Teams and organizations

AI training for managers, measured in week 12.

Pocket Square's AI Enablement Program is a 12-week program that teaches a group of managers to use AI on the work they already do, with the tools you already pay for. Scope and price are set on a free call.

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A line of people walking uphill toward an open door

Does this sound like your team?

  • You bought AI licenses. Usage dropped after the first month.
  • A few managers use AI every day. Most never started.
  • Nobody is sure what is safe to paste into which tool.
  • The training day went well. By Friday, nothing had changed.

Rules before pilots

Before anyone tries anything, we agree on what is safe. What data can go into which tools. What needs a human yes. Who owns each workflow once it works.

The core rule never changes: AI drafts. You hit send.

What we measure

Two numbers. How many hours of work a week your managers no longer do by hand. And which workflows are still in use in week 12.

We don't count logins or AI usage.

How the 12 weeks work

  1. Stretch 1

    Understand

    Learn the work. We sit with each manager and map where their week goes, and which parts AI could take off their plate.

  2. Stretch 2

    Apply

    Apply AI to it. Managers use AI on their own real tasks, with us beside them. No sample exercises.

  3. Stretch 3

    Activate

    Bring it back to the team. Each manager teaches what worked to their own people, so the change spreads past the first group.

Why 12 weeks? Training days fade by Friday. Real change takes three stretches: learn the work, apply AI to it, then bring what works back to the team. Most programs skip the third part. Ours is built around it.

What your organization keeps

  • Written rules for AI use: what data goes where, and what needs a human yes.
  • A playbook of the workflows that worked, written for your team.
  • A named owner inside your team for each workflow, so nothing depends on us.
  • A week-12 report: what changed, what is still in use, and what to do next.

No new platform to buy. We work on the tools you already have. If a tool we recommend pays us, we tell you in one line. After the first group, later groups can go through a Workshop.

Questions about data and approvals are answered in the FAQ. Formats for later groups are on the pricing page.

We run this way ourselves

Two systems from our own companies.

A company handbook AI can read

We rebuilt the company handbook so AI can read it. Along the way, it found the places where the company contradicted itself.

An inbox that sorts itself and learns

Every hour, AI sorts the inbox. When I move something, it learns from the correction.

It never changes a sorting rule without asking first.

Talk it through first

On a free call we ask how your team works today. If the program is not the right fit, we will say so.
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I take on two or three new clients a month, so I can actually do the work myself.