5 Ways To Avoid Awkward Conversations DCL #51


The holiday season is upon us in full swing, which means spending time catching up with friends, family, and acquaintances.

And with that comes those inevitable, sometimes awkward, conversations about your career and your job search.

The job search is hard enough without bearing up under the scrutiny of others.

That’s why I wanted to devote this issue of Design a Career You love to talking about how to navigate those innocent, but somewhat awkward questions about your career.

Here are five easy-to-use tips to move through these moments with grace and ease:

1️⃣ Keep it Simple and Positive: When asked about your career or job search, keep your response concise and positive.

You don’t have to share all the details with everyone who asks, reserve that for the people in your life who you know will encourage you and are invested in your career.

For the rest, focus on the aspects of your work that you enjoy or recent accomplishments you’ve made on the job search.

It’s amazing how sharing something small and positive can shift the tone of the conversation away from the details you’d rather not share.

2️⃣ Shift the Focus: Another tactic is to generously redirect the conversation to the other person by asking about the other person's career or interests. People love talking about themselves, and this strategy not only helps avoid awkwardness but also shows your interest in them.

You may be surprised by what you discover… it could lead to new leads or networking opportunities.

3️⃣ Have a Go-To Story: I cannot stress this tip enough.

Prepare a brief, interesting story or anecdote about your career or job search that you can share.

A funny or engaging experience related to your work and search can make the conversation more enjoyable for both parties.

Insert this into the conversation before transitioning back to the other individual.

4️⃣ Practice Diplomatic Responses: Sometimes, questions about your job might border on sensitive topics. Hello Aunt Mary!

Prepare diplomatic responses in advance to gracefully navigate inquiries about promotions, salary, or career changes without feeling uncomfortable.

Remember, you can always say “I’m not comfortable sharing those details, but I am… [insert something related that you’re excited about and comfortable sharing].”

No one else will hold up your boundaries for you so this is an important moment to graciously and strongly hold up what you’re willing and not willing to share.

If the other party gets frustrated, remember that this is a reflection of them and not of your actions.

5️⃣ Embrace the Change: If your job situation has changed recently, embrace it! You don’t need to have everything figured out. Be honest about your journey and share your excitement about new opportunities.

Even if you’ve been laid off for some time, focus on what you’ve been able to accomplish with your new found time. Share your new insights and ideas for the future.

BONUS TIP: If you ARE feeling discouraged about the job search, share what’s actually going on with a trusted friend before heading into a holiday gathering. That way you’ll feel seen and heard before having to answer questions from people you’d rather not share the details with.

Better yet, if your friend is also going to be there, enlist their help to shift the focus of the conversation. Don’t feel like you have to tackle this alone.

Remember, these conversations are just small moments in the larger festive picture.

Use them as opportunities to connect and share, and if things get a bit awkward, it's okay! Hold up your boundary, shift the focus or graciously transition to a conversation with someone new.

From the bottom of my heart, I’m wishing you a holiday season filled with joy, laughter, and stress-free conversations!

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🤗 Celebrate with our community

This week I'm celebrating all my clients who are still in the MIDDLE of their job search.

Some are just starting, others are knee deep in networking conversations and still more are preparing for important interviews.

Here's to you this holiday season! 2024 is going to feel incredible because of your investment NOW on your job search.

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🥳 Celebrate with me

This week I presented my second masterclass for the month called The Job Search Masterclass, and shared my best tips to strategically and systematically run your job search. Thanks to everyone who joined! There was so much goodness coming out of the comments, it left with me a warm, fuzzy feeling inside.

I'm also thrilled to be taking some time off to be with my family this week. We are excited to head to the mountains. Yay for a winter wonderland. I find that some of my best ideas hit while I'm in nature... so stay tuned for 2024!


When you’re ready, here are some ways I can support you:

​NEW Book FREE 1:1 Career Strategy call with me Start your New Year off right by gaining clarity on your next career steps.

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