leadership · whole group · offline + online
The Leader Checkup.folder
Feedback flows down easily and rarely up. The team speaks; the leader listens without defending. Then one real change, with a follow-up date.
// kit v2: a stage-ready 12-slide HTML deck (presenter drawer, run-of-show clock, round timer, built-in QR) · poker-spec print-and-cut cards with backs and blanks · an A3 wall poster · a participant workbook and a one-page session sheet, A4 and US Letter with bookmarks · a machine-readable artifact template.
A leadership session, built as a complete workshop folder: a timed run sheet, printable cards, a 12-slide deck for the screen, a participant workbook and a one-page session sheet — and a mechanic that turns “I am overloaded” into exactly one real hand-off, with an owner, the support they get and a review date.
The props are poker-spec print cards (63.5 × 88.9 mm, bleed and cut guides) with branded backs and a blank; the deck is a single offline HTML file with a presenter drawer, a round timer and its own QR engine. Nothing in this folder needs a projector, and nothing needs an account to download.
the run sheet
// this is the guide file, word for word — read it here, run from it here. the .md at the bottom of the page is the same text, offline.
Folder: `the-leader-checkup` · Category: leadership · 3–10 people · 25 min · offline + online · print props · tool pack License: CC BY 4.0
A 25-minute, 3–10 person leadership tool. Feedback flows down easily and rarely up, so a leader who only hears what's filtered learns wrong. This is a structured upward checkup: the team names what's working, what quietly blocks them because of how the leader shows up, and one ask — and the leader's only job is to listen without defending, then commit to one change.
Objectives
By the end of the activity, participants will have:
- Said out loud — as behavior plus impact, not character — one thing that quietly blocks them, and heard it land without a rebuttal.
- Watched a leader listen without defending, reflect back what was actually heard, and ask one clarifying question instead of explaining.
- Left with exactly one commitment carrying a follow-up date, and a shared list of what the team will watch for.
When to use this activity
- A leader keeps learning the wrong things because everything that reaches them has been filtered.
- A new leader who wants the truth early — run the keep-only pass first and earn the rest.
- You have 3–10 people under or alongside one leader, 25 minutes, and a relationship worth protecting.
Keep · Block · Ask
| Card | The sentence it forces | Why it's shaped that way |
|---|---|---|
| Keep doing | "When you ___, we ___ — please don't stop." | what works gets named before anything is asked to change |
| Blocking | "When you X, we Y." — behavior, then impact | character talk closes the room the moment it opens; "when decisions change late, we lose a day" doesn't |
| One ask | "Next quarter, could you ___?" | a request that is concrete enough to be declined honestly |
The leader's fourth card — the commitment — is the only one the leader writes.
Setup
- 3–10 people who report to, or work under, the same leader.
- A circle of chairs or one shared board. The leader sits where they can hear everyone but does not run the meeting.
- The card faces from `the-leader-checkup-prop-cards.pdf`: a "working — keep doing" card, a "blocking — when you X, we Y" card, a "one ask" card, "the leader's commitment" card, and a blank (see The card below).
- Put `the-leader-checkup-activity-poster.pdf` on the wall so the two rules — "the leader listens, no defending" and "blocks are behavior + impact, not character" — stay visible.
- No projector, no account, no online form. Online, the cards live on a shared board.
- Print one `the-leader-checkup-worksheet.pdf` per group — the one-page artifact sheet the room fills while it talks.
- Put one `the-leader-checkup-workbook.pdf` at each seat if people want their own copy; the sheet above is the group version.
- Optional: open `the-leader-checkup-slide-deck.html` in any browser to run the 12-slide deck on the wall (S opens the presenter drawer, T starts the round timer); `the-leader-checkup-slide-deck.pdf` is the same deck for print.
How to run it
| Time | Phase | Facilitator does | Participants do |
|---|---|---|---|
| 0–7 | Write | Hold the silence; nobody reads aloud yet | Each person writes silently: one thing working (keep doing), one thing blocking (when you X, we Y), one ask. The leader writes too — including a self-critique |
| 7–15 | Speak & listen | Enforce the rule the moment the leader flinches: no defending, no explaining | Round-robin. The team speaks; the leader listens — this is the whole discipline of the exercise |
| 15–20 | Reflect back | Keep it a check, not a rebuttal | The leader says what they actually heard, and asks one clarifying question |
| 20–25 | Commit | Refuse a second commitment; make the first one observable | The leader commits to one concrete change, with a follow-up date. The team names what they'll watch for |
Then run the debrief — see `the-leader-checkup-debrief.md`.
The card
The sheet from `the-leader-checkup-prop-cards.pdf` (poker spec, 63.5 × 88.9 mm, bleed and cut guides, branded back, blanks) carries five faces: working — keep doing; blocking — when you X, we Y (the sentence template is the safety mechanism: behavior first, impact second, character never); one ask; the leader's commitment — filled in by the leader, last; and a blank for your own prompts. Every voice writes before anyone speaks; the cards go to the center of the circle, not to the leader.
Failure modes
- The leader starts defending. The first defense teaches everyone to edit the truth from now on. Rescue: enforce the rule — park explanations until after the round; a single defense costs more than any block said aloud.
- The team gives only "everything's great." Rescue: the leader goes first with a real self-critique: "what do I do that makes your job harder?" Buying honesty costs the leader going first.
- "Blocking" turns into a character attack. Rescue: reframe to behavior + impact — "when decisions change late, we lose a day," never "you're chaotic." The room can only stay open if it stays about actions.
- The commitment is "I'll try harder." Rescue: reject it gently and name the observable version — what changes, by when, and what the team will see when it happens. Ten promises are a performance; one is a change.
Variations
- New leader, first month: run only the "working / keep doing" pass so what's already good gets reinforced before anything is asked to change.
- Peer version: two leads check up on each other; the listening rule is just as hard sideways.
- Quarterly: repeat on a rhythm; the follow-up date from last time is the first thing you check.
Facilitation notes
- The leader is not the facilitator. Someone else runs the clock and the rules; the leader sits in the circle to hear, not to manage.
- Writing before speaking is the safety design — silent cards stop the first two loud voices from framing the whole room.
- Watch where three or more people write the same block; that's a pattern, not a complaint, and it deserves the middle of the debrief.
- End on the follow-up date spoken aloud with an owner in the room. A date nobody holds is how checkups quietly die between quarters.
Put it on the wall
Print `the-leader-checkup-activity-poster.pdf` (A3) to put the run of show, the two rules — listen without defending, behavior plus impact — and the keep / block / ask frame on one wall while you facilitate.
Props in this folder
- `the-leader-checkup-prop-cards.pdf` — poker-spec print sheet (63.5 × 88.9 mm, bleed and cut guides): the five card faces, branded back, blanks
- `the-leader-checkup-guide.md` — this run sheet
- `the-leader-checkup-debrief.md` — eleven numbered debrief questions with what each targets, plus failure modes of the debrief
- `the-leader-checkup-worksheet.pdf` — the one-page session sheet, print-and-fill: keep / block / ask from every voice, plus the leader's one commitment and follow-up date
- `the-leader-checkup-workbook.pdf` — participant workbook: the sheet in plain words, the artifact as fill-in pages, session notes, a before-you-leave page
- `the-leader-checkup-slide-deck.html` / `.pdf` — the 12-slide deck for teaching or projecting: presenter drawer (S), round timer (T), built-in QR, print fallback; the `.pdf` is the same deck for print
- `the-leader-checkup-run-sheet.pdf` — the print edition: this run sheet + the debrief, bound as one A4 document with bookmarks
- `the-leader-checkup-activity-poster.pdf` — the whole activity on one A3 wall sheet: run of show, the two rules, watch-outs
- `the-leader-checkup-tool.json` — machine-facing file (not listed in the download table): the artifact as a machine-readable template: columns, flow, fields, prompts, watch-outs
- `the-leader-checkup-start-here.md` — one page, thirty seconds, then print and go
- `the-leader-checkup-license.md` — what you may do with all of this: run it, copy it, translate it, rebrand it; keep the attribution line
- `SKILL.md` — machine-readable manifest for AI agents
- `*-Letter.pdf` — US Letter editions of the print documents
Agent version
Every file in this folder has a stable public URL — an AI agent can fetch the props, the debrief and this run sheet with three curl commands (see `SKILL.md`). The paper version itself needs no screen at all: no projector, no accounts, just a circle, five cards and one leader learning to listen.
the debrief sheet
// the debrief questions, in full — the .md version prints on one page for the room.
Eleven questions, three failure modes of the debrief itself, one rule: the leader speaks first and defends nothing. Use with `the-leader-checkup-guide.md`. The debrief runs after the commitment, while the cards are still in the center of the circle.
How to run this debrief
- Sort the cards on the table into three piles — keep, block, ask — before anyone talks; the piles speak before the people do.
- The leader answers first. Their honest surprise or pull-to-defend sets the safety ceiling for everyone else.
- Finish on the commitment: say what changes, who watches, and when it gets checked, in that order.
For the leader
1. The real surprise.
"What did you hear that genuinely surprised you?"
→ Proof the filter broke at least once; if nothing surprised the leader, the room wasn't honest yet.
2. The pull to defend.
"Where did you feel the pull to defend or explain — and what did you want to say?"
→ The discipline named from the inside; saying the unsaid defense out loud is how the next checkup gets easier.
3. The repeated block.
"Which block showed up for more than one person?"
→ A pattern, not a complaint — the item that must anchor the commitment.
4. Real change or try-harder?
"Is the one change you committed to real, or a promise to 'try harder'?"
→ The difference between a sentence and a test; the room is allowed to reject the vague version.
For the team
5. Was it safe?
"Did it feel safe to be honest? What made it safer, and what made it riskier?"
→ The checkup's own instrument reading — the safety is the product as much as the feedback is.
6. Heard or waited-on?
"Did the leader actually listen, or wait to respond? People can tell."
→ Uncomfortable, load-bearing; run it even when the answer will sting.
7. The unsaid thing, finally said.
"What did the leader hear that you'd been carrying for a while without saying?"
→ The delayed relief measure; naming it in the open shrinks it.
8. Making the next one easier.
"What would make the next checkup easier to be honest in?"
→ The improvement loop — the answer usually costs the leader something small and specific.
For the commitment
9. What exactly changes.
"What exactly will be different, and how will you all know?"
→ Observability; a commitment nobody can see is a mood.
10. Who holds the date.
"Who owns the follow-up date, and what happens if it slips?"
→ The date needs a name that isn't the leader's; slipping needs a pre-agreed response, not a new guilt cycle.
11. The sentence each person leaves with.
"What's the one sentence each person says aloud before leaving?"
→ The public close; it should be repeatable at the follow-up without embarrassment.
Failure modes of the debrief
- It drifts into a performance review. Blocks start getting scored and ranked. Rescue: keep every question on behavior + impact and the single commitment — titles, ratings and "overall" belong to a different room entirely.
- The leader hijacks reassurance. After each block, the leader explains how hard they're working. Rescue: the leader speaks first, then listens — the rule from the run carries over; two reassurance rounds end the debrief early rather than let it hollow out.
- The commitment debriefs itself to death. Ten follow-up questions water down one promise until it means nothing. Rescue: the commitment gets exactly one test and one date; everything else waits for the next quarterly checkup.
Who is The Leader Checkup for?
A leader who wants an honest read on how they're landing, not another filtered status report — and a team where feedback flows down but never up. It needs 3–10 people and 25 minutes; it runs on a shared board online.
What does it produce?
A keep / block / ask set the leader genuinely heard, and one concrete leader commitment with a follow-up date. No pre/post measure; the artifact is the commitment and the honesty it took to make it.
Can my AI agent use this folder?
Yes. Every folder ships a SKILL.md skill file: frontmatter for matching plus runnable prep commands — fetch the cards, pull the debrief. The three-step workflow (discover, install, run) lives on the skills page, every folder ships a one-command zip bundle, and the machine index is skills.json.
Is it really free?
Yes — CC BY 4.0, no account, no email wall inside a folder. Download it, run it, copy it, rebrand it for your own workshop. Attribution keeps everything free.
make it yours
This checkup needs no online form and no account — a circle and cards. The card prompts are the one file to change: rename keep-doing / blocking / one-ask / commitment to how your team talks, and reprint at poker spec; the leader-listens-no-defending rule stays. The license spells out what you may change.
Files in this folder
All files are free under CC BY 4.0. Attribution: “The Leader Checkup · WorkshopSkill · CC BY 4.0.”