Redesigning a website because it "feels tired" is an expensive way to change your mind. Redesigning because it's costing you enquiries is an investment. The trick is telling the difference, and there are seven reasonably objective signals.
One: it's slow. Open your site on a phone, on mobile data, having cleared the cache. If the main content isn't visible in about two seconds, you're bleeding visitors. Speed problems are sometimes fixable without a rebuild — oversized images and unused scripts are the usual culprits — but when the underlying platform is the bottleneck, patching stops working.
Two: it's awkward on mobile. Not "it technically works", but genuinely comfortable: readable text without zooming, tappable buttons, forms that don't fight the on-screen keyboard, no horizontal scrolling. The majority of your visitors are on a handset, and a site designed for desktop with mobile bolted on afterwards always shows.
Three: you can't update it yourself. If changing a phone number or adding a case study means emailing a developer and waiting a week, your website will slowly drift out of date, because nobody wants to raise a ticket for a typo. Content that can't be maintained won't be.
Four: it doesn't say what you do now. Businesses evolve faster than their websites. If your site still leads with a service you've deprioritised, targets a customer you no longer want, or omits the profitable thing you started doing two years ago, every visitor is being told the wrong story.
Five: no measurable enquiries. Not traffic — enquiries. If you can't say how many the site produced last month, you're flying blind. If you can, and the answer is roughly zero despite reasonable visitor numbers, the site is failing at its one job.
Six: it's a security or maintenance liability. Out-of-date plugins, an unsupported framework, no SSL warnings you've learned to ignore, a hosting bill for a machine nobody has patched in three years. Sooner or later this becomes an emergency, and emergencies are the most expensive way to buy a website.
Seven: you're embarrassed to send people to it. This one sounds soft, but it's a genuine commercial signal. If you find yourself apologising for the site before a prospect looks at it, or avoiding sending the link at all, your most credible salesperson has been taken out of service.
Three or more of those and it's time. But before you commission anything, do the unglamorous work, because a redesign that skips it will fail attractively.
Decide what the site is for. "Generate qualified enquiries for two specific services" is a brief. "Modernise our online presence" is a mood. Write down the one or two actions you want a visitor to take and judge every design decision against them.
Then find out what's currently working. Look at which pages bring people in, which ones precede enquiries, and which search terms already send you traffic. It's remarkably common for a redesign to quietly delete the page responsible for half the leads because nobody checked. Keep the URLs, redirect anything you change, and preserve the content that earns its keep.
Sort the content before the design. Most website projects run late because copy isn't ready, not because design is hard. Write the words first and the layout gets easier, faster and better.
And plan for after launch. A site is not a monument. Budget a little time each month for adding case studies, answering the questions customers actually ask, and improving whichever page loses the most people. A modest site that's tended beats a beautiful one that's abandoned, every single time.
If you recognised one or two signs on that list, don't rebuild. Fix the specific problem, and put the money into content and follow-up instead. Redesign when the platform itself is what's holding you back.