How to converse with the CEO during lunch?

Question

Twice the CEO of our company sat next to me (also across from me) during lunch in the company. He asked some general informal questions which I answered but didn't ask him anything in return. I want to know whether I should ask him questions or not.

If yes what can/should I ask? Or how shall I converse with him during the lunch when he is sitting next to me (or across from me)?

Additional Info: Company is 14 years old, much like a start up although not exact.

Note: I didn't ask this question on workplace as I think it is more of an interpersonal skill owing to be an informal serendipitous or coincidence of having lunch with the CEO rather than a pre-planned formal lunch having professional elements.

Answer 1

This may sound a little naive, but ... why not just forget he's the CEO for a while and talk to him like a friendly stranger you met on a train? Everyone has hobbies, or something interesting they did last weekend, and is usually willing to share. Maybe you did something interesting lately; tell him about it.

Look ... you're talking about being put in a social situation. You're not angling for a promotion, or trying to solve a problem. You just want to pass an hour in companionship, yes? The CEO part really doesn't factor, except to the extent you might decide not to tell any racy jokes.

I had a situation like this, and it came out that CEO was into building boats. So we talked about boats, that led to fishing, and so on. Of course I'd always wondered about this, so I ended up asking what his daily workday was like. Turns out my notion that "the CEO answers to no one" isn't quite accurate...

Answer 2

A lot would depend on whether the CEO is a friendly type and open to informal conversation with a junior staff member during lunch.

In my personal experience in Indian culture, this is an uncomfortable situation: very senior officers are often remote and preoccupied and they might well ask us a question but they may not appreciate being asked a question in return.

The risk with being bold and asking this senior officer something, whether professional or personal, in the Indian context (though I am not specifically familiar with the IT sector) is that they might later remember us as being 'forward' or 'lacking sufficient respect' -- but this is probably not a problem in the USA!

You can also possibly commit a blunder by asking something that irritates the person, unless you are very familiar with their likes and dislikes. This actually happened:

Hospital Director to his PA: Do you know, that English Student person is impertinent. We met in the lunch room and he actually asked me whether I like music! I hate music, it's such a waste of time. You keep an eye on him. I didn't like his forward attitude and familiar way of asking me these questions...

Of course I have also been lucky to have extremely kind and friendly superior officers.

So I should advise you to keep it polite and formal unless the CEO is exceptionally friendly and he explicitly encourages you to have an informal conversation.

Answer 3

CEOs are generally very busy people and probably won't have time for long chats over lunch. He asked you some general whatabouts, and you nicely answered them. That is good.

You, at the same time, felt a little uncomfortable as to whether or not you should ask him something in return. That's okay. Since he was in a casual mood, you could've asked him one or two casual questions, tops; preferably something not about the job. Then again, there's no compulsion to do so. Be cool, answer his questions well. Trying to force a question to him will undoubtedly make things awkward.

Since I assume you two aren't friends outside of the workplace, I recommend you don't ask too personal questions. :)