As a CEO or founder, planning a sabbatical can be a daunting task. However, a study chronicled by Inc. Magazine (2017) suggests sabbaticals have the power to help stress test an organization to prepare for a leadership succession. A sabbatical is more than just taking time off, it involves ensuring your organization remains stable and continues to thrive in your absence. A well-structured sabbatical plan not only sets the stage for a smoother exit transition but also empowers your team and strengthens the organization’s resilience.

Here, we outline ten crucial steps to help you create an effective sabbatical plan.

  1. Succession Planning

Identify Potential Successors

Start by identifying and grooming potential successors within the organization. This may involve mentoring, providing leadership training, and gradually giving them more responsibilities. This step is essential to ensure that the organization has capable leaders who can take the reins during your absence.

Develop a Transition Plan

Create a detailed transition plan that outlines how the transition will occur. This plan should include timelines, key milestones, and the roles of different stakeholders in the process. A well-defined plan will provide clarity and direction, alleviating any uncertainties that may arise during the transition.

  1. Documenting Knowledge and Processes

Create Comprehensive Documentation

Ensure that all critical processes, workflows, and key information are well-documented. This includes standard operating procedures (SOPs), strategic plans, and institutional knowledge. Comprehensive documentation serves as a valuable resource for your team and successors, ensuring continuity in your absence.

Knowledge Transfer

Conduct knowledge transfer sessions where you share insights and critical information with your team or designated successors. These sessions foster a deeper understanding of operational nuances and strategic priorities, empowering your team to make informed decisions.

  1. Empowering the Team

Delegate Responsibilities

Begin delegating your responsibilities to your team members. This not only reduces dependency on you but also empowers your team to take on more leadership roles. Delegation helps in building a sense of ownership and accountability among team members.

Build Leadership Skills

Invest in leadership development programs and executive coaching to enhance the skills of your team members. These programs prepare them for higher responsibilities and equip them with the tools needed to navigate challenges effectively.

  1. Establishing Clear Communication Channels

Open Communication

Maintain open lines of communication with your team about your plans for the sabbatical and eventual exit. Transparency helps in building trust and prepares the team mentally for the upcoming changes.

Feedback Mechanism

Implement a feedback mechanism to gather input from your team and stakeholders. This can help in identifying potential issues early and addressing them proactively, ensuring a smoother transition process.

  1. Strengthening Organizational Culture

Reinforce Values and Vision

Ensure that the organization’s values and vision are well-entrenched in the culture. This will help maintain continuity in your absence and provide a strong foundation for decision-making.

Promote a Collaborative Environment

Encourage a collaborative and supportive work environment where team members feel valued and motivated to contribute to the organization’s success. A strong organizational culture fosters resilience and adaptability, essential traits during transitions.

  1. Engaging External Advisors

Consult with Experts

Engage external advisors or consultants (perhaps Flourish Executive Counseling and Coaching) to provide an objective perspective on the transition process. We can offer valuable insights and help address any blind spots, enhancing the effectiveness of your sabbatical plan.

Board Involvement

Involve the board of directors or advisory board in the planning process to ensure their support and guidance. Their involvement can provide additional oversight and strategic direction.

  1. Testing the Waters

Trial Sabbaticals

Consider taking shorter trial sabbaticals to test how the organization functions in your absence. These trials can highlight areas that need improvement and help in making necessary adjustments to your transition plan.

Monitor and Adjust

Use these trial periods to monitor the organization’s performance and make any required adjustments. Regular reviews and fine-tuning ensure the transition plan remains robust and effective.

  1. Setting Up a Timeline

Define Clear Timelines

Establish a clear timeline for your sabbatical and eventual exit. Communicate this timeline to all relevant parties to ensure everyone is aligned and prepared for the transition.

Milestones and Checkpoints

Set up specific milestones and checkpoints to review progress and adjust as needed. Regular check-ins ensure that the transition remains on track and any issues are addressed promptly.

  1. Financial Planning

Ensure Financial Stability

Make sure the organization is financially stable and has the necessary resources to support the transition. Financial stability provides a solid foundation for implementing your sabbatical plan and ensures the organization can continue to operate smoothly.

Review Financial Policies

Review and, if necessary, update financial policies and practices to ensure they are robust and sustainable. This step is crucial for maintaining fiscal responsibility and accountability during the transition.

  1. Personal Preparation

Reflect on Your Goals

Take time to reflect on your personal goals and what you aim to achieve during your sabbatical and post-exit. Clarity on your objectives will guide your actions and decisions throughout the transition.

Seek Personal Development

Engage in activities that promote your personal development and well-being, preparing you for life after your leadership role. Personal growth ensures that you are well-equipped to embrace new opportunities and challenges beyond your current position.


Creating a sabbatical plan as a leader involves strategic foresight, meticulous planning, and proactive engagement with your team and stakeholders. By following these steps, you can ensure a smoother exit transition, empowering your organization and paving the way for continued success in your absence.

Ready to start planning your sabbatical and ensuring a seamless transition? Work with Angela Sasseville of Flourish Executive Counseling and Coaching to prepare for your business exit.


Inc. Magazine. NEWSLETTERS SUBSCRIBE INNOVATE Need A Succession Plan? Take A SabbaticalLong periods of time off let you test people for the next role. Nov 20, 2017.