One of our favorite projects at Chalkbox Creative is a website redesign. While the scope of the challenge might be daunting to you as a company, to us it’s an exciting challenge. We love juggling design and technology to renovate an old, tired website into something new and productive.
But we also know that a website redesign is a big decision. You want to make it with as much information as you can gather. That’s why we’ve put together this Mega Guide.
We want to walk you through a lot of the decisions and challenges you’ll face. Along the way, we’ll point out why we think our Seattle agency is a great resource for your next website project. And we’ll keep updating this guide periodically to cover even more ground.
It’s a scary thing to redesign a website, but don’t worry. We’re here to help.

When is it time for a website redesign?
The first step in a website redesign is to decide if it’s necessary. We all know by now the importance of a user-friendly website that represents your brand well and converts traffic into sales. And presumably your site has been doing that for some time. Is it time to refresh it? How do you know?
At Chalkbox we find it helpful to ask some simple questions to clarify where you are.
1. Do you want to show off your website?
When customers ask about your website, do you find yourself trying to make excuses and apologies? “It’s not complete, it hasn’t been updated in a while, you see the thing is…”
If you want to hide your website, you’ve got your answer. It’s time for a change.
Imagine instead how you could talk about your business if you were confident in your site and eager for your customers to use it? Your website shouldn’t be a source of guilt or embarrassment; it should be a source of sales.
2. Does your site look obviously outdated?
Have you ever stumbled across a website that clearly hasn’t been updated in a very long time? The style is old, it probably doesn’t work well on your phone, and the impression you leave with is one of neglect. You might even ask, “Are they still in business?”
If your site hasn’t been redesigned since 2003, you can skip this section and go straight to how to choose a designer. It’s time!
But a lot of businesses are in a less obvious situation. Sure, it’s been a few years, but maybe it still looks ok? It’s time to look at your site with fresh eyes. Talk to your customers or talk to colleagues and ask them to give you honest feedback. Especially seek out younger people from Generation Z. If you repeatedly hear that your site looks and feels dated and old, then a website redesign is probably needed.
3. Does your website represent your current brand identity?
Sometimes a site can function fine, but still not capture the identity of the company it represents. Often sites are designed by one team, and then maintained by a mishmash of employees and freelancers or agencies. Over the years, that can lead to the site drifting away from what it really needs to look like.
At Chalkbox, we see this frequently. We’ve helped many companies get their brand and site into alignment. A website redesign might be required to reset the site and get it reflecting your brand identity perfectly.
4. Does your website convert?
Finally, we reach this key question. Are you seeing results? Are you getting traffic, and is that traffic turning into leads and eventually customers?
A beautiful site that doesn’t convert is missing the point entirely.
If you’re seeing conversion rates drop and leads dry up, your statistics are telling you it’s time to consider a redesign.

Who should handle the website redesign? An agency or a freelancer?
We’re going to assume you’ve come out of the previous section with the realization that it’s time to consider a redesign. However, many websites include dozens to hundreds of pages and have years of history and content, along with specialized solutions for your particular needs. It’s not an easy thing to change. You need professional help. But from whom?
When it comes to website redesign assistance, the most common decision will be between freelance designers and creative agencies. What are the differences between freelancers and agencies? What are the potential benefits and drawbacks of each? And when should you choose one over the other?
Freelance designers
Freelancers work solo and look primarily for short-term contracts or one-off assignments. Many wear several different hats and are comfortable with an array of project types—such as brand development, web design, print layout, etc. Some freelancers are moonlighting from their 9-5 job, others are between jobs, and some freelance full-time. They can be hired directly by clients or even by creative agencies for specific tasks.
Creative agencies
Creative agencies come in many sizes, from small and agile to large and complex. Large organizations might have multiple teams of individuals who are highly specialized in their roles; meanwhile, mid-sized and small agencies often have generalists who take on many different aspects of a given project. Agencies typically have greater bandwidth than freelancers and can take on multiple projects at the same time. They also are likely to have a project manager or someone dedicated to facilitating the work and making sure deadlines are met.
Benefits and drawbacks
Freelancers, even highly skilled ones, tend to be best suited for smaller projects—in terms of both scope and budget. While they may have the ability to do anything, the issue often boils down to whether they have the capacity to do it. Remember, we’re talking about a single person, and their schedule might be very full (particularly if they are moonlighting). If you have a long-term project, or want to cultivate a trusted design resource you can call on down the road, you could run into availability issues with a freelancer. However, they can be more cost-effective compared to an agency. And some take a more personal approach that could suit your specific project
Agencies are built to take on bigger, more complex projects, and frequently offer related services beyond design, such as strategy. They typically have additional resources to draw on as well, which can give you access to expertise a freelancer might not be able to provide. Another key advantage is that agencies don’t have the capacity challenges freelancers often face, making it easier to maintain a lasting relationship. That means your design team can build up institutional knowledge over time, so you’re not starting over with every subsequent project.
Where does Chalkbox fit into all of this?
We are an agency, but we’re on the smaller side—which allows us to take on complex projects while still offering our clients a personal approach. Our owner (Josh) and senior designer (Adam) have a few decades of combined experience and a successful record working on a wide variety of projects: brand identity, web and mobile design, print design, events, even illustration. That, along with our stellar project manager (Luke), means we’re equipped to work on projects of almost any scale, from small one-offs to much larger and/or longer-term initiatives.
We think that positions us perfectly to help our clients with their website redesign needs.

How do you choose a website redesign agency?
Choosing an agency is the first step on a very big journey. And it might be the biggest decision you make through the whole process. So how do you decide? Here are a few things to keep in mind.
1. Chemistry is key.
When you’re looking at the portfolios of various website design agencies, you should keep something in mind. While it’s great to see what an agency has accomplished for another company in the past, you have to make your decision based on what they can do for your company now and in the future.
That means digging into things like their process, their communication skills, and the general compatibility you feel when talking with them. An agency that “gets” your company is simply going to produce better work than one you struggle to connect with.
A great portfolio is proof of good work in the past. A great relationship will lead to great work now and for years to come.
2. How do you like to work?
Part of that quality of comfort comes with working together in a way that fits your company. For example, since Chalkbox is based in beautiful Seattle, WA, we’re perfectly positioned to meet personally with thousands of companies in our area. So whether you’re a professional services company in downtown or an educational institution in Kirkland, we’re here for you. If you’re Puget Sound-based and working with a local digital and web design agency is important to you, then Chalkbox is a great fit.
However, many of our clients come from outside Seattle, also. We’re completely comfortable with virtual meetings and long-distance collaboration.
3. Check the reviews.
Now more than ever, people rely on social proof to make big decisions. Make sure to look at reviews of any potential agency partner and see what previous experiences others have had. We’ll put our reviews up against anyone.
4. Look beyond size.
Often companies think “bigger is better” when it comes to a design agency. Unfortunately, they then find out that they’ve been given to the “C” team yet are still paying “A” team prices (note: our “A” team is our only team). Smaller agencies can bring a more personal touch to the relationship, so don’t count them out!
We love where we are positioned at Chalkbox to help medium- and small-sized businesses take their next step for website redesign. The best way to start is with a conversation. Let’s see where it goes from there.
Do you charge an hourly rate or by the project?
At Chalkbox Creative, we almost always work on a fixed project fee because we feel that’s the best way to operate. Not only does it make it easier for our clients to budget, but it also allows us to do the work the way it needs to be done. We don’t worry about “billable hours.” Instead, we focus on how we can best serve the client.
Compared with hourly billing, a fixed project fee gives you more cost certainty while allowing you to consider other factors—such as the experience and skill of the designer, whether you will actually like working with them, and so on.
And as you’re considering those factors, at Chalkbox, we’re considering how to complete your project (and exceed your expectations) while staying within your budget. We evaluate things like the deliverables, the time and research required to create them, and what you want to spend.
You should get what you need at a price that works for both of us. We think project-based fees are the best way to do that.

How is the Chalkbox Studio website redesign process different?
Across various design agencies and freelancers, you’ll find a process with many familiar elements. Every website redesign agency will talk to you, find out your needs, produce a concept, refine the design, and then deliver a product. While the basic steps may be similar in theory, you also know that your experience can vary wildly, both in the process and in the final outcome. So, what makes Chalkbox stand out? How are we different from other agencies?
1. We emphasize research.
Research is the deep informational dive that we believe should precede all creative work. We want to develop an understanding of a client’s business, with a particular focus on their audience and their competitors.
It’s only through the process of research that we understand what we need to create—and what NOT to create.
Too many designers are in a rush to start sketching. When we are preparing for a website redesign, we want to first understand who the site users are, what information they’re looking for, and what sort of experience they need. Then we can design the right solution for your actual situation.
2. We’re all about content-first design.
A website is a tool to communicate. Its success or failure will be judged by how well it communicates, informs, persuades, and connects with the customer.
That means the key element of any website will always be the content. It’s the voice of your brand speaking to the world.
What are you going to say?
Design for design’s sake doesn’t make sense on a website. That’s why we prioritize content when building your site. No one needs fluff. No one wants purposeless pages. We’ll work with you to make sure you’re saying exactly what you want and need to say. Even more, we want the site to then convey that content perfectly to the user.
There’s a lot more we could say. We could talk all day about our process and why we believe it’s the best approach. In the end, you need to feel comfortable with us and know your project is in good hands.

Is this all about design? What else goes into it?
Too many agencies approach a website as purely a design challenge rather than a multi-layered combination of design, strategy, branding and technology.
Chalkbox understands the complexity of a website redesign project.
That’s because we’re more than just designers. We’re designers who code, communicators who strategize, and branding experts who understand the real world.
1. We’re designers who code.
A website is a unique type of design challenge. Unlike other media, a website is a combination of design and underlying code. It’s way beyond pretty pictures or slick features.
A website not only has to look good, it has to function well.
Chalkbox understands the requirements of digital design. As designers who can code, we live in both worlds. We won’t waste time with showy designs that are impractical or kill the user experience. At the same time, we won’t prioritize the functionality to the detriment of a top-notch design experience.
2. We’re builders who strategize.
Through our research process and continuing conversations about your business, we make sure your redesigned website is aligned with your business strategies and goals.
If the website isn’t a vital part of your communication strategy, it’s not done.
We don’t want to build something that simply exists. It has to fulfill vital functions in your business processes. What do you want your customer to know about you? What action do you want them to take? How does the website help achieve those goals?
3. We’re brand experts who understand the real world.
We’ve built a business on creating brand identity packages for companies in the Seattle, WA area and beyond. We know branding. We appreciate the harmony that comes when your website fits perfectly within a larger corporate identity. But that’s never the whole goal.
In the real world, SEO matters. Accessibility matters. Conversions matter.
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- The prettiest, most brand-aligned site in the world won’t matter if people can’t find it. So we build with SEO in mind, to make the site speak to Google and giving you the best chance to get found by searchers.
- As a business you can’t afford to turn away customers, so why would we build something that is inaccessible to sight issues or other disabilities? So we build with accessibility in mind, to make the site as widely available as possible.
- And finally, a pretty site that doesn’t convert is just that… pretty. So we build with conversions in mind, giving your customers a clear path to the goals you’ve set.
As we are designers, you might think it pains us to say a website redesign goes way beyond just design. But that’s the fun of it, isn’t it? The challenge to merge great design and visionary strategy and real-world functionality is thrilling. It’s the only way to build a great website.
Are you ready for a website redesign?
You’ve persevered through more than 2,600 words to get here. You must be considering a website redesign. Contact us and let’s start talking.