The ability to take a step back and analyze a website is harder then it may seem. But if the site you are looking at hasn't been updated in 2 or 3 years, it is easy enough to look at what other sites in the same space are doing and see that the site needs updating.
When it comes time to update a website, we sit down with website owners and go over page by page where the website is now, and where the owners want the site to go. We help set expectations on what the website is able to do, and where it needs to go.
Whether the site is 1 year old or 5 years old, we sit down and make sure that it is up to date in all of the ways that it needs to be, and that it is up to current standards.