The short version: Broken on a phone, no updates in years, a contact form no one checks and a copyright date frozen three years ago are the real signs, not a feeling that something newer exists. The harder question is what sits behind the dated look: a brochure site is a straightforward rebuild for a web designer, but an old ASP.NET application running your bookings or records in the background is a different job, and that one is mine.
Six signs it is actually outdated
Open it on your phone first. If text runs off the edge of the screen or you have to pinch to zoom just to read a paragraph, the site was built before responsive design was standard practice, full stop. Check the address bar for a padlock or a certificate warning, an expired or missing HTTPS certificate is a five-minute fix left undone for years. Look at the footer: a copyright year stuck two or three years in the past is a small tell that the admin panel has not been opened since. Check whether the contact form goes anywhere a person reads, a surprising number of small business sites have a form emailing an inbox that was closed when someone left. And ask whether the site tells a visitor what they came to find out, your prices, your service area, a way to book, rather than a paragraph about your "commitment to excellence" from 2016.
If the contact form is the weak point rather than the design, that is worth fixing on its own before touching anything else, and the post on answering enquiries the same day covers exactly that.
A stale marketing site vs an old application wearing one
Here is the split, because I do not build websites, this one is the exception. A five-page brochure site with a dated look, some old photos and a form no one checks is a straightforward job for a web designer or a modern site builder, and that is not my lane. But some "old websites" are not brochures at all, they are a custom ASP.NET application from a decade ago handling bookings, quotes or customer records behind a front end that looks like a website. If that is what you have, rebuilding "the website" misses the point, because the real problem is the ageing system underneath it, usually talking to a SQL Server or Access database untouched since it was installed.
That second case is a legacy migration, not a redesign: the interface moves into a modern Power Apps or Power Pages front end while the data migrates into Microsoft 365, priced the same way as any other legacy move, a fixed $8,000 to $18,000 for a firm under 20 staff, migration included. The SQL Server migration post and the Access end-of-support post both cover what that involves.
When it is not worth touching
If the site loads properly on a phone, the padlock shows, and the enquiry form gets checked daily, changing it is a distraction dressed up as a project. Outdated is a specific, checkable list, not a vague sense that a competitor's site looks flashier. Work through the six signs above before you spend anything, on either a redesign or a migration.
Common questions
Is it worth rebuilding an old ASP.NET website?
Depends what is actually inside it. A static brochure site built in old ASP.NET WebForms is a straightforward rebuild for a web designer. If it is a genuine application handling bookings, quotes or customer records behind that dated front end, that is a legacy migration, not a redesign, and a fixed band of $8,000 to $18,000 for a firm under 20 staff is the more honest way to think about the cost.
How do I modernise an old company website without losing my content?
Copy every page's text and images out before anything else starts. A rebuild only needs the words and pictures, not the old code behind them, so any competent designer or a DIY builder can carry that content into a new, mobile-correct template without losing a testimonial or a price list.
Why does my old website look broken on a phone?
Almost always because it was built before responsive design was standard, using a fixed pixel width meant for a desktop screen, so a phone just shrinks the whole page instead of reflowing it. That is a template-era problem, not a content problem, and a modern site builder fixes it without you rewriting anything.
Is it really the website, or what's behind it?
If a designer can fix the look, that is not a conversation for me. If what is old is the system behind the front end, a booking tool, a customer database, a quote form wired into something from another decade, book a free 30-minute call and I will say plainly which one you have.