is 30-90 days of bug fixes included. “Lifetime warranty” is marketing nonsense. “No warranty” means you’re paying for fixes on day one.
Watch for these phrases in contracts:
“Reasonable revisions” with no definition of what reasonable means. This gives the agency unilateral power to decide when you’ve asked for too much.
“Support at our discretion” or “as resources allow.” This means nothing is actually guaranteed.
“We retain ownership of templates, frameworks, or reusable components.” This could mean parts of your site aren’t actually yours.
Auto-renewing maintenance agreements with vague scope. Know exactly what you’re paying for monthly and what happens if you want to leave.
You don’t need a lawyer to review every contract, but you should understand what you’re agreeing to before you sign.
Red flags that should make you walk away
They act like an order-taker, not a consultant.
Good agencies push back. They tell you when your ideas won’t work or when there’s a better approach. If every idea you have is “great,” they’re selling, not advising. If you say “make the logo bigger” and they just say “okay,” that’s a problem. You’re paying for them to protect the user experience, even from you.
The pitch team disappears.
Senior people in the sales meeting should be working on your project. If “the team will be assigned” after signing, you’re buying a bait and switch.
They can’t explain their strategic thinking.
“We think this approach will work best” without explaining why is a red flag. Expertise should be explainable. If they can’t articulate reasoning, they may not have any.
They promise guaranteed results.
“Page one of Google in 30 days.” “Guaranteed ROI.” “We’ll double your traffic.” Anyone promising specific outcomes they can’t control is lying or naive.
They badmouth competitors.
Confident agencies don’t need to tear down the competition. They explain their approach and let you decide. Trash-talking signals insecurity.
They use high-pressure tactics.
“This pricing is only available today.” “We’re about to raise rates.” “We only have one slot left.” Manufactured urgency is a red flag. Good agencies stay busy through reputation, not pressure.
They won’t show you their failures.
Every agency has projects that didn’t go well. Unwillingness to discuss them suggests they haven’t learned from them or won’t take responsibility when things go wrong with you.
Green flags that suggest you’ve found a good partner
They ask better questions than you do.
Before making recommendations, they want to understand your business model, competitive position, customer acquisition costs, and growth goals. Design and technology questions come later.
They challenge your assumptions.
When you suggest something, they ask why. They offer alternatives. They tell you when your instincts might be wrong. They treat you like a peer, not a revenue source.
They explain their thinking.
Every recommendation comes with reasoning. You understand not just what they want to do, but why they believe it will work for your specific situation.
They’re excited to learn about your business.
They ask about challenges, competitors, customers. They want to understand what makes you different. They’re curious, not just taking orders.
They connect everything back to business outcomes.
Good agencies measure success in terms that matter to your business: leads, revenue, market position, competitive advantage. Not just traffic or rankings or engagement.
They’re willing to lose the sale.
They’ll tell you if timing is wrong, if budget is mismatched, if you’d be better served elsewhere. They value fit over revenue.
The reverse interview: what good agencies ask you
Pay attention to what they want to know. It reveals how they think.
Questions good agencies ask:
- What does success look like for this project? How will you measure it in 12 months?
- Who are your top 3 competitors and what are they doing better?
- Walk me through how you acquire customers today. What’s working and what isn’t?
- Who needs to be involved in decisions, and how do you typically make them?
- What’s your relationship with your current marketing efforts? What’s working?
- Have you worked with agencies before? What went well and what didn’t?
- What’s the internal capacity for supporting this project with content, feedback, and decisions?
- Can we talk to your sales team?
That last one matters more than most people realize. If an agency only talks to marketing leadership but never asks to speak with the people actually selling your product, they’re going to build a brochure, not a sales tool. Your sales team knows the real objections, the questions prospects actually ask, the language that resonates. An agency that ignores that input will create something that looks good but doesn’t convert.
Questions that signal trouble:
- Leading immediately with design preferences and visual examples
- Focusing on features rather than goals
- Not asking about measurement or success criteria
- Assuming they know your industry without asking about your specific situation
If an agency jumps to solutions without understanding your business, they’re not thinking strategically. They’re applying what worked elsewhere without validating whether it fits you.
The vibe check matters
After all the questions, trust your gut.
How trustworthy do they feel? How secure in their process? How flexible? Did they make you feel heard? Did they push back where appropriate?
Consider:
- Are you excited to work with them, or just satisfied they can do the job?
- Do they seem like partners or vendors?
- Would you want to grab a beer with them?
Past agency frustrations usually come from misalignment between what was sold and what was experienced. If the sales conversation feels different from how they describe their work process, that’s a warning sign.
The best partnerships start with honest conversations. If you’re getting polished sales pitch instead of real dialogue, that’s likely what you’ll get throughout the project.
Putting it all together
You don’t need to ask every question in this guide. Pick the ones that matter most for your situation.
If you’re concerned about strategic depth: Focus on discovery process questions, what designers learn from research, and how they make recommendations.
If you’re concerned about execution reliability: Focus on past project reality, timeline and budget history, and change order patterns.
If you’re concerned about working relationship: Focus on who does the work, how communication happens, and what their clients say about the experience.
If you’re concerned about value: Focus on what you own, what’s included versus excluded, and how they measure success.
The goal isn’t to grill agencies. It’s to have real conversations that reveal whether you’re a good fit for each other. The best partnerships happen when both sides know what they’re getting into.
Good agencies will appreciate these questions. They’re tired of competing on portfolio prettiness and want to talk about how they actually work. If an agency is defensive or dismissive about this level of inquiry, that tells you something too.
Need help thinking through your specific situation? Let’s talk.
