A leader's greatest weakness can be avoiding difficult conversations with employees they care about. This avoidance, meant to protect feelings, instead builds resentment and fosters an entitled culture. Direct, kind candor is essential for healthy relationships and business growth.

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The biggest professional and personal problems often stem from a lack of candor. Withholding honest feedback to "keep the peace" is a destructive act that enables bad behavior and builds personal resentment over time. Delivering the truth, even when difficult, is a gift that addresses problems head-on and prevents future failure.

True kindness in leadership isn't about avoiding confrontation. According to Figma's CEO, it's a leader's duty to provide direct, even difficult, feedback. Withholding critical information is ultimately unkind because it lets problems escalate, harming the individual and the team in the long run.

A leader's desire to be liked can lead to a lack of candor, which is ultimately cruel. Avoiding difficult feedback allows underperformance to fester and makes an eventual firing a shocking surprise. This damages trust more than direct, consistent, and tough conversations would have.

Kindness and candor are not opposites. When leaders establish a culture of kindness, employees trust that direct, constructive feedback comes from a place of positive intent. This trust makes difficult conversations more effective and better received, as it's seen as an act of care.

The most selfish thing a leader can do is withhold feedback because giving it would be uncomfortable. In that moment, you are optimizing for your own comfort at the expense of your colleague's growth. High-performance teams require radical candor, which is fundamentally an unselfish act.

A leader's failure to deliver difficult feedback, even with good intentions, doesn't protect employees. It fosters entitlement in the underperformer and resentment in the leader, leading to a toxic dynamic and an inevitable, messy separation. True kindness is direct, constructive feedback.

True kindness in a leader is not about avoiding confrontation to be 'nice.' Dylan Field argues it's a leader's duty to deliver direct, even hard, feedback. Withholding it is fundamentally unkind because it lets issues fester, ultimately causing more harm to the individual and the team.

Vaynerchuk, famous for his direct communication, reveals his biggest professional failures stem from an inability to be candid with people he likes most. This created a jarring experience for employees who were praised one day and fired the next because critical feedback was withheld.

Daniel Lubetzky argues that niceness (politeness) can be detrimental in the workplace as it avoids necessary, difficult feedback. True kindness requires the strength to be honest and provide constructive criticism that helps colleagues and the organization grow, even if it's uncomfortable.

Many leaders are candid in broad strokes but fail to have direct, difficult conversations with individuals they personally like. This avoidance stems from a desire not to hurt feelings but inevitably leads to underperformance and greater problems down the line.