With this in mind, I don't know if he's become my confidant because he genuinely likes me, because he's trying to find the lie of the land or if he's testing me in some way. It makes me feel uncomfortable, because my loyalties are divided between him as my boss, and my colleagues (and friends). What would you do in my position?
A: You should give him the benefit of the doubt. As a new CEO, with a demanding brief and some unfamiliar senior colleagues, he probably finds talking to you extremely helpful. By helping him you'll be helping your friends and colleagues as well. I very much doubt if he's testing you.
If he seems to be fishing for your opinion of individual colleagues, whether junior or senior, you should tactfully but firmly decline to play. If he's truly a decent guy, he'll understand your reticence and think well of you for it.
Only if he starts putting on the pressure should you seriously begin to doubt his motives - at which point you might need to find a different way to get to work.
Jeremy Bullmore is a former creative director and chairman of J Walter Thompson London. His book Another Bad Day at the Office is published by Penguin at £6.99. Address your problem to Jeremy Bullmore at: firstname.lastname@example.org. Regrettably, no correspondence can be entered into.