Here's What I'd Tell a Friend
If a friend told me they were about to hire a web developer, I'd sit them down for 10 minutes and walk them through the stuff that actually matters. Not "check their reviews on Google" (though sure, do that too). I mean the questions that separate someone who'll build you something great from someone who'll ghost you in month two.
I'm a web developer. I know how this industry works. And I know how many business owners get burned because they didn't know what to ask.
So here's the cheat sheet.
Start With Their Portfolio (But Look Deeper Than Pretty)
Every developer has a portfolio. The question isn't whether it looks nice. It's whether it looks relevant.
What to actually look for
Similar projects to yours. If you run a bakery in Burlington and their portfolio is all fintech dashboards, that's a mismatch. Ask them to walk you through a project similar to yours, start to finish. How did it begin? What problems came up? How did they solve them?
Real businesses, not just mockups. Click the links. Are those sites actually live? Do they load fast? Do they work on your phone? A portfolio full of screenshots with no live links is a yellow flag.
Results, not just visuals. The best developer I could hire for my own business isn't necessarily the one with the flashiest portfolio. It's the one who can say "I built this site and the client's leads went up 40%." Ask about outcomes.
Red Flags That Should Make You Pause
I've heard enough horror stories from clients who came to me after a bad experience. Here's what they wish they'd caught early:
- No contract. Ever. If someone wants to start work without a written agreement, run. A contract protects both of you.
- Vague pricing. "It depends" is not a quote. You should get a clear scope document with line items before any money changes hands.
- They can't explain things simply. If a developer can't describe their process without drowning you in jargon, that's going to be a problem for the entire project. You'll never feel confident about what you're paying for.
- The timeline is suspiciously fast. A custom website in 3 days? Unless it's a single landing page, someone's cutting corners. A realistic timeline for a solid business website is 2 to 6 weeks.
- They don't ask you questions. A good developer should be grilling you about your business, your customers, and your goals before they talk about code. If they jump straight to "here's what I'll build," they're not thinking about what you actually need.
Questions About Process and Timeline
These are the questions that reveal how someone actually works. Not what they claim on their website, but what happens day to day.
Ask these:
"What does your process look like from kickoff to launch?" You want to hear something structured. Discovery, design, development, review, launch. If they can't articulate a process, they don't have one.
"How will we communicate?" Email? Slack? Weekly calls? You need to know you can reach this person and that they'll respond within a reasonable timeframe. I tell my clients they can text me. That's not normal for agencies, but it's normal for a freelancer who actually cares.
"What happens if the project goes over the timeline?" Things come up. Scope changes, feedback takes longer than expected, life happens. What matters is how they handle it. Do they communicate proactively, or do you find out the project is delayed when you chase them?
"How many revision rounds are included?" This is where a lot of disputes happen. Get it in writing. Two rounds of revisions is standard. Unlimited revisions sounds nice until you realize it usually means the developer is padding the price to cover it.
The Money Questions
Don't be shy about this. You're running a business.
"Is this a fixed price or hourly?" Both models work, but you need to know which one you're in. Fixed price means you know the total cost upfront. Hourly means it could shift. For most small business websites, fixed price is better because it forces clear scope.
"What's included in the price, and what's not?" Hosting? Domain setup? Stock photos? SEO basics? A $3,000 quote that includes none of that is very different from a $4,000 quote that includes all of it.
"What are the payment terms?" 50% upfront and 50% on launch is common and fair. If someone wants 100% upfront, that's a red flag. If someone wants nothing upfront, they're either desperate or not serious.
Who Owns the Code?
This is the question most people forget. And it's one of the most important.
Ask: "Do I own the code and the design when the project is done?"
The right answer is yes. You paid for it, you own it. But some developers (and a lot of agencies) retain ownership of the code and essentially license it to you. That means if you ever want to leave, you're starting over from scratch.
Get it in the contract. Full ownership of all code, design files, and content transfers to you on final payment.
While you're at it, ask about your domain name and hosting accounts. Are they in your name or theirs? I've seen business owners lose access to their own domain because it was registered under their developer's account. Set up your own accounts and give your developer access. Not the other way around.
What Happens After Launch?
A website isn't a "build it and forget it" thing. It needs updates, security patches, and occasional fixes.
"Do you offer ongoing support?" Some developers build it, hand it over, and move on. Others offer maintenance plans. Neither is wrong, but you need to know which one you're getting.
"What does maintenance cost?" Monthly retainers for small business sites typically run $50 to $200/month. That covers updates, backups, minor changes, and keeping things secure. It's worth it.
"What if I need changes six months from now?" You want someone who'll still be around. This is actually one of the biggest advantages of working with a local freelancer in the GTA rather than an overseas contractor. If I build something for a business in Burlington and they need a change next year, I'm right here. I'm not disappearing.
How to Evaluate Technical Skills When You're Not Technical
You don't need to understand code. But you can ask smart questions that reveal competence.
"What technologies will you use, and why?" You don't need to understand the answer in detail. What you're listening for is whether they can explain their choices in terms of your business needs. "I use Next.js because it loads fast and Google ranks fast sites higher" is a good answer. "I use what I use" is not.
"Is the site going to be fast?" Ask them how they'll ensure performance. Look for specifics like image optimization, caching, and clean code. Then, after launch, test it yourself at PageSpeed Insights. If it scores below 80, something went wrong.
"Will it be mobile-friendly?" In 2026 this should be a given, but you'd be surprised. Over 60% of web traffic is mobile. Ask to see the mobile version during the review phase, not after launch.
"Is it going to be accessible?" This means people with disabilities can use your site. It's not just the right thing to do. In Ontario, it's required under the AODA. Ask if they follow WCAG guidelines. If they look at you blankly, that tells you something.
The Freelancer vs. Agency Question
I've written about this in detail, but the short version: for most small and medium businesses, hiring a freelancer is the better move. You talk directly to the person building your site. No telephone game, no layers of account managers, and significantly lower cost for the same quality of work.
The exception is if you need a large team working simultaneously. Design, development, copywriting, paid advertising, all at once. That's what agencies are built for.
For everything else, find a good freelancer.
The Bottom Line
Hiring a web developer doesn't have to be stressful. Most of the bad experiences I hear about could've been avoided if the business owner had asked a few direct questions upfront.
You don't need to be technical. You just need to be clear about what you want, upfront about your budget, and willing to ask the uncomfortable questions before you sign anything.
Want to run through these questions with me? I'm happy to chat. Even if you end up hiring someone else, I'll give you an honest take on what you need and what it should cost.