> Its the guy that always reaches for the menu bar instead of learning keyboard shortcuts

I think judging someone based on their computer habits like being a command-line guy versus a GUI guy might be a risky thing. I'm a command-line guy through and through, but my newest boss comes from a different background and is very GUI-focused, and I think it would be easy to assume he's mediocre based on his choice of tools and such, but the results are more what matters.

That said, he seems like a pretty stubborn guy and I've definitely seen some warning signs on being resistant to change.