The Exit Strategy: Lasting Legacies Beyond Goodbye

In professional settings, from small nonprofits to the highest levels of government, there is an age-old trope: leaders cling to power. Anyone in professional spaces has a story or two about a boss who aged out of the role years before they actually retire.

Unfortunately, this is not just an issue in governance, but in everyday life. People nowadays struggle to say goodbye correctly. Relationships end without closure, inheritances are left unwritten, and friendships fall apart in unnecessary fights.

As a culture, we’ve forgotten that every story has an ending and that endings actually matter.

In the modern world, people often have an aversion to endings, associating them with failure and loss. James Rowe, the author of Radical Mindfulness, writes extensively about the fear of death and the role it plays in activism and leadership. In Rowe’s article on the 2024 Presidential Election in the United States, he clearly articulates how both leading candidates failed to confront their own mortality properly.

This inability to adapt to circumstances and recognize one’s limitations is also organizational. Carleton University’s PANL Perspectives website hosts a guidebook titled “It’s Time to Go: A Self-Guided Workbook to Assist with Nonprofit Organizational Closure.” Sometimes, a business, nonprofit, or grassroots coalition needs to come to an end; yet, being prepared to ensure that staff, volunteers, board members, or supporters are ready is a huge challenge.

In essence, it is essential for activists and change-makers of all kinds to engage in transition planning. Below are three tips for people in any position, from the top of an organization to the bottom, to keep in mind.

Plan for the end from the beginning

As someone who has worked in the nonprofit sector for nine years, I have had a fair share of contract roles. The expectation is that you will be in a single position for one or two years, and because of the high turnover rate, there is little guidance on how to approach your role. For instance, organizations rarely provide training manuals for specific positions.

A successful training manual must be carefully crafted from the outset and continually maintained. Everyone in a technical role should start documenting from the very beginning. By doing so, you address potential knowledge gaps as they arise, avoiding a rush at the end of a contract.

Be an inclusive leader: no gate keeping

A good leader will have two or three tentative replacements ready to go at a moment’s notice. A resume is never a good indicator of leadership. Often, when an organization rehires a key position, there is a steep learning curve, and a resume is not a good indicator of who can take on increased responsibility.

To determine who a good replacement is, you need to see them up close. Involve potential successors in your work constantly, even if you are not planning to leave. Regardless of what happens, sharing responsibility makes your work better in the moment and shows you who your staff are.

The benefits of non-hierarchical work structures and decentralization are not just ethical; they are also the most strategic approach to take. The less an organization depends on a single person, the more resilient it is. Teach all staff, volunteers, and supporters the applicable skills, give them responsibility, and transfer institutional knowledge early.

Create systems that outlast you

No person, no matter their qualifications, is as good as an airtight system. When leaving a role, do so with organized files, catalogued emails, and an airtight contacts list. Most professionals find that there is a constant battle to set up systems, as throughout the workday, a million individual crises arise.

It is essential to set aside time throughout the workweek to focus on system upgrades. Even a morning a week is worth it. Additionally, discuss any knowledge transfer systems you have in place for fellow staff. A system is only helpful if someone can take your place relatively quickly without starting from scratch, and the more coworkers that understand a system, the better.

Conclusion

Closure is an attitude, not an action. Effective leaders, staff at all levels, and people in general need to carry with them the understanding that they are not immortal. As I have mentioned before, time is a continuum, and if you learn from history, you do not make the same mistakes twice.

Likewise, if you develop effective systems, prepare for the end from day one, and train the people around you, the ending becomes a lot less of a challenge for you and your mission.

In all, the lessons discussed in this post are intuitive and have more to do with overcoming the human ego than they do with anything else. If you are humble, think long-term, and focus on the betterment of others rather than yourself, you will do fine. It is important to remember that our careers and lives are not determined solely by our own communities, but by the ones that come after us.