10 Questions You Must Ask Before Hiring a Web Designer
What You'll Learn in This Article
Hiring a web designer can feel a little like a gamble if you are not sure what to ask on that first call. You know your business matters, you know your website matters, but you might not feel confident leading that conversation yet.
That is exactly what this guide is here to help with.
In this installment of the Confident Client Series, I am walking you through 10 essential questions to ask before hiring a web designer, plus a bonus question that can give you even more peace of mind. These questions are grouped into four main categories: process, communication, pricing, and post-launch support.
By the end, you will be able to walk into any discovery call or consultation prepared, calm, and ready to make a smart hiring decision instead of crossing your fingers and hoping for the best.
I am Meg, a Squarespace web designer, and for this series, I’ll be your Confidence Catalyst. I help successful women service providers and creative professionals bridge the gap between their expertise and their online presence so they can show up confidently online.
If you are already wondering whether you are ready for this step, you might also like my guide on 5 essential questions before hiring a web designer, which helps you decide if now is the right time to bring in help.
If you prefer to watch or listen along, you can follow the series on my YouTube channel.
Now, let’s get into the questions you will want to bring to your next discovery call or designer interview.
Why These Questions Matter For Your Discovery Call
Once you decide you are ready to work with a designer, the next decision is who to hire. That first discovery or interview call is where most people get stuck. You show up, chat about your business, maybe talk about colors and styles, then hang up and realize you still do not know if this person is actually the right fit.
These questions will help you:
Understand how the designer works.
See how you will communicate and collaborate.
Get clear on pricing, scope, and money details.
Know what happens after your site launches.
Think of this as your interview guide. You are not just being chosen as a client, you are also choosing a partner for your business.
The questions are grouped into four categories:
Process
Communication & collaboration
Pricing & investment
Post-launch support
Keep a notebook handy or use an AI meeting recorder so you can jot down answers and compare designers later.
Category 1: The Web Designer’s Process
First up, you want to understand how the designer actually works. Their process needs to match your needs, your schedule, and your working style.
Question 1: What Does Your Typical Timeline Look Like From Start To Launch?
This question reveals how they manage their workload and how they set expectations. It also helps you understand whether their schedule really fits your life and your business.
You might hear answers like:
A shorter, focused project, for example, 2 weeks, with:
1 week for design
1 week for revisions and launch
A longer multi-week process, like 8 weeks, where they may:
Spend a week on strategy
Spend a week on the initial build
Spend another week on revisions
and also be working with multiple clients at once during those weeks
Any of these setups can work. What matters is that they give you clear phases with specific timeframes so you know what is happening when.
Red flag to watch for:
If you ask about the timeline and only get, “Well, it depends,” with no explanation of what it depends on, that is a problem. It is fine if timing changes based on factors like page count, content readiness, or custom features. It is not fine if they cannot explain any of that.
If you want to see an example of a clearly outlined project timeline and phases, my own custom Squarespace website design services page walks through how a structured build works, from strategy to launch and support.
Question 2: How Many Clients Do You Work With At Once?
This question tells you how much attention and focus your project will get.
Some designers, like me, work with one client at a time, so that project has full focus during the build window. Other designers may work with 3, 5, or more clients at once. Neither approach is wrong.
What you want to know is:
Where will your project fit in their current workload?
Will you feel supported or like “just another task” on a very long list?
Red flag to watch for:
If they cannot or will not answer how many clients they work with at a time, that can signal disorganization. If they do not know how many projects are on their plate, it will be very hard for them to manage your timeline well.
Question 3: What Do You Need From Me, And When?
A solid designer will have a clear structure for what they need from you and when they need it. This is often called “homework,” and it is a key part of keeping the project on track.
They may need:
Your photos
Your website copy
Testimonials
Your service packages and pricing
Brand assets like logos and colors
A strong answer might sound like:
Complete a content workbook by day 3.
Provide photos by day 5.
Give feedback within 24 hours during revision rounds.
This is helpful because you know exactly what you are responsible for and when those pieces are due. It makes planning your schedule much easier.
Red flag to watch for:
If the answer is something like, “Just send me whatever you have, whenever,” that is a recipe for delays, frustration, and a website that drags on instead of launching on time.
If you are still weighing whether to DIY or bring in help, you might also like this breakdown on when DIY web design becomes a budget drain.
Category 2: Communication & Collaboration
Next, you want to understand how you will actually work together. A mismatch in communication styles can quietly wreck a project, even when the design skills are great.
Question 4: How Will We Communicate Throughout The Project?
Different designers prefer different tools and rhythms. Some love Zoom calls, some prefer email only, and others use tools like Slack or a client portal with chat features, which is my method. A client portal keeps everything, including files, communications, and tasks, all in one place.
You want to find out:
How often you will communicate.
What tools you will use (Zoom, email, messaging app, portal).
How quickly you are expected to respond.
How quickly they usually respond.
What happens if you have an urgent question.
Whether they offer any after-hours support.
If you know you need frequent check-ins, quick replies, or more hands-on support, you want to choose a designer whose communication style matches yours. Hiring someone who only checks email twice a week when you were expecting daily updates will cause a lot of stress for both of you.
Question 5: How Many Rounds Of Revisions Are Included?
This one protects you from scope creep, surprise fees, and endless “almost there” versions of your website.
A clear and healthy answer might look like:
Two rounds of revisions on the full design.
Minor tweaks included.
Major changes after two rounds count as additional rounds and may incur extra fees.
That gives everyone a shared understanding of the boundaries.
Red flags to watch for:
“Revisions are unlimited.”
This sounds generous, but often means there are no real boundaries or process. Projects can drag on for months because no one knows when “done” actually is.“Revisions cost extra,” with no clear definition of what counts as a revision and what counts as an extra change.
You want those lines defined, not discovered on your final invoice.
Question 6: What Happens If We Disagree On Design Direction?
This question helps you see how they balance your vision with their professional expertise.
You want a designer who:
Listens to your goals and preferences.
Uses their expertise to support the strategy.
Is willing to explain why something might not work for your goals.
Still treats the project as a collaboration.
A strong answer might sound like:
“If you have concerns, we will absolutely discuss them. Sometimes I might push back if a choice conflicts with your goals or the strategy we set for your website and business. Ultimately, we will work together to find a solution.”
You are hiring an expert for a reason, but you also deserve to feel heard and involved.
Red flags to watch for:
“Whatever you want, I will just execute it.”
This means they are not actively applying their expertise. You could hire almost anyone for that.“I am the expert, just trust me.”
This dismisses your input. That is not collaboration, and it is usually a sign that they are not interested in aligning the site with your real-world needs. You know your business. They know strategic web design.
If you want to see a range of collaboration options and support offers all in one place, the web design and SEO services overview page lists several paths you can consider.
Category 3: Pricing & Investment
Money conversations can feel uncomfortable, but clear details here prevent resentment and shock later. You should never feel unsure about what you are paying for.
Question 7: What’s Included In Your Price And What Costs Extra?
You may have (hopefully) already seen pricing on the designer’s website and know if they are in your budget, but this is your chance to confirm all the details live.
You will want to ask what is included in the base price, such as:
Design and development
Number of pages
Number of revision rounds
Any training or handoff sessions
Launch support
Then ask what is NOT included or could cost extra, for example:
Domain registration
Hosting
Third party app integrations
Additional pages beyond the package
Copywriting
Branding
Ongoing maintenance
You are not being difficult by asking this. You are simply making sure you know where your investment goes and what you might want to budget for later.
If you are still comparing website platforms and plans, you might also find this Squarespace Business Plan review and pricing guide helpful while you are planning your total website costs. You can also find current Squarespace pricing information here.
Question 8: What’s Your Payment Structure?
Most designers do not expect the full amount on day one. Instead, they break the project into payment milestones.
Common payment structures include:
A third to book your project, a third at the beginning of the project, and the final third at launch.
A 50 / 50 split, half upfront and half at launch.
Full payment upfront, which some designers require.
These are all valid payment structures. What matters is that:
You know how much you are committing to.
You know when each payment is due.
The structure fits your budget and timeline.
Question 9: What Happens If The Project Goes Over Time? Do I Pay More?
Life happens. You might get sick, your schedule might change, or your content might take longer than expected. The same is true on the designer’s side.
You want to understand:
What happens if delays are on their end.
What happens if delays are on your end.
How scope changes affect the timeline and pricing.
A thoughtful answer might sound like:
If delays are on the designer’s side, there is no extra charge.
If you are late with content or feedback, the timeline may need to be adjusted, and you might need to be rebooked for a different date, but the price stays the same.
If you request major scope changes beyond the original agreement, that may cause delays, rescheduling, and additional fees.
You are listening for clear policies and a clear schedule of when rescheduling or extra costs might kick in. Tip: These should all be clearly outlined in your contract, too.
Red flag to watch for:
If they have no clear policy or cannot explain what happens when a project runs long, that is a sign you might face surprises later if something goes off track.
Category 4: Post-Launch Support
Your website launch is not the end of your relationship with your designer. At least, it does not have to be. The period after launch is often where you realize what you still want to learn and where you might need extra help.
Some designers offer structured support. Others hand everything over and say goodbye on launch day. Others, fall somewhere in the middle. You want to know which one you are signing up for.
Question 10: What Kind Of Support Do You Offer After My Website Goes Live?
Ask what happens once the site is live, including:
Any training sessions or handoff calls.
How long you can reach out with questions.
Whether they offer a window of email or phone support.
Whether they provide tutorial resources.
Whether they have ongoing maintenance packages, retainers, or support ticket options.
Common examples might include:
A live or recorded handoff session with training on how to use your site.
A few weeks to a month of email support after launch.
Optional retainers for ongoing requests and updates.
What you need will depend on how comfortable you feel managing your website yourself. If you know you want someone available for quick updates or training, that is helpful to share on the call too.
For faster, focused support on an existing Squarespace site, you might also be interested in a Squarespace Design Day VIP experience, which is a one day intensive option some clients use after launch for updates and improvements.
Bonus Question: What Happens If I’m Unhappy With The Final Result?
This bonus question gives you a lot of insight into how the designer handles problems.
A confident, professional designer will answer by connecting back to:
Their revision process.
Any refund terms.
Their overall problem-solving approach.
If they get defensive, seem offended, or shut down the conversation when you ask this, that is very telling. A strong designer will appreciate that you are taking your project seriously and will be glad you asked.
Signs You’ve Found The Right Designer
As you run through these questions, you are not just listening to the words. You are also noticing how you feel.
Some good signs:
You feel heard and respected.
They answer clearly and do not dodge questions.
They explain things without making you feel silly or behind.
Their process feels organized and calm.
On the other hand, if they seem annoyed by your questions, get defensive, or keep everything vague, that is usually your cue to keep looking.
If you are still in the early planning stage of your website, you might also like this guide on 3 key things before building a wellness website, especially if you are in the wellness space, but it’s a great basic guide no matter what industry you’re in.
How To Use These Questions To Choose Your Designer
Here is a simple way to use this list once you start booking discovery calls:
Make note of the questions.
Keep them on a notepad, in your phone, or in a document you can glance at during your call.Record or write down answers.
Take notes by hand or use an AI meeting recorder so you can compare later without relying on memory.Compare designers after your calls.
Ask yourself:Who made me feel the most confident?
Who listened well and asked thoughtful questions back?
Who had a process that felt aligned with how you work
Who do I trust with my business and my brand?
Decide, or keep looking.
If none of the designers you spoke with feel like a strong “yes,” it is completely okay to keep looking. This is not something to settle on just to get it over with.
If you are thinking, “I would really like to work with someone who already thinks this way,” you are welcome to explore my custom Squarespace web design solutions or other services and book a free discovery call.
Final Thoughts And Next Steps On Hiring A Web Designer
Hiring a web designer does not have to feel like a gamble. With the right questions, you can turn that discovery call into a clear, grounded conversation that helps you choose someone who understands your goals and has a process that supports you.
The core idea is simple: you are allowed to ask questions and expect clear answers. Doing that will attract the kind of designers who respect your time, your business, and your investment.
If you have a favorite question you always ask before hiring a web designer, or one you wish you had asked in the past, share it. Your insight might help someone else feel more confident too.
And if you are curious about fast turnaround options, stay tuned for the next part of this series, where I talk about Design Day or VIP Day rates and whether they are a good fit for busy service providers like you.
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