Executive Transition Fund

Executive Transition Roadmap

What We Are Learning

The NSI funders are continually evolving their understanding of key readiness factors and transition planning considerations in close partnership with grantee partners, including: an informed and engaged board, a departing leader who is personally ready, and a plan in place for the transfer of key knowledge and relationships, among others. Participants have also reported the importance of peer exchange to share practices and resources, to combat isolation and to normalize feelings around transition. To view more of what we have collectively learned in greater detail, please click on the four Transition Roadmap phases below to see a list of likely transition activities and key considerations within each. 

Links to tools and resources to help guide you through your process.

Phase I: Early Transition Planning

Likely Activities:

  • Departing executive informs the board
  • Transition timeline is established
  • Transition committee of the board is created
  • Organizational culture assessment
  • Board evaluation & development
  • Staff restructuring & development
  • Transition plan & budget drafted

Phase II: Pre-Recruitment

Likely Activities:

  • Make decisions regarding staff restructuring, right-sizing the role, or co-leadership models
  • Consider strategic benefits of interim executive engagement
  • Vet transition consultants/search firms (Learn more)
  • Identify key stakeholder groups and seek input
  • Draft/update job description
  • Engage coach for departing leader to facilitate the process of documenting institutional knowledge and letting go
  • Ongoing Board development & unconscious bias training
  • Ongoing Staff development
  • Establish communications plan, design announcement collateral, contact key funders
  • Plan transition-related fundraising campaign and/or farewell event
  • Refine transition plan & budget

Phase III: Recruitment

Likely Activities:

  • Coaching for outgoing executive
  • Communicate transition plan with staff
  • Make public announcement
  • Launch search
  • Conduct interviews
  • Execute plan for key funder outreach/hand-offs
  • Establish a plan for staff support and change management support
  • Ongoing Board development
  • Ongoing Staff development
  • Finalize terms of post-transition engagement with outgoing executive and/or exit compensation agreement
  • Finalize plan for a transition-related fundraising campaign and/or farewell event
  • Finish documenting the outgoing executive’s institutional knowledge
  • (Re)Consider strategic benefits of interim executive engagement
  • Refine transition plan & budget

Phase IV: Offboarding / Onboarding

Likely Activities:

  • Coaching for board chair
  • Executive farewell and/or welcome event(s)
  • Set clear expectations of communications and meeting schedules between the board chair and the incoming executive
  • Establish an agreed-upon onboarding plan with the incoming executive (listening/learning, assessment, alignment, etc.)
  • Introduce incoming executive to staff and key external relationships
  • Orient incoming executive with full board; share priorities and receptiveness to changes
  • Provide candid communication with an incoming executive about any potential “landmines”
  • Coaching for the incoming executive
  • Coaching senior staff with new roles
  • Consulting contracts to complement incoming leader's skill sets, or conduct organizational assessments to expedite onboarding process

Key Considerations during Each Phase

Phase I: Early Transition Planning

Key Considerations during this Phase:

  • Readiness: Is the departing executive ready personally, financially, and professionally to transition? What factors are influencing this readiness? Link to relevant report and link to relevant self-assessment tool

  • Timeline: How proximate is the anticipated departure? What are the major factors that will dictate this timeline? Is there flexibility?

  • Strategy: Does the organization have a current strategic plan? How might this transition be an opportunity or challenge in meeting those goals?

  • Staff Development: Is the executive’s job description reasonable, or does the role need to be right-sized in order to set the next leader up for success? How might senior staff roles evolve as a result of the transition? What support will staff need to successfully adapt to these new roles? What decision-making processes could senior staff be brought into now, to support their growth in anticipation of the transition? How much staff time will be required to navigate the transition? Link to relevant resource

  • Board Development: Is this a founding, governing, or institutional board? How much oversight have they had over the executive? Will the board need to step up to support a new leader (what about a first-time executive director?) Link to Nonprofit Board’s Lifecycle resource

  • Culture: How does leadership characterize the organizational culture and current climate? Can the organization articulate its guiding values? Are there signs of dysfunction (staff attrition, multiple sub-cultures that don’t align, etc.) What elements of culture should be protected, and what needs realigning during the transition? How centralized is the power in the organization? How attached is the organization to the departing leader? Link to relevant podcast

  • Alignment: Are board and staff operating with the same value/within the same culture? Are board and staff on the same page for what they are looking for in an executive? Are they looking for a change; and if so, how do they articulate the needed changes? What qualities and skill sets are of greatest importance to each group?

  • Equity & Representation: Do the board and staff reflect the community served? Does the organization have explicit values or goals around diversity, equity, accessibility, inclusion, and belonging? If so, how should they show up in recruitment/hiring and onboarding practices? How recently has the board gone through an unconscious bias training together? What organizational culture and values alignment work needs to be done to set a new BIPOC leader up for success? Link to relevant report

  • Financial: What is the current financial position of the organization? How dependent are the funding relationships on the departing executive? When should key funders be brought into the conversation?

  • Plan: Is there a phased transition plan that addresses development and planning, successful exit, recruitment, onboarding and support? What are the priority transition activities, who needs to be involved, and when? Link to relevant checklist

  • Fundraising: What are the transition-related expenses that need to be budgeted for? Is the organization willing and able to contribute internal resources towards the transition budget? How might transition-related fundraising needs dictate the timeline for going public with the transition?
Phase II: Pre-Recruitment

Key Considerations during this Phase:

  • Interim Executive: How might the transition timeline, strategic goals related to the transition, and organizational culture change needs suggest the need for an interim executive? Are additional compensation expenses being budgeted for interim or acting executive during transition period?  Link to relevant resource

  • Internal Candidate: If the board is inclined to conduct an external search despite strong internal candidate(s), what are their reasons, and how might they be informed by unconscious bias? Link to relevant NPQ Article

  • Recruitment Support: To what extent does the board desire to/have the capacity to execute outreach and recruitment activities? If a full-service search firm is not desired or financially feasible, what project management/facilitation/outreach support is needed

  • Internal Candidates: Do you anticipate there may be internal candidates? If so, what communication strategies can the search committee use to ensure a fair process and earn staff buy-in and trust in the ultimate decision

  • Board Dynamics: How do you run meetings? Who speaks the most during meetings? How are board leadership roles determined? Have newer members been properly onboarded? Have board members had time to build trust and thus the ability to navigate difficult conversations with one another? How might virtual meetings during the pandemic have impacted these dynamics in recent years?

  • Setting Boundaries & Expectations: How might the process be best communicated with the outgoing executive, board members not on the search committee and with senior staff to collect necessary input, establish clear boundaries, and pave the way for buy-in on the ultimate decision?

  • Co-Leadership: What organizational development activities should precede a co-leadership model decision to set co-directors up for success? How might the recruitment process be designed to allow for a successful partnership? What are the benefits and trade-offs to a co-leadership model, and how are they being communicated to stakeholders? How might cross-race, cross-gender, or intergenerational partnership dynamics show up? Link to relevant article

  • Communications Strategy: How are you framing the transition for key partners as an opportunity for organizational growth and greater alignment with organizational values? What are ways that you can communicate a message of strategy and proactiveness versus vulnerability and reactiveness? How might you call upon funders to protect their investments by leaning in during this moment.

  • Vetting a Search Firm: See table below

Vetting a Search Firm

Questions to Ask:

Did They Ask You About…

Does the Scope of Work Include:

Questions to ask References:

Phase III: Recruitment

Key Considerations during this Phase:

  • Equitable Search and Interviewing: What are equitable search and interviewing practices? What training would be helpful for the search committee before meeting with candidates? Link to relevant resource

  • Documentation: What institutional knowledge should be readily accessible to senior staff, board members, and the incoming executive that isn’t already? (Consider relationship/knowledge of donors and partners, senior staff responsibilities, passwords, organizational memberships, decision-making framework, links to archival documents, etc.)

  • Setting a BIPOC Leader Up for Success: When recruiting a BIPOC leader for a historically white-led organization, anticipate what ways unconscious bias may show up, and what ways the organization can operationalize and institutionalize values of inclusion and belonging in advance of onboarding? Link to relevant report

  • Exit Compensation: What are the options for a Board interested in compensating a founder or long-tenured leader (particularly one that has been historically undercompensated)? What are the relevant legal and risk management questions? Link to relevant article

  • Selling the Job: How is the opportunity being pitched to strong candidates and who is best apt to communicate this message? How can board members be appropriately deployed to assist recruiters in attracting applicants in such a competitive employment market?
Phase IV: Offboarding/Onboarding

Likely Activities during this Phase:

  • Coaching for board chair
  • Executive farewell and/or welcome event(s)
  • Set clear expectations of communications and meeting schedule between board chair and incoming executive
  • Establish an agreed upon onboarding plan with the incoming executive (listening/learning, assessment, alignment, etc.)
  • Introduce incoming executive to staff and key external relationships
  • Orient incoming executive with full board; share priorities and receptiveness to changes
  • Provide candid communication with incoming executive about any potential “landmines”
  • Coaching for incoming executive
  • Coaching for senior staff with new roles

Key Considerations for during this Phase:

  • Setting Healthy Boundaries: If outgoing executive will remained involved in another capacity, what are ways that clear boundaries can be set so that the engagement is at the discretion of the next leader (examples: create new email address for outgoing leader, establish restrictions on who may contact outgoing leader, set a defined end date for engagement (even if open to extensions). Link to relevant article; Link to Roles & Responsibilities Resource
  • Co-Leadership Facilitation: If adopting a co-leadership model, how might the directors benefit from both individual coaching and a shared facilitator to establish the partnership (respective roles, decision-making protocol, etc.) Link to relevant article
  • Executive Resourcing: Does the incoming executive need a leadership coach, executive mentor(s), or consultants to conduct organizational assessments to identify gaps in organizational effectiveness (such as internal financial controls)? Link to relevant resource
  • Change Management: In what ways are staff processing the change, and what space is being given for individual/group processing and support? How might the use of ceremony/events serve the organization’s need for reflection and processing? Link to relevant resource
  • Prioritization: How might staff-championed priorities compete with board-championed priorities? How can the incoming executive set clear expectations by charting organizational capacities against needs
  • Performance Evaluation: How often and who from the board is meeting with the incoming leader for the first 18 months? What checkpoints and key milestones can be established from the beginning, and who will be ultimately responsible for performance evaluation? Link to relevant article