Rise Above Routine with Darren Mann

A Conversation with Darren Mann on Leadership, Failure, and Growth

Summary

In Episode 59 of The Clear Voice, James Groom and Michael Boese talk with leadership coach, speaker, and author Darren Mann about leadership growth, failure, daily habits, communication, mentorship, and the importance of rising above routine.

Darren shares lessons from his project management career, his transition into coaching, and the core ideas behind his book, Rise Above Routine.

Leadership Rarely Breaks Down All at Once

Leadership rarely breaks down in one dramatic moment. More often, it settles into routine. The calendar fills up. Emails stack up. Meetings take over the day. The urgent begins to crowd out the important. Before long, leadership can become a cycle of reacting, checking boxes, solving immediate problems, and trying to keep up. That pattern affects leaders in every field, but it is especially familiar in city government. City Managers, Assistant City Managers, police chiefs, fire chiefs, finance directors, public works directors, HR leaders, and other executive staff often operate in environments where pressure is constant and expectations are high. Darren Mann’s message in this episode is a useful reminder that leadership growth cannot be accidental. Leaders have to be intentional about their habits, support systems, communication, and willingness to learn from failure.

From Project Management to Leadership Coaching

Darren spent 15 years in project management, including high risk and high value projects. That background shaped how he thinks about leadership. Project management requires goals, planning, communication, accountability, and follow through. Those same skills matter in leadership, especially for executives and department heads who are responsible for moving teams, projects, and organizations forward. Darren explains that project management eventually taught him how to manage and lead his own life. That lesson applies well beyond the private sector. In local government, leaders are constantly balancing competing priorities, resident needs, council expectations, staff development, budgets, infrastructure, public safety, and long term organizational health. Without a clear sense of direction, leaders can stay busy without actually moving forward.

Leadership Starts With Self Management

One of Darren’s practical habits is setting priorities the night before. He recommends identifying three important priorities for the next day while also leaving room for interruptions. That is a realistic approach for leaders because interruptions are part of the job. For city executives and department leaders, the day rarely goes exactly as planned. A personnel issue, public complaint, emergency response, council request, budget concern, or operational problem can quickly shift the schedule. The goal is not to eliminate interruptions. The goal is to lead with enough clarity that the most important work still gets attention. Leaders who cannot manage their own priorities will struggle to help others manage theirs.

Failure Is Not the End Point

Darren talks openly about an early leadership failure when he was promoted into management at 25. He had been a strong employee and a top performer, but the transition into managing people was much harder than expected. He did not know how to ask for help. He did not have the right support system. He also did not fully understand what the management role would require. That story matters because many organizations make the same mistake. They promote a top performer and assume that technical skill will automatically translate into leadership ability. Sometimes it does. Often, it does not happen without support. This is a real issue in city government. A strong police officer may not automatically become a strong sergeant. A skilled firefighter may need help becoming a company officer. A talented finance employee may need support moving into director level leadership. A high performing department employee may know the work, but still need coaching on communication, delegation, accountability, and leading former peers. Promoting people into leadership without a transition plan is unfair to the employee and risky for the organization.

Top Performers Need Leadership Support

One of the best practical takeaways from the episode is that organizations should not just promote people and hope they figure it out. Darren recommends having a transition plan for new leaders. That means clear expectations, training, mentoring, honest feedback, and someone they can talk to before small issues become larger failures. This is especially important for cities preparing employees for future executive leadership. The next generation of City Managers, police chiefs, fire chiefs, directors, and senior staff will need more than technical experience. They will need judgment, communication skills, emotional intelligence, resilience, and the ability to develop people. Leadership development should begin before the promotion, not after the struggle becomes obvious.

Leaders Need Support Systems

A major theme in the conversation is the importance of mentors, coaches, counselors, peers, and trusted advisors. Leadership can become lonely. As people move higher in an organization, they often have fewer people they can speak with openly. They may have employees, peers, and elected officials around them, but not always a trusted outside voice who can help them process decisions, pressure, and blind spots. Darren describes the value of having an inner circle. These are the people who provide support, accountability, perspective, and honest feedback. For local government executives, that kind of support is not a luxury. It is a stabilizer. City leadership requires difficult decisions. Public sector executives are often managing limited resources, competing priorities, political pressure, staffing challenges, and public expectations. Leaders who try to carry everything alone are more likely to burn out, isolate, or miss important feedback. Strong leaders build support before they need it.

Acceptable Failure Versus Repeated Mistakes

The episode also addresses the difference between healthy failure and inexcusable repeated mistakes. Darren supports the idea of a failure friendly culture, but he makes an important distinction. Failure can be acceptable when people are learning, trying, improving, and moving forward. Repeating the same mistake without growth or accountability is different. That distinction is important for city leaders. Public service requires accountability. Mistakes can affect employees, residents, public trust, budgets, safety, and service delivery. Leaders should create environments where people can learn and grow, but they also have to set clear expectations and address repeated performance problems. A healthy culture does not punish every mistake. A healthy culture also does not ignore patterns.

Sharing Failure Builds Trust

Darren also makes the case for leaders being willing to share their own failures. That does not mean oversharing or making every conversation about personal setbacks. It means being honest enough to show people that growth often comes through difficulty. When leaders only talk about success, they can feel distant or impossible to relate to. When they share what they learned from failure, they create connection. This matters in public sector leadership because credibility is built over time. Employees are more likely to trust leaders who are honest, self aware, and willing to acknowledge that they have had to grow too. Leaders do not lose credibility by admitting they have learned hard lessons. They often gain it.

Communication Is Not the Same as Connection

One of the strongest parts of the episode is Darren’s discussion about communication and connection. A leader can talk a lot and still fail to reach people. A leader can sound polished and professional, but if there is no trust, no listening, no common ground, and no real connection, the message may not land. Darren points to listening, eye contact, body language, and finding common ground as important parts of connection. The point is simple. People need to feel heard before they are likely to fully hear you. That is a major leadership lesson for city executives and department heads. Whether a leader is speaking with employees, elected officials, community members, applicants, or partner agencies, communication is only effective when it connects. The best message in the world can fall flat if people do not believe the leader understands them. Everyone communicates. Effective leaders connect.

Servant Leadership Requires Accountability

The episode also includes a practical conversation about servant leadership. Darren and Michael both make an important point. Servant leadership is not weakness. It is not avoiding hard conversations. It is not simply being nice. It is not a generic answer to give during an interview. Real servant leadership is about seeing value in people, adding value to people, and helping develop leaders around you. But it still includes accountability. That distinction matters because the phrase servant leadership is used often in public sector leadership. It sounds good, but leaders need to be able to explain what it actually means in practice. A servant leader can support employees and still set clear expectations. A servant leader can care about people and still address performance problems. A servant leader can develop others and still make difficult decisions. The strongest leaders usually have more than one leadership style. They know when to coach, when to support, when to direct, when to correct, and when to make the decision.

Consistency Compounds

Darren also talks about daily leadership habits and John Maxwell’s Rule of Five. His daily practices include reading, reflecting, writing, leading, and adding value to someone. The power is not in doing those things once. The power is in doing them consistently. Leadership growth is usually not the result of one book, one conference, one class, or one inspirational moment. Growth comes from repeated habits that compound over time. A leader who reads every day grows in perspective. A leader who reflects every day grows in self awareness. A leader who writes every day clarifies thought. A leader who adds value to someone every day builds influence. In local government, consistency also builds trust. Employees notice whether leaders follow through, communicate regularly, prepare well, treat people fairly, and remain steady under pressure. Consistency is not flashy.It is foundational.

Asking for Help Is a Leadership Strength

Another major theme in the episode is the courage to ask for help. Darren explains that many leaders struggle with this because of fear of rejection. That fear may come from earlier life experiences, past disappointments, or a long standing belief that they have to figure everything out alone. That mindset can hold leaders back.Leaders who will not ask for help may stay stuck longer than necessary. They may miss opportunities for mentoring, feedback, growth, and connection. They may also unintentionally model unhealthy independence for the people they lead. Asking for help does not make a leader weak. It shows self awareness. For current and aspiring city executives, this is an important point. The leaders who grow the most are often the ones willing to ask better questions, seek advice, invite feedback, and learn from others who have walked the path before them.

Rising Above Routine in Public Service

The conversation closes with advice for leaders who feel stuck in routine. That question fits public service well. City government can be deeply meaningful work, but it can also be exhausting. Leaders face staffing shortages, budget pressure, public criticism, infrastructure demands, community expectations, council priorities, emergency issues, and constant operational needs. Routine can become a survival strategy. But leadership is not just about surviving the work. It is about developing people, strengthening organizations, serving communities, and making decisions that leave things better than they were before. Darren’s advice is to seek support, ask for what you need, get out of the comfort zone, and invite honest feedback from people who know you well. That is a strong message for any leader who feels stuck. Rising above routine does not always begin with a major life change. Sometimes it begins with one honest conversation, one mentor, one better habit, one act of reflection, or one decision to connect more intentionally with the people you lead. Leadership growth starts when routine is no longer enough.

Connect with Darren Mann

Darren Mann is a leadership coach, speaker, and author of Rise Above Routine.

Email: dmann@dmanncoaching.com
Website: https://dmanncoaching.com/
Book: https://dmanncoaching.com/rise-above-routine-ebook
LinkedIn: https://www.linkedin.com/in/manndarren/

Connect With Clear Career Professionals

Clear Career Professionals is a Texas-based municipal executive search firm specializing in City Manager search services, municipal executive search, and local government leadership consulting for cities and counties across Texas and the United States. Clear works with communities to recruit City Managers, City Administrators, Assistant City Managers, Police Chiefs, Fire Chiefs, Finance Directors, HR Directors, and other senior municipal leaders.

Clear’s approach, known as the Clear Way, is a candidate-focused recruiting model designed to attract both active and passive candidates while maintaining strong communication throughout the process. This includes consistent engagement with applicants, clear expectations, and a commitment to transparency for both candidates and hiring organizations.

In addition to executive search services, Clear provides leadership development and training, organizational reviews, executive coaching, interim leadership placements, promotional assessments, compensation studies, and strategic consulting. These services are built to help cities and counties strengthen internal operations, develop future leaders, and align organizational structure with community expectations.

Clear also produces The Clear Voice podcast and PositionCast™ episodes, which are designed to elevate leadership conversations and bring executive-level career opportunities to life. These platforms provide insight into local government leadership, organizational culture, and the real-world challenges facing today’s public sector executives.

Clear partners with city councils, county commissioners, and executive leadership teams seeking experienced professionals who can guide growing communities, manage complex organizations, and deliver strong public service outcomes.

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