Why Success Can Be Harder to Handle Than Failure

In a recent episode of the Some Goodness podcast, leadership expert Steve Graves sat down with host Richard Ellis to explore a paradox in leadership development. Drawing from decades of experience working with thousands of leaders, Graves revealed a counterintuitive truth: many leaders actually handle failure better than success. This conversation sparked important insights about how success, while desirable, might pose greater challenges to leadership effectiveness than failure.

The Hidden Dangers of Success

Success, while desirable, carries with it several potential pitfalls that can derail even the most promising leaders. Graves identifies four primary dangers that leaders must actively guard against:

1. Overinflated Abilities When success becomes consistent, leaders can fall into the trap of overestimating their own contributions while undervaluing the roles played by their team, timing, and circumstances. This distorted self-perception can lead to poor decision-making and strained relationships within the organization.
2. Entitlement Success can breed a sense of entitlement that fundamentally alters how leaders view their role and responsibilities. "Don't bother me with the details," becomes a common refrain, as leaders begin to see themselves as above certain tasks or responsibilities. This attitude not only damages relationships but can also create dangerous blind spots in leadership.
3. Addiction to Success The neurological rewards of success – those dopamine hits that come with wins – can create an unhealthy addiction to achievement. This addiction might drive leaders to compromise their values or take unnecessary risks to maintain their winning streak. As Graves notes, while everyone needs wins, becoming overly dependent on positive outcomes can be dangerous in a world where not every encounter can result in victory.
4. Complacency Perhaps the most insidious danger of success is the comfort it brings, potentially leading to reduced innovation, decreased vigilance, and a false sense of security.

The Formation Factor

One of the most compelling concepts Graves introduces is the idea of "formation" in leadership development. He argues that leaders must grow who they are at the same rate as what they're doing. This synchronous development of character and capability is crucial for sustainable leadership success.

"It's really important that leaders grow who they are at the same rate of what they're doing," Graves emphasizes. This means that as leaders advance in their careers and take on greater responsibilities, they must simultaneously develop their personal character, emotional intelligence, and self-awareness.

Building Resilience Through Feedback

A critical component of handling both success and failure effectively is creating an environment that welcomes honest feedback. Graves advocates for implementing regular 360-degree feedback systems, but with an important caveat: the culture must make people feel safe providing honest, objective feedback.

Leaders need to demonstrate that feedback won't result in retaliation or damage relationships. As Graves colorfully puts it, team members need to know they're "not going to get spanked" for providing honest insights about a leader's blind spots.

The Data Point vs. Trend Line Perspective

When it comes to handling failure, Graves offers a practical framework for analysis: distinguishing between data points and trend lines. A single quarter of missed targets or a failed initiative represents a data point, while consistent underperformance over multiple quarters indicates a trend line.

This distinction helps leaders respond appropriately to failure:

• For data points: Focus on specific circumstances and lessons learned
• For trend lines: Consider deeper structural issues, such as unrealistic goals or misaligned resources

The Power of Self-Reflection Without Self-Destruction

Graves emphasizes the importance of balanced self-reflection following failure. Leaders should examine their role in the outcome without assuming total responsibility for every failure. Sometimes, as he points out, "other people just win." The key is finding the balance between accountability and acceptance.

Building Stronger Teams Through Success and Failure

One of the most powerful antidotes to the dangers of success is building and empowering strong teams. This requires:

• Genuine comfort with hiring people smarter than yourself
• Willingness to empower talented team members
• Security in your leadership role
• Active solicitation of diverse perspectives

Future-Proofing Leadership

The insights shared by Graves point to several key practices for maintaining effective leadership through both success and failure:

1. Regular self-assessment of how success might be affecting your leadership style
2. Establishment of strong feedback mechanisms
3. Continuous investment in personal growth and character development
4. Maintenance of perspective during both victories and setbacks
5. Creation of a culture that values honest communication

The Path Forward

Success and failure are both essential teachers in the leadership journey. The key is maintaining perspective and using both experiences as opportunities for growth. As Graves suggests, the most effective leaders are those who can navigate both extremes while staying grounded in their values and committed to continuous personal development.

The challenge for modern leaders isn't just achieving success – it's maintaining their effectiveness, humility, and growth mindset once they've achieved it. By recognizing the potential pitfalls of success and actively working to counter them, leaders can build more sustainable, resilient careers and organizations.

In the end, perhaps the most valuable insight is that neither success nor failure defines a leader. Instead, it's their response to both that shapes their leadership journey and ultimate impact.