When is it actually time to redesign?

Straight answer first: most redesigns happen because somebody got tired of looking at the site, not because the site stopped working. That is an expensive reason, and it is worth separating from the reasons that actually pay for themselves.

Here is the honest split.

Reasons that are worth the money

• It does not work properly on a phone. Most people who look you up are on a phone. If they have to pinch and zoom to read your number, you are losing work every week and have been for years. This alone justifies the job.
• Nobody can contact you easily. No visible phone number, a form that goes to an inbox nobody checks, or an address that is three clicks deep. Every enquiry you never received was paid for by this.
• It is slow. If it takes more than a few seconds to appear, a good share of people leave before they see anything at all. They do not tell you they left.
• What you sell has changed. You have dropped a service, added two more, moved into a new area, or your prices are years out of date. A site describing a business you no longer run costs you the enquiries it misdescribes.
• You cannot change anything yourself. If updating a phone number means emailing someone who may or may not reply, you do not really control your own site. That gets worse with time, not better.
• It is built on something abandoned. Old platforms stop getting security updates, and a hacked site is a much worse day than a redesign.

Reasons that usually are not

• You are bored of it. You look at your site far more than your customers do. They see it once, get what they need, and leave. Your boredom is not a business problem.
• A competitor got a new one. Theirs might be worse. A prettier site that is harder to use loses to a plain one that answers the question.
• Someone cold-called and said it looks dated. They say that to everyone. It is a sales script, not an audit.
• It is a few years old. Age is not a fault. A five-year-old site that loads quickly, works on a phone, and gets people to call you is doing its job.

The middle option most people miss

There is a lot of room between "leave it alone" and "start again", and it is where a good chunk of sites actually belong. If the structure works and the site loads properly, you can often get most of the benefit by rewriting the copy, replacing the photos, fixing the contact routes, and tightening the pages that matter. That is a fraction of the cost and a fraction of the disruption, and it carries none of the ranking risk of a full rebuild.

The question worth asking is not "does this look current" but "is this losing me work". If the answer is no, put the money into something that brings work in instead.

How to tell, in about ten minutes

Open your site on your own phone, on mobile data rather than your office wifi, and try to do what a customer would do. Find out what you charge. Find out whether you cover their area. Call you. Time it.

If any of those is awkward, slow, or impossible, you have your answer, and you know exactly which part to fix. If all three are quick and easy, your site is fine and the money belongs somewhere else, like your Google Business Profile, which for a lot of local businesses does more work than the website does.

If it is the whole thing that needs doing, a redesign is the job. If it is one or two of those, it is not.