Imagine this scenario: You just lost your job. Your friend asks you to go to the best nightclub in town with him. Reluctantly, you go, and once there, you realize that the Head of Human Resources of your dream employer is also at said club. Your luck seems to be getting even better: your friend is good friends with this person and wants to introduce you to him. Could things get any better? Well, they might, but they can also get much, much worse.

Like oil and vinegar?

Many say that business and pleasure do not mix, at least not well. But in reality, those that are fortunate enough to find happiness and satisfaction in their employment will attest to the fact that all too often, business and pleasure can be stirred in the same cocktail glass. Whether or not this cocktail goes down smooth depends on your understanding of exactly how much business is actually conducted while out for pleasure.

A time and place for everything

There are times when one has to be serious and professional, and then there are times when one can get crazy and live life to the fullest. After all, first impressions are usually carved in stone, so make sure that you’re in the right mode when you hit the town — be it for business or pleasure. Conversely, do not be shy about letting both sides come out. After all, ceteris paribus (all other factors remaining constant), employers prefer to hire people who can have fun and deliver the goods.

Stay alert

You can begin the night on purely social terms and then run into a potential client, competitor or even a future employer. The key is to respect that your counterpart is also out for an evening of fun, so you shouldn’t necessarily turn the conversation into a business dialogue; you must keep it light (while remaining professional) but be ready to switch into corporate mode every now and then. If you can alternate between the two and keep it light and interesting, you will impress whoever you run into. Anything else can be downright annoying, especially after a hard and stressful day at the office.

Round of drinks please

For what it’s worth, you have to be realistic about the fact that you are all out in a setting different from the office or boardroom. Whether you are with ladies or gentlemen, there is a new variable in the “mix”: alcohol. Sooner or later, the liquor will flow and your chance to adjust the pace of the evening will arrive. If you want to lighten things up a bit, order some drinks.

And by the way, chances are that the people you’re out with have the means to rack up quite a tab, so the key is not showing off how much you’re spending or flaunting the fact that you can afford to buy others a round, but rather placing the emphasis on your personality and ability to show others a good time. That is what will set you apart. Anyone can pick up a tab, but not everyone can entertain…

Don’t get drunk, and schmooze with the right people…

Find the comfort zone

Ideally, it is also helpful if you remain less than tipsy. Let others sweat the next day about what they might have done. But as the evening progresses and everyone loosens up a bit, you must assess exactly how much — if any — business is to be discussed. After all, people go out to get away from work, right? Yes, to some extent, but another reality is that a large majority are also attached to their profession, and pride dictates that they have something to add about their work or prospects. Add a dash of lemon-flavored vodka and the challenge will be shutting them up… Absolut-ely.

Know your audience

If you are taking potential clients out for dinner and drinks, make sure to do your homework; after all, nothing will help you gain their business more than showing them that you have an intricate knowledge of their business. If you happen to run into them once you’re already out and haven’t yet had the opportunity to do your research, make sure to ask questions.

This is advantageous because: a) you have been drinking and should keep your talking to a minimum; b) if they talk, they may disclose more than they should, thus giving you an edge in later negotiations; c) people tend to promise things when they drink (at least more so than when they’re in a sober state), so if they insist on doing business with you, chances are that they will follow through, and; d) in life, you will be judged on the kinds of questions you ask, so the more you inquire, the better.

Quality versus quantity

Simply mentioning where you work can sometimes be enough to establish a primary contact, as long as you follow up during the work week — at some point, you’d probably do better by saying less and listening more.

All it takes to make a new contact is an introduction, a handshake or even a one-minute exchange. In the aforementioned example the Head of HR, you need not ramble on about your resume at the bar. The fact that a mutual friend referred you is already a plus (just make sure to follow through at a later date and name-drop about how you met him).

It’s like dating

Trying to maintain the upper hand when conducting business alongside pleasure is not all that different than meeting women while you’re out on the town. Women are usually out to have a good time and depending on the setting, they can either be actively looking for men or simply wanting to have fun with the ladies. The key is understanding the setting and the decorum it calls for

Moreover, if you do meet a lady who catches your eye, your goal is to get her interested enough in a follow-up, not necessarily to seal the deal. The same applies to business. You have to leave something for the workweek (and leave them wanting more).

Make sure that it’s acceptable to talk business according to the setting and company, if it’s not, then you will be seen as too serious, rather than a guy who knows when to leave his work at his office desk. The key is not to initiate business talk, but have the others start by asking questions about your line of work. Once they’ve opened that door, the floor is yours to ask the others whatever questions you might have.

Ultimately, while you should not push the business agenda too much while out, you do need to understand that things rarely fall into your lap: you have to go get them and make things happen… on that note, what’ll you have to drink?

Ash Karbasfrooshan is also the author of Course To Success, available at