Putting the Pleasure in Business Entertaining

by Sima Matthes (New York City)

I am a fearless public speaker. I know this to be my strength, and marvel at the number of otherwise well-spoken and intelligent women who identify public speaking as their greatest business fear. I certainly understand; I was not always this confident.

I also understand because I have my own fear—well, not fear, but substantial discomfort—of business entertaining. I dislike small talk, and find it draining to be one-on-one with someone with whom I have nothing in common except a business interest. Put me before hundreds, no problem; face-to-face, I have to pretend there’s a crowd in order to get through.

I am awed by the skills of some of my colleagues and friends, moving with ease from business event to business event. At each, they are engaging, “on” and relaxed. How fortunate that I had them to turn to when, recently, I found myself faced with the prospect of an important dinner out with potential clients.

Michelle, a VP at a large public relations firm, suggested cultivating relationships with your favorite local places. She has a list of ten restaurants that she takes time to patronize regularly. She has one or two that have a great brunch, another that allows her to pre-select the menu when there’s only an hour available for lunch, and more than a few that can accommodate larger groups for dinner. She greets the staff warmly, tips the maitre d’, and knows the menus well enough to order and make recommendations confidently. She takes the time to confirm the reservation herself—no delegating of this critical task—and makes sure that the wait captain knows that she’s the host of the meal.

These relationships allow her to request the privacy she requires for particular meetings, and to pre-select the menu. She usually arrives early, positions herself at the proper place at the table, then meets her client or guest at the captain’s station without disrupting the table setting. If she meets her guest at the table, she stands as they arrive, gives them a firm handshake, and invites them to sit in the best seat, the one that looks out into the room.

Michelle and my friend Larra—a partner in a prestigious law firm—recommend tipping 20 percent or more, particularly as you’re building your relationship with those restaurants. Larra says that rather than sulk about a problem and stiffing the wait staff, cultivate the ability to speak up kindly and professionally for the resolution you seek.

Larra regularly arrives fifteen minutes before her guests, and arranges to pre-pay the bill. She takes care to handle even the smallest detail, including tipping the coatroom attendant. She makes it her job to smooth over every problem, and allow her guest a carefree experience.

She offers her guests a “beverage” rather than a “drink.” This may seem like just semantics, but many of her corporate clients discourage drinking, especially at business lunches. This is an important detail—knowing the corporate culture of your industry and your client’s company.

Another friend, Candace, related an anecdote about a $700 business lunch for four people early in her career. It seems that she was unaware that she could set limits discreetly, and found herself with clients who knew no limits. After their third expensive bottle of wine, she realized she was in trouble. When the credit card bill arrived at her firm, a lesson followed the reproof: Set the limits on hospitality by casually suggesting an appetizer and some of the items on the menu. Discuss the menu with the wait staff, and then defer to your guest. If your guest orders an expensive item on the menu, you should as well. You want your guest to feel comfortable with his or her choice.

It occurs to me that the turning point in my fear of public speaking came the day I realized that with preparation and timing, I could get through even the biggest presentation. I expect that the same is true for business entertaining: preparation and timing are the keys to success.