How Leaders Can Persevere and Thrive in the Face of Constant Second Guessing

Advisory | Glenn L. Friedman | Sep 07, 2022

“Success it not final. Failure is not fatal. It is the courage to continue that counts.” –Winston Churchill

Leadership is not a destination. Ideally, leadership is the beginning of a journey that can be extremely rewarding, but also frustrating. It’s not for the faint of heart.

Most people aren’t prepared for the frustrating parts of leadership.

It is human nature to be critical and leaders are second-guessed more than anyone. Keep in mind that there is leadership at every level of an organization, from C-suite positions to senior partners to department managers and supervisors. The more decisions you make, the more criticism you receive.

The Impact of Constant Second Guessing

The sad reality is that very little criticism will be accompanied by a solution. I’m not talking about a viable solution. I’m talking about any solution. As solutions are the responsibility of leadership.

Criticism often comes from people who don’t have all the facts. They don’t understand the context by which a decision was made. It’s a leader’s responsibility to add context.

As a leader, you have to accept the fact that complaints and airings of grievances will be directed at you. It’s important not to personalize the airings of these grievances. Although criticism comes with the territory, you are human and can easily personalize any criticism. It can hurt. It can wear on you.

Criticism may seem hollow on the surface, but a good leader will always listen. Some criticism will have no merit. Some will have substance, even if you have to dig deep to find it. Your job as a leader is to identify valid criticism and make changes when necessary.

Keys to Navigating Criticism and Succeeding as a Leader

Leaders don’t receive much empathy for the challenges they face but, again, you’re human. It’s lonely at the top, as the old saying goes, and much of that loneliness and lack of empathy stems from constant criticism.

Leaders need to remember the full quote about leadership and loneliness:

“It’s lonely at the top, so you better know why you are there.”

Leadership is not about ruling a kingdom. Some people step into a leadership role and say, “I’m the boss (a horrible term), and I can do whatever I want.”

Leaders who take that approach are the loneliest.

Your most important function as a leader is to serve people. You serve your clients and the communities where they live. You serve your team and their families. You serve the organization and its investors and shareholders. You serve your business partners.

Of course, leadership will still come with lonely moments. However, you’ll feel less lonely if you have a moral compass and focus on meeting the needs of real people inside and outside your organization.

When you value people, people are more likely to value your leadership. They may not always agree with you, but they’ll trust and respect you.

This isn’t just true when leaders have to make difficult decisions. Having a moral compass will help leaders maintain trust when they inevitably make the wrong decision. Even when you’ve made decades of good decisions, critics will latch onto the bad ones. Regardless, leaders have to own the good and the bad with humility and transparency so the entire organization can move forward.

That said, the right decision is not always popular. Leaders need to believe in their convictions when they know they’re doing the right thing, even in the face of constant criticism. Communicate the reasoning behind the decision and share the full context to reduce assumptions and second-guessing. The long-term positive impact of a good decision that’s unpopular will always outweigh short-term frustration.

The Reward of People-Focused Leadership

The last thing I want to do is discourage people from pursuing leadership positions. The positive experiences from my time as CEO of Prager Metis CPAs far outweigh the negative.

People-focused leaders can change lives. They can drive positive change in communities. They can support families, and not just financially. They can support their team’s career advancement and education.

Yes, the criticism leaders face can be frustrating and deflating. As Churchill said, however, it’s the courage to continue that counts. That courage and perseverance bring the greatest reward.


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