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Q. I tend to do a fair amount of client entertaining but always wonder if I could be doing a better job of it. Ball games and dinners are what I do most often – are there other things that others do that you think are better? What do in-house attorneys tell you about what they prefer?

A. This is a timely subject, as a lot of entertaining goes on in the summer and fall. Initially, I note that the subject is actually broader, as in-house counsel often have their own entertainment budgets (and internal guidelines that also limit what types of gifts, including meals, they can accept), so they, too, wrestle with this at times. Let’s take this step-by-step.

Who is your target client/guest?

Some entertaining is done for goodwill reasons that may result in intangible benefit to your organization. This is an important part of any business, but needs to be done in a coordinated fashion, as there is no need for 11 different partners to take out the same person or group of persons from the same company. A firm’s management team should be able to devise a plan for much of this type of entertainment.

The more important aspect of entertaining, especially for individuals, focuses on answers to two key questions: (for private practice attorneys) who can hire you, and (for in-house lawyers) who can directly help your company?

As to the former, I am consistently surprised that many private practice lawyers do not focus more on just this point. Sometimes this stems from a fear of getting outside of a comfort zone, which leads someone to take Joe Assistant GC, who happens to be a neighbor, to dinner. This can result in a nice night, but, if Joe has no hiring authority or no connection to your practice area, it most likely is an abject waste of your firm’s entertaining dollars. Instead of the slam-dunk dinner with Joe, step back and think of those who could actually hire you (and your firm) and map a plan as to how you will approach them.

The in-house side of the equation is more complex than one may imagine. There is a perception that private practice lawyers will line up 20 deep for a chance to get business from an in-house lawyer. This may be true in many cases, but the “best of the best” in private practice only have so many hours to bill any one year. As such, there can often be a competition of sorts to ensure that one’s company will be on the short list that will get that lawyer’s time and the “A-group” of lawyers when a need arises. Savvy in-house lawyers, who plan ahead, are cognizant of this and will make an effort to stay in touch with, and entertain such lawyers when feasible.

Know your client/target.

My discussions with big business-getters and high-profile in-house attorneys reveal a number of constants, one of which is that they leave very little to chance. In this realm, that entails knowing as much as they can about the person they intend to entertain. This can be difficult at the outset of a relationship, as one may not know much about the interests of the other. However, careful listening (which includes making notes of discussions you have had with that person – such as what he did this past weekend, activities of his children, etc.) is a very useful tool. If you have been in this person’s office, make mental notes (and then memorialize them later) of what you saw (such as memorabilia, mementos, etc., all of which offer some key clues as to the person’s interests).

A general counsel of a major company here laughed when I asked him about this subject. He cited the example of one person interested in getting business from him who has, with almost clocklike precision, called him at year-end to offer to bring him to a basketball game. There are two fundamental reasons why he always politely declines: He doesn’t like basketball, and he barely knows this person and would be loathe to spend two to three hours with him in such a captive setting.

An additional consideration is that you should determine whether it makes sense to invite someone’s spouse (or significant other). This can be quite important, as a spouse can have an unseen but important impact in this arena. The nature of the activity and what you learn about your guest will help decide this. If the spouse or significant other does attend, make sure that you (and not just your spouse) pay legitimate attention to this other person. This can make a huge difference in the long run and not just in the couple’s recap of the event on the ride home.

Your goals.

This one is simple but often forgotten. Your primary objective is to do something that will be fun, interesting, and/or enriching for your guest. It is not the opportunity to get the firm or company to foot the bill for something you have been longing to do, but which may be of no interest to your guest. Secondary objectives are that you want to put your guest in a pressure-less situation (so forsake making the big pitch) and hopefully will spend time together that enables this person to get to know you better. If your guest walks away having had a nice time and thinks you are a nice guy/woman, your time was a success. This sets the stage for closing the deal (or getting more business, if that’s the case) later.

What to do?

My suggestions here are split into two areas: entertaining in your home area and out of town (presumably in the home town of your guest/client).

As to the former, especially if your client/guest is not from your town, try to think of an activity that is distinctly local (and thus may be more memorable than a dinner in the local iteration of a chain restaurant). If it is a sporting event, one-of-a-kind contests (a PGA tour stop, big college football game, professional tennis tournament or similar activity) are likely to be interesting, especially as that particular event cannot be repeated in the person’s hometown. Similarly, timing your invitation to coincide with a date on when that person’s favorite team will be in your town is also a draw for many sports fans.

If you have a situation where the relationship is in its incipient stages, you can try to avoid the scenario despised by the general counsel mentioned above. Rather, think of activities where you will spend time together but your client/guest will have time to explore, listen (or watch) or think on his own. Some examples include going to a unique venue that interests your guest (such as the Barnes Foundation for an art lover or a well-regarded private golf course for the passionate golfer); a well-reviewed opera, play or show; buying tickets to listen to an acclaimed speaker who your guest has mentioned who will be in town, or, in the case of a meal, in a spot that is distinctly local (perhaps a venue like the Waterworks). The list is almost endless and is only limited by what you don’t know about your client or guest.

Things can change significantly when you are on your client or guest’s home turf. It is essential to remember how precious that person’s time is, particularly since he will be in the midst of his normal routine and has all the attendant duties that go with it. As such, as much as this person may like you or may appreciate the invitation, the prospect of missing a child’s sports contest or school play, getting home much later than usual, or missing some valued time with a spouse, can weigh heavily in his decision.

As a result, this may tilt the balance toward inviting a spouse, as it takes a piece of the time away from home puzzle out of the equation. You also should consider, if possible, picking an earlier time, as this mitigates the late-night syndrome. As to an activity, research what is going on in this other town. Many persons know little about hot new events in their own towns, as they are so engrossed in their routine that they are become a bit oblivious. Internet travel sites and online newspapers for that city are just two fertile sources for activities that just may surprise (and excite) your client or guest.

Have fun – if you do, your client or guest likely will – and it will be time well spent.

FRANK M. D’AMORE is the founder of Attorney Career Catalysts, http://www.attycareers.com, a Pennsylvania-based legal recruiting, consulting and training firm. He is a former partner in an AmLaw 200 firm, general counsel in privately held and publicly traded companies, and vice president of business development. He can be reached at [email protected].

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