Free Succession Planning Crossword and Word Search for Nonprofit Leaders
The Leaving Well crossword and word search are two free, printable puzzles that teach 16 leadership transition terms—including succession, interim, continuity, and legacy—to nonprofit executive directors, board members, and funders.
Every executive director, founder, and board chair will leave someday. The only question is whether it happens on your terms or in a crisis. Most organizations have never talked about it, partly because nobody shares the same vocabulary for it.
That's where a puzzle helps. It's a low-stakes way to find out who in the room knows these words, who doesn't, and where your organization has a gap. Print one for your next board meeting, leadership team retreat, or grantee convening.
Download the puzzles
Both puzzles are free, print-ready PDFs with an answer key included.
Leaving Well Crossword: 16 clues across and down, from "the plan for who leads next" to "what too many organizations don't have until the resignation letter lands." Answer key on the last page.
Leaving Well Word Search: 16 terms in a 15-by-15 grid, hidden across, down, and diagonally. Answer key on the last page.
Download the word search (PDF)
Best for: board meetings, leadership retreats, funder convenings, cohort sessions, and new-board-member orientations.
The 16 leadership transition terms, defined
Candor: Saying the true thing without sugarcoating it. Transitions go better when a board and an executive can be honest about timing and readiness.
Chapter: A leader's time at the organization, with a beginning and an end. Treating tenure as a chapter makes leaving a normal part of the story.
Continuity: Mission carried through change, no matter who is in charge. It's the goal of every transition plan.
Exit: A departure, ideally planned well in advance. It can be a retirement, a resignation, or an unexpected loss.
Funded: The part of a transition plan most often forgotten or missing: real money set aside for interim leadership, a search, and overlap.
Grief: What a team feels when a leader goes, even when the departure was planned. Name it early so it doesn't surface as turnover or conflict.
Interim: A temporary leader who keeps the organization steady between executives.
Leaving Well: Our framework and brand name: a planned, steady, mission-protecting approach to leadership departures.
Legacy: What a leader leaves behind, whether they planned it or not.
Plan: What too many organizations don't have until the resignation letter arrives.
Readiness: Being prepared before the departure, not after.
Search: The hiring process for the next executive leader.
Steward: Someone who looks after the organization, regardless of title.
Succession: The plan for who leads next, best made before anyone needs it.
Transition: The stretch between one leader and the next.
Trust: What honesty builds and secrets erode. It's the asset a transition spends fastest.
How to use the puzzles with your board, team, or grantees
Give people five minutes, then use what comes up as the conversation.
At a board meeting: Hand out the crossword as an icebreaker. Afterward, ask which words took the longest and whether the board has a written succession plan.
With your leadership team: Use the word search to open a retreat session. Then ask who, besides the executive director, could step in for 90 days if needed.
At a funder convening or cohort session: Use either puzzle as a warm-up, then ask grantees what is funded, planned, and written down.
For new board members: Include the crossword in your orientation packet so everyone starts with the same language.
Why shared language matters before a leader leaves
Organizations that can't name the parts of a transition usually can't plan for one. When an executive director gives notice, boards often discover they don't know the difference between an interim leader and a successor, haven't set money aside, and haven't decided who is in charge of the search.
A shared vocabulary doesn't replace a plan, but it makes starting one easier. It lets a board chair say "we need to be funded for an interim" and have everyone understand the ask. It also helps funders ask better questions of the organizations they support.
If the puzzles show a gap, that's useful. You're finding it while you still have runway.
Frequently asked questions
What is succession planning for a nonprofit?
Succession planning is deciding in advance who will lead, who will step in temporarily, how a search will run, and how it will be paid for when a leader leaves. A planned approach turns a departure from an emergency into a managed transition.
What does "interim executive director" mean?
An interim executive director is a professional temporary leader who keeps an organization steady between executive employees. They manage operations, support the board, and help prepare for the next leader.
Where do I start if my organization has no transition plan?
Start with a conversation, not a document. Use the puzzles to get your board talking, then book a Transition Readiness conversation at with us here.
People leave. Be ready.
Every executive director, founder, and board chair will leave someday. Start planning while you have runway.
Get prepared at ChooseLeavingWell.com.