Five Subtle Signs You’re Doing Workplace Conversations All Wrong

Written & Contributed by Ed Hess

Oakland, CA (March 2021)—Good workplace conversations matter. They’re the vehicle through which business gets done, of course. But Ed Hess says good conversations aren’t just about conveying information. They’re about creating conditions for people to be able to innovate, continually learn, trust each other, think critically, and consistently bring our Best Selves to work.

“Every conversation either adds to these favorable conditions or detracts from them,” says Hess, author of Hyper-Learning: How to Adapt to the Speed of Change (Berrett-Koehler Publishers, September 2020, ISBN: 978-1-523-08924-6, $29.95, “If you’re a leader, nothing is more important than how you talk to employees.”

What’s more, people desperately want to feel connected, especially now when so many are working remotely. Helping employees feel like they’re an integral part of a caring, trusted team is not just a nice thing for companies to do; it’s more like a survival strategy, says Hess.

“The highest levels of performance require that people care about and understand each other and feel cared about and understood in turn,” he notes. “That happens only through the right kinds of conversations—those designed to make meaning and spark ongoing learning. Any company that wants to stay competitive has to ensure they happen.”

While most of us know these things on some level, most leaders make the same mistakes over and over in our approach to conversations and meetings. A few red flags to watch out for:

You’re focused on getting to a solution fast. Hess says great conversations are about building trust and camaraderie, making people feel “safe” enough to take risks, and thinking critically rather than clinging to assumptions. This takes time and that’s okay. Quick “solutions” may not only be wrong, they likely don’t serve your interests long-term.

You’re “all business” (or worse, in a bad mood). The best, most productive conversations and meetings happen when everyone is in a state of positivity and inner peace. This is more likely to happen when you connect with them on a personal level, asking about family, interests, hobbies, etc. When everyone is tense and anxious, you’ll never achieve that connective intelligence and flow that’s vital to innovation.

You TELL a lot more than you ASK. Telling sends the message that I know more than you. Telling is a power play. Sometimes, of course, you have to explain your position—but Hess says this still doesn’t require telling. Rather, it requires sharing, which basically means you make it clear that you are not expressing certainty but offering up questions or concerns.

You shut down (or at least discourage) those who say what you don’t want to hear. Humans are wired to be speedy thinkers who seek confirmation, affirmation, cohesiveness, and homeostasis. We don’t like contradictory information. Our egos send us into defensiveness, denial, and deflection. This goes against the main point of Hess’s book: We must be able to learn, unlearn, and relearn over and over again (and we surely can’t do this if we can’t stay open to things we don’t want to hear).

People leave conversations with hurt feelings. People vary quite a lot in what they find emotionally hurtful. Some are very sensitive to the slightest perceived insult even if it is unintentional. Always err on the side of respecting the dignity of each person. It doesn’t matter that you don’t think your words or behavior are hurtful. Never critique the person, only the idea—and do it in a respectful way that starts out with the parts you agree with.

“It’s not easy at all to change how you approach conversations,” admits Hess. “But the first step is always self-awareness. If you see these red flags in yourself or in other leaders, take it seriously because it is certainly impacting the performance of your organization.”

About the Author:

Edward D. Hess is a professor of business administration, Batten Fellow, and Batten Executive-in-Residence at the Darden School of Business and the author of Hyper-Learning: How to Adapt to the Speed of Change. Professor Hess spent 20 years in the business world as a senior executive and has spent the last 18 years in academia. He is the author of 13 books, over 140 articles, and 60 Darden case studies. His work has appeared in over 400 global media outlets including Fortune, European Business Review, HBR, SHRM, Fast Company, WIRED, Forbes, Inc., Huffington Post, Washington Post, Business Week, Financial Times, CNBC Squawk Box, Fox Business News with Maria Bartiroma, Big Think, WSJ Radio, Bloomberg Radio with Kathleen Hays, Dow Jones Radio, MSNBC Radio, Business Insider, and Wharton Radio. His recent books and research have focused on Human Excellence in the Digital Age: A New Way of Being; A New Way of Working; Humanizing the Workplace; and Hyper-Learning.

For more information, please visit

About the Book:

Hyper-Learning: How to Adapt to the Speed of Change (Berrett-Koehler Publishers, September 2020, ISBN: 978-1-523-08924-6, $29.95) is available at bookstores nationwide and from major online booksellers.

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