16 Questions to Answer Before Starting a Website Redesign

Matt Pusateri
11 min readNov 9, 2015

One common misconception I’ve often heard is that a website redesign is smaller project than creating a new website. People underestimate the challenges of reworking an existing site, and, as a result, wind up frustrated, disappointed, and unsatisfied with the result.

A new site can be anything: like a new house, it can be built from the ground entirely the way you’d like it. But a redesign poses different challenges: you’re dealing with something that already has a foundation, architecture, decorations, and things living inside it. You can change it, remodel it, but there are limitations and challenges. You rarely need just a fresh coat of paint: more often, you need to scrape off old ugly wallpaper, break down some walls, add rooms, replace plumbing. Sometimes you need to gut the whole place and rebuild almost everything.

A redesign is often a harrowing and challenging experience: all the more reason to make sure you’re doing it right… or if you really need to do it at all. So before you start, here are the essential questions to answer.

Big Picture Questions

1. Do you really need a redesign?

What’s wrong with your current site? What is broken? Are there significant, meaningful problems with the site that need to be addressed? If you can’t name those problems, you can probably stop here.

If you’re itching for a redesign just because your website feels “stale” or isn’t as flashy as some other site you visited, that’s probably not a good enough reason to start ripping pixels up. Improving the look and feel of a design is important — and can be a big part of a redesign — but shouldn’t be the only reason you’re re-doing your website.

A redesign should solve problems and help your company or organization do something better: increase sales, grow a readership, promote more sign ups. It shouldn’t just be to add the latest cool visual gimmick to your site.

2. What is the goal?

If you can identify meaningful problems with your current site, the next question to answer is what are the goals to address them? Be concrete and specific. Some examples:

  • “Make it easier for visitors to subscribe to our newsletter and double our subscribers before the end of the year.”
  • “Make our website more usable and readable on mobile devices.”
  • “Promote our events better and boost our sign ups by at least 25%”
  • “Encourage readers to share our stories on social media and increase our social network sharing by 50% by the end of the year.”
  • “Sell more of our books directly from the website than we did last year.”

3. Who is this site for?

Who is currently visiting your website? (If you don’t have basic analytics in place yet, don’t start a redesign until you do.) What do you know about your visitors/users? If they aren’t your target audience, then who, ideally, would be? Who do you want to connect with your website? A helpful exercise here can be to define and describe the “persona” of a target user.

4. What do current site visitors/customers complain about? What are they asking for?

Many clients I work with already know the answer to this question. Typical complaints are things like:

  • The website is unreadable on an Android device
  • They try to sign up for a workshop, but the form doesn’t work
  • The navigation is too confusing and they can’t find what they’re looking for

If you don’t know what users want or don’t like about the current site, ask them

Ask them to answer a short survey. Ask for suggestions in a post. Ask followers in a tweet. If you have an email list, send a special message asking for feedback and suggestions. With tools like Survey Monkey, MailChimp, and Google Forms, there’s no excuse for ignorance about what your current visitors like and don’t like about your current site.

5. What do you want someone to know or understand about you within five seconds?

Research consistently show that most people typically leave a website between 5 and 15 seconds of first visiting it. This means you’ve got a very small window of time to hook someone before they click away to Facebook or Buzzfeed.

So let’s be pessimistic for a moment and assume that your user WILL leave after a few seconds. Given that, what is the one thing you want that person to know or understand about yourself, your organization, or your company during that fleeting moment? An effectve website can communicates some key information in that short opportunity. Some examples:

  • We raise money for blood donations and emergency relief
  • We are a nonprofit working to reduce child hunger
  • We sell organic cupcakes
  • We review mobile apps

6. When someone comes to your site, what one thing you want them to do first

You might have a website loaded with articles and tools and resources, but, If someone comes to your website — and doesn’t stay long — what would be the one thing you’d want to them to do? Do you want their email? Do you want them to sign up for a free trial? Do you want them to play your latest video? However you answer that question, your redesign needs to focus on that as a primary goal.

This isn’t to suggest that you don’t want to strive to encourage engaged users who explore your site thoroughly and return often — everyone does — but as a starting point, it’s important to focus on the most critical thing you want a visitor to do if they come to your site.

7. What tone do you want to convey?

An effective website conveys the persona of your organization or company; it sets the tone for how you should be perceived. A bank or insurance company may want to convey trustworthiness and security. A dating site may want to communicate fun and optimism. A nonprofit that rescues pets may want to convey warmth and hope. Before you can really make informed decisions about the visual design of a site — the colors, typography, and art — you need to know what you want those elements to communicate. I’ve seen clients take the reverse approach: they see a website they like, even if its for a very different type of product or service, and try to apply it to their site, even if it’s a clear mismatch in terms of the personality and tone.

If you’re about to embark on a redesign, start with some general concepts to build around when it comes to the tone and style of your site. Once those are established, making decisions about aesthetics and visuals becomes less subjective and more driven by the organization’s goals.

8. Is the site structure generally sound?

Going back to the house analogy, sometimes you look at a house with “good bones” — all the key structural elements are good, and the improvements are mostly secondary things: replacing carpets, repainting walls, and updating some appliances. A redesign of a site with “good bones” might focus primarily on tackling presentational elements: making the site look better on small screens and tablets, improving typography, cleaning up icons, etc.

But often, a redesign needs to first rebuild the underlying structure of a website: changing or adding types of content, rethinking the way content and stories are organized, coming up with a newer, more intuitive navigation system. If a redesign needs to handle this kind of change, it’s important to tackle the big issues before getting into the smaller stuff. You don’t pick out new paint colors before figuring out how many rooms you need to add to the building. Tackle the big stuff first.

9. Do you have a CMS? If so, is it the right one?

A surprising number of websites still operate without any kind of content management system (CMS), the digital equivalent of an old car held together with duct tape and twist ties. I also see many websites running on an outdated, custom-build CMS that they outgrew years ago. Other sites run on a modern CMS, but it isn’t working well for them. Or it’s too difficult or frustrating for their team.

When you’re about to launch a redesign, this is a big question to answer first. Switching to WordPress or Drupal may be a worthwhile move that will offer many benefits, but it may likely impact the cost and scope of the project. It also may require additional time to train staff and get them comfortable with a new CMS before the site relaunches. Planning for this at the outset will help keep your time and budget expectations realistic.

Visual & Design Questions

10. What are the visual and branding requirements (if any)?

A redesign is rarely a wide-open, anything-goes creative exercise. A company or organization often has existing branding elements that need to be incorporated in the design, such as a logo, a color palette, or company typefaces.

The problem is that sometimes, a redesign is well underway when the stakeholders responsible for these brand and style guidelines get involved in the project. The last thing you want to find out two weeks before launch is that the color or logos you have been working with can’t be used.

Before any redesign begins, it’s important to get these requirements on the table from the start. If you’re not sure, ask. Surprises are fun for birthday parties, not design projects.

11. What sites are visually inspirational?

I always ask clients to provide examples of websites they admire for one reason or another. More importantly, I ask them to explain why they like them. While you never want to copy someone else’s website design, it is very helpful know what websites (or elements of websites) are appealing.

I ask this not because we would ever clone someone else’s design, but to get a sense of what a client likes. It might be a whole site, or part of it (“I really like how this site navigation is big and floats a the top”). It can help guide discussions of what elements and approaches would work with the redesign, especially in the service of the big answers provided above.

For example, someone might like how The New Yorker features it’s top stories. This can lead into a conversation about what they like about it and how a similar approach might work — or might not — for their content.

A second reason this question helps is that it can allow you to clarify your terms early on. One thing I learned early in my design career is that words like “bold” or “modern” or “friendly” mean very different things to different people, especially people who aren’t designers. These words are dangerously subjective. A better approach is to see what a client perceives to be “bold,” “modern,” or “friendly” through their inspirations. And again, that information can help steer the visual design in the right direction.

12. How will this look on different size screens?

Today, the same website is expected to look good on a 27-inch iMac or the phone in your pocket. You can’t just leave that to a developer to “figure it out”

Ten years ago, when I designed mock ups of websites for clients, I’d show one size for the content: something that would fit on a “typical” computer monitor. Designing for the web was still a lot like designing for print: you had a canvas and created a design to fit it.

Today, the same website is expected to look good on a 27-inch iMac or the phone in your pocket. You can’t just leave that to a developer to “figure it out” — you need to think about how the site will be experienced at different sizes. With my clients, I tend to favor the shirt-size analogy: we can’t design for 50+ specific mobile devices, but we can decide how the site will adapt at a few basic sizes: small, medium, large, and extra-large. If you wait until late in the project to start thinking about these different ways of rendering the website, it becomes more challenging to build.

13. Will you be expanding this new design to other media & social media networks?

A web presence used to start and end with your website, but now, it often extends well beyond it: to Facebook, Twitter, YouTube, Instagram, and in email campaigns. A new look and feel for your site may demand changes to those as well. Don’t wait until you’re about to launch a site to think of all the other places your content lives in the digital universe: think ahead and plan for how to roll out updates to all those other media as well at the same time.

A little early planning, and it can be easy to generate new banners and icons to fit these other networks at the same time art is being finalized for the website. Too often, organizations forget about all these other places until right before (or after) a redesign goes live. And the result is a mad scramble to ask a designer to relocate the the source files and create all these additional files and images. Since you already know you’re likely to need all of these things: make it part of the redesign project.

Getting It Done Questions

14. Who has time to do the work?

Once you’ve answered all the above questions and have a clearer picture of what you’re looking to do with a site redesign, the biggest remaining question is to figure out who will do all this work? Do you have enough in-house experience or time to do it? If you have an in-house digital team, are they free to make this a primary focus for the next few weeks or months?

If the answer to either of those questions is “no,” you might need to consider getting outside help.

15. Where is the content going to come from? Who is going to create and edit it?

It’s cliché to say “content first,” but I’ve worked on more than my share of ambitious web projects for sites that had no practical content plan. Months of design, code, and review went into a big design project, and then after the site launched, there was no one in charge of making sure the site was kept fresh with new, compelling content.

Sites like these can become very expensive brochures on a digital coffee table. And before long, they become irrelevant.

Several projects I worked on planned to rely on “user-generated” content, and to this day, I’ve almost never seen that work.

The best sites I’ve worked on almost always were built with a clear vision for who would write and edit content for it well ahead of time. If anything, they already had a surplus of content, or a wealth of overlooked great content, and the redesign was vital to help better showcase the work.

If you can’t say how and where the ongoing content for your site is going to come from, you’re probably not ready to move forward with a website redesign.

16. After the redesign, who will manage and update the site?

Similar to the question about who will create content, do you have a clear plan for who will manage the site after it goes live? If you need to change some visual elements of the site, can you do it yourself? If not, do you have someone who can make those adjustments for you?

Are you comfortable updating your CMS and plugins yourself? Are you prepared to backup the site and restore it in the event of some emergency? Are you able to review and assess the site analytics to see who’s coming to your site and what they’re doing when they get there? Again, if you or your staff are on top of this, great. But if not, you should have a plan in place for learning to handle this, or for having someone from the outside on contract to help as needed on short notice.

A website redesign can turn a stale, ineffective website into an engine that grows businesses, audiences, and boosts sales. Done right, it can become a powerful tool. But to to do one right, always make sure you’ve asked the right questions; they’ll point you to the right solutions.

Originally published at flyingdogcreative.com on November 5, 2015.

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Matt Pusateri

Develops content & communications. Film & poker geek. Outmatched dad of two girls.