Connected AI Workflow Pilot Checklist
Considering connecting AI to your finance, sales, marketing or document systems? Use this checklist before allowing an AI assistant to access business data or perform actions.
Connected AI can access business data and carry out actions across multiple systems. Before connecting AI to any business tool, work through this checklist to reduce the risk of incorrect outputs, over-broad access, approval failures and data issues.
Connected AI can act on business information. Give it only the access and authority the workflow genuinely requires.
Business case
- Define the specific problem the workflow is solving.
- Choose one workflow to pilot — do not connect everything at once.
- Define what success looks like before you start.
- Identify a named person responsible for the workflow and its outputs.
Data
- List the information the workflow needs to access.
- Remove access to information the workflow does not need.
- Check the quality and completeness of the data in connected systems.
- Identify any confidential data — customer records, financial data, employee information.
Permissions
- Use named accounts to connect services — not shared administrator credentials.
- Enable MFA on all connected accounts.
- Apply least privilege: grant access only to what the workflow requires.
- Avoid using administrator accounts with broad access to set up connectors.
Actions
- Keep all outputs in draft initially — no automatic sending or publishing.
- Define approval thresholds: who must approve before any action proceeds.
- Prevent unrestricted payment actions without explicit named authorisation.
- Prevent automatic sending of external messages without approval.
Testing
- Test with normal, typical records.
- Test with incomplete or missing records.
- Test with duplicate records.
- Test with unusual edge cases.
- Record every error, not just successes.
Security
- Review data-processing terms for Claude and each connected service.
- Check data retention settings — how long is workflow data kept?
- Confirm audit logs are available for the workflow.
- Confirm offboarding process: what happens when the workflow owner leaves?
- Confirm the connector can be disabled quickly in an emergency.
Review
- Measure time actually saved — compare against the manual process.
- Review feedback from the users doing the approvals.
- Review any incidents or unexpected outputs.
- Decide to expand, amend or stop based on evidence — not on demonstrations.
Plug-and-play does not mean risk-free. The easier AI is to connect, the more important it becomes to control what it can see and do.
Plain-English Takeaway
Choose one low-risk workflow. Limit data access. Control permissions. Keep initial actions in draft. Test with real and imperfect data. Review the results before expanding.
Downloadable guide
Download the Connected AI Workflow Pilot Checklist
A one-page printable checklist covering business case, data, permissions, actions, testing, security and review — everything to check before connecting AI to business systems.
Download PDFFree download. No email address required.
Want the full business explanation?
The Technology Intelligence article covers why this matters, where it helps and what to watch out for.
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