By Abby Rosenswaike
By: Abby Rosenswaike
When a senior executive announces they’re leaving, most organizations immediately focus on operations, communications, and the legalities involved in a separation: employment agreements, handoff logistics, how to word the announcement. HR tends to get brought in after those conversations have already happened, and that delay costs organizations more than they realize.
The First 48 Hours
Not all departures carry the same risk, and the response needs to reflect that. Anjeanette Gunter at Just Bridges has mapped executive exit types across two factors that tend to determine where the real vulnerabilities are: how planned the departure was, and how much alignment exists around it.
An unplanned exit due to sudden illness, burnout, or an emergency means the first move is a knowledge audit. What lives only in this person’s head, and how do you get it out before they’re gone? A contentious or board-directed exit means you’re managing competing narratives and unclear authority at the same time. HR needs to be in the room, because if we’re not, someone else is already controlling the narrative.
Whatever the exit type, I push to hold a full staff meeting the same day. People need to hear from leadership directly, before they hear it from each other. You won’t be able to share everything, but you can communicate who is leading right now and that there is a plan.
Communication and the Cost of Waiting
There is a common pattern where leadership tries to control a narrative and ends up damaging the trust they were trying to protect. It tends to happen through delay, vague statements, and the belief that staying quiet buys time for more planning.
Gunter uses the term “Founder Drift” to describe what happens when a leader gradually disengages without a formal announcement. Responsibilities become murky, and staff start filling in the blanks themselves. Even in a planned exit, sitting on information too long produces the same effect. People do not tolerate ambiguity well, especially when it touches their jobs and the stability of the organization they work for.
I’ve seen this play out at a school where a principal resigned and then quietly told individual teachers she was leaving because she was unhappy with the organization. There was no formal communication from leadership, just her version of events moving through the building without any counter-narrative. She eventually took a group of teachers with her to another district.
When I advise leaders who want to wait before communicating, I frame it as organizational risk rather than an HR preference. The cost of a trust breakdown is far higher than the discomfort of an early, honest announcement. HR’s role is to co-author the communications strategy, not to implement someone else’s version after the fact. That means advocating for the same-day all-staff meeting, explicitly revisiting the organization’s mission and vision, conducting stay interviews, and reassuring staff directly that their jobs are not at risk.
The 60-Day Stabilization Window
The 60 days following an executive departure can either protect an organization or unravel it. It’s helpful to break that window into three phases of roughly twenty days each.
The first phase is about alignment: a written transition plan is in place, knowledge transfer begins immediately, the board has full visibility, and internal and external communications have gone out. The second phase shifts to operations: grant funders, vendors, and key board relationships are informed, an organizational calendar is built with all deadlines and compliance obligations documented, and a centralized reference is created so people know who does what and who to contact. The third phase is about close-out: interim or successor leadership is fully established with clear decision-making authority, complete systems access, and enough context to lead effectively from day one.
One failure mode worth naming is what Gunter calls the Symbolic Exit: when someone steps down in title but retains informal authority. It is not a 60-day problem. It can persist for years. I worked with a startup founder-CEO who suffered a serious illness and had to step down. There was a planning period on paper, but the leadership team had difficulty translating it into an actual plan. Decisions got rushed, deadlines were missed, and morale dropped significantly. The business survived, but only through outside intervention, and it was permanently shaped by how the transition was handled.
The 60-day framework only works if succession infrastructure already exists before the departure. If you are building the bench from scratch when someone announces they are leaving, the window is already compressed.
What a New Leader Needs on Day One
The difference a structured handoff makes is significant. I supported an organization as their Chief People Officer was preparing to leave. She had been there since the beginning and had built most of the HR and operations infrastructure from the ground up. I came in 30 days before her last day and walked into a fully developed transition file: systems access, a cyclical calendar with action steps and background notes, a reference guide for every key relationship. That file allowed me to do what I was actually brought in to do.
Beyond documentation, a new leader needs real cultural intelligence: the actual norms, informal power dynamics, and current staff sentiment. An org chart does not tell you the difference between stated culture and lived culture. They also need genuine stakeholder context, not just names and titles, but an understanding of who the key players are and what they expect from this role.
One practice I have seen work well is “empathy interviews”: 15-minute one-on-ones with every staff member in the new leader’s first 60 days. Thoughtful incoming executives ask questions like, “What brought you to this organization? How do you see your role connecting to the mission? What do you do outside of work?” Staff view it as a leader who is there to understand them, not just manage them. When I’ve seen this happen, the dynamic noticeably shifts, even for staff who were anxious about the transition.
On hiring: a fast hire almost always creates problems down the line. I have seen organizations bring in candidates with strong backgrounds and strong references who were not equipped for the specific cultural context they were walking into. In one case, a leader who gave feedback publicly, in an environment where feedback was delivered privately and direct communication was the norm, lost the confidence of the staff within months. Understanding the work culture, communication norms, and community context of the organization you are hiring into is not optional. The approach I advise is to hire slow, and move fast if it isn’t working.
The Bigger Picture
Leadership transitions surface everything that is underdeveloped in an organization: succession planning, documentation, communication infrastructure, and cultural onboarding. The organizations that handle them well are not necessarily the ones that move fastest. They are the ones where the people strategy was already in place before anyone announced they were leaving. HR’s job is to build that infrastructure in advance and to be present when it matters.
References
Gunter, Anjeanette. Founder Exits in Nonprofits: Types, Patterns, and Structural Dynamics. Published by Just Bridges