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This chapter illustrates the consequences that can result from a mismatch between leadership style and organizational contexts required to encourage genuine investigation and exploration – particularly in topical areas relevant to the enterprise’s business model. This cautionary tale suggests not only that leadership approaches need to complement the necessary conceptual challenges involved in rigorously defining relevant problems and strategies in order to sustain organizational success; ideally, it should also align with the strengths and goals of the teams led. Thus, a senior marketing, communication and sales leader may not support the creative research and evidence-based, user-centered design necessary to nurture innovation within, for example, a future-oriented research and development team. Such cultural misalignments have been well framed by classical theories of leadership as well as by empirical comparisons of enduringly successful companies with more transient corporations.

Two of the many requirements for being a Servant Leader are compassion and understanding. In this chapter, the author examines the individual, group, and organizational lessons learned after a verbal confrontation between two executives in the lady’s restroom. The author examines what can happen when Servant Leadership fails and how, when people move up the stages of conflict, they get further away from the foundational elements of being a Servant Leader.

The time has come to reflect on the warning signs, decisions made, and repercussions of those in leadership of a financial services company which collapsed in the wake of the financial crisis during the mid-2000’s. The author was a divisional technology executive of this firm at the time, close enough to the top of the organization to observe the actions of those in charge. The author’s observations over a period of years eventually led her to resign from her position to enter a doctoral program only a few weeks before the company’s demise. The impetus behind the author’s resignation was her feeling that the decisions and actions of those in leadership violated her personal values. In this account, the author offers her personal reflections and the repercussions of this experience, followed by a deconstruction of this tragic leadership failure which includes references to the leadership literature.

This chapter revisits and examines the experience of working with a new senior level administrator who failed to understand their role on the team. This was further compounded by the administrator’s inability to establish trust and rapport, assimilate into an established organizational culture, and empower staff. Additionally, this administrator’s style could best be described as managing instead of leading. This failure to assess and learn the group dynamics of the team resulted in a lack of buy-in and a visceral decrease in team morale. Change was swift and fast, but not transformational. Within 14 months of the hire of the new senior administrator, two office support staff assistants resigned and four of the six associate/assistant directors within the office resigned. Within two years, the senior administrator resigned. The authors will provide remedies that will assist future leaders in similar situations in making better decisions, as well as provide examples of ways to connect with staff and implement change together.

Leaders have a profound impact on the work lives of the employees they supervise. This chapter explores the experiences of employees whose leaders exhibit toxic behaviors and the impact of this toxicity on employee engagement. The authors report the findings of a qualitative study involving in-depth interviews with 13 participants. First, the authors describe the participants’ experiences before and after experiencing toxicity. Next, the authors outline three critical toxic leadership styles: the nightmare (leaders who have unbalanced emotional control and who are overly fond of power), the pretender (leaders whose authenticity and integrity seem low, who play different characters depending on the circumstances), and the runaround (leaders who change directions too often or give unclear instructions). Finally, the authors address organizational, leadership, and individual strategies to identify and remove toxic leaders from the workplace.

Failing to effectively play their leadership role can have a devastating effect not only on leaders, but also on the group or team they are responsible to lead, as well as on the organization or organizations they belong to and/or serve. In the following example of a leadership failure, the author’s inability to come to the plate to play her required role as a leader had a negative impact on her professional standing, as well as on a number of individuals who she was called to lead. This example illustrates the necessity to master “leading oneself” prior to leading others. Cleaning out the cobwebs in one’s own psyche and mastering emotional intelligence are pre-conditions for effective leadership. This is especially true when leading in a foreign cultural context as this chapter shows. A leader always faces the possibility of having to deal with individuals who bring out those inner parts of oneself that have not yet been dealt with and healed. This chapter focuses on the importance of the key ingredient of leading oneself, namely emotional intelligence. Within emotional intelligence, the author examines her leadership failure in relation to self-awareness and self-regulation while leading a US government foreign assistance project. She highlights the negative impact on her leadership of fear that arose from unresolved past conflicts remaining in my shadow side. “Self-betrayal” emerged as a key factor also in her leadership failure.

A change in leadership can often be stressful for an organization. Miriam, the Founding Executive Director of a supporting foundation for a rural hospital, was primarily a servant leader, providing volunteers and staff with the tools needed for successful fundraising. As the initial Executive Director for this small nonprofit organization, she established an organizational culture that fit the needs of the community; volunteers became accustomed to that culture and the organization flourished. Upon Miriam’s retirement, her replacement brought a very different type of leadership rooted in hierarchical structures and authoritarianism. Accustomed to a more supportive organizational culture, many volunteers flatly refused to work with the new executive director. He exacerbated the problem by refusing to acknowledge any missteps he might have taken and was not receptive to any ideas not his own. He was not supportive of staff or even the organization’s own board members. The new executive director was accustomed to being in control and misunderstood managing the needs of multiple stakeholders. He moved too quickly to consolidate his own power without consideration of the organization’s needs. He tried to instill a “heroic” leadership style in a culture of shared leadership. The credibility of the organization suffered as a result, not only among volunteers and hospital staff, but, as they talked within the community, publically as well.

Impactful leadership requires an investment in the self and others. Blinded by past success, this leader’s story explains examples of a failed attempt to learn how to navigate a new industry culture with hidden political landmines in the organization, communicate effectively in a hierarchy, and ultimately realize she might not have been a fit for the organization. This chapter will provide examples of the leader’s story of challenging organizational politics and relational aggression in the workplace. Through many conflicts and barriers to effective leadership, this chapter provides key insights of leadership self-awareness, wellness, communication blind spots, and organizational strategies to build trusting leader–follower relationships. Living in a volatile, uncertain, complex, and ambiguous (VUCA) world today, the ability to build strong trusting relationships between leaders and followers and peers is vital to success as a leader and organization. The leader must learn from failure and innovate from lessons learned. To lead within a VUCA world, the time to invest in continuous leadership development is strongly recommended.

Founder’s syndrome is when one individual holds disproportionate power and influence in an organization. It is not limited to the founder of an organization and can be found particularly in dominant and charismatic organizational leaders. While the nonprofit leader in this case was not a founder, he was highly charismatic and was granted as much authority as a founder. He became reluctant to share power, even when it was clear he needed help to build the capacity of the organization. The board of directors did not feel it necessary to check the executive director’s power because he had been so successful in growing the organization up to a point. When it was discovered he was having an inappropriate affair with a subordinate employee, however, the board did ask him to resign. Yet it allowed him to name his successor, and accepted the executive director’s nomination of the employee with whom he had an affair. Board and staff of nonprofit organizations have obligations to act in good faith in the governance of the organization and to enforce the duties of care and obligation. This requires transparent communication. Without two-way symmetrical communication maintained throughout the organization, this executive director abused the power granted him for his own gain.

A faith-based international nonprofit and its newly hired, narcissistic CEO are examined in this chapter. The CEO made up his own rules acting contrary to many leadership, financial, and HR practices, as well as ignoring the law. As difficulties mounted, there was little to no outcry. Until his abrupt departure seven years later, the CEO operated with impunity. The authors analyze the CEO’s tenure through four lenses – the leader, the followers, the environment, and their faith perspective. As a narcissist, the CEO quickly created a toxic environment and stayed one step ahead of everyone else. Employees were most often compliant and the few who were not found themselves stripped of their position as an example to the onlookers. With the Board in transition, there were no checks and balances and, coupled with a perception of instability, the environment was advantageous for a narcissist. Each of these three lenses was influenced by the faith system which the organization and its employees espoused. Faith-based compliance and organizational silence created an open door for the narcissistic leader and resulted in great damage individually and collectively. The authors offer lessons for individuals, groups, and organizations working under a narcissist.