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Invited To Lunch With Your Boss’s Boss? Here’s Exactly What To Do

Sharing a meal with a senior executive can feel awkward or nerve-racking. But do these four things, and you’ll turn it into a career opportunity.

Invited To Lunch With Your Boss’s Boss? Here’s Exactly What To Do
[Photo: nd3000/iStock]

You’ve just been asked to join your boss’s boss or another one of your company’s senior executives for lunch. Feeling excited? Nervous? You might be asking yourself, “Is this business, or is it social? What questions should I ask? What should I wear? What should I order?”

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Relax. It’s just lunch–but it’s also an opportunity to advance your career, as long as you know how to take advantage of it. Do these four things, and you’ll sail right through, without sounding too rehearsed or overeager to impress.


Related: Here’s What To Say When You’re Stuck In The Elevator With A Senior Exec


1. Ask (Nonspecific) Questions

This can be a great chance to make a good impression, but your main goal should be to build a relationship. Chances are you don’t have a close working relationship with the senior leader you’ll be chatting with, but you should resist the urge to show off all your skills and knowledge in one go–this isn’t a job interview.

Instead, come prepared with a handful of smart questions to ask, demonstrating your interest in getting to know your boss’s boss as a person, not an embodiment of her high-level position. For example, let’s say you work in retail and are meeting a senior executive for the company. Chances are they’ll have a lot to say on the subject of leadership, so you might consider asking, “What’s some of the best leadership advice you’ve kept going back to when making big decisions in your career?” That’s broad enough to give the exec a chance to decide how much to disclose, while showing her that you’re interested in who she is.

You should also ask questions that can help you get an idea of the executive’s vision going forward. Again, don’t be too specific–avoid asking what’s going to happen in your division next year or next quarter, for instance. Instead, ask something like, “What are some of the innovations you think will be most important in the future?” This shows you’re interested in how your boss’s boss thinks, rather than putting her on the spot to give you an answer.

2. Share How The Company Is Helping You Grow

Another smart move for lunch with a senior leader is to give an example of how the company is helping you grow. Don’t just share details about your job duties or favorite projects you’ve worked on, though. Discuss a highlight from a company “extra” that you felt was valuable, like a training program, an offsite event, etc.

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This can help you demonstrate that you appreciate what the company is doing to invest in your career, without taking a deep dive into the specifics of your role. Remember, your goal is to build a rapport, not deliver a scorecard. He probably doesn’t want that kind of detail, but he does want to know you. And above all, he wants to know that you want to know him. If you don’t give the impression that that’s the case, you’ll miss your chance at developing a potentially valuable mentor inside your organization.


Related: Let’s Be Real–You’re Never Getting A Mentor, So Do These Six Things Instead


3. Be Ready To Answer, “What Could We Be Doing Better?”

One of the questions you’ll likely be asked is some version of, “What could we be doing better?” You don’t want to say, “Nothing! Everything’s great!” But you also don’t want to dig into the particulars of your day-to-day gripes. Your biggest problem may be that one of your colleagues is constantly dropping the ball, but now is not the time to vent. Instead, use your lunch as a chance to get feedback on ideas you have that could benefit both you and the company.

For example, let’s say you work in patent law and want to be involved in earlier planning stages where you feel you could add value. Tell her that you have some ideas and would appreciate her feedback. This puts the senior executive in an advisory role, where she’s likely to be most comfortable. Letting her know your ideas about a certain problem area is a great way to answer the “What could we be doing better?” question in a solutions-focused way.

4. Plant A Seed

Finally, plant a seed for one of your long-term goals with the company. Again, avoid being too direct. All you need to do is drop a hint by telling a story or giving an example of something that you’d be excited to do in the future. Maybe you want to be selected for a global assignment. Try to find an opportunity to mention your trip abroad–talk about how much you learned and that you have a big appetite for new experiences. Then mention how eager you are for a global assignment–but keep it light. You just want to connect the dots, not hammer a nail.

What do these four tactics have in common? They’re all about being strategically indirect so that you don’t put the executive in an uncomfortable position. If you can avoid getting too specific and keep everything as positive as possible, you’ll have a pleasant lunch and lay the foundation for a good relationship you and develop in the future. This way your next lunch meeting will open the door wider to new career possibilities.

About the author

Anett Grant is the CEO of Executive Speaking, Inc. and the author of the new e-book, CEO Speaking: The 6-Minute Guide. Since 1979, Executive Speaking has pioneered breakthrough approaches to helping leaders from all over the world--including leaders from 61 of the Fortune 100 companies--develop leadership presence, communicate complexity, and speak with precision and power.

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