AI Executive Checklist

A practical, step-by-step guide to implementing AI in your organization. Review the checklist below, then print it to use in meetings and planning sessions.

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AI Executive Checklist

From JAKT.AI - AI Strategy Without the Complexity

How to Use This Checklist

1.Review each section summary to understand the strategic context

2.Check off completed items or write target dates next to each task

3.Use the notes sections to capture decisions and action items

4.Share with your executive team and AI implementation partners

Quick Progress Overview

1. Set ambition and guardrails
2. Build a use case portfolio
3. Choose models and platform
4. Architecture and controls
5. Delivery method
6. Evaluation and quality
7. Upskilling and change
8. Compliance snapshot
9. Metrics and ROI
10. 8-week pilot plan

Key Success Metrics

1. Set ambition and guardrails

Section 1 of 10

Completion Date:

Clarify the outcomes you want in the next 12 months and the rules you will not break. This creates focus and prevents tool-first projects.

Action Items

Define 3 to 5 business outcomes: revenue, cost, risk, or cycle time

Target Date:
Owner:

Name an executive sponsor and product owner for each outcome

Target Date:
Owner:

Write non-negotiables for privacy, security, and human oversight

Target Date:
Owner:

Approve a lightweight AI governance model with monthly portfolio review

Target Date:
Owner:

Notes & Action Items

2. Build a use case portfolio

Section 2 of 10

Completion Date:

Source ideas from journeys and bottlenecks, score them consistently, and balance quick wins with strategic bets.

Action Items

Source ideas from customer journeys, operations logs, finance, and supply chain

Target Date:
Owner:

Score every idea on impact, feasibility, and risk using one rubric

Target Date:
Owner:

Place ideas on a 2×2: quick wins, scalable wins, strategic bets, deprioritized

Target Date:
Owner:

Select 3 quick wins and 2 strategic bets with clear exit criteria

Target Date:
Owner:

Notes & Action Items

3. Choose models and platform

Section 3 of 10

Completion Date:

Decide where you need speed versus control. Most teams start hybrid: a managed LLM with retrieval over governed data.

Action Items

Decide buy, build, or hybrid based on control needs, latency, and cost

Target Date:
Owner:

Select a primary LLM and a backup model with routing rules

Target Date:
Owner:

Stand up retrieval over governed data with a vector index

Target Date:
Owner:

Define SLOs per journey: accuracy, latency, and cost per task

Target Date:
Owner:

Notes & Action Items

4. Architecture and controls

Section 4 of 10

Completion Date:

Stand up the minimal rails for safety and operability so pilots can scale without rework.

Action Items

Data layer: sources documented, access controlled, lineage tracked

Target Date:
Owner:

Orchestration: prompts, tool use, eval harness, rollback plan

Target Date:
Owner:

Security: identity, secrets, audit logging, policy enforcement

Target Date:
Owner:

Observability: telemetry, usage analytics, cost caps, feedback loops

Target Date:
Owner:

Notes & Action Items

5. Delivery method

Section 5 of 10

Completion Date:

Ship a thin slice for one role and one task. Keep a human in the loop until quality is proven, then expand scope.

Action Items

Ship a thin slice for one role and one task before expanding scope

Target Date:
Owner:

Keep human-in-the-loop until SLOs are met and monitored

Target Date:
Owner:

Add guardrails: input validation, output filters, rate limits, PII redaction

Target Date:
Owner:

Document purpose, data, risks, and owners for each AI feature

Target Date:
Owner:

Notes & Action Items

6. Evaluation and quality

Section 6 of 10

Completion Date:

Make quality measurable. Use golden sets and weekly evals to prevent regressions and build trust.

Action Items

Create a golden test set for accuracy, safety, and edge cases

Target Date:
Owner:

Run weekly offline evals and track drift

Target Date:
Owner:

Pilot with 5–10 users, then 25–50 with A/B tests

Target Date:
Owner:

Tie every release to one measurable business KPI

Target Date:
Owner:

Notes & Action Items

7. Upskilling and change

Section 7 of 10

Completion Date:

Raise fluency at the top and skills at the edge. Celebrate shipped wins and retire legacy processes.

Action Items

Hold executive sessions on AI economics, risk, product patterns, and ROI

Target Date:
Owner:

Run a practitioner bootcamp on prompts, retrieval, tools, and evals

Target Date:
Owner:

Publish simple playbooks and internal examples

Target Date:
Owner:

Celebrate shipped wins and retire legacy processes

Target Date:
Owner:

Notes & Action Items

8. Compliance snapshot

Section 8 of 10

Completion Date:

Keep a simple register of AI uses and map controls to recognized frameworks. Track timelines for your regions.

Action Items

Maintain a register of AI use cases with risk tier and controls

Target Date:
Owner:

Map practices to recognized frameworks and standards

Target Date:
Owner:

Track regulatory timelines that apply to your footprint

Target Date:
Owner:

Train staff on responsible use and incident handling

Target Date:
Owner:

Notes & Action Items

9. Metrics and ROI

Section 9 of 10

Completion Date:

Agree on the math with Finance before launch. Publish a monthly scorecard with inputs, outputs, and outcomes.

Action Items

Inputs: adoption by role, time on task, automation rate

Target Date:
Owner:

Outputs: accuracy, latency, completion rate

Target Date:
Owner:

Outcomes: revenue lift, cost reduction, risk loss avoided, customer NPS

Target Date:
Owner:

Finance signs off on baselines and the ROI method

Target Date:
Owner:

Notes & Action Items

10. 8-week pilot plan

Section 10 of 10

Completion Date:

A proven tempo to go from idea to scale decision without stalling.

Action Items

Week 1 – Scope and success metric

Target Date:
Owner:

Week 2 – Data access and thin slice design

Target Date:
Owner:

Week 3 – Retrieval and tool wiring

Target Date:
Owner:

Week 4 – Evaluation harness and golden set

Target Date:
Owner:

Week 5 – Pilot to 5–10 users with human in the loop

Target Date:
Owner:

Week 6 – Fixes and guardrails

Target Date:
Owner:

Week 7 – Expand to 25–50 users, measure ROI

Target Date:
Owner:

Week 8 – Go or no-go with scale plan and de-risking

Target Date:
Owner:

Notes & Action Items

Implementation Summary

Key Decisions

Next Steps

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