Leaders who lose their way

By Priscilla Rosenwald

We have been intrigued with long-term leaders and their ability or inability to continue to be innovative, inspirational and inclusive over time. More often, our experience with many long-term leaders has been that their tenure exceeds their abilities, and this finding has been confirmed by Bill George, celebrated author of True North, who speaks of “why leaders lose their way”.

As transition consultants, we encourage organizations to robustly assess their impact, direction and the effectiveness of their leadership. Leadership tenure does not automatically confer success – despite the status and prestige. This can easily be witnessed in the unlimited tenure of politicians, legislators and judges. Often they develop a sense of entitlement, and when these political leaders and legislators fall from grace, it is always because they “lost their way”. The same is true of organizational leaders, whether it is a large profit-driven business or a mission-driven nonprofit they are leading. In the end, it is their organizations that suffer.

George points to leaders being trapped by external gratification as the source of their fulfillment. Leaders who focus on external gratification instead of inner satisfaction find it difficult to stay grounded. They reject the honest critic who holds a mirror to their face and speaks the truth. Instead, they surround themselves with supporters telling them what they want to hear. Over time, they lose the capacity for honest dialogue, and people learn not to confront them. They often choose to listen only to people who reinforce their views, and miss opportunities for wise counsel and authentic conversations.

See if you recognize bosses or colleagues in these archetypes:

Imposters – They rise to leadership through the ranks using cunning and aggression to cover poor leadership skills. When they have acquired power, they are unable to act decisively.

Rationalizers – They blame external forces or subordinates when challenges arise. Without wise counsel, they often resort to desperate measures.

Glory Seekers – They define themselves by money, fame, glory and power, in lieu of building sustainable organizations.

Loners – They believe they can and must make it on their own. They reject feedback while their organizations unravel.

Shooting Stars – They move up so rapidly in their careers that they never have time to learn from their mistakes. When they arrive at the top, they are prone to make irrational decisions.

It is not difficult to spot these leaders who have lost their way, although their peers and colleagues often refrain from honest and challenging dialogue. From our perspective, it is the role of the board to assess and monitor the performance of the organization’s chief executive. If the board is unable to have effective and authentic conversations about how the leader is empowering others, by promoting innovation, inspiration and inclusion, they are not serving as solid stewards of their for-profit and non-profit organizations. It is the responsibility of the board leadership to know that the chief executive is engaged in honest, meaningful dialogue with their employees and their stakeholders. As stewards, they should be mindful of when the chief executive has lost their way to ensure that the organization, not just the leader, is thriving.

Too frequently, we see boards held hostage by long-term leaders, whose tenure is at best tenuous.

“What Lies Beneath” – Inside Leadership Transition in a Charter School

By Susan M. Poglinco and Priscilla Rosenwald.

The authors collaborated on this article as a result of a partnership forged between a charter school Board Chair (Poglinco) and a retained Executive Search Leader (Rosenwald) of Leadership Recruiters with experience leading searches for organizations at critical crossroads. The two worked together for more than a year to launch an internal search committee, select a new leader and CEO, and get through the onboarding process in this 600 student charter school located in a large city in the northeast. This article chronicles some of the expected and unanticipated challenges they encountered.


Leadership transitions and organizational change can be difficult under the best of circumstances. Striking a balance between maintaining areas of success and achievement with the promise of a new direction for a school can be delicate. Change in leadership is, indeed, a painful thought. But avoiding or postponing leadership change could put the school in long-term jeopardy. What is most important is that the facts are faced and parameters put in place to ensure the school will continue to thrive and stand on its own without the current leadership; the school’s vitality and sustainability are the key factors to be considered.

When a long-term leader has been in their role for a decade or more, the board often defers to them for all organizational information, decisions and direction. Frequently, long-term leaders who have not had authentic performance conversations with the board leadership believe that the organization is theirs to oversee – until they get tired of showing up. The organization is often held hostage to the retirement considerations of the chief executive, who may no longer be leading the school into the future.  Boards are frequently remiss in not having regular performance expectations and comprehensive performance reviews with long-term school leaders. The performance review would focus on the health and sustainability of the school, and have input from the major stakeholders, including the senior leadership team.


The charter school board understood the need for professional guidance and engaged an executive search firm. Without any prior leadership continuity planning, the leadership transition at the charter school required collaboration with the board leadership and the organization’s senior leadership in a transparent and inclusive way. Effective planning and processes had to be put in place to redirect and ensure an effective transition to new leadership.

In conjunction with Leadership Recruiters, we anticipated that change management might be an initial challenge as began an organizational assessment. We rolled out a leadership inventory questionnaire/planning tool and met with staff at the school to create a position description reflective of the demanding CEO role. One thing was immediately clear – many staff expressed a readiness for a change of leadership and welcomed the change. First Tip Off – The prospect of change was uniformly welcomed among teachers and other school staff.        

Outgoing CEO’s Backstory

At the time of the search, the CEO of the school had been in the role for close to a decade. He was committing to a new professional chapter in his life, and had been working toward that chapter for a number of years while in the CEO role at the school. The last two years at the school had been increasingly difficult, and the CEO was admittedly tired.

The Board

The CEO enjoyed a collegial relationship with the immediate past Board Chair. While a few tricky issues came up during her two-year term, she united the nine-person board and fostered a productive working relationship with both board members and the CEO – the status quo was maintained and the school was getting by on the surface. The board was comprised of committed members with good intentions, but board members were in need of strategic direction/capacity building to prepare them for the search and the imminent organizational transition.

The CEO publicly announced he was departing soon after the new Board Chair started her term. The new Board Chair was action-focused and charged with leading the search and the board through a complicated year. She started asking the kinds of questions that no one had ever asked of past board leadership or the CEO. A methodical audit of all aspects of the school revealed that there were inconsistent policies and procedures and less documentation than expected across critical aspects of the school. Second Tip Off – At the board level, while hunches existed that internal systems were not fully realized, the new Board Chair quickly confirmed that the state of affairs was worse than expected. (*Tide started to turn here)  

Leadership Team

The CEO presided over an 8-person Leadership Team in what might be called a “servant leader” model – defining his devotion to the school as “a calling.” Cloaked in humanity and service, the CEO inarguably had good intentions. Yet, the strategic and operational execution of a coherent and consistent academic agenda was often clouded by two persistent and inescapable realities within the school – school climate/student discipline and a challenging financial outlook for the school. At the helm of the Leadership Team, the CEO was overwhelmed. He neither promoted excellence nor tolerated dissent among Leadership Team members. Third Tip Off – Leadership Team members had the latitude to make decisions not because they earned it or had proven they could handle it, but out of benign neglect from a CEO who was consumed with the school’s financial challenges above all else.


Most school staff characterized communications from the administration as inconsistent or non-existent. Fourth Tip Off – The CEO and Leadership Team were cloistered from the rest of the school staff. Leadership team decisions were communicated poorly with little rationale or transparency, or sometimes not at all.  All the staff lamented the lack of transparency.


Across the school, there were few accountability systems – for teachers, Leadership Team members, students, or the CEO. Fifth Tip Off – While teacher observations were performed by the Principal, academic performance, especially among a core of failing students improved little. As far as instructional quality, it was variable teacher to teacher and there were no systems in place to rectify that variation. Chief among staff complaints was the lack of enforcement of a code of conduct and students not being held accountable for bad behavior. This was viewed as the province of the Dean of Students and the Principal, and not a shared responsibility across Leadership Team members and all school staff. It was then revealed than in a decade of service, the CEO had no record of written performance reviews by the board. The executive committee reported to review the CEO annually, but there was no paper trail, or stated performance objectives.

School Climate/Discipline

Disciplinary issues continued to rise among students in both numbers and severity, escalating into a series of events that was emblematic of all of the previously mapped out tip offs colliding. These events (which included a key leadership team member taking an abrupt leave of absence) were not communicated to the board until after the fact. Sixth Tip Off – (CEO lost good will of most board members after this.)

Human Resource Issues

In preparing to mount a national search for a new CEO, the executive search leader instructed the Board Chair that she needed an organizational chart that reflected the Leadership Team structure, because potential candidates would ask for that as they progressed through the candidacy pipeline. In addition, the Board Chair needed to track down job descriptions for all 8 Leadership Team members. She soon discovered that there was no organizational chart, no job descriptions for Leadership Team Members, and no documented formal review processes – no performance evaluation system. Seventh Tip Off – The Board Chair had to act quickly and outsource a short turnaround project with an HR consultant to get the necessary documents so the search could proceed and provide accurate organizational information about the school. (Board Chair intervened in basic operations of school out of necessity, not choice, because of impact on search.)

School Finances

The set up at the school had the CEO working with a charter school subcontractor who acted as Business and Finance Manager, resulting in an over-emphasis on dire financials at the risk of all other aspects of school performance or approaches to revenue enhancement. Eighth Tip Off – The internal COO had no responsibility for the financial systems, and revenue generation was the responsibility of a contracted fundraising professional. The alliance formed between the CEO and the Business Manager mutually reinforced the intractable nature of the financial challenges the school faced, and took the emphasis away from the academic and instructional aspects of the school, where the school was under-performing. Everyone was complicit in this, and entreaties to move beyond this discussion by the Board Chair were met with hostility from both the CEO and the Business Manager. The outgoing CEO was more aligned with a subcontractor than the Board Chair or the board, and as a result, all other aspects of the school suffered.

The Search Process

The search consultant and Board Chair led an engaged search committee, with representation from the faculty. Information gathered from the organizational assessment, and additional HR and financial due diligence, guided the leadership profile for the next CEO, as well as concurrent planning for system changes at the school, led by the Board Chair. During the transition, the outgoing CEO was encouraged to prepare for the knowledge transfer to his successor, and was subsequently honored at public events celebrating his tenure once the new hire was announced. The new CEO and Board Chair have engaged during the on-boarding process to prepare the school for change – leading to viability and sustainability.

Essential Takeaways

No amount of planning can prepare the Search Chair for “What Lies Beneath” over the course of the search process

Unforeseen challenges emerge during a search that will require decisive action and an independent thinker able to see beyond competing agendas. That is why it is critical to hire an experienced executive search professional and listen to them. This partnership cannot be understated. A capable executive search professional will act as a compass and ally, and coming from the outside – they will see dynamics that may escape you.

Strong leadership is best shared across all board members during a critical transition

The Search Chair can lead the process, but should be backed up by search committee members and board members in addressing the unforeseen challenges that may come up during the search process. A Search Chair aims to run a successful search. If pre-existing organizational circumstances put that at risk, it should be all hands on deck among board members.

Money is always an issue, it is never the ONLY issue

Demystify school finances – strike a balance between engagement and overemphasis. Board composition should deliberately include at least one or two board members with a background in school finance or accounting. The CEO should be engaged in the finances of the school, but not to the detriment of all the other pieces of the puzzle. The academic mission of the school and the instructional program are key to attracting additional funder/donor dollars and corporate support.

Incoming leaders will inherit “legacy challenges” with both school staff and the board

“Legacy challenges” like persistent academic failure among students and lower student enrollment numbers are two interconnected areas the new CEO has had to contend with immediately. Board composition analysis identified a need for two or three new board members with legal, HR or financial expertise.

Final Reflections

If you liken a charter school to the puzzle Jenga ™ (https://en.wikipedia.org/wiki/Jenga) – once you pull one piece out of the tower, the integrity of the entire structure is affected and weakened. In the different headings in this article from presenting the leadership transition to staff, the Board, the Leadership Team, Communications, Accountability, School Climate/Discipline, HR Issues, Finances – each section is a piece of the puzzle and constructs part of the tower. Yet within each building block there was a “Tip Off” that hinted at “what lies beneath” in the transition process. It is that which lurks underneath and reveals itself gradually that bedevils even the most efficient and effective transition processes.


Every “Tip Off” in the sequence threaded throughout this article was problematic on its own, but the interconnectedness of these puzzle pieces is what made the transition process at this charter school more complicated than anyone could have predicted from the onset. It’s fair to say that charter schools are not perfect places, they are not run by infallible human beings, or governed by stellar boards. It is our hope that in the depiction of the perfect storm – demonstrated by this school’s organizational transition, that one comes away with a strong sense of the realities required to prepare for leadership change.

Don’t Skip Succession Planning for Your Board

Succession and transition planning have become increasingly important as nonprofit boards and funders are more focused on ensuring that organizations can function effectively if a leader departs. The entire emphasis is on the professional leader, with little attention paid to how the board manages its own transition. It is critical to have a succession plan in place for professional leadership, but equally important for the board to pay attention to its own development and succession planning. Good nonprofit governance supports the creation of a process at the board level. Here are some questions to focus your thinking:

1. How does your board recruit new directors?
2. How are members assessed and groomed for potential leadership roles?
3. What board committees and roles do directors need to participate in before they can serve effectively as officers?
4. Is there a plan in place for board leadership to ensure a smooth transition to new officers?
5. Are there contingency plans in place to manage a scenario such as the incoming board chair’s company transfers him or her to a new position on the other side of the country?

If the board is not practicing good governance, and succession plans are chaotic or worse, non-existent, this may present an even greater risk to the organization’s sustainability than a lack of planning at the chief executive level. If your organization experiences a leadership transition, it may be hard to attract good candidates. Talented professionals interested in nonprofit senior leadership roles are careful to complete their due diligence, and they typically start with a review of the organization’s financial status and board governance practices.

As a new CEO, you can assess the senior team and make changes, moving people into different roles or out of the organization. Addressing a poorly performing board of directors is another matter. It is nearly impossible for a chief executive to make any rapid changes in the composition of a board, particularly if the number of directors is at maximum under the current bylaws. Good candidates may steer clear of an organization with a non-performing board.

Which organizations might be at risk? Nonprofits with

  •  boards that experience excessive turnover, poor governance practices and no orderly plan for recruiting and orienting new members
  •  boards where the majority of directors are high-powered members of the business community who are disengaged, or who serve on so many boards they lack the time to be effective for any one board;
  •  boards that are required to have a specific number of government or political appointees;
  •  founder led boards where the officers or the president have served for many years, the governing bylaws are outdated, don’t include term limits or a process for evaluating the board’s performance.

What processes work well? Here are some examples:

The synagogue board on which I serve has a comprehensive and orderly process for developing board members and exposing potential board leaders to all aspects of governing the synagogue. There are three Vice Presidents, and each has several committees under their supervision. The committees under each Vice President are progressively more comprehensive, with the First Vice President overseeing critical operational areas they must learn about before becoming President, such as Budget-Audit, Development and Fundraising, Facilities and Human Resources. Each Officer serves at least two years in their roles, with Treasurer and Secretary often serving longer if they don’t aspire to higher level leadership. By the time a board member becomes President, they are well grounded in all aspects of both board governance and synagogue programs and operations. They have the opportunity to build their leadership skills and connect broadly with committees and other constituents.

The board of a women’s funding federation rotates board members through the officer levels to develop leadership skills and organizational knowledge. Directors may spend one or two years in the Secretary or Treasurer roles, and two years are required in the Vice Chair and Board Chair roles. The immediate Past Chair spends another year on the board and focuses on board governance and recruitment. This type of progression enables directors to learn about the organization, develop relationships with donors and enhance their leadership skills. The immediate past Board Chair collaborates with current board and professional leadership to identify potential board leaders from among the directors, and works to engage new members, either through committees as a step to board membership, or directly onto the board if appropriate.

You don’t have to put these exact processes in place, but your board does need to think strategically about managing its own succession planning. Be proactive in putting a plan in place – it can benefit board recruitment and ensure a robust candidate pool if a leadership transition at the chief executive level occurs.

For more information about creating board or leadership succession and transition plans, contact TransitionWorks at 610-892-8035.

By Lesley Mallow Wendell