How To Master The Art Of Difficult Discussions With Your Boss

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Jan. 19 2024, Published 8:10 a.m. ET

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We’ve all been there – that moment when you need to have a heart-to-heart with your boss, but the idea of it makes your tongue swell and your palms sweaty. Whether it’s asking for a well-deserved raise or addressing a conflict with a colleague, having difficult discussions at work is a skill we could all stand to sharpen from time to time.

Here are a few tips on how to approach and navigate difficult, but necessary, conversations with your manager at work:

1. Embrace the awkward.

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Let’s be real, uncomfortable conversations are a part of professional life. Instead of avoiding them, embrace the awkwardness. We often get caught up in how we anticipate the other party will respond and most of our hesitation is based on what we think might happen. Whatever the topic of the conversation, you have two responsibilities: to communicate clearly and to remain professional.

Get comfortable being uncomfortable and think of it as a chance to develop your communication skills. The more you practice, the better you’ll become and the less you’ll sweat these interactions.

2. Get your facts straight.

Before initiating any kind of difficult conversation, do your homework. Whether it’s about your achievements, project successes, resource needs, or addressing personal conflicts, having your information ready gives you a leg up from the beginning. Going into these tough talks armed with facts gives your position a solid foundation to build from vs. coming from an emotional space or merely stating your opinions with no facts. Before you speak up, be sure you can back it up.

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3. Choose your battles wisely.

Not every issue is worth fighting over. Pick your battles (and how loudly you fight them) wisely, and concentrate on what truly matters. When you do decide to speak up, choose your words carefully. Take a sec to think about how important each issue really is and be assertive without being confrontational. By choosing which battles to dig your heels into, you can save your energy for the conflicts that genuinely need it.

4. Seek solutions, not just problems.

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It’s easy to turn a difficult talk into a venting session, but let’s aim higher. Instead of just highlighting problems, bring potential solutions to the table. When applicable, come into the conversation with ideas. It shows you’re a problem-solver, not a problem-finder.

And it’s not just about looking good. Being proactive will show your boss that you’re a team player and helps create a vibe where everyone works together, focusing on solutions and making the workplace more suggestion-friendly.

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5. Embrace feedback.

Remember, feedback isn’t a one-way street. Embrace constructive criticism as a way to elevate your career. Instead of seeing it as a setback, treat it as your golden ticket to level up and evolve into the unstoppable force you’re destined to become in your professional journey. Embracing feedback helps you identify your areas for improvement so don’t just hear the feedback – absorb it, learn from it, and watch how it launches you towards bigger and better opportunities.

Addressing Difficult Conversations With Confidence

In the end, mastering difficult workplace conversations isn’t just about surviving them. It’s about taking charge of your professional narrative and shaping your path to success. So, go ahead, embrace the uncomfortable, and let your confidence shine through!

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By: Carri Helman

Carri is a recovering long-term corporate employee turned freelance copywriter. Although she earned a degree in business and spent almost 20 years in automotive manufacturing and quality engineering, she knew the 9-to-5 corporate grind wasn’t her final destination and launched her copywriting business in 2021. Carri is also a multiple myeloma care partner and advocate, working closely with global organizations and pharmaceutical companies like the International Myeloma Foundation and Pfizer. She is also the content manager and editorial director for the nonprofit Health, Hope, 𝄞 Hip-Hop, which focuses on health equity in underserved communities.

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