Session 1 of 4

How AI Works in Business

From Prompt to Governed Decision

Duration60 minutes
AudienceC-level executives
FormatLive demonstration on one screen. Participants watch; laptops are not needed.
DatasetDataCo Supply Chain, sanitized extract
OutputEach participant places one AI initiative on the AI Readiness Rubric

Workshop Concept

One business question. Five layers of enterprise AI.

Session 1 uses the DataCo supply chain dataset to follow one late-delivery problem through five rounds. Each round adds a capability that separates enterprise AI from a chatbot: structured instructions, business context, working tools, continuous operation, and governed authority.

Opening

Our delivery data tells us more orders arrive late than on time. The board wants to know where, why, and what to do about it. Over the next hour we will ask that same question five times. Each time, we give the AI one more thing it needs to be useful: clearer instructions, business context, real tools, the ability to run on its own, and rules about what it may and may not do.

The DataCo Dataset

One slide. The key point: this is line-level data — each row is a single order line, not an order summary.

FieldExampleNotes
Order Id76255One order may have multiple lines
order date1/15/2017
Shipping ModeStandard ClassStandard Class · Second Class · First Class · Same Day
Customer SegmentConsumer / Corporate / Home Office
Category NameCleats, Men's Footwear, FishingDataCo product categories, not aggregated
Department NameFan Shop, Apparel, Golf, Technology
Delivery StatusLate delivery / Advance shipping / Shipping on time / Shipping canceledHistorical outcome
Days for shipment (scheduled)4Promised shipping window
Days for shipping (real)7Actual days taken
Order Profit Per Order25.50Behaves as line-level profit in this extract
Order Region / Order CityWest of USA / Los Angeles
Late_delivery_risk1Historical flag. It equals Delivery Status = Late delivery on every row, so it is an outcome, not a prediction

Important for analysis. Order-level metrics such as unique order count or order-level late rate require deduplication on Order Id. Delivery Status, actual shipping days and Late_delivery_risk are historical outcomes, not predictions.

What the data actually shows

The facilitator should know these numbers before going live. The AI will surface them during the demonstration. Derived Evidence

CutResult
Company-wide late rate54.8% of 180,519 order lines, and the same at order grain across 65,752 orders
By shipping modeFirst Class 95.3% late · Second Class 76.6% · Same Day 45.7% · Standard Class 38.1%
Share of order lines by modeStandard 59.7% · Second 19.5% · First 15.4% · Same Day 5.4%
By product category50 categories, every one between 47.7% and 60.1%
By region23 regions, every one between 48.8% and 58.0%
By customer segmentConsumer, Corporate and Home Office within 0.4 points of each other

What this means on stage: ranking categories or regions produces lists whose differences are noise — every category is within four points, every region within ten. The only real lever in this data is shipping mode, and the premium services are the late ones. Layers 1 and 2 are designed so the room discovers this live.

Facilitator note. Load the dataset into your AI tool before the session. Paste the prompts below rather than typing them live.

Layer 1 — Prompt Engineering

5–15 minutes

Three steps to working with AI: prepare, prompt, and polish. The facilitator introduces the framework, then demonstrates each level live.

Step 1 — Define your objective

Before writing a single prompt, answer four questions:

QuestionWhat it means
Outcome and outputWhat decision do you need to support, and what form should the deliverable take?
AudienceWho will see or act on this output? Their level of detail shapes your prompt.
Information to provideWhat metrics, documents, or datasets must you feed the AI? It cannot use what it does not have.
Scope and limitationsWhat can AI do here, and where does human expertise need to take over?

Skipping this step is the most common mistake. A well-defined objective is worth more than a clever prompt.

Step 2 — Build the prompt

A prompt is assembled from building blocks. Not every use case needs all of them — the specificity of your desired output determines which to include.

Building blocks

BlockPurpose
Task descriptionTell the AI what you want it to do. Be concise and direct.
RoleThe perspective or expertise the AI should adopt for this task.
BoundariesWhat to include, what to exclude, and where to stop.
ContextBackground the AI needs to generate a relevant response. Narrows down the space of possible outputs.
Specific requirementsFormat, length, structure, metrics to include, or standards to follow.
ReasoningAsk the AI to explain its logic, show trade-offs, or justify its recommendation.

Prompt types

Three levels of prompt structure. Each adds building blocks as the task demands more precision.

TypeBuilding blocksWhen to use
BasicTask description + ContextQuick lookups, simple summaries, first-pass exploration
FocusedTask description + Role + Context + Specific requirementsStructured analysis, formatted reports, audience-specific outputs
ComprehensiveTask description + Role + Boundaries + Context + Specific requirements + ReasoningExecutive decisions, high-stakes recommendations, cross-functional work

Prompting tip. Not every use case requires every building block. Start with what your output demands and add blocks only when the result falls short.

Live demonstration — the same question, three prompt levels

The facilitator now runs three prompts against the DataCo dataset. Each corresponds to a prompt type above.

Demo A — Basic prompt

Prompt type: Basic (task description + context)

PromptClick the text, then ⌘C or Ctrl+C
Using the attached DataCo supply chain dataset,
what are the top late delivery products?

What happens. The AI has the data, so it pulls real product names — but the output is an unstructured paragraph with no ranking, no percentages, and no clear takeaway. It mentions a few categories without explaining why they matter.

Facilitator asks the room

Would you take this to a board meeting?

Lesson. The AI has the data but no direction. A minimal prompt produces a minimal answer — real numbers buried in a shapeless paragraph that no executive can act on.

Demo B — Focused prompt

Prompt type: Focused (task description + role + context + specific requirements)

PromptClick the text, then ⌘C or Ctrl+C
You are a supply chain analyst.

Using the attached DataCo supply chain dataset, identify the top 10
product categories with the highest late delivery rate.

Output a Markdown table with exactly three columns: Category Name,
Total Order Lines, and Late Delivery Rate (%).
Sort by late delivery rate descending.

What happens. The AI returns a ranked table with real numbers from the dataset. Lacrosse leads at 60.1%, followed by Pet Supplies, Cameras, Strength Training and Music; the tenth entry sits near 56%. It looks precise and actionable.

Facilitator asks the room

This looks useful. But is it a decision, or just a sorted list?

Lesson. A specific prompt produces specific numbers — but numbers are not insight. What the room does not yet see: every one of those ten categories sits within four points of the company average. The ranking is noise.

Demo C — Comprehensive prompt

Prompt type: Comprehensive (all six blocks: task description + role + boundaries + context + specific requirements + reasoning)

PromptClick the text, then ⌘C or Ctrl+C
You are a supply chain analyst presenting to the CEO.

Using the DataCo dataset, analyse late delivery patterns and produce:

1. Top 10 product categories by late delivery rate (% of order lines late)
2. For each: the total profit associated with late order lines
3. Compare late-delivery rates across shipping modes
4. One actionable recommendation per category to reduce delays

Boundaries: base every finding on the dataset provided. Do not
speculate beyond what the data supports. If a pattern is ambiguous,
say so.

Format as an executive summary with a table. Flag any category where
late delivery rate exceeds 50% as CRITICAL. Keep it under 500 words.

Before generating the table, think step-by-step in a brief paragraph
about how the 50% threshold interacts with the baseline company average.
Then apply the threshold exactly as given.

For each recommendation, explain the reasoning: what evidence supports
it, what trade-off is involved, and what would need to be true for it
to work.

What happens. The AI returns a structured executive brief — prioritised, quantified, with per-category recommendations. Two things surface that no one expected.

  • 49 of 50 categories are flagged CRITICAL — because the company-wide late rate is 54.8% and the threshold sits below it. The AI followed the instruction precisely. The result is useless precisely because it did.
  • Item 3 uncovers the real story. First Class 95% late, Second Class 77%, Standard Class 38%. The premium shipping modes are the late ones — and this only appeared because the prompt happened to include a shipping-mode comparison.
Facilitator asks the room

Would you take this to the board now? And what would you still need before acting on it?

Lesson. Prompt structure matters — role, constraints, format, and reasoning direction produce a markedly better output. But this prompt applied a bad threshold flawlessly and found the one useful pattern by accident. Better instructions improve direction. They do not replace missing context or missing evidence.

Step 3 — Polish and iterate

No first prompt is final. After reviewing the output, refine with follow-up prompts: ask the AI to add what is missing, go deeper on a specific section, or change the format.

Then apply human expertise — check for accuracy, question the assumptions, verify the ethics, and make final edits before the output leaves your hands. AI drafts; you decide.

Prompting is iterative. You can always polish with a follow-up prompt. But the human must know the limitations of the tool, review every output, and own the final result.

Layer 1 debrief

Show all three outputs side by side. The gap is visible in seconds.

Key takeaway

Most organisations are still at Step 1. The same AI and the same data produce radically different results depending on how the question is asked.

Facilitator guide — why the 50% threshold is a trap

The threshold in Demo C is deliberate. It is the moment that proves precise instructions do not compensate for flawed human logic or missing business context, so it is worth walking the room through slowly.

The flawed human assumptionFlag any category above 50% late as CRITICAL. To an executive writing the prompt, 50% sounds like a reasonable bar for a severe problem.
The mathematical realityThe company-wide late rate is already 54.8%, and 49 of the 50 categories sit between 47.7% and 60.1%. The threshold was set below the average.
The useless outputThe AI flags 49 of 50 categories as CRITICAL. When almost everything is critical, the categorisation cannot prioritise anything.

How to explain it

  1. Highlight the literal execution. The AI did exactly what it was told. The prompt applied a bad threshold flawlessly, which proves the tool will confidently execute poor instructions.
  2. Ask the pivotal question. “Would you take this to the board now? And what would you still need before acting on it?”
  3. Deliver the core lesson. The comprehensive prompt structure — role, boundaries, reasoning — improved the formatting and direction of the answer. It could not replace missing context or missing evidence.
  4. Reveal the real insight. Point at the story the AI found by accident: the premium shipping modes are the delay drivers. First Class 95.3% late, Second Class 76.6%, against Standard Class at 38.1%.

If the AI refuses the threshold. The added “think step-by-step, then apply the threshold exactly as given” line makes the model announce the flaw before complying, which is the stronger demo. A model may still argue for a better threshold instead of applying it. If that happens, take the win: it is the same lesson from the other direction, and the follow-up is “good — now who at this company decides what the threshold should be?”

Layer 2 — Context Engineering

15–25 minutes

Now we move from answering a question to understanding a business. The AI receives the same data, plus the company’s rules, targets, and constraints. Everything below that is not in the dataset is a controlled workshop assumption.

Step 2.1 — Add business context

PromptWorkshop ScenarioClick the text, then ⌘C or Ctrl+C
COMPANY CONTEXT:
- We are a B2B distributor serving corporate and home office segments
- Our SLA commitment: delivery within scheduled shipping days
- Board KPI: reduce late delivery rate from 54.8% to below 30% in 6 months
- Current allocation by order lines: Standard Class 59.7%, Second Class
  19.5%, First Class 15.4%, Same Day 5.4%
- Budget constraint: logistics cost cannot increase more than 12%

DATASET: [DataCo supply chain data attached]

Given this context, analyse our late delivery problem and recommend a
phased action plan that stays within budget. Prioritise by profit impact.

Format the plan into three phases: Immediate (0-30 days), Short-Term
(30-90 days), and Medium-Term. For each phase, explicitly state the
expected budget impact against the 12% ceiling.

The 54.8% starting rate and the four allocation percentages come from the data Derived Evidence. The SLA, the board target and the budget ceiling are invented for the exercise Workshop Scenario.

What happens. The recommendations change completely. The AI will not propose shifting volume to premium shipping — it now knows both the budget ceiling and the fact that premium modes are the late ones. Expect it to move volume toward Standard Class, the cheapest and most punctual mode in this data, and to prioritise the segments named in the context.

Facilitator asks the room

Same data, same model, completely different recommendation — because it now understands the business. What other context would change the answer again?

Lesson. Context engineering is the practice of giving AI your company’s rules, KPIs, constraints, and priorities. This is where enterprise AI separates from consumer AI.

Step 2.2 — Add historical context, or memory

PromptWorkshop ScenarioClick the text, then ⌘C or Ctrl+C
PREVIOUS ANALYSIS (Q1):
- We shifted 15% of Second Class volume to Standard Class in West of USA
- Result: late deliveries dropped 8% in West of USA but increased 3% in
  US Center
- Root cause hypothesis: the Standard Class carrier has limited US Center
  capacity

Given this history, update your recommendations. Do not repeat strategies
that failed. Account for regional carrier capacity differences.

Provide a "Revised Action" table contrasting the Q1 approach with the new
approach for US Center.

What happens. The AI adjusts course. It keeps the direction the data supports, avoids the approach that failed in US Center, and proposes different tactics for different regions.

Lesson. Enterprise AI without memory will repeat the mistakes the organisation already paid to learn from.

Layer 2 debrief

Key takeaway

Anyone can access the same AI model. Your competitive advantage is the context you give it — your rules, your constraints, your history.

Layer 3 — AI Workflows and Tools

25–35 minutes

The AI stops answering and starts working. It now has access to tools: code execution, charting, document generation.

Step 3.1 — Multi-step workflow, live demo

PromptClick the text, then ⌘C or Ctrl+C
WORKFLOW:
1. Query the DataCo dataset: pull all order lines flagged as late delivery.
   Drop any rows with null values in the target columns.
2. Segment by: region, shipping mode, customer segment, product category
3. Generate a visual dashboard with 4 charts. Use a consistent corporate
   colour palette (navy and gold) and label every chart axis clearly:
   - Late delivery rate by region (bar chart)
   - Shipping mode vs delay days (box plot)
   - Profit associated with late deliveries by category (treemap)
   - Trend: late delivery rate over time (line chart)
4. Identify the three strongest combinations associated with late
   delivery (e.g. Standard Class + West of USA + a specific category)
   and state what additional evidence would be required to establish
   causation
5. Draft an email to the VP of Logistics summarising findings with
   the dashboard attached

What happens. The AI produces analysis, four visualisations, a pattern assessment, and a draft email to the VP of Logistics — in one uninterrupted flow.

Facilitator asks the room

That took the AI sixty seconds. How long would it take your team?

Lesson. AI with tools becomes a work multiplier. Without them, it can only talk about the work. With them, it does the work.

Step 3.2 — Tool awareness

Point out what the AI just used:

  • Code execution — ran Python or SQL over the dataset
  • Visualisation — generated the charts
  • Document generation — drafted the email
  • Data retrieval — queried specific subsets
Key takeaway

An AI model without tools is a consultant with no laptop. It can advise, but it cannot deliver.

Layer 4 — Agentic AI

35–43 minutes

Until now, every action required someone to type a prompt. Now the AI operates on its own schedule.

Step 4.1 — The autonomous agent scenario

Agent definitionWorkshop ScenarioClick the text, then ⌘C or Ctrl+C
Name: Supply Chain Monitor
Trigger: Runs daily at 6:00 AM

INSTRUCTIONS:
1. Pull yesterday's delivery data
2. Calculate late delivery rate by region and shipping mode
3. Compare to the 30% target KPI
4. IF any region exceeds 50% late delivery rate:
   - Analyse contributing factors (carrier, product mix, volume spike)
   - Generate alert with supporting evidence
   - Draft recommended action
   - Send summary to VP Logistics
5. IF all regions are below 30%:
   - Log "All clear" and update weekly trend tracker
6. Every Friday: generate weekly performance summary with trend analysis

Show the output. Walk through a bad day and a good day. In the historical data, most regions sit between 53% and 58% — so the alert is today’s reality and the all-clear is the target state.

Facilitator asks the room

This agent runs every morning without being asked. But it depends on clean data, reliable execution, and well-defined exceptions. Who monitors the monitor?

Lesson. Agentic AI operates across time without being prompted. The executive question is not how many agents you deploy, but what each one may access, recommend, and execute.

Step 4.2 — Beyond a single agent

Organisations rarely run one agent. What they run is a small set of specialised agents in a hub-and-spoke arrangement, not a peer-to-peer network negotiating with itself.

Specialised rolesEach agent handles one distinct task: demand forecasting, delivery monitoring, carrier optimisation, cost control.
Centralised outputThe agents do not message each other. Each feeds its findings and alerts into one executive summary, which is the only thing a person reads.
Governing boundariesOrganisational guardrails bound every agent. The defining question for each is what it may access, decide, and escalate.

The structure is what keeps this manageable. Several agents contribute to one unified picture for leadership, without unchecked interaction between the agents themselves.

Facilitator asks the room

If four agents disagree, who reconciles them — and does that person see the disagreement, or only the summary?

Layer 5 — Guardrails and Human Authority

43–55 minutes

AI capability is no longer the constraint. The question is now: under what conditions, with what evidence, and with whose authority.

Step 5.1 — What could go wrong?

ScenarioWhat went wrong
AI recommends cancelling all First Class shippingNo cost or contract constraint applied, so it breaks customer commitments
AI sends the alert to the wrong executiveNo access control, so information leaks
AI bases a recommendation on corrupted dataNo data validation, so garbage in, garbage out
AI recommendation violates a vendor contractNo legal or compliance context, so liability
AI optimises for speed and ignores carbonNo sustainability guardrail, so misaligned KPIs
Facilitator asks the room

Which of these has already happened in your organisation — or could happen tomorrow?

Step 5.2 — The governance layer

Guardrails for supply chain AIWorkshop ScenarioClick the text, then ⌘C or Ctrl+C
DECISION AUTHORITY:
- AI MAY: Generate reports, send alerts, draft recommendations
- AI MAY (with approval): Adjust shipping mode allocation up to 10%
- AI MAY NOT: Change carrier contracts, override SLA commitments,
  communicate to external partners

DATA RULES:
- Must use data less than 24 hours old
- Must flag if any data source is missing or incomplete
- Must show confidence level for predictions

EVIDENCE REQUIREMENTS:
- Every recommendation must cite specific data points
- Must show "what if" comparison (current vs recommended)
- Must include risk assessment for each action

ESCALATION:
- If late delivery rate exceeds 60%: escalate to COO immediately
- If recommended action exceeds budget by >5%: requires CFO approval
- If pattern is unprecedented: flag for human review, do not auto-act

AUDIT:
- Log every decision, recommendation, and data source
- Weekly governance review of all AI-generated actions

Lesson. Guardrails define what AI may do, under what conditions, and with whose authority. Without them, no AI deployment is trustworthy enough to operate.

Step 5.3 — Executive self-assessment: the AI Readiness Rubric

Each participant evaluates one of their own AI initiatives against six dimensions.

DimensionLevel 1 · Ad hocLevel 2 · StructuredLevel 3 · Enterprise
InstructionsVague, generic promptsSpecific, formatted, role-basedConstraints, reasoning direction, output standards
ContextNone, general knowledge onlyDataset providedBusiness rules, history, KPIs, constraints
ToolsChat onlyData analysisMulti-tool workflow: query, visualise, draft, send
OperationHuman runs every requestScheduled tasksAgent monitors and acts within defined authority
GovernanceNoneBasic access controlDecision authority, evidence rules, escalation, audit
Evidence“AI said so”Data-backedCited, compared, confidence-scored, peer-reviewed

Facilitator exercise, 3 minutes. Pick one AI initiative you are responsible for. Where does it sit on this rubric today? Where does it need to be in six months — and what is the first gap to close?

Close

55–60 minutes

The key question, answered

What does AI need before it can support a real business decision?

  1. Clear, structured instructions — prompt engineering
  2. Your business reality — context engineering
  3. The ability to do work — tools and workflows
  4. Continuous operation within a defined scope — agentic AI
  5. Rules, evidence and human authority — guardrails and governance
Closing statement

The AI model is the engine. You would not put an engine on the road without steering, brakes, and a driver. Now you have seen what the full vehicle requires — and you know where your organisation stands.

Facilitator Cheat Sheet

TimeLayerEnergyParticipant action
0:00–0:05Opening: business question and datasetSet the stakesListen, orient
0:05–0:15Layer 1 · Prompt engineeringHighWatch the demo, react to the differences
0:15–0:25Layer 2 · Context engineeringMediumSuggest what context to add
0:25–0:35Layer 3 · Tools and workflowsHighEstimate the time saving
0:35–0:43Layer 4 · Agentic AIMediumDebate what AI should decide
0:43–0:55Layer 5 · Guardrails and governanceCriticalSelf-assess with the rubric
0:55–1:00CloseHighCommit to one next step

Materials needed

  • AI tool with the DataCo dataset pre-loaded
  • Large screen for the live demonstration
  • Pre-written prompts ready to paste. Do not type live; it kills momentum
  • Printed rubric cards for each participant, optional but high impact

Labels used in this session

LabelMeaning
Source DataActual values or columns from the sanitized DataCo extract
Derived EvidenceComputed from the DataCo extract
Workshop ScenarioInvented business fact created for the exercise, not from the dataset