Hi Molly,

I just started a new job, and at my company (which is on the smaller size), the CEO takes every new employee out for lunch during his or her first month.

My lunch with him is scheduled for next Thursday and I’m pretty nervous—both about not making a fool of myself in front of him and about having enough conversation material for the full hour. Any advice?

O

Hi O,

Congrats! That is awesome that someone senior at your company wants to take you out to lunch, and it’s hopefully an encouraging sign that your company is a place where this sort of behavior is the norm. Your lunch will be a great chance to learn more about your CEO and new team, and it’s a huge opportunity for the CEO to get to know you and for you to shine as a new employee.

Here’s my advice for acing the small talk, having a professional lunch, and ending things on a great note.

Pre-Meal: Prepare for the Conversation

First, don't be intimated by someone else’s job title—be confident and be yourself (this is pretty true in every situation, in fact). Remember, your CEO likely takes new employees out to lunch because he wants to get to know the people at your company on a personal level. He’s probably also used to his new hires feeling nervous, and hopefully knows how to put people at ease.

That said, you can prepare for the meeting by thinking about what the CEO might ask you and talking to other new employees about the questions they’ve been asked. Is he likely to ask about your work experience? Where you’re from? Ideas you have for the company? Things that have stuck out to you in the first few weeks? I can almost guarantee he’ll ask you about your career goals or where you see yourself in five years, so have an honest and thoughtful answer ready.

But also remember that in these types of networking situations—where one person is much more senior than the other—the junior person does a lot of the question-asking and the executive a lot of the advice-giving. So, also have questions for him ready. Do some pre-meeting research on his background and tailor your questions so they’re relevant to his specific experience (think “What was it like coming from a large company to our smaller one?” not “Tell me about your career path”). Not only will you look more prepared, you’ll definitely have a more productive and interesting conversation.

During the Meal: Dress (and Eat) to Impress

Now, remember this isn’t just a casual lunch with a co-worker—so leave your phone in your bag, mind your table manners, and dress nicely (though within the realm of what you normally wear to work).

Also, it’s always important to be respectful of time constraints, but this is especially true in a situation where the other person is more senior than you. So be on time to the meal, watch for his cues for when it's time to leave, and don’t order an appetizer or dessert unless he does first.

On the flip side, if the lunch is going well, you don’t want to feel stressed about getting back to the office ASAP. Make sure to not to schedule anything immediately before or after the lunch so you don’t feel like you need to rush back, and let your boss know where you’ll be. (Believe me, your boss will understand if you end up taking a two-hour lunch break because you’re with the CEO!)

 

Post-Lunch: Thank You and Next Steps

Just because taking employees to lunch is something the CEO always does, doesn’t mean you shouldn’t let him know that you appreciate his time. Say thank you twice: once in person and once with a short follow-up email afterward. I always like to reiterate some interesting part of the conversation in follow-up emails—i.e., “I so enjoyed your story of your first job and grad school professor”—something to personalize your interaction and show you were paying attention. This is also a great chance to remind him how excited you are to work for his company and be part of the team.

Remember—this is a great opportunity to put your best foot forward at your new office and to have fun learning from someone who’s obviously very successful. Good luck!

xoxo, Molly

Have a question for Molly? Email molly@smartprettyandawkward@gmail.com.

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