Surrounding yourself with agreeable people may feel good, but it's not the right way to lead. Encourage your subordinates to challenge you.
A recent opinion on the U.S. withdrawal from Afghanistan suggests that President Joe Biden surrounded himself with a cadre of advisors unwilling to challenge his view. Key people in his intelligence and military leadership were reportedly the classic yes-men, unwilling or unable to challenge the beliefs of their boss, and in the worst cases, becoming steadfast cheerleaders rather than capable experts.
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This is certainly not unusual, and we've seen many political and professional administrations in which high-level leaders fall victim to a cadre of yes-men and -women. As leaders advance, they often grow increasingly distant from the people they are nominally leading and come to rely on a shrinking circle of close advisors. This can be effective if those advisors are willing and able to articulate a variety of viewpoints and data, especially when those views and data conflict with their boss' thinking; however, it can handicap a leader if that leader pushes them toward becoming yes-men.
Whether in politics or the professional space, as if this were not challenging enough, most key lieutenants owe their positions and authority to the leader that carried them along in their rise to power. Your subordinates likely feel some combination of gratitude and obligation to you that may color their thoughts, opinions and how much they share. Suppose you intentionally or unintentionally create an impression that you don't want bad news. In that case, this sense of loyalty will exacerbate self-censorship, ultimately resulting in a team that only provides good news and serves as an echo chamber rather than a valuable sounding board.
Identifying the problem
The best leaders I've worked with enjoy the intellectual sparring that comes from their peers and subordinates, where their beliefs and approaches are thoughtfully and intelligently challenged. They seek—and often demand—that their most trusted advisors regularly challenge their thinking. This is not done in some misguided notion of playing devil's advocate just to be a contrarian, but with the expectation and assumption that their advisors will likely improve their thinking and ultimately help them produce better outcomes.
If you find your team regularly agreeing with your unmitigated brilliance and echoing your ideas back to you with little more than a few semantic changes, you may have created a culture of yes-men around you. Perhaps even more nuanced is when you've unintentionally anointed a single individual as the team skeptic, who is the only individual expected and allowed to challenge your thinking among the sea of yes-men. While having a team skeptic is better than a collection of agreeable head-nodders, it's a lonely and thankless position that relies on a single brain to challenge and clarify your thinking, rather than soliciting the best your team has to offer. Too often, the team skeptic becomes team punching bag and ultimately becomes yet another yes-man or -woman.
Fixing the yes-men problem
The most significant roadblock to correcting a team of yes-men is assuming that the team is the problem, rather than the leader. If you find yourself surrounded by yes-men, it might be tempting to believe the team is the problem and replace them. However, a culture of yes-men usually comes from the leader, who knowingly or unintentionally communicated that they only want good news and agreement from subordinates.
It can be difficult to self-assess and identify this tendency, and by nature of having created a culture of yes-men, it will be difficult for your team to stand up and speak their minds. Use a trusted peer outside your organization, an external coach, or attempt to have one-on-one conversations with some of your team members, realizing that this is the least reliable option.
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Once you've identified that you have indeed created a culture of yes-men, seek to address the source of that behavior: your leadership. While simple in concept, it will take diligent, long-term effort to allow your team to offer their best thinking when it's controversial or goes against what you have previously articulated. Start by actively soliciting multiple team members for their thoughts, and encourage respectful and focused conflict around the idea—not the speaker—before you share your position. Set the example by stating your approach and then highlighting alternatives that you explore with an open mind.
It may take several months, but you'll find your team gradually becomes willing to challenge you. While this can be uncomfortable in the moment, you'll get better thinking, more robust tactics, and you'll ultimately become a more effective leader when your team is willing to put forth their best ideas without consideration of whether their leader might be offended, insulted or downright dismissive. It might be comfortable being surrounded by a team of yes-men, but it's robbing you of being the best leader you can be.
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