The Conversations Business Leaders Can’t Afford to Avoid

Christina Wing
December 8, 2025

Some of the most consequential conversations in business are also the ones leaders are most tempted to postpone. Topics like compensation, career timelines, succession, personal circumstances, or values can feel uncomfortable — yet avoiding them often creates more risk than addressing them directly.

A recent HR Morning article, “5 Tips to Talk About the Weird Things at Work,” draws on insights from Wingspan Founder Christina Wing’s Harvard Business Review article, Let’s Talk: Why It’s Time to Stop Avoiding Taboo Topics at Work. Her research reinforces a simple idea: trust, clarity, and alignment are built through honest dialogue.

In her HBR article, Christina outlines five principles for navigating sensitive workplace conversations more effectively:

People already talk at work — about sports, travel, weekend plans, and everyday updates that feel safe and neutral. What’s often left unsaid are the conversations that shape trust and long-term success: where people are headed, what matters to them, and what they need in order to thrive. Business leaders who are willing to engage in those conversations with authenticity, empathy, and intention don’t just reduce discomfort — they create environments where honesty, alignment, and trust can take root.

Read the full article below:

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About Christina Wing

Christina founded Wingspan Legacy Partners to help Founders and Families navigate the intersections between Family dynamics, business operations, wealth, legacy and philanthropic impact.