Dear Frank:

I am a mid-manager in a large city organization. I just attended an all-managers meeting where the city manager shared a few leadership lessons that she learned the hard way and wished that she would have known as a younger manager. It occurred to me that many of us emerging leaders could benefit from learning from senior leaders what they wished they could have told their younger selves. Maybe we current managers could avoid the same mistakes.

My response:

Great idea! I, too, wish that I could have shared with my younger self a number of leadership lessons that I learned after much adversity. As a result of your query, I contacted a variety of colleagues, both active senior managers and those who are retired but actively engaged in their “encore” phase. (See the contributor list at the end of the article.) I asked them what they wish they would have known as a younger leader. The lessons have been compiled as themes in various categories, including two mini-case studies.

Leadership Lessons

Followers choose to follow. As younger leaders, several contributors thought team members would follow them simply because they were formally in charge or had great ideas. People may have indicated that they would follow, but there was no active support. One city manager learned the hard way that “you can’t lead by fiat”— essentially, a leader must engage with their team and build consensus rather than just dictating actions.

You achieve nothing without a good team. Many of the contributors tended to be “lone wolf” leaders. They eventually discovered that to achieve anything of importance, a leader must build a team, develop a vision with others of where the team is headed, rally people toward that vision, and follow as well as lead.

Leadership is a humbling experience. One contributor concluded (thankfully) that “leadership is a learnable skill.” You learn how to exert positive influence through trial and error after experiencing many situations when people decided to truly follow or not. As younger leaders, we often assumed people had the same values, motivations, and goals that we did. To lead and get everyone aligned in the same direction (oftentimes not precisely your direction) takes much relating, conversations with others, and openness to other perspectives. It is a humbling experience.

Relationships matter. Several senior managers acknowledged that as younger managers they were focused on results, especially related to serving the governing board and their interests. While many results were achieved, they failed in fully serving the organization and the community. In forcing results, they failed to realize the importance of building strong relationships with staff and community stakeholders. They came to realize that one achieves results through relationships. Without strong relationships and engagement, one ultimately fails.

Patience is your friend. As younger managers, many of us felt we knew the answer and had the solution and thus made quick decisions based on our good instincts. Over time, we often discovered that problems were more complex than we anticipated, and many stakeholder groups had their own values and preferred solutions. Consequently, it was often better to fully delve into the issue, consult with different professional staff and key stakeholders, and evaluate options before rushing to a quick decision that may likely need to be reconsidered later.

There is wisdom in the crowd. Before taking a position, determining a course of action, or speaking out, it is often prudent to listen to many different people and perspectives, including ideas and concerns from staff, elected officials, community stakeholders, and other agency leaders. You will undoubtedly learn of implications that you may not have considered on your own.

People need to get their fingerprints on the solution. Several contributors noted that you will fail as the leader if you come up with most of the solutions and decide most issues. People need to influence the decision and get their “fingerprints” on the solution so that it’s owned by them and so that they commit to achieving the outcome. One contributor stated: “People will underwrite what they help write.”

Organizational Management Lessons

Seek shared leadership. Many chief executives discovered that they could not do it all. It is often stated that city/county management is akin to a three-legged stool, and to be successful, chief executives must spend sufficient time and energy effectively interacting with (1) governing board members, (2) employees, and (3) community. That is impossible. There is not enough time in the day.

Therefore, while you must spend some time with each of the groups (especially the governing board), you need to partner with other senior managers to help interact with the three groups and represent and promote the direction of top management. For instance, if the public works director has good communication and people skills, he may be the best executive manager to engage employees in a new city-wide initiative.

Mitigate the natural “silo” mentality of departments. As a result of many experiences, good chief executives have learned to continually demand and reinforce an organization-wide perspective and behavior of departments. The community, as well as the governing board, expect the organization to act in a unified and coordinated way, not as a group of separate entities. Any important issue cannot be solved by one department alone.

Focus on the middle. Several chief executives stated that success happens (or not) in the middle. While you may have a great vision or push worthwhile change initiatives, nothing of significance occurs unless mid-managers embrace the change. Engaged mid-managers connect employees to the vision from the top. They also connect the top to the bottom, communicating to top management the concerns of line employees. Consequently, contributors learned over time that they needed to spend time with mid-managers and engage them in the change.

Relentlessly communicate the value of the organization’s work and each employee’s contribution. To engage employees, senior managers must communicate on a daily basis why the work of the organization is important and how it makes a difference in people’s lives every day. In interacting with individual employees, it is necessary to make a clear connection between the employee’s individual work and the ability of the organization to fulfill its mission.

Consider mistakes as part of the path forward. Effective managers have learned that perfection is not possible in any work group or organization. While managers need to have high expectations, mistakes and errors will happen. If efforts by staff are well-intentioned, mistakes can lead to learning and better performance. No organization can address the big problems of the day without taking some risks and making some mistakes. The key is taking a few steps forward, seeing what works and what doesn’t, and fixing things up and learning as you go. Organizational members observe how managers respond to mistakes. If managers overreact, employees naturally become very cautious.

Confront performance problems. Several senior managers indicated that their preferred style of managing direct reports was coaching and mentoring. However, they learned that sometimes performance problems do not get better with time even with coaching and performance improvement plans. The senior manager often waited too long (especially if the staff person was a long-tenured employee or had support from other employees or community groups). By not acting sooner to terminate the employee, the performance issue remained or grew worse to the detriment of the organization or the community.

Recognize your role to serve as one voice for the entire jurisdiction. Some chief executives suggested that their organizational and community leadership roles were changing in the face of term limits and especially the advent of district elections. Given the short-term perspectives of some elected officials and the limited views of governing board members elected by districts, the chief executive has learned that he or she must often advocate for the longer-term view and become the voice for the entire community, as well as uninvolved constituencies.

Navigating the Politics of Local Government

Think politically, act non-politically. As younger managers, most contributors knew that they must stay out of politics and remain politically unaligned. Therefore, we go to great lengths to act non-politically by sharing all information at the same time with each and every governing board member and avoiding surprises. We also avoid the perception that we are aligned with a particular governing board faction, even if we share policy perspectives.

However, with some experience in the political and messy world of local government, most managers learned that they had to “think politically” (or strategically) if they were going to be effective leaders. To think politically requires that you get to thoroughly know elected officials and their motivations, values, fears, and aspirations (even if they are not aligned with yours). In other words, you must have “positive regard” for them even if you disagree. The more of a relationship you can develop with political actors, especially elected officials, the easier it is for them to understand and somewhat appreciate what you are trying to achieve. Relationships usually must precede problem-solving.

Frame issues differently for different political actors. Part of thinking politically is “framing” the issue differently for different elected officials and any of their constituencies. A blue frame brings out the blue in a painting. A red frame brings out the red in the same painting. So how do you talk about an issue so that the political actor considers the positive possibilities given his or her interests? For example, if you are recommending the funding of a clean energy project, do you frame it as “saving the planet” or “creating new jobs”? Which frame better resonates with the elected officials and other political actors?

Augment the data with a compelling narrative. Managers focus on what they know. Over time, managers discover that elected officials tend to focus on what they believe. We managers seek hard data and evidence. Elected officials are more comfortable with stories and narrative. Consequently, effective managers not only provide data but also put a human face on an issue and share stories aligned with the data. (See Career Compass #50, “Storytelling: A Powerful Way to Communicate and Lead.”)

Know when to push forward and when to pull back. As a city manager, I often tended to push forward on a decision even when it would result in a major conflict or a split council. I failed to adequately learn when to pull back and present a proposal at a later date when there was more support or a greater readiness to consider the recommendation.

Avoid disagreements with elected officials that become “personal.” It is easy for a policy dispute to become personal. A disagreement that becomes personal turns into a real danger zone for the manager. If you feel that your relationship with a councilmember is spiraling out of control, several managers suggested that you be open to another councilmember providing mediation or seek the advice of your coach or a trusted city/county manager colleague.

Embrace criticism. In the political world of local government, chief executives and senior staff are often criticized (if not abused). Senior leaders have learned to consider and even embrace criticism. As one contributor noted, “there is a gem in every criticism.” (See Career Compass #31, “Political Savviness” and Career Compass #102, “Responding to Public Criticism.”)

Interacting with Community Groups

Understand that public hearings do not effectively engage the public. One contributor learned that “public hearings are the worst forum for problem-solving.” They just bring warring tribes together. The community stakeholders must be engaged in advance of public hearings. Authentic community engagement assumes that the professionals provide good information, listen to the values of the stakeholders and their concerns and ideas, acknowledge what they heard, and let people get their fingerprints on the solution. Then public hearings can confirm the solutions developed.

Engage the typically non-involved. One contributor emphasized that it’s important to ask, “Who’s missing from this conversation?” This question will help the leader and staff to reach out and engage all voices in the community. To do so, identify which people and organizations have access to and positive relationships with underrepresented members of the community. When dealing with a “wicked” adaptive challenge, these groups can help the local government engage those typically not involved and thus create a more inclusive public conversation.

Demonstrate to people how you have incorporated their input. One of the biggest complaints about local government staff is that “they don’t listen to us.” Consequently, effective leaders have learned to show people to the extent possible how their ideas have been incorporated and concerns addressed.

Self-Management

Understand thyself. Contributors strongly suggested that leaders must manage themselves if they are going to effectively lead others. To do so, they must first be self-aware about their values, motivations, attitudes, and behaviors—and how those impact others.

Don’t feel responsible for things you cannot control. As younger leaders, we often cared too much and took responsibility for things outside of our control. We had to learn to let go of issues and concerns outside our realm of control or influence, especially when things don’t go our way.

Set boundaries. You and you alone are responsible for monitoring and metering your work efforts. Do not expect elected officials to encourage you to work less on weekends and holidays, spend more time with family, exercise more, or take a needed vacation. You must take control of your work and personal lives. Set expectations early in your tenure and create boundaries.

Keep the work in perspective. If work stresses are affecting your health mentally, emotionally, physically, and/or spiritually, get help! Don’t assume that you can just “tough it out.”

Take care of yourself. Plan, schedule, and commit to family activities, exercise, and hobbies that refresh you and make you a better leader and person. Stated one seasoned city manager, “If you don’t take care of yourself, you can’t take care of others.”

To give you a sense of some lessons learned the hard way, here's a mini case study from my own leadership experience.

Mini Case Study #1: Frank’s Police Oversight Experience

During my time as city manager of Palo Alto, California, a number of residents and nonresidents (including some activists) came to city council meetings, complained about racial profiling by the police, and demanded better oversight of the police department (PD). During the public hearings, some residents shared personal stories of mistreatment by the police.

As city manager, I did not perceive much hard evidence supporting the claims. The police chief was a leader in addressing racial profiling. She had initiated the placement of video cameras in all police vehicles to record all encounters in the field. (This was before bodywear was introduced.) All police officers also underwent diversity training. Finally, the chief insisted on reports of any field encounters, including racial data. Quarterly profile reports were then shared with the city manager and city council. Over my tenure, there were no significant harassment or racial-related complaints filed against the police.

To eliminate racial profiling and related offenses by the police, the complainants demanded that the city council directly oversee the police (instead of the city manager) or that the council appoint a citizens commission to oversee the PD. I was very concerned about these demands:

• I did not see any hard data supporting these demands.
• I felt that any change would undercut the council-manager form of government.
• I believed that any change to police oversight would politicize policing.

Therefore, I did not support the demands of the anti-police activists and strongly recommended that we continue with my oversight of the PD as city manager.

During the council discussions, one of the nine councilmembers suggested establishing a contract with an independent police auditor with expertise in police-related laws and practices. The auditor could review all resident complaints, determine their factual basis, and make any recommendations for training, new policies, or officer discipline. The auditor would report directly to the council (and not the city manager).

The police chief and I were verbally attacked by the activists during the public hearings, and they demanded that the city council fire us. It was a very difficult and stressful time for me, but I maintained my support of the PD.

After a few meetings, the council decided to ignore my recommendation and voted to hire an independent police auditor. In the process, I lost much credibility with the councilmembers. However, because I had a large bank account of trust with the council, I managed to survive as city manager.

What do I wish that I knew back then? What did I learn from all this adversity?

I learned that soft data (stories, personal experiences, narratives) are as important as hard data (official police complaints, police statistics). In fact, stories often trump hard evidence and provide real insight.

My job as city manager was to help the council respond in a positive fashion to the demands of the public. I didn’t do my job by offering the council an acceptable solution responding to the complaints. I only considered the three options in respect to police oversight: (1) PD reporting directly to the council, (2) PD reporting directly to a citizens commission, and (3) continuing city manager oversight of the police chief and the PD. When under personal attack and much distress, we often limit our thinking. In such a situation, we must widen the options. I did not do that.

In hindsight, the police auditor was the perfect solution. Since the inception of the auditor, their review of any resident complaints often supported the police behavior. When there was a problem, they recommended new training, a change in police policy, or discipline of the officer. All their reports go directly to the city council and are public information.

While I was courageous in standing up for the police and resisting any politicizing of the police, I became part of the problem. Because of all the personal attacks against me and the resulting distress, I did not respond well and did not perceive a way out of all this mess (contracting with a police auditor). I took things personally. Most importantly, in my role as a leader, I did not help the PD adapt to new realities until they were forced to.

Mini Case Study #2: Developing a Dog Breeding Ban/Mandatory Spay Neuter Ordinance

One of the contributors provided the following story:

In my first leadership role as animal control coordinator for the county, I faced an immense challenge that would shape my understanding of effective leadership. I was tasked with leading a technical advisory committee composed of diverse community stakeholders including animal breeders, Humane Society staff, veterinarians, and others to create an implementation plan for a groundbreaking ordinance: the nation’s first dog breeding ban and mandatory spay neuter law.

Our committee met for months, and those initial meetings were often contentious, requiring security from the sheriff’s office to maintain order. Despite the challenges, we persevered, ultimately crafting a consensus proposal that we believed included the interests of all. However, when we presented our work to the board of supervisors, we were met with disappointment. The board members expressed that our proposal lacked the strength and impact they desired and ultimately rejected it in favor of an alternate process that we had not been privy to.

I still remember the feeling of devastation I had walking out of that meeting. This experience became a powerful lesson in the necessity of aligning stakeholder efforts with the governing body’s expectations from the very beginning. As a young leader, I had naively assumed that achieving consensus within our committee would ensure that our proposal was valued and approved. However, I should have prioritized ongoing communication with the board throughout the process, ensuring we were in sync with their vision and goals.

If I could advise my younger self, I would emphasize the importance of establishing a clear line of communication with decision-makers and seeking to understand their interests from the outset. Regular checkpoints would have provided insight into their expectations, allowing us to adjust our approach accordingly. Effective leadership involves not only facilitating collaboration among stakeholders but also managing relationships with decision-makers to ensure your work is aligned with their vision.

What Are You Learning About Leadership?

Leadership is a learnable skill. What lessons from these senior managers resonate with you? What lessons are you learning the hard way? How are you making adjustments in your behavior? How are you sharing what you have learned?

DR. FRANK BENEST, ICMA-CM (RETIRED) is a retired city manager and currently serves as a local government trainer and ICMA’s liaison for Next Generation Initiatives. He resides in Palo Alto, California. (frank@frankbenest.com)

Contributors:

Valerie Barone, city manager, Concord, California
David Biggs, former city manager, Orinda, California (retired)
Anil Comelo, city manager, St Helena, California
Kevin Duggan, former city manager, Mountain View, California (retired)
Melissa Diaz, city manager, Redwood City, California
Peggy Flynn, city manager, Petaluma, California
Ed Everett, former city manager, Redwood City, California (retired)
Rod Gould, former city manager, Santa Monica, California (retired)
Derek Johnson, county executive, Marin County, California 
Dan Keen, former city manager, Vallejo, California (retired)
Dominic Lazzaretto, city manager, Arcadia, California
Tess Lengyel, executive director, Alameda County Transportation Commission, Oakland, California
Brian Loventhal, city manager, Campbell, California
Kevin O’Rourke, former city manager, Fairfield, California (retired)
Peter Pirnejad, city manager, Los Altos Hills, California
Laurel Prevetti, former town manager, Los Gatos, California (retired)
Dan Rich, former city manager, Mountain View, California (retired)
Ed Shikada, city manager, Palo Alto, California
Christina Turner, city manager, Morgan Hill, California
Donna Vaillancourt, former HR director, San Mateo County, California (retired)
Kevin Woodhouse, city manager, Pacifica, California