Dining with the Boss: Top Ten No-No's

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There's something wonderful about dining with the boss. Whether it's a quick business lunch or a celebratory dinner, it makes you feel special - like an insider. But, to be honest, it can also make you feel...well...a little uncomfortable. It's not exactly a relaxing experience. You've got to be on your best behavior. So, instead of getting yourself all worked up, take a look at our list of no-no's. Avoid these things and your dining experience will be smooth sailing. Of course, if you find yourself stumbling head-first into one of these scenarios, excuse yourself and reclaim your composure.

1. Office Gossip-Fest

Most problems that arise while dining with the boss are conversational - and for good reason. Most of us aren't really sure what to talk about when we're not in the office. Our first instinct is to rely on what we know we have in common. People can be an easy target. This is dangerous territory! Talking about others when they aren't present is a recipe for disaster. You could easily find yourself sharing private or inappropriate information unwittingly. To be safe, steer clear of conversation that revolves around others.

2. Gripe Session

Don't use this dining experience as an opportunity to gripe about others or work in general. Just because you have the boss's ear, doesn't mean you should take it as a chance to air your grievances. If asked a direct question regarding a topic about which you have complaints, be diplomatic and use tact to express your opinion. But move on quickly. This isn't the appropriate forum for such a serious discussion.

3. Binge Bragging

Just as you don't want to spend the whole meal griping, you also don't want to go overboard telling your boss how great you are. Sure, a little self-promotion never hurt anyone. But this isn't a free invitation to recite your many triumphs. A few well-timed anecdotes are certainly worthwhile. Just be cautious that you aren't dominating the conversation with proof about why you deserve a promotion.

4. All Business

Your boss, believe it or not, is a person with a life outside the office. Don't fall into the trap of thinking the entire conversation should revolve around business. Find ways to connect that have nothing to do with work. Ask questions and show a sincere interest in getting to know your boss as a person. Think sports, hobbies, family, vacations. These are topics that most people love talking about and they provide ways for you to bond while potentially discovering something new about each other.

5. Overly Personal

While you want to use this as an opportunity to get to know your boss as a person, and vice versa, you still want to be cautious about sharing too much. This is a professional meeting - it's not a date. So don't go overboard with personal details. If you find yourself sharing stories about your messy divorce, your recent therapy session, or your mother's alcohol problem, you've gone too far.

6. Manners Slob

While it's probably not expected that you act five-star formal, you don't want to look like a complete slob either. Brush up on your table manners (and take our quiz to make sure you're up-to-par). Good dining etiquette is a sign of respect for the person you're with, and it shows maturity and professionalism.

7. Alcohol Excess

This almost goes without saying but - just to be clear - alcohol must be carefully monitored at any business event. That's not to say that you can't have a glass of wine. But be responsible. And make sure that it's appropriate for the situation. This is a judgment call and, if you're not sure, it's best to simply abstain.

8. Dress Distress

A meal with the boss should be treated just like a day in the office wardrobe-wise. A nice suit or slacks and a button-up shirt are perfectly appropriate. Women: avoid short, revealing dresses. It's just not professional and others may get the wrong idea.

9. Wait-staff Woes

Your server at the restaurant may not be perfect. It happens from time to time. When dining with the boss, it's more important than ever to remain patient and respectful. How you treat those who wait on you in a restaurant is a sign of your overall demeanor towards subordinates.

10. Big Deal Bill

When the bill arrives, don't make a big thing of it. If you're dining with your boss for business purposes, it's expected that he or she will take care of it. This shouldn't make you feel uncomfortable, so don't make an attempt to reach for your credit card.

Lastly, be sure that the location is business appropriate and, when making reservations, notify the host or hostess that this is a business meeting. While dining with the boss is a common occurrence in many companies, for some, the idea carries "implications". Avoid causing any confusion and, if you feel like there may be something unprofessional about the situation, graciously decline the invitation.

Next time you're planning a meal for your boss or with your boss, book your table on OpenTable.com, the easiest and fastest tool available for making restaurant reservations. It's free, instant and confirmed. Plus, you can earn dining rewards points and redeem them for OpenTable Dining Cheques.


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