Squiggly Careers 3 Hard Work Conversations & How To Handle Each One with Confidence
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Dec 2, 2025 
Join Amy Gallo, a journalist known for her expertise in workplace conflict, Celeste Headlee, a communication strategist, and Dr. Sunita Sah, a researcher on ethical leadership, as they tackle the art of difficult conversations. They discuss transforming irritation into curiosity and using affirmations to stay grounded. Gallo highlights preempting team conflict, while Headlee shares strategies to counter defensiveness. Sah introduces a framework for speaking up that aligns with personal values, empowering listeners to navigate tensions confidently.
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Conflict Is A Career-Defining Skill
- Conflict is inevitable and career-defining; avoiding it limits progression.
- Useful conflict signals a healthy team and surfaces necessary hard truths.
Set Team Norms To Prevent Pointless Conflict
- Discuss team working norms early to avoid pointless resentment like lateness or tone clashes.
- Use explicit agreements to build compassion and prevent simple style clashes from derailing work.
Flip Irritation Into Curiosity
- When irritation rises, shift to curiosity by asking genuine questions to open the other person up.
- Start difficult conversations with a question to set a collaborative tone and engage others.
