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I'm having lunch with my CEO in a couple of days. I'm an Engineer who's pretty involved in a product that the company sells, but I don't know too much about the business side of things.

My company is mid-sized, about 1500 people. I sit in the same office as the CEO, but do not interact with him on a regular basis.

I won this lunch with the CEO in a contest and it's just one-on-one (no one else from the company will be there).

What are some good topics of conversation for a software engineer to have with the CEO of a company?

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    This might also be a good question to ask your manager, as they know your company much better than we do. – David K Aug 19 '15 at 20:17
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    Do your homework first. Look at the CEOs Linkedin profile and find areas of common experience and interest. For fluff, find out if he is a sports fan or whatever. Executive assistants can be very helpful for this sort of thing. Always be nice to them, they've got tough, tough jobs. – Spehro Pefhany Aug 19 '15 at 20:17
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    You will find this answer of mine beneficial I think - workplace.stackexchange.com/a/47862/2322 - it's very related (probably not quite a duplicate given circumstances you are meeting under) – enderland Aug 19 '15 at 21:12
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    As an aside, I'd advise you not to drink any alcohol, even if it is offered. – camden_kid Aug 20 '15 at 10:41
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    You "won" this lunch? Why is this a big deal? If I were you, I'd just say "No, thank you, got some other plans" (<- playaaah!) – Renae Lider Aug 21 '15 at 6:29
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Since you say that you won this one-on-one lunch with the CEO as some sort of prize, I wouldn't go in expecting to spend the whole time talking business. With 1500 people in the company, the CEO would probably like to get an idea of who his or her employees are, so you could expect to make some small talk at first. Your CEO may ask that old standby, "So, tell me a little bit about yourself." This gives you an opportunity to mention your '80s cover music garage band, your pig-calling hobby, your collection of artisan shave mugs—whatever you don't mind sharing about yourself, that might prompt more conversation. Look for clues of polite disinterest as a hint to move on to another topic, or ask a question in return.

If your CEO wants to get your impression about some aspect of the business, he or she will probably ask a question about that. Feel free to be open about what parts of the corporate strategy you have any clue about, and what parts are a mystery. Your CEO may very well love to explain these things to you, to show an employee just how savvy and capable their CEO is.

On the other hand, your CEO may want to talk about sports, television, gluten-free diets, hiking in the Rockies, monster trucks, cross-fit, cross-stitch, David Cross...

The safest thing may be to start the conversation with the standard introductions and pleasantries and then, assuming your CEO doesn't immediately take control of the direction of conversation, ask: "So, what kind of conversation did you have in mind, business talk or something more casual?"

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    "...your '80s cover music garage band, your pig-calling hobby, your collection of artisan shave mugs..." Brilliant. Simply brilliant. – T.J. Crowder Aug 19 '15 at 22:23
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    The last paragraph sounds very wise to me! – Kevin Aug 19 '15 at 22:37
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    Also doesn't hurt to do some background check on the CEO to see where both you and his interests cross, so you have something in common to talk about. Just DON'T FAKE interests, as by the time someone climbs to a 1500 head-count-company CEO, he probably has the skillz to smell a fake. – Mindwin Aug 20 '15 at 15:35
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    @Mindwin I agree on both counts. Don't fake management knowledge, either. If you don't know about the corporate strategy, A) and you're interested in it, ask questions about it; B) and you're not interested in it, don't bring it up. – Air Aug 20 '15 at 15:37
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    I would stress that, even were the CEO to turn the conversation towards the business, to keep away from the company politics and your section/division/team, etc. Comments made by you, even those you expected to be off-hand, will find their way back to bite you squarely in your third point of contact. – CGCampbell Aug 22 '15 at 20:26
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As this is a prize won, I doubt the CEO will be interrested in a deep analysis of the company. It will be a light conversation, small talk. Most likely about the non-workplace side of you. If the CEO is known to be proud of his daughter's showjumping, ask how that is coming along.

But the most important part, take small bites. There is nothing worse than having the CEO asking something where you realize that you have the most amazing answer ever, but you just have to chew for 2 more minutes, before you can answer. If you usually eat at lot at lunch, maybe have a little extra at breakfast or a snack mid-morning.

And remember to breath deeply, with your belly, the best cure against being nervous.

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    Do you frequently find yourself chewing a single bite for two minutes? o.O – Lightness Races in Orbit Aug 4 '16 at 23:49
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Like every other leader, the CEO is human and its natural for you want to impress and be a bit star struck. Treat him like he's human and not so much like he's a god. Contrary to many autocratic egotistical executives of the past, a good leader doesn't see himself as disconnected from the rest of the world or being owed esteem. Many are happy when they are simply treated with the same context as any normal person. Simply treat him like you would a good colleague and let your character speak more than your words. If he's not doing a lot of talking, take an interest in him and his hobbies, how he got to where he is. Then you can casually lean into conversations about what his recommendations might be to someone wanting to follow the path to the corner office, or what you think he would find useful to know from other levels in the company.

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Treat this as a networking opportunity. It is not a chance to gripe about nuances in the workplace or pitch some big idea you have about projects. Simply get to know him as a person and find some common ground to carry a friendly conversation. As an engineer he does not expect you to know about business related topics just as you don't expect him to know about detailed programming.

This is your chance to put a real live person behind your name badge. If you treat it as a networking opportunity then what you talk about at the lunch can be a segue to approaching him in the office.

He's a person like anyone else in the company, just he's the one that signs your paycheck. ;)

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    "Oh, I just entered the contest for the free lunch..." – sixtyfootersdude Aug 20 '15 at 21:58
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    Hah... then order the most expensive item on the menu. – Acumen Simulator Aug 20 '15 at 22:06
  • Yea ahhhhh just give me the most expensive thing on the menu stuffed with the second most expensive thing. – emory Aug 21 '15 at 21:06
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You may be tempted to throw out some big idea you have, but try to read the room first. He may just want to eat lunch, and not discuss anything business-related. So the most important thing you can do is listen at first, not talk. He will almost certainly ask you about yourself and what you do. Do some research to see if you have anything in common. Even if you have nothing in common, there's got to be something interesting he does that you can ask about.

There may be some expectation that you are supposed to ask for career advice or some nugget of CEO wisdom/insight. That's the prize, right? Try to think of something to ask. Or, if you can't think of anything, prepare a good answer if he asks why you don't have any questions for him. Cover yourself, or it could get awkward.

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Let him guide the conversation in the direction he wants. I have had CEOs who only wanted to talk personal stuff at lunch and others who couldn't leave business alone for ten seconds.

What you need to do is prep both ways and be ready to do either. What you need to be careful of is that you make a friend and not a political enemy because he has much more organizational power than you do. This is a great opportunity to impress a person who has control over your salary, your benefits, and your continued employment at that company.

On the personal side, try to stay away from religion or politics or anything that he might find controversial. It is safer to talk about how much fun you had at Comic Con than how much you hate Donald Trump and find out afterwards that he just contributed $10,000 to Trump's campaign.

On the business side, be ready to talk about things that are going well and project successes you have been a part of. If he wants to talk about how your group contributes to the business, you need to sound knowledgeable about both your professional specialty and the overall business of the company. This is your chance to become very visible and it can help you greatly or harm you.

Perhaps be ready to talk about some things you think could be improvements (ones your boss would approve of, whatever you say in this situation is going straight to him after if the CEO asks you what ideas for improvement you have). If you have an idea that could open a new market for the business, that is a great thing.

Same goes if he asks specifically for anything that is not working well, pick something your boss would love to get fixed and not something he has been opposing.

You might consult your boss about things he might want brought up if the opportunity presents itself. Tell him you want to make a good impression for the whole department and ask his advice about what to say if the CEO wants to talk business. Your boss might be thrilled to have the chance to have someone informally bring up something he hasn't been able to get past the gatekeepers below the CEO.

Try not to bad mouth anyone. No matter how much you think the VP of HR is an incompetent jerk who has figuratively raped multiple employees, it won't go well for you if you actually say that. Especially if the person in question is a C-level employee who was probably doing his or her best to implement the policies the CEO wanted.

If he does ask you to suggest something that the company can make better, be prepared to make a business case for your suggestion. Tell him why it is important and what the company bottom line will get out of it or what serious problem that it will solve. It helps here if you are aware of other things going on in the company. For instance if you know that they just had trouble in an audit or certification process due to an issue, a suggestion for how to fix that is perfect. Do not suggest anything that costs money but has no apparent benefit outside the Programming department (yes we would all love to have three monitors and brand new equipment and a chance to play foozeball during the work day, unless you can make a case for how that will improve things for the external or the internal customers of your services, then now is not the time to suggest it.

Even if he doesn't buy off on the change suggested, the fact that you presented it in business terms not usually associated with development staff is going to impress him.

2

Ask him about himself: how his day is going, what kinds of things are coming up for him on the business side. If he travels for work, you can use an upcoming or a recent trip as a topic. You probably shouldn't start with personal questions, but as you warm up, you can segue from work talk to getting to know him. Maybe his recent trip was to an area you've visited, or he just gave an external presentation on a topic that interests you professionally.

If he loves talking about himself, he may talk your ear off the whole time and he'll feel flattered and well-liked when lunch is over. If he's more reserved or prefers to flip it to "What about you?", take it as an invitation to talk about yourself for a little bit, but keep asking him questions to find points in common.

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The one area that has burned me in the past, even as just a rank and file employee, is knowing where the company makes it's money. So get in some general hobbies type questions (expect them to be expensive hobbies, like helicopter skiing or racing Ferraris), but also some business questions about where the company makes it's best profit, and where they see things going in the next 5 years. It can give you very valuable insight into what the company values, and this is what the CEO's job is, looking to the future and maximizing profit.

I learned the hard way that pushing a product that required very little in the way of configuration and enhancement was the wrong approach for our company. While being able to save money on deployment and hosting, I missed that the lion's share of our revenue and profit came from billing customers for customization. Now that wasn't sustainable either, so I also learned that we probably didn't have that long before things fell apart and I moved on.

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