Field Guide · 30 Days

The Activation
Playbook.

Three phases. Nine moves. Five rituals. Six anti-patterns. The minimum viable set of things a leader actually does to shift a culture from rollout to movement. No frameworks worth printing on a mug. Start Monday.

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30
Day arc
09
Moves
05
Rituals
06
Anti-patterns
Phase 01 · Days 1–10

Surface the truth already in the room.

Stop pretending the rollout hasn't started. 75% of your people are already using AI in private. Your first job is to make the shadow visible — without punishment.

"We don't have the answers. We have a direction and a willingness to figure it out with you. I'd rather we be wrong fast together than right slowly apart."

Say this out loud
01

Run the Shadow AI Amnesty

A 45-minute all-hands. One question: what are you already using AI for that nobody on this call knows about? No slides. No recording. No retaliation. Document every workflow that surfaces.

02

Map the actual workflows

Pick three roles. Shadow them for an afternoon. Find the seams — the handoffs, the rework, the rituals that exist because someone, sometime, decided they should. These are the leverage points.

03

Name the four fears, out loud

Relevance. Trust. Capability. Identity. Put them on a slide. Say the words. Watching a leader name the unspoken halves the room's anxiety on the spot.

Phase 02 · Days 11–20

Build the safe-to-fail sandbox.

Movements need a place to try things before they're load-bearing. Without a sandbox, every experiment becomes a referendum on someone's job.

"This experiment is allowed to fail. If it fails, we share what we learned. If it succeeds, we share what we did. Either way, the next person goes faster."

Say this out loud
01

Fund 10 experiments at $0 ROI required

Pick ten people closest to the work. Give each a small budget, a coach, and 90 days. The only deliverable is a public writeup — what they tried, what they learned, what they'd do next.

02

Stand up the weekly Show Your Work forum

30 minutes, every Friday. Three people share one prompt, one workflow, one failure. No prep slides. Just screens and stories. Record nothing. The room will fill itself.

03

Pre-write the failure announcement

Draft, today, the email you'd send when an experiment fails publicly. Share the template with the team. The whole point is to lower the cost of being wrong.

Phase 03 · Days 21–30

Shift the operating system.

Tools spread on their own. Cultures don't. By day 30, the conditions that make AI compound should be visibly embedded in how you operate, hire, promote, and measure.

"Here is what we believe today. Here is what we believed last quarter that we no longer believe. Here is what we don't yet know. The document will keep changing because we will keep learning."

Say this out loud
01

Change one promotion criterion

Add "evidence of reinventing your own work with AI" to the next promotion cycle. One line. People optimize for what gets people promoted.

02

Replace one adoption metric

Kill license utilization as your headline number. Replace it with a workflow metric — hours reclaimed, cycle time cut, decisions made faster. Measure reinvention, not consumption.

03

Publish the org's evolving stance

A living document. One page. What you believe about AI, what you're trying, what you've changed your mind on. Update every 90 days. Sign your name.

Operating Cadence

Five rituals that do the work.

Movements run on cadence, not memos. These are the only five recurring practices you actually need.

01
Weekly · 30 min

The Friday Demo

Three demos. No decks. One prompt, one workflow, one lesson. Voluntary. Recorded only if the presenter opts in.

02
Weekly · Async

Prompt of the Week

One person publishes a prompt they actually used, with the input, the output, and what they'd change. Shipped in #ai-in-practice, not buried in a wiki.

03
Monthly · 45 min

Failure Forum

Three people present an experiment that did not work. Goal is pattern recognition, not post-mortems. The org learns where the walls are.

04
Quarterly · 1 page

Stance Update

Leader publishes the current organizational stance on AI. What's changed. What's still uncertain. Signed, dated, public.

05
Quarterly · 60 min

Identity Hours

Small-group conversation, manager-led: what does it mean to be good at your job now? No agenda. Coaching, not communications.

Stop / Start

Six trades that change the system.

Every item on the left is seductive because it's familiar. Every item on the right requires you to give something up.

Instead of
Mandatory enterprise-wide training
Do this
Voluntary peer demos with the people already winning
Mandates breed compliance theater. Demos breed envy — the productive kind.
Instead of
A center of excellence that owns AI
Do this
A network of practitioners that owns their workflow
Centers of excellence become bottlenecks. Distributed ownership becomes the operating system.
Instead of
Measuring license utilization
Do this
Measuring workflow reinvention
Logging in is not learning. You can buy seats. You cannot buy reinvention.
Instead of
A polished 18-month roadmap
Do this
A public 90-day stance you'll happily revise
Certainty you don't have erodes the trust you need. Honest uncertainty compounds it.
Instead of
Pilot → evaluate → scale
Do this
Many small bets → public learning → emergent scale
Pilots filter for safety. Movements filter for energy. You need energy.
Instead of
Communicating the change
Do this
Coaching through the identity work
Communications answer "what." People are asking "who am I now?" Coaching is the unlock.
Measurement

Stop measuring this. Start measuring that.

You will get what you measure. Pick numbers that reward reinvention, not consumption.

RetireAdopt
% of licenses activated% of teams that reinvented a workflow this quarter
Hours of training completedNumber of workflows publicly demoed
Survey: "Do you feel supported?"Survey: "Did you try something this month that scared you?"
Adherence to the roadmapVelocity of belief change in leadership
Number of approved use casesNumber of experiments that failed publicly
The Conversations

Four sentences to keep in your back pocket.

Most of activation is interpersonal, not institutional. These are the lines worth rehearsing.

With your skeptic
"You're right that we don't know if this will work. That's exactly why we're keeping the bet small and the learning loud. What would you need to see in 60 days to update your view?"
With your early adopter
"You're already two steps ahead. I don't want you to slow down — I want you to teach. What would it take to make your workflow legible to the team?"
With your anxious high performer
"Your craft isn't disappearing. It's relocating. The question I want us to sit with is — what part of your judgment is now the most valuable thing you do?"
With your board
"We're optimizing for learning velocity this year, not headline ROI. The companies that compound are the ones whose people reinvent their own work. That's the line we're measuring."
Get in Touch

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