A Checklist for Onboarding a New Nonprofit Leader

One of the most important things a mission-driven organization is called to do from time to time is to onboard a new chief executive after having selected him or her. This leader may be called its executive director or its president or its president/CEO. This is especially important when the new leader is replacing a long-tenured one, and even more important when the outgoing executive is the founder. (I have written elsewhere about the special considerations that apply when replacing a founder to help ensure that the usual pitfalls are not experienced.)

Unlike in corporate America, most nonprofits don’t have a battery of consultants and human resource staff to guide the process. Resource constraints usually preclude access to such experts. But it is important, even in a resource-constrained environment, to do as good a job as possible with the process in order to minimize distractions to achieving the organization’s mission.

I was recently helping a client with its founder transition process, and as a result developed the template below which constitutes a new leader onboarding checklist and an outline of a confidential transition memo which is an important part of that process.

1. After the offer is verbally made (normally by the board chairperson) and accepted by the candidate, a formal offer letter should be extended describing all details of the job and related terms, with the job description attached. An onboarding plan should be presented in draft form shortly thereafter, and then finalized after getting input from the new leader.

2. The organization should define the role going forward for the outgoing leader, and ensure that all key stakeholders, especially the incoming leader, understands and supports those roles.

3. One on one meetings with each board member and senior staff member should be scheduled, and position descriptions for each role should be provided to the incoming leader in advance. (Recent performance evaluations for the staff, if available, can be provided later.)

4. An all hands meeting with staff is planned and held (if more than a dozen or two are on the payroll). Otherwise, integrating the new leader into one of the first staff meetings after they are appointed can suffice.

5. Weekly one on one meetings with the board chair should be scheduled for as long as desired by the incoming leader.

6. Meetings should be set up with key funders (with files about those relationships shared in advance).

7. Meetings should be planned and held with key programmatic allies, with the key relationship manager accompanying the new leader if desired.

8. A comprehensive Briefing Book should be prepared that contains the organizational budget for the current year, bylaws, recent board agendas/pre-reads/minutes (anything sensitive in the minutes about the incoming leader and process of choosing them can be redacted), board member job description, officer job descriptions, date of expiration of current board terms, current year and 2022 organizational budgets, agreements and funding history with program partner, human resources and financial/procurement manuals, registrations with local, state and national authorities including IRS determination letter and state fundraising registrations (or at least where to find them), the exit interview with the predecessor, recent trip reports by staff, consultants and board members, and other material identified by the candidate or the board.

9. Needed equipment (e.g., a laptop) should be identified and procured bearing in mind the preferences of the incoming leader. An email account and other online access should be created or arranged, and the process for getting help on information technology issues should be explained clearly. The office they will work out of should be cleared and cleaned to allow for an easy move into it.

10. An organizational public announcement of candidate’s appointment should be published, including strong endorsements by the outgoing leader and the board chairperson. This could be a single press release or it could be in multiple formats, including videos, blog posts, newsletter articles, and more. A community meeting involving partners, beneficiaries, and government officials — online or traditional — can be arranged to augment the process of welcoming the new leader.

11. A Transition Memo should be prepared by the outgoing leader and presented to the incoming leader in draft form. It can then be discussed, and any missing items identified and included in a final version. The transition memo is a confidential, detailed and candid assessment and analysis of the organization’s people, systems, and history by the outgoing leader, with additional elements such as passwords to databases and social media accounts added as appendices. The past performance and future potential of each board member, funder, key volunteer, and program partners/allies is analyzed in depth. The only person who should read this beyond the author is the incoming leader. An outline of a transition memo appears below.

12. Any recently adopted governance and operational reforms should be summarized and presented to the candidate with the rationale for each reform. Other proposed reforms may be presented in draft form, with final approval pending input from the incoming leader.

13. Introductions should be made to others if requested by incoming leader, such as to former staff, former board members, past funders, and any consultants or active volunteers who have served the organization.

Outline of a Leadership Transition Memo (Described in #11 Above)

1. General organizational history (including and especially the stories few know and fewer tell).

2. Confidential description of the current board as a whole (workstyle, culture, areas of strength and weakness, trends, etc.) and of each individual member, including their participation patterns and preferences, likes and dislikes, who they get along with and don’t, strengths and weaknesses as a director, and most importantly, you recommendations about how to best engage them and why.

3. A confidential and detailed description/analysis of each senior staff member, and a less detailed description/analysis of the dozen or so most senior/important staff beyond the senior team.

4. A similar exercise (in a bit less detail perhaps) about past board members and other active volunteers and allies who are not major donors

5. A similar exercise for top 10–15 donors, adding texture and color to whatever is in the donor database. How would you recommend the new leader engage each of them and why (and all relevant background).

6. A similar exercise for the most important allies, including their key staff and board members. This may include people in government, academia, or think tanks.

7. A similar exercise (which can be less detailed) for key vendors (companies and/or people).

8. A description of the biggest opportunities and risks you see for the organization in the next 2 years and why. Include risks related to disgruntled former staff, board, and donors speaking ill of the organization or even taking legal action against it.

9. Ideas you have had about the future of the organization that you haven’t had time to implement that you think merit consideration.

10. Processes to improve the organization that you started but that are incomplete, on hold, thwarted, or nearly complete and what needs to happen next in your opinion.

11. Suggestions people have made (and likely will continue to make) that make no sense to you, and why.

12. Human Resources (HR) policies or practices that are not captured in the HR manual (if one exists).

13. Donor stewardship policies and practices (especially if they are not formally captured in any document in the briefing book).

14. Typical organizational calendar (arc of the year): what happens in the first quarter and why, what happens in the second quarter, etc. Also, how the calendar could be rationalized/improved and attempts to do so in the past and how they panned out.

15. Budget process in recent years and how it can be improved (if at all).

16. What you think the new leader should be most focused in on their first 90 days and first 180 days, and what things may be tempting to focus on that should, in your view, be deprioritized or put off, and why.

17. Key accounts and passwords (or how to locate them).

18. Any other words of guidance for a successful tenure as the organization’s leader.