Home For School Leaders
For School Leaders
Reading your staff's interviews, coaching each person, and following up.
AI integration is a continuous-improvement problem, not a policy problem. A policy says what is allowed. A diagnostic shows where your people actually are, and where to invest next.
Running the diagnostic#
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Ask each staff member to take the interview with the AI tool they use most. It takes about twenty minutes. Open the interview
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Collect the records it produces. Every record uses the same format, so they can be loaded together.
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Read them in two passes with the analysis prompt below: once for the institution, once for each person.
Two disciplines govern both passes. Placement rests on behavioral evidence — what a person demonstrably does, not what they claim or aspire to — and when the evidence is ambiguous, the placement goes to the lower stage. Where the interviewing model drew on saved memory or past chats, that record is weighted above self-report, because it shows actual use rather than a person's account of it.
Treat every placement as a starting position for reflection, not an evaluation. A model's reading of an interview is a first draft; your conversation with the person is the review.
Two passes over one dataset#
The submissions are loaded together and analyzed in two passes. The first is aggregate: it produces the picture a leadership team needs to decide where to invest — where the organization actually sits, what people do with AI, what they want to do and cannot, and where current practice is quietly risky. The second is individual: for each staff member it produces a short analysis and a set of development artifacts they keep using after the exercise ends.
Pass one: the institutional picture
The aggregate pass returns the distribution of staff across the twelve cells, the same distribution broken out by department, the most common things people actually do with AI, their stated aspirations and blockers, the places where uncritical use is institutionally risky, and the outliers worth learning from. It also surfaces patterns the administrator did not think to ask for.
The shape is more telling than any single number.
The institutional risk sits in the upper-left: the cluster of fluent, heavy users whose verification has thinned (Integrated and Generative engagement at Receptive treatment). The cautious corner — low engagement with careful handling — is not a danger but an opportunity cost: seasoned judgment the organization is underusing. Naming which corner is which is what turns a distribution into an investment decision.
Pass two: personalized development artifacts
For each person the second pass produces three things. The artifacts are calibrated to placement, which is the whole point. A Functional user is not pushed toward system prompts; a Generative user is not handed beginner advice.
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Email
A short email names where their practice sits and gives a single most-leveraged next step.
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Coaching prompt
A reusable prompt the person pastes into their own tool going forward keeps the development on a regular cadence.
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Custom instructions
Stages 1 and 2 only
For the least-engaged staff, a draft set of custom instructions scaffolds better use without asking them to learn prompt design first.
The analysis prompt#
Loaded into a project workspace with the submissions, this is the prompt that produces both passes. Part one runs first; the per-person artifacts run afterward, in small batches so the administrator can catch and correct any drift toward generic phrasing.
Fill in the bracketed parts for your school.
You are helping me analyze diagnostic interviews from approximately [number] employees of [school name], [one-line description of your school]. Each submission captures a snapshot of an employee's engagement with AI tools.
Your work has two parts: aggregate analysis (for an in-service follow-up) and individual analysis (for personalized follow-up to each employee).
FRAMEWORK — The Engagement-Discernment Grid
Engagement (mode of use):
1. Peripheral — AI sits at the edge of the work. Use is occasional or exploratory, and no regular task depends on it.
2. Functional — AI handles discrete tasks on demand, such as drafting a message or looking something up, but it is not built into how the work gets done.
3. Integrated — AI is part of recurring workflows. It is a routine partner in core work like communication, grading, and content preparation.
4. Generative — AI is something the person builds with: custom tools, configured context, and new workflows that extend what they can produce.
Discernment (how wisely AI use is judged):
A. Receptive — Output is trusted by default. Little scrutiny is applied, and understanding of AI's limitations is thin.
B. Critical — Output is scrutinized after it is produced: compared against a source and checked before use. Discernment as hygiene.
C. Prudent — Judgment comes first: whether AI belongs in the task, how it should be used, and what must stay human. Discernment as architecture.
The columns differ in when judgment happens, not in how much effort it takes. Two people can check output the same way and still sit in different columns.
Place each employee in one cell. Base placement on behavioral evidence in the structured fields and narrative — what they actually do — not on their self-claims or aspirations. Be conservative; when ambiguous, place at the lower stage. Some submissions will include data the interviewer LLM pulled from saved memory or past chats; weight that more heavily than self-report, since it reflects actual usage.
PART 1 — AGGREGATE ANALYSIS
Produce:
- Distribution across the 12 cells (count and percentage per cell)
- Distribution by role or department
- Top 5 use patterns: what people actually do with AI, with example phrasings drawn from the data
- Top 5 stated aspirations
- Top 5 stated blockers
- Discernment red flags worth surfacing — places where receptive use is institutionally risky (e.g., grading, parent communications, theological writing)
- Outliers in either direction. Especially: anyone placed at Generative. These are people I should learn from. Quote them.
- Three patterns I should highlight that I might not have anticipated. Surprise me.
Write Part 1 as a memo of about 1,200 words. Prose with selective bullets where they genuinely serve clarity. Do not pad. Cite specific quotes from submissions where they make the point better than your summary would. The audience is me — [your role] — preparing for an in-service follow-up presentation.
PART 2 — PER-EMPLOYEE OUTPUT
Do not generate Part 2 until I ask for it, and do it in batches of 10 employees at a time. For each employee, produce two required artifacts and one conditional artifact.
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Artifact 1 — Email to employee (~250 words):
- Subject line that is specific, not generic
- One sentence naming where they are on the grid, in plain language (describe the behavior; do not name the cell directly)
- One paragraph reflecting what stood out from their interview, specific to them
- One paragraph on the single most leveraged next step for them, with a concrete example tailored to their actual work
- For employees at stages 1 or 2: include a closing line directing them to their custom instructions draft (Artifact 3)
- For employees at stages 3 or 4: close with a pointer to the coaching prompt
- Tone: direct, warm, specific. Do not flatter. Do not list "areas for growth" — pick one thing.
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Artifact 2 — Coaching prompt (~300 words):
A prompt the employee pastes into their LLM going forward to keep developing. It should:
- Establish a coaching persona calibrated to the employee's current stage. Do not push a Functional user to think about MCP servers. Do not patronize a Generative user.
- Reference their specific role and the work they actually do, drawn from the submission
- Set up a periodic check-in cadence ("every Friday, ask me what I tried this week and what I noticed")
- Push them diagonally — toward both more sophisticated engagement and more discernment
- For Receptive users: build in a verification reflex they have to perform out loud before leaving any chat where output will be used
- For high-engagement + Receptive users: emphasize discernment exercises (catching errors, naming tasks they should refuse AI for)
- For Prudent + low-engagement users: nudge toward experimentation with a specific, low-stakes first step drawn from their stated role and work
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Artifact 3 — Draft custom instructions (STAGES 1–2 ONLY; omit for stages 3–4):
Generate a ready-to-use custom instructions block the employee can paste directly into Claude (Settings → Profile → Preferences) or ChatGPT (Settings → Personalization → Custom Instructions). Format it as two sections matching each platform's standard fields:
"What would you like Claude/ChatGPT to know about you?"
"How would you like Claude/ChatGPT to respond?"
Ground the draft in:
- Their actual role and stated primary work activities
- Any tools, communication patterns, or tasks named in their interview
- Their current discernment level — keep verification prompts and guardrails visible in the instructions if they are Receptive, lighter-touch if Critical
Keep the draft short enough to be non-intimidating (under 200 words total) but specific enough to be immediately useful. Do not include aspirational features they have not demonstrated readiness for.
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Begin Part 1 when I paste or upload the submissions.
Reading and coaching individuals#
Choose a position to see how it shows up in an interview, how to coach it, and what to avoid.
Generative · Receptive
4A: Active Risk
If adoption is over-rewarded culturally, the pressure leads here. Cognitive offload becomes cognitive debt.
How it shows up
Many tools built, few checks, and recognition for adoption.
How to coach
- Change what is rewarded: praise checking and boundaries, not volume.
- Require human review on any tool others use.
- Pair them with a 4B or 4C builder.
What to avoid
- Holding them up as the model for adoption.
- Banning their tools outright, which loses the skill and the goodwill.
Generative · Critical
4B: Rigorous Builder
How it shows up
Strong builds and strong testing. Boundaries are absent or set after the fact.
How to coach
- Ask whether a tool should exist in every review conversation.
- Involve them in setting policy.
- Pair them with a 4C builder.
What to avoid
- Treating quality control as sufficient.
- Sending more build requests without a purpose review.
Generative · Prudent
4C: Wise Builder
How it shows up
Builds with written purpose, retires tools that don't serve, and is sought out by colleagues.
How to coach
- Give them a formal role in guidance and peer coaching.
- Protect their time.
- Ask for help setting school-wide boundaries.
What to avoid
- Making them the sole AI authority.
- Letting others defer to them instead of developing their own judgment.
Integrated · Receptive
3A: Capable but Uncritical
The primary institutional risk by prevalence. If an employee is customer-facing, AI discernment is non-negotiable.
How it shows up
Fluent, frequent use in core work. Vague about checking. Errors are caught by others. Probe for silent verifiers before concluding.
How to coach
- Treat this as the top priority by prevalence.
- Build checks into shared workflows rather than relying on personal promises.
- Start with customer-facing staff.
What to avoid
- Celebrating productivity alone.
- Public correction, which drives silence.
Integrated · Critical
3B: Diligent Integrator
How it shows up
Frequent use and specific stories of caught errors, but few stated boundaries. Signs of checking fatigue.
How to coach
- Affirm the checking habit.
- Introduce task triage as relief, not more work.
- Have them model checked workflows for others.
What to avoid
- Adding volume.
- Treating checking as the finish line.
Integrated · Prudent
3C: Intentional Integrator
How it shows up
Articulates boundaries and reasons. Checks are targeted. Use is routine.
How to coach
- Invite them to lead peer learning or a pilot.
- Ask them to draft department guidance.
- Support building if they want to grow upward.
What to avoid
- Pressuring toward Generative as if it were required.
- Loading them with mentoring without giving them time for it.
Functional · Receptive
2A: Unchecked Convenience
How it shows up
Comfortable, frequent task-level use. Can't describe checking beyond a skim. Errors have reached others.
How to coach
- Make source-checking a team norm rather than a personal correction.
- Give a simple three-fact checklist.
- Celebrate caught errors.
What to avoid
- Shaming errors, which drives use out of sight.
- Rewarding speed or volume until checking is in place.
Functional · Critical
2B: Careful Practitioner
How it shows up
Talks easily about errors caught; struggles to name tasks kept for themselves. Checking is strong on high-stakes work and lighter elsewhere.
How to coach
- Praise the checking habit specifically, because it is real.
- Ask how they decided to use AI for a given task, and listen for whether the decision came before or after.
- Offer the decision log as an experiment, not a requirement.
- Pair them with a 2C or 3C colleague to compare stays-human lists.
What to avoid
- Pushing for more AI use before boundaries exist.
- Treating accuracy checks as the finish line.
- Handing them a list of boundaries instead of having them build their own.
Functional · Prudent
2C: Measured Practitioner
How it shows up
Names boundaries quickly, with reasons. Checks output. Use is limited by time or policy, not uncertainty.
How to coach
- Remove obstacles: clarify policy and protect time.
- Ask them to share their boundaries with colleagues.
- Invite them into pilot groups.
What to avoid
- Treating low volume as low skill.
- Assigning them more discernment training they don't need.
Peripheral · Receptive
1A: Untested Trust
How it shows up
Few examples of use. Describes outputs used without mentioning any checking. Vague about how AI fails.
How to coach
- Frame checking as professional rigor, not technical skill.
- Pair them with a 1B or 2B colleague on one shared task.
- Give explicit permission and time for low-stakes trials.
What to avoid
- Pushing for more use before checking is in place.
- Mistaking unfamiliarity for principled caution (1C).
Peripheral · Critical
1B: Wary Sampler
How it shows up
A few specific examples, each with checking. Low frequency. No stated principle behind the low use.
How to coach
- Affirm the checking habit by name.
- Offer time and explicit permission to give AI one recurring job.
- Ask what would make AI useful in their work.
What to avoid
- Labeling them resistant.
- Pairing them only with enthusiastic adopters who don't check.
Peripheral · Prudent
1C: Passive Caution
Risk: stagnant growth as the broader culture develops. Tradeoff: opportunity cost as tools become more capable.
How it shows up
States reasons and boundaries clearly. Few or no recent examples of use. The position hasn't changed in a long time.
How to coach
- Honor the conviction publicly and invite it into school conversations.
- Ask them to help write boundary guidance.
- Offer one low-stakes task to test against their own standard.
What to avoid
- Treating them as resistant or behind.
- Pressuring for volume, or letting their view stand as a veto.
After the assessment#
- Review before sendingGenerate the individual artifacts in batches of ten and read each one before it goes out. Catch drift toward generic phrasing early.
- Pick one thingEach email names where the person's practice sits and one next step, not a list of areas for growth.
- Keep a cadenceThe coaching prompt sets a weekly check-in the person runs with their own tool, so development continues after the exercise ends.
- Invest by cornerUse the aggregate picture to decide where training, time, and permission go: checks for the fluent and uncritical, opportunity for the cautious.
- Coach to the positionUse the notes for each position above in the conversations that follow.
Let's talk
If you are thinking through how your school uses AI, I would be glad to talk. I have run this diagnostic with a full staff and worked through what comes after: the conversations, the coaching, and the decisions about where to invest.
Whether you want a single conversation or someone alongside your team as you work through it, write to me. No pitch, just a conversation about where your school is and what would help.
Will Mead
Email Willw.mead@enlightiumacademy.com
Always Discerning.