03 — Resources

Pitching AI to Your Boss

A fill-in-the-blank pitch planner for administrative professionals, ops leads, and anyone who's spotted an AI tool worth adopting and needs to bring leadership along. This is the same planner used in the Using AI Safely workshop.

The goal: pitch responsibly. Lead with value, then address security, policy alignment, and rollout — before they ask.

A — The pitch planner

Five blanks to fill in before the meeting.

1. Tool name

"The tool I'd like to introduce is __________."

Example: Clockwise, ChatGPT, Microsoft Copilot, Otter.ai.

2. The value

"This tool helps us __________. It could save us approximately ____ hours per week by __________."

Example: "Automate calendar scheduling across teams. Could save us 3 hours per week by reducing back-and-forth scheduling emails."

3. Security safeguards

"The tool uses __________ to ensure data protection. We will limit access through __________."

Example: "End-to-end encryption and SOC 2 compliance. Role-based permissions and admin-controlled settings."

4. Company policy alignment

"This tool is __________ the company's approved list. It aligns with our current policies by __________."

Example: "Not currently on the approved list, but it aligns with our policies because we won't input PII and access is restricted to authorized users."

If no AI policy exists yet: "We currently don't have an AI policy, but this tool gives us an opportunity to define safe usage practices moving forward."

5. Implementation plan

"We will monitor usage by __________. Team training will be conducted through __________."

Example: "Tracking activity logs and reviewing access monthly. A 30-minute walkthrough and a documented best practices guide."

B — Sample dialogue

What it sounds like in the room.

Admin: "We've identified an AI tool that could save us 5 hours per week by automating scheduling. It uses secure, encrypted systems to protect sensitive data."

Boss: "How do we know it won't expose confidential information?"

Admin: "We've vetted the tool — it's on our approved list and follows IT's encryption standards. We'll set access permissions and review usage monthly."

C — After the pitch

Three questions to debrief.

  1. 01What worked well in the conversation? Capture the language and framing that resonated.
  2. 02What objections were hard to overcome? These are the gaps you fill in for the next pitch — usually security, cost, or policy alignment.
  3. 03What would you do differently next time? Often: lead with security upfront, or bring a specific use case the boss already cares about.

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