Roast & Rise

Published by Roast & Rise

The Team AI Academy: Upskilling That Changes Real Work

Build a 30-day AI academy that changes how work gets done.

Turn scattered training links into a structured academy built around roles, cohorts, and live work. You will leave with the core tools to run the first 30 days and see whether AI skills are reaching the workflow.

Scattered course cards converge into a structured path of evidence, practice, changed work, and a final decision gate.
Turn a library of learning into a 30-day system that reaches real work.

Course thesis

AI upskilling works when it is run as a change programme tied to real work. With more than half the workforce needing reskilling within four years and AI skills carrying a reported 62% wage premium, optional course libraries are too passive. A structured, role-based academy gives people a weekly reason to apply new skills and gives the company evidence of changed work.

What you leave with

By the end, you will have a team baseline, one role-based track, a weekly practice ritual, and a scoreboard for proving changed work.

For

Founders, HR and people leads, and managers accountable for an AI adoption target across a team or company.

Workflow

Run a team fluency baseline, build role-based tracks around recurring workflows, operate weekly live-work practice sessions, and track visible evidence of application through a 30-day cohort.

Change

Replace passive course distribution with a 30-day academy cohort in which every participant applies AI to a recurring workflow each week and presents one changed work product.

What you can do

Use these as checks while you move through the plan.

Diagnose team AI fluency through evidence from real work.

Design a role-based learning track around one recurring workflow.

Run a weekly ritual that turns instruction into immediate application.

Measure adoption through visible workflow evidence and changed work products.

Chapters

01

Find the Real Skill Gap

Diagnose AI fluency through recent workflow evidence, then isolate the capability gap the academy should address.

A recent work document passes through four evidence checkpoints before one precise capability gap is isolated.
Start with recent work. Isolate the capability gap the academy can address.

A useful baseline starts with work evidence. Confidence surveys reveal how people feel. Course completions reveal exposure. Neither shows whether someone can apply AI safely and repeatedly inside a real workflow.

Choose one recurring task for each participant or role group. Review a recent work product and ask how the task was completed. Score four capabilities: framing the task, selecting useful context, evaluating the output, and integrating the result into the workflow. Use one shared scale from zero to three: no evidence, attempted, repeatable, and repeatable with verified quality.

The evidence matters more than the number. A low score should point to a visible constraint, such as weak instructions, missing source material, shallow review, or an isolated experiment that never reaches the final work product. That constraint becomes the skill gap the academy must address.

Keep the scorecard narrow. It is a curriculum decision tool, not a verdict on someone’s value or future potential. Record where evidence is unavailable and name the assumption that needs validation during the first practice session.

Quality checklist

Uses a recent work product as evidence.

Links every score to one recurring workflow.

Names one specific capability gap.

Marks unsupported judgments as assumptions.

Common mistakes

Scoring general AI enthusiasm instead of demonstrated capability.

Averaging scores until role-specific gaps disappear.

Treating limited tool access as a learning failure.

Using the baseline for performance appraisal.

Checkpoint

Can you name one evidenced fluency gap and the recurring workflow it blocks for every participant?

Exercise

Score One Workflow, Not the Whole Person

  1. Choose one participant or role group and one recurring weekly workflow.
  2. Review one recent work product and capture how AI was used, if at all.
  3. Score the four capabilities from zero to three using observable evidence.
  4. Name the single gap that most limits better work, plus any assumption to validate.
  5. Set one cohort priority that the next role-based track must address.

Use this at work tomorrow

Ask one team member to walk you through a recent recurring task and score the evidence together.

02

Build Tracks Around the Work

Convert one role's diagnosed fluency gap into a focused sequence of skills, live practice tasks, and observable work outputs.

One evidence gap is transformed into a narrow role-specific sequence of skills, live tasks, outputs, and a changed work product.
Build backwards from the work product. Give every skill a visible job.

The baseline scorecard showed where fluency breaks inside real work. Use that evidence to build a track for one role and one recurring workflow. A shared catalogue may support the programme, but it cannot define the path. Different roles face different decisions, source material, risks, and standards of quality.

Design backwards from the changed work product due on day 30. Name what the participant should produce, then identify the smallest capabilities needed to produce it well. Each capability becomes a skill in the track. Each skill must immediately connect to a live task from the selected workflow and leave behind an observable output.

Sequence by dependency. Start with the capability required for the next one to work. Keep the track narrow enough to practise during the 30-day cohort. Extra topics create motion without transfer.

A useful track has a clean chain: baseline gap, required skill, live practice task, observable output, changed work product. That chain makes curriculum decisions visible. It also gives the weekly ritual something concrete to run and the later scoreboard something meaningful to measure.

Quality checklist

One role and recurring workflow anchor the track.

Every skill addresses baseline evidence.

Practice tasks use current work.

Outputs can be reviewed without self-reporting.

Common mistakes

Copying the same track across different roles.

Adding broad AI topics because content already exists.

Teaching tool features without a workflow decision.

Treating an untested assumption as a confirmed gap.

Checkpoint

Can each skill in your track be traced from a baseline gap to a visible piece of changed work?

Exercise

Build One Role Track

  1. Choose one role, its scored fluency gap, and the recurring workflow from your baseline.
  2. Define the changed work product that should exist by day 30.
  3. Name two essential skills required to create it. Add a third only when dependency demands it.
  4. Pair each skill with one live task and one observable output.
  5. Mark any weak evidence as an assumption to validate in week one.

Use this at work tomorrow

Draft the first two skill-to-task links for one role using its baseline scorecard.

03

Make Practice the Programme

Turn the role-based track into a weekly live-work ritual that produces application evidence and a committed next use.

A live work artifact moves through a repeating weekly cycle of brief input, application, review, evidence capture, and next use.
Keep instruction short. Let live work carry the session.

A role-based track only changes work when practice enters the working week. The weekly session is the delivery mechanism: a protected moment where participants apply one target skill to a task already on their desk.

Keep instruction brief. Most of the session belongs to doing, reviewing, and committing. Participants arrive with a live task from the workflow selected in their baseline scorecard. They use the week’s skill to change that task, then capture evidence before leaving. Evidence could be a revised work product, a tested prompt with its result, or a documented decision that improved the workflow.

Peer review should judge usefulness, not performance. Ask whether the application made the output clearer, faster, safer, or easier to reuse. Choose the criterion that matches the diagnosed gap. When the work falls short, the participant records what to adjust next time.

Close with a specific next-use commitment tied to the same recurring workflow. Name the task and deadline. This turns a workshop into a cadence. Across four weeks, the cohort creates a visible trail of application that the next chapter can measure. Where quality or time improvements are claimed, treat them as assumptions until the team compares real before-and-after evidence.

Quality checklist

Most session time is spent applying the skill.

The task comes from the selected recurring workflow.

Review uses one relevant quality criterion.

Evidence is captured before participants leave.

Common mistakes

Letting demonstrations consume the practice block.

Using fictional exercises instead of current tasks.

Turning peer review into tool troubleshooting.

Accepting vague promises to practise later.

Checkpoint

Can every participant leave the session with work evidence and a dated next-use commitment?

Exercise

Build the Weekly Practice Ritual

  1. Take one skill-to-task link from the role-based track you built.
  2. Choose a live task participants can safely bring and change during one session.
  3. Time-box brief instruction, application, peer review, and evidence capture.
  4. Write one review question linked to the diagnosed fluency gap.
  5. Define the next-use commitment each participant records before leaving.

Use this at work tomorrow

Book the first cohort session and ask each participant to bring one live task from their selected workflow.

04

Measure Work That Changed

Build a visible scoreboard that turns cohort evidence into decisions about what to scale, revise, or stop.

Evidence passes through separate participation, application, and changed-work gates before reaching scale, revise, or stop routes.
Attendance shows reach. Changed work gives the programme a decision.

A full session can still leave the workflow untouched. Your scoreboard must reveal whether people attended, applied the skill, and changed a real work product. These are separate signals.

Participation shows reach. Record active cohort members and attendance so you can spot access or scheduling problems. Application shows transfer. Count a participant only when they provide evidence that AI was used in the recurring workflow selected during the baseline. A verbal claim is too weak. Use a link, screenshot, prompt record, process note, or reviewed output.

Changed work products show the programme’s result. By day 30, compare a participant’s earlier output with a reviewed version produced through the track. Describe the observed change in work terms such as time taken, clarity, accuracy, usability, or risk. Where no reliable comparison exists, label the claim as an assumption to validate.

Keep the scoreboard visible to the cohort and update it after each weekly ritual. Use counts and rates together. A percentage can flatter a tiny cohort; a count exposes the base. Avoid ranking individuals. The purpose is programme judgment: scale a track with repeated application and credible work change, revise one with participation but weak transfer, and stop one that produces no useful evidence.

Quality checklist

Every rate includes its underlying count.

Application entries link to a selected workflow.

Changed outputs include reviewed before-and-after evidence.

Each track has an owner and decision date.

Common mistakes

Treating logins or course completion as adoption.

Changing definitions midway through the cohort.

Publishing individual rankings that distort behaviour.

Claiming productivity gains without a reliable comparison.

Checkpoint

Can your scoreboard support a clear scale, revise, or stop decision using visible workflow evidence?

Exercise

Build the Visible Skills Scoreboard

  1. Open the baseline scorecard, role track, and evidence captured in the weekly ritual.
  2. Create three columns: participation, weekly application, and changed work products.
  3. Enter current counts, rates, and links to evidence; mark unsupported outcomes as assumptions to validate.
  4. Add one scale, revise, or stop decision for the track, with a review owner and date.

Use this at work tomorrow

Publish the cohort’s first participation, application, and changed-work-product counts with links to the underlying evidence.

30-day path

Days 1–3: Name the cohort, adoption target, included roles, and work evidence that will count.

Days 4–7: Run the fluency baseline and choose one recurring workflow for each participant or role group.

Days 8–29: Launch role-based tracks, hold four weekly live-work sessions, and update the scoreboard after each session.

Day 30: Review changed work products, capture what improved, and decide which tracks to scale, revise, or retire.

Success signals

Baseline coverage: every enrolled participant has a scored workflow and named fluency gap before practice begins.

Weekly application rate: every active participant shows evidence of applying AI to their selected workflow each week.

Changed-work-product rate: every participant presents one before-and-after work product by day 30.

Adoption lift: compare live-work application with any available self-directed learning baseline, clearly marking gaps where prior data is absent.

Reflection prompts

Where does this topic show up in real work?

What behavior should change first?

What evidence would prove this Riseplan worked?

Manager checklist

Choose one owner for the behavior change.

Use the exercise on live work.

Review the output before scaling the habit.

Decide what changes after 30 days.

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