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The Holidays & Your Career: 4 Awkward Scenarios & How to Handle Them

Ah, the holidays. They bring smiles, laughter, and many cringe-worthy moments among family and friends. Do you have an uncle that appears to listen and repeat every other word, a cousin that brags too much, or a well-meaning but overbearing friend who can’t help but to ask questions about your job search within earshot of anyone in the room? If yes, you are not alone — in fact, you are in good company! (Ever wonder why movies with cringe humor tend to sell out over the holidays? It’s not the acting that’s magical; it’s that so many people can relate!)

If you’re in an active job search, you may feel especially vulnerable to such awkward moments. Here are four predicaments or conversations — and how you can gracefully handle any of these challenges if they apply to you.

1. You left one job without another one, and you are getting asked “why?”

Suggested approach: Avoid discussing how you feel about it. State the facts and lead out the adjectives. “When I was hired, the company had 40 employees. The company let 18 people go. My schedule changed from 40 hours a week to 14 hours a day. This was my new schedule for five months. Since I left in September, three different people have been hired to do my job. One is still there.

Why This Works: You’re not complaining. You are just saying what happened.

2. You’re between jobs and have a relative who can’t get past that. Uncle Charlie has asked you three times what you are doing. When he comes back after getting seconds from dinner, he asks “what are you doing for work?” You say, “I’m looking for a new opportunity.” He opens his eyes wide, smacks his forehead with the palm of his hand and says, “Still?”

Suggested Approach: Play offense, not defense.

What to do? Volunteer to help out in the kitchen and switch conversations–fast! Find someone who makes you laugh, wait ten minutes, and say “Charlie…look at what I’m doing with ________?”

Why This Works: You show that you can keep your head up, that you can keep smiling — but also that you’re not willing to be the family scapegoat.

3. Your cousin is a rock star, or a rocket scientist. Either way, Aunt Mary is so proud that she won’t stop talking about it. “I just don’t know that I’ve ever met someone so talented, have you?”

Suggested Approach: Congratulate your cousin, but give props to other people. “She’s one of the most talented persons to hit the family tree in three generations. I’d also like to introduce you to [other family member]. Have you seen his [unique skill]?”

Why This Works: You show your appreciation for others and your ability to work effectively in a team — all important criteria for teams and work environments.

4. Your best friend keeps saying she’ll introduce you to a friend who can get you hired at your dream company. But she’s been saying that for six months and nothing has happened.

Suggested Approach: Go ahead and apply for a job with the company now. If you see the job on StartWire, connect your LinkedIn account and see if you have any mutual connections. If yes, reach out to your network and see if you can request an introduction. If no, let your friend know you’ve applied for [insert title] position and you’d appreciate a follow-up by [insert date].

Why This Works: You are taking initiative and moving forward–not waiting for something to happen!

¬†Over the next month, we’ll be tackling the holiday job search. Got anything in particular you’d like us to tackle? Send it along!


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