Beyond Yes Men: How Great Leaders Build Cultures That Challenge Them

Rhetta Standifer • August 6, 2025
A group of people with diverse skin tones are in a circle with their hands stacked in a gesture of teamwork and support.

Good leadership requires you to surround yourself with people of diverse perspectives who can disagree with you without fear of retaliation.

- Doris Kearns Goodwin, American biographer, historian


From a cultural standpoint, organizations should work to create an atmosphere that values and emphasizes tolerance, openness, and psychological safety. Employees should feel safe and free to ask questions, offer ideas, take risks, and make mistakes. Whether this happens is largely dependent on leadership — leaders who aren’t afraid to hear opinions and thoughts that might challenge/differ from their own. Goodwin notes this in her quote.


As she describes in her book, Team of Rivals, Lincoln built his cabinet around people who had been his political rivals. Why? Because he wasn’t interested in “yes men”; he wanted people who made him think. One big clue that you are dealing with a weak leader is when he/she surrounds themselves with people who only agree, never question. Enter groupthink.



Make sure your organizational culture represents a diverse, strong culture of people who all want to make the company successful and are willing to contribute their own unique perspective and experiences to make it happen.

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