When does a business decide to invest in a website redesign? According to Jonathan Denwood in WP-Tonic 119, the only two reasons compelling enough are envy and fear. The fear usually involves something like a potential loss of search ranking (think Google’s Mobilegeddon or the upcoming penalties on pop-ups) or sales. Envy comes in when a company’s biggest competitor has an amazing new website that makes them look bad.
To that I would add frustration: if the current site is broken, and provides a bad experience either for the site owner or for the site’s visitors, it’s time to think of a redesign. While it’s possible to add features a WordPress site doesn’t have without completely redesigning the site–that’s what plugins are for–if a site is doing a lousy job fulfilling its original function, it’s not likely going to handle the added functionality very well.
Watch the entire spirited discussion here.