> "This is truly a nightmare scenario for any CEO: do you take the risk and proceed with the better user experience/product at the expense of short term numbers–with no promise that the better design will actually lead to long-term benefits–or do you scrap the new design and start over?"
Would the simplified, modern design have led Yahoo into a new era of profitability? Maybe. Or maybe they'd just have a nicer site that made less money for a year.
Our team made a site that made less per visitor, but we felt like it was a better-looking and more useful site. We decided to stick with it and work out the kinks, but ~6 months went by without reaching our old sites' benchmark. There was a ton of pressure on me to make it work or admit defeat and revert. I nearly gave in as the stress built, but eventually revenue surpassed the old site. I later learned that I was almost fired over it.
My story has a happy ending, but just barely. I have sympathy for the people making these decisions.