Riseplan from Roast & Rise
AI Readiness Pilot
From scattered experiments to one useful pilot
Choose the workflow where AI can create value now, design the human-in-the-loop routine, and prove in 30 days whether it should scale.
Course thesis
AI readiness is not a maturity label or a list of tools. It is the operating ability to choose one real workflow, describe the current work clearly, decide where AI may assist, protect human judgment, and measure whether the new routine improves speed, quality, confidence, or customer value.
What you leave with
A ranked opportunity map, one selected pilot, a human review routine, risk rules, a live-work exercise, and a 30-day scorecard for scale, redesign, or stop.
Learner
Founders, operators, product leads, and team managers preparing a first serious AI workflow without turning the company into a tool experiment.
Workflow
Workflow discovery, pilot selection, human-in-the-loop design, live practice, quality review, and 30-day adoption measurement.
Behavior
Move from scattered individual AI experiments to one owned pilot with explicit inputs, review criteria, quality gates, risk boundaries, and a decision rule for what happens next.
Outcomes
What the learner should be able to do after finishing this public Riseplan.
Map repeated work by trigger, input, handoff, decision, output, owner, and current friction instead of starting with a tool.
Score AI opportunities by value, workflow clarity, data readiness, risk, and team energy so the first pilot is useful but contained.
Design a human-in-the-loop routine that names what AI drafts or checks, what humans decide, and how feedback improves the workflow.
Run the routine on live work and capture what breaks, what improves, and what must be clarified before asking more people to adopt it.
Use a 30-day scorecard to decide whether the pilot should scale, be redesigned, or stop because the evidence is weak.
Chapters
01
Map the Work
Find the repeated decisions, documents, handoffs, and customer moments where work slows down or quality varies.
Start with the work, not the model. A useful AI pilot usually appears inside a repeated workflow: preparing a proposal, summarizing a customer call, triaging support tickets, drafting a report, comparing research notes, checking a document, or moving context from one person to another.
The best signal is visible friction. Look for delays, repeated copy-paste work, inconsistent quality, missing context, senior people answering the same questions, or customer-facing work that depends too heavily on one person's memory.
A workflow map should name the trigger, inputs, steps, handoffs, decisions, outputs, owner, current pain, and the standard for good work. Without that map, AI adoption becomes opinion-based because nobody can compare before and after.
Do not select the most exciting use case first. Select the workflow where the team can explain the current routine, provide examples, name the risk, and tell whether the result became better.
Worked example
A consulting team notices every proposal starts with the same hunt through old notes, call transcripts, and proof points. The workflow map shows the real bottleneck is not writing. It is missing context before the first draft.
Artifact template
Trigger: what starts this workflow?
Inputs: what information must be available?
Handoffs: who touches the work before it is done?
Friction: where does time, quality, confidence, or context leak?
AI assist: where could AI draft, summarize, compare, classify, or check?
Quality checklist
The map names a repeated workflow, not a broad department.
The current standard for good work is visible.
The proposed AI assist is tied to one workflow moment.
Common mistakes
Listing tools before describing the work.
Choosing a one-off task that will not teach the company anything reusable.
Checkpoint
Can someone outside this workflow read the map and understand where the pilot would start?
Exercise
Run a 45-minute workflow inventory with one team.
List five repeated workflows. For each, capture the trigger, inputs, steps, handoffs, output, owner, current friction, risk level, and what good would look like. Mark where AI might draft, classify, retrieve, summarize, compare, or check quality. End by choosing the two workflows where improvement would be visible within 30 days.
Artifact
Workflow map with friction points and candidate AI assists.
Use this at work tomorrow
Pick one live workflow and ask the people inside it: where do we lose the most time, confidence, quality, or context?
02
Choose the Pilot
Score candidate workflows by practical value, risk, readiness, ownership, and team energy before choosing one move.
The right pilot is narrow enough to run and meaningful enough to matter. If it is too broad, nobody owns it. If it is too small, nobody learns anything the company can reuse.
Score each candidate on five dimensions: business value, workflow clarity, available context, risk, and team energy. A strong first pilot has visible value, a clear routine, available examples, manageable risk, and people who want to try.
Avoid pilots where the output cannot be judged. If the team cannot say what a good answer, draft, summary, or decision looks like, AI will only make the ambiguity faster.
A pilot decision memo should also explain what was not selected. This prevents the team from treating every possible AI use case as urgent at the same time.
Worked example
The team scores proposal drafting, support triage, and meeting summaries. Proposal drafting wins because examples are available, quality is reviewable, and a better routine would affect revenue quickly.
Artifact template
Candidate workflow
Value score with evidence
Workflow clarity score with evidence
Context availability score with evidence
Risk score and stop condition
Decision: test now, park, redesign, or reject
Quality checklist
Every score includes one sentence of evidence.
The selected pilot has a named owner.
The memo explains why tempting alternatives are not first.
Common mistakes
Picking the highest-value workflow even when nobody can judge output quality.
Treating every AI idea as urgent.
Checkpoint
Would the team still choose this pilot if they had to show the first result in 30 days?
Exercise
Score five opportunities against a readiness matrix.
Create a 1-5 score for value, workflow clarity, context availability, risk, and team energy. Write one sentence of evidence for every score. Choose the pilot with the strongest balance and write why the other options are parked, unsafe, too unclear, or better suited for later.
Artifact
Pilot decision memo.
Use this at work tomorrow
Choose one candidate pilot and write a one-paragraph reason it is worth testing now, including the risk that would make you stop.
03
Design the Operating Loop
Define the exact routine for requesting AI help, reviewing output, protecting quality, and improving the workflow.
AI readiness depends on operating design. The important question is not whether AI can produce output, but how people will request, inspect, improve, and use that output inside the real workflow.
Every pilot needs quality gates. Decide what AI can draft or suggest, what a human must review, what must be escalated, and what should never be automated. Write these rules before the pilot starts.
The loop should be visible: input, AI assist, human review, final decision, feedback, and improvement. If feedback disappears, the workflow will not get better because the team only sees isolated outputs.
Use examples, not only instructions. Show one weak input, one better input, one acceptable output, and one output that must be rejected. This makes quality teachable.
Worked example
For proposal drafting, AI creates an outline from discovery notes and proof points. A human checks customer specificity, unsupported claims, scope promises, tone, and next action before anything reaches the prospect.
Artifact template
Workflow trigger
Context AI receives
Output AI may draft or check
Human decision owner
Quality rules
Escalation boundaries
Feedback log
Quality checklist
The human decision cannot be confused with the AI assist.
Claims that need verification are named.
Feedback has a place to go after each use.
Common mistakes
Writing prompts but no review routine.
Letting feedback disappear into private edits.
Checkpoint
If the AI output is plausible but wrong, which rule catches it before use?
Exercise
Write the first human-in-the-loop routine.
For the selected pilot, define who starts the workflow, what context AI receives, what AI produces, who reviews it, which quality criteria apply, which claims need checking, what cannot be delegated, and how improvements are logged after each use.
Artifact
Pilot operating checklist.
Use this at work tomorrow
Write three quality rules that must be checked before any AI-assisted output from this pilot is used in real work.
04
Practice on Live Work
Use the pilot routine on a real but low-risk work item and record what the first attempt teaches.
A pilot becomes useful when it touches live work. Synthetic examples can help training, but they rarely reveal the missing context, unclear ownership, tone problems, and edge cases that block adoption.
Choose a work item with enough realism to matter and low enough risk to recover from mistakes. The first run should create learning, not pressure to prove the whole AI strategy.
Review the result in three layers: input quality, AI output quality, and human decision quality. Often the problem is not the model; it is unclear context, weak examples, or missing review criteria.
Capture changes immediately. If the team waits until the end of the month, the details that would improve the routine will be forgotten.
Worked example
The first live proposal outline saves 20 minutes but invents a proof point. The review note shows the routine needs a required evidence section before the model is allowed to draft claims.
Artifact template
Live work item
Input quality notes
AI output quality notes
Human changes made
Trust, hesitation, and rejection signals
Routine change before the next run
Quality checklist
The practice item is real but recoverable.
The review separates input problems from AI output problems.
At least one routine improvement is captured immediately.
Common mistakes
Practicing only on synthetic examples.
Judging the model without checking whether the input was usable.
Checkpoint
What changed in the routine because of this live run?
Exercise
Run the routine once on a real work item.
Choose one live example. Run the routine from input to final decision. Record what context was missing, what AI handled well, what required human judgment, what quality checks caught, and what should change before the second run.
Artifact
Live pilot review note.
Use this at work tomorrow
Test the routine on one low-risk item and ask the reviewer what they trusted, what they changed, and what made them hesitate.
05
Measure the First 30 Days
Use behavior, speed, quality, adoption, confidence, and business effect signals to decide what happens after the pilot.
Measurement should start before the pilot begins. Capture the current baseline so the team can distinguish real improvement from novelty, enthusiasm, or a one-off good result.
Use a small scorecard. Measure speed, quality, adoption, confidence, and business effect. Not every pilot needs a full ROI model, but every pilot needs a decision rule.
The point of 30 days is learning. At the end, decide whether to scale the workflow, redesign the loop, narrow the use case, improve the knowledge base, or stop because the evidence is weak.
Make the decision visible. Teams lose trust when pilots drift. A clear review turns experimentation into operating discipline.
Worked example
The proposal pilot tracks draft turnaround, reviewer rewrite percentage, salesperson confidence, and whether follow-up quality improves. At day 30, the team scales only if speed improves without lowering specificity.
Artifact template
Baseline measures
Target measures
Weekly review rhythm
Quality signal
Adoption signal
Business or customer-value signal
Scale, redesign, narrow, or stop rule
Quality checklist
The scorecard includes speed and quality, not only activity.
A decision rule exists before the pilot starts.
The final decision can be explained in one paragraph.
Common mistakes
Calling usage adoption even when quality has not improved.
Letting the pilot drift without a day-30 decision.
Checkpoint
What evidence would make stopping the pilot the disciplined choice?
Exercise
Create the pilot scorecard and review rhythm.
Define three baseline measures, three target measures, a weekly 20-minute review agenda, and one final decision rule. Include one quality measure, one adoption measure, and one business or customer-value signal.
Artifact
30-day pilot scorecard.
Use this at work tomorrow
Write the one metric and one quality signal that would make this pilot obviously worth continuing.
30-day path
Week 1: inventory workflows, choose two candidates, and select one pilot with a named owner.
Week 2: write the human-in-the-loop routine, quality gates, examples, and risk boundaries.
Week 3: run the pilot with two to five people on low-risk live work and improve the routine after each use.
Week 4: review the scorecard, decide scale, redesign, or stop, and document what the next workflow can reuse.
After 30 days: convert the pilot into a maintained operating routine only if quality, adoption, and business signals support it.
Success signals
One AI pilot is chosen with a clear owner, workflow, scope, and stop condition.
The team can explain exactly when AI helps, when humans decide, and what quality rules protect the work.
Baseline and target measures exist before broad rollout begins.
At least two live-work reviews improve the routine before any scale decision.
The 30-day review produces a clear scale, redesign, narrow, or stop decision.
Reflection prompts
Where are we experimenting with AI without ownership, quality rules, or a decision moment?
Which workflow would become noticeably better if turnaround, consistency, or context improved?
What output would be risky, embarrassing, or useless if we automated too casually?
What evidence would make this pilot worth scaling beyond the first team?
Manager checklist
Name the pilot owner, reviewer, weekly review moment, and final decision date.
Check that the workflow has baseline measures before testing starts.
Make quality rules and escalation boundaries visible to everyone involved.
Require live-work review notes before adding more people to the pilot.
Decide at day 30: scale, redesign, narrow, or stop.
Want this shaped around your company?
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