'Tis the season: the office and work holiday party season that is. For some, holiday parties are a welcome opportunity to connect with industry colleagues, co-workers and clients. For others, the forced obligation to socialize with those with the power to promote or influence workflow can cause extreme anxiety. Just how much fun should you really have at a "work" party is the perennial (really awkward) question.

In thinking how to best navigate the nuances of the season, I turned to Jennifer Johnson Scalzi, Founder of J. Johnson Executive Search (JJES), a recruitment and strategy consultancy specializing solely on placing marketing, business development and communications professionals into law firms. Jennifer is also the President, Northeast Region Board of Directors of the Legal Marketing Association. Over the past 17 years in the legal profession, she's attended more than a few holiday parties and participated in numerous "secret santas" - and has observed the recurring challenges many people face this time of year. "

There are four typical scenarios people face when it comes to work and the holidays" says Jennifer, "and if you arm yourself with a plan for those tough situations, you can open yourself up to the opportunities this time of year has to offer... and maybe even enjoy yourself in the process."

Scenario 1: I'm going to an industry holiday event where I don't know anyone.

  • Don't wait for people to come talk to you. Remember that there are other people in the same position as you. Throw them a lifeline by approaching them and introducing yourself.
  • Find a beverage (sparkling water works just as well as a glass of wine) to have something to hold on to and to give yourself a minute to collect yourself before you circulate the room.
  • Plan ahead! Find a purpose in advance of the party - such as volunteering to help at the event (handing out nametags, greeting guests, etc.). Helping out at the event enables you to socialize with a purpose.

Scenario 2: I want to give my supervisor/client/colleague a gift but don't know what is appropriate.

  • Use the level of the relationship as your guide. Jennifer notes that if there is a personal element, it's appropriate to give a more thoughtful or tailored gift. If your relationship is strictly professional, keep the gift simple.
  • Think carefully before sending an extravagant gift to someone you have not done business with (as Jennifer accurately points out, it could appear as though you are trying to buy their business or pressure them into a working relationship).
  • Identify local sources that align with you, your client or your company's values. Charitable giving can be a sincere gift when the cause is close and personal to the recipient's heart- something in their life that drives them or they are actively involved in.

Jennifer also points out that gift-giving is appreciated year-round and doesn't need to be limited to the holidays. "You have a better chance of standing out and demonstrating your thoughtfulness if you send a birthday or business anniversary gift [than being another obligatory seasonal gift]" notes Jennifer.

Scenario 3: I'm in a conversation that won't end or is otherwise uncomfortable.

  • There are plenty of ways to politely excuse yourself from a conversation- "I need to: use the restroom, check in with my babysitter, touch base with another colleague before I leave, refill my drink..." Be positive, and gracious when you excuse yourself from the conversation.
  • In the festive environment, some colleagues may over-share. If a supervisor, client or colleague shares too much information ("that could be anything from terminations, promotions, bonuses, personal feelings about colleagues, potential mergers, etc." notes Jennifer) keep it to yourself.
  • Offer some casual assistance if you sense your colleague may be enjoying the holiday season too much. Grab a water together, guide the conversation if you are mingling with others, make a joint trip to the hors d'oeuvres table, or offer to call a second cab if you are getting one for yourself.

Scenario 4: I'd like to reach out to a group of people with a holiday greeting.

  • As with gifts, Jennifer points out that the more personal your note, the meaning it has to the recipient. Handwritten notes may take longer to execute (than simply hitting send), however it creates a stronger personal connection, which is worth the extra effort.
  • Try to not make anyone feel like a box on your checklist of things to do, warns Jennifer. Don't simply sign your card, but include a note about a deal you've done together, a trip you know they're taking, or your anticipation for a joint project that you'll be working on together in the new year.
  • If you choose to send a mass email, look for a way to make it worthwhile for the recipient. Make it funny, interactive, or include some heartfelt and original thoughts on the value of your relationships.