The Big Question for Seasoned Executives: When is the Right Time to Leave?

All executives share the desire to step out of their role on a positive note and help the organization flourish under new leadership. But deciding when to leave is not easy for most executives, and it is especially challenging for those who devoted a significant part of their career to building and/or transforming an organization. The significant changes over the past two years can make this decision even more complicated.

So how do you answer the big question? Here are the top five things nonprofit executives should think about when determining the right time to leave.

1. How is the organization performing?

Is the organization in a growth period, adjusting to recent growth, or rebuilding after a difficult period? Does the organization have a sustainable strategy for the next few years? What does the organization need and want from its executive during this cycle? Do you want to and are you able to offer that leadership?

2. How are your relationships within the organization?

Is there a positive working relationship between you, the board, managers, or staff? If so, this is a great sign that you are enjoying your role and it is working for the organization. If relations are strained, consider the source of that strain. Do you and/or members of your organization believe you are still the right person for your role? Are people wondering if you will have the energy needed to be effective for much longer?

3. What are your personal and professional goals beyond leading this organization?

Over time, a leader’s perspective and goals change. Setting personal goals and paying attention to what activities energize you helps inform how long you should plan to stay. Do you need a vacation, a sabbatical, or a real change? What’s next for you?

4. How will I know it is time to move on?

Are there organizational milestones pending, such as the development of a new program or a fundraising campaign that you want to complete? When these milestones are reached, do you want to sign up to lead the next big agenda item for the organization, or is that a good time to consider a transition? What signs can you look for that show you have completed what you set out to do and it’s time to begin planning a transition?

5. What can I do now to make sure both the organization and I are ready for a planned or unplanned departure?

Do you have a rainy day fund for unexpected expenses or events? Are you clear on what you need to do to prepare financially for the long term? As for the organization, is it ready for unplanned departures of key leaders? Is there an emergency leadership continuity plan and a succession policy for the chief executive and other key leaders?

Enlisting help with planning your eventual exit is tricky business. You don’t want to lose control over when you depart your executive role. Unfortunately, these concerns too often stop executives from taking steps to prepare for a transition until it is too late to make a difference. Early attention, years before departure, to the question above greatly increases the odds of a successful transition when it occurs.

If you have any questions about this article or how we help your organization with transition and leadership planning, contact Karen Schuler at [email protected].