Lessons from Leaders on Leadership

Insights from Conversations with Cynthia Kurtz and Philip Hawkey

Leadership is often discussed in theory—frameworks, models, and best practices. But the most meaningful lessons emerge from lived experience.

In a recent conversation with Cynthia Kurtz and Philip Hawkey, two accomplished leaders who have served as city managers in Pasadena, we explored what leadership truly looks like in complex, high-stakes environments. Their insights offer powerful guidance not only for those in public service but for anyone navigating leadership today.

Below are some of the most compelling lessons from our discussion.

1. Leadership Is Navigating Complexity—Not Avoiding It

Leadership in local government is not a neat, linear experience. It is layered with competing priorities, diverse stakeholders, and constant scrutiny.

As Philip described, leaders in public service must balance:

• The expectations of elected officials
• The needs of the community
• The realities of internal teams
• The voices of critics, advocates, and constituents

Often, these perspectives are not aligned.

Leadership, then, is not about eliminating complexity—it is about learning to operate effectively within it.

2. You Serve Many Masters—But Must Stay Grounded

One of the most striking realities of public leadership is the circular nature of accountability.

You serve:

• The community
• The employees
• The elected officials

Yet those same groups influence one another—and ultimately determine your success.

This requires a strong internal compass. Without it, leaders can easily become reactive or fragmented.

Integrity and clarity of purpose become essential anchors.

3. Trust Is the Foundation of Everything

Both Cynthia and Philip emphasized a core truth:

If trust is lost, leadership is lost.

Trust is built through:

• Honesty (even when difficult)
• Consistency
• Transparency—balanced with discretion
• Follow-through

And importantly, trust is fragile.

As Cynthia noted, a single breach—especially dishonesty—can permanently undermine a leader’s credibility.

4. Listening Is a Strategic Skill

We often think of leadership as speaking, directing, and deciding.

But in practice, listening is one of the most powerful leadership tools.

Cynthia described her approach during city council meetings:

Listen deeply—not to win an argument, but to find alignment.

Rather than focusing on where people disagree, effective leaders:

• Identify common ground
• Build from shared priorities
• Guide groups toward consensus

This is not passive listening—it is active, intentional, and strategic.

5. Decision-Making Requires Courage

A recurring theme in our conversation was the necessity of making decisions—even without perfect information.

Many leaders hesitate, waiting for:

• More data
• More certainty
• More consensus

But as Cynthia wisely stated:

You will never have all the data.

Leadership requires:

• Making the best decision possible with available information
• Owning mistakes when they occur
• Adjusting course quickly and transparently

Progress depends on movement—not perfection.

6. Leadership Is About Process, Not Just Outcomes

In both planning and governance, process matters as much as results.

How decisions are made:

• Builds (or erodes) trust
• Shapes team engagement
• Influences long-term success

Leaders who focus only on outcomes risk overlooking the very mechanisms that make sustainable success possible.

7. Not Everyone Will Like You—And That’s Okay

This may be one of the hardest lessons for leaders to accept.

In highly visible roles:

• Everyone has an opinion
• Everyone evaluates your performance
• And not all feedback will be positive

Cynthia put it plainly:

If your measure of success is making everyone happy, you will always feel like you’re failing.

Effective leaders shift their focus from approval to impact.

8. Leadership Is Ultimately About Service

At its core, leadership—especially in public service—is about contributing to something larger than oneself.

Philip reflected on the fulfillment that comes from:

• Improving communities
• Solving real problems
• Supporting others

This sense of purpose is what sustains leaders through complexity, criticism, and challenge.

9. Leadership Can Be Learned—Start by Stepping Forward

For those considering leadership roles, Cynthia offered practical advice:

Volunteer.

In volunteer settings, you quickly learn:

• Whether you step forward or stay back
• How you handle responsibility
• How you work with others

Leadership is not discovered in theory—it is revealed through action.

Final Thoughts

Leadership is not a position—it is a practice.

It is shaped by:

• The choices we make
• The relationships we build
• The integrity we demonstrate
• And the courage we bring to uncertainty

The experiences shared by Cynthia Kurtz and Philip Hawkey remind us that leadership is both demanding and deeply meaningful.

And perhaps most importantly:

It is always a work in progress.

To hear these insights in their full context—and gain even more perspective from this rich discussion—watch the full episode on YouTube.