When Leaders Leave by Priscilla Rosenwald & Lesley Mallow Wendell

When Leaders Leave

by Priscilla Rosenwald and Lesley Mallow Wendell


At some point in the life of every existing organization, the leader leaves. This can be especially poignant when it is a non-profit organization’s founder or long-term leader. This departure generates abundant questions:

– Is the organization prepared for the leaving?
– How can it best prepare?
– And, if necessary, how quickly can it prepare?
– Can the needs of the leader and the organization align in a way to benefit both in the transition and post-transition?

And the biggest question: How can we, as an organization, grow and thrive from this leadership transition?

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When Leaders Leave offers real-life advice on how to prepare before and during a significant leadership transition. The book offers the real experiences and learnings developed from hundreds of client organizations and interviews gathered through the work of Priscilla Rosenwald and Lesley Mallow Wendell from TransitionWorks.

When Leaders Leave takes readers through the many possibilities that may occur – from an emergency departure of the executive director to an unqualified board member applying for this critical role. The book focuses again and again on how to learn from the mistakes others have experienced, avoid the pitfalls and take the path that will align stakeholders, staff, and board while graciously supporting the current leader’s departure and avidly promoting the new leader coming to the helm.

Priscilla Rosenwald

Priscilla Rosenwald

Lesley Mallow Wendell

Lesley Mallow Wendell







This book is about that change in leadership, which often strikes fear at the very heart of an organization. It can throw the board, staff and leadership into turmoil. Learn how successful organizations can gain the stability and the resiliency to respond to changes in both their internal and external environments.
Chapter 1: Start Where You Are
The best way to prepare for change is to start before it happens. The first step is to realistically assess how the organization currently responds to change. By taking the Change Readiness Survey and identifying challenges, organizations can begin to have a creative and productive conversation about how to manage the inevitability of change.
Chapter 2: Align the Legacies
The organization was created with a particular mission and vision for its work, often by a founder or long-term leader driven completely by passion. As the organization matures, the leader’s role evolves. The board must continue to assess the current and future direction of the organization and ensure that the leader’s goals align with the organization’s sustainability.
Chapter 3: Helping the Leader Find His or Her Way
The deliberate review of the executive director’s personal and professional goals will ensure that the organization can achieve its mission.
Chapter 4: Plan for Succession. Plan for Success
Typically, an organization needs two types of succession plans — an emergency succession plan (a roadmap for continued operations in the event of an unplanned absence) and a comprehensive succession plan (a process for cultivating and developing leadership talent).
Chapter 5: Kickstart the Leadership Transition
Active transition planning should begin as soon as it becomes known that the founder or long-term leader will be leaving. This planning, usually done 12 to 18 months in advance of the departure, is a collaborative effort between the board, the board’s transition planning committee and the leader often with guidance from an external transition consultant.
Chapter 6: Reach for the Sky
An executive transition is a unique moment to shape the future of the organization. In a transition, organizations learn that by powering through change and moving into a positive place, they can own their resiliency, which, in turn, reduces the fear of change and allows opportunities to be embraced.
Chapter 7: Smooth Sailing
Leadership transitions require attention and support especially during the onboarding process. To ensure long-term success the board, new chief executive and staff, must work to develop their professional relationship during the first three to six months.
Chapter 8: Moving Forward
One of the most important aspects of organizational life is to recognize that change is a constant. The responsibility of every organization is to be prepared for change through a realistic and timely assessment of where it stands now, where it wants to be now, and where it wants to be in the future. Good leaders have the vision and detail focus to execute on the organization’s growth and sustainability.