Most of us have held back a hard conversation and told ourselves it was the kind thing to do. In “Why Good Leaders Start Conversations Others Avoid,” Forbes contributor Rodger Dean Duncan talks with Wingspan Founder Christina Wing about when that kind of silence stops being polite and starts costing people something.
Her starting point is simple. Silence becomes a problem when it protects the comfort of the person in charge instead of the people they lead.
Kindness or avoidance?
Christina tells the story of a former Harvard Business School classmate she calls Maya, a high-performing consultant who had just come back from parental leave. Her manager noticed she seemed tired, decided a promotion would come at the wrong time, and gave it to someone else without ever asking her. Maya might have turned it down, but it was her call to make.
“We tell ourselves we’re being kind when we hold back difficult feedback, but often we’re sparing ourselves the discomfort and calling it grace.”
Christina’s test for leaders is to ask who the silence is serving. If the timing never seems right, or a conversation keeps getting rehearsed but never scheduled, that’s usually a sign. She likes the phrase “clarity is kindness.” Being vague can feel gentler in the moment, but it keeps people from responding to things that affect them.
Leaders have to go first
Many organizations describe psychological safety as a place where employees feel free to speak up, which puts most of the weight on the employee. Christina thinks leaders need to raise the uncomfortable subject first, own their mistakes, and ask the questions other people hesitate to ask. Drawing on the work of her Harvard colleague Amy Edmondson, she points out that a team without disagreement isn’t necessarily a healthy one. “A team where everyone’s comfortable and no one disagrees isn’t safe,” she says. “It’s just quiet.”
Curiosity over persuasion
Plenty of hard conversations stall because both people walk in trying to win. Christina describes an MBA student who kept trying to convince his parents he shouldn’t join the family business. On one trip home he tried something different and asked them why it mattered so much. Their real worry was losing closeness with their son if his career took him far away. Once that came out, they found a middle path. He joined the board, came to in-person meetings every other month, and often stayed through the weekend.
“The perfect words matter far less than people think. What matters is being the person who says, ‘Can we talk?’ and then actually does.”
Christina writes more about these ideas in her book, Unspeakable: The Taboo Topics We Avoid and How to Talk About Them, which offers practical ways to start the conversations most of us put off. You can learn more about the book at christinawing.com/book.
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