Earlier quoted context omitted.
Why would you have history of what you searched 2 years ago? I automatically clear my history every day. It sounds like a privacy issue when someone gets your phone.
Maybe he never does anything on his work machine that would cause privacy concerns?
And while that’s not my policy, I’ve worked in security long enough to know... anything you do on your work computers is already being watched by the security team. Web proxies and log aggregation go a long way, especially with web proxies being able to decrypt SSL traffic on-the-fly.