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Full Retreat Agenda
Leadership TrackTuesday, Sept 15 · 2:55 – 3:55 PM

What Are We Doing About AI? Leave With the Answer.

When the board asks "what are we doing about AI?" don't say "exploring." Leave with the first workflow, owner, guardrails, and success measure already chosen.

About This Session

Turn the day's demos into an operating plan your company can actually run. See the same workflow side by side as a reusable prompt with human review and as a tool-connected agent with triggers, approvals, and measurement — then design the first lift for your own business.

What We'll Cover

  • Reset the frame: maturity belongs to each workflow, not one company-wide label
  • Side-by-side reveal: the same weekly management job at two AI maturity levels
  • Workflow heatmap: classify three real jobs and choose the best first lift
  • Lift design sprint: trigger, data, tools, owner, approval gate, and exception path
  • Red-team the design: permissions, failure thresholds, audit trail, and human handoff
  • Write the baseline, 90-day target, and graduation test

You Leave With

Your first AI workflow plan — owner, guardrails, success measure, and 90-day launch target

Who Should Attend

CEOs, owners, and executive directors who keep getting asked what the company is doing about AI — by the board, by employees, or by their own gut. This is the Leadership Track capstone: the hour where the day's demonstrations become an operating plan.

Part of a Full Day of Hands-On AI Training

This workshop is one of 20 at the AI Business Retreat — a one-day, hands-on AI training for business at The Island in Spooner, Wisconsin, within driving distance of Minneapolis–St. Paul, Eau Claire, La Crosse, Duluth, and Hudson. Can't make the drive? Every session, including this one, streams live for remote attendees.

Presenters and final session materials are being finalized and will be announced closer to the retreat.

Session Details

When
Tuesday, Sept 15, 2026 · 2:55 – 3:55 PM
Track
Leadership Track
Where
The Island · Spooner, WI (or attend live remote)
Who it's for
The Leadership Track capstone — for CEOs, owners, and boards

One registration covers the full retreat — every session, every track.

For CEOs & Owners

See the whole day mapped for your seat →

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ChatGPT, Claude, or Grok: A Straight-Answers Buyer's Guide

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Leadership Track10:50 AM – 12:00 PM

The Owner's Cockpit: Every Number That Matters, One Screen

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What Are We Doing About AI? — Questions & Answers

The best first lift is a workflow that's frequent, measurable, and painful — weekly reporting, lead follow-up, or document preparation are common winners. This session has you classify three of your real jobs on a workflow heatmap, pick the best first candidate, and design the lift: trigger, data, tools, owner, approval gate, and exception path.
Six things: a named owner, defined permissions for what the AI can read and do, an approval gate where a human signs off, failure thresholds, an audit trail, and a success measure with a baseline and a 90-day target. That's the difference between an AI experiment and an operating plan a board will accept — and it's exactly what you design in this hour.
This workshop is part of the AI Business Retreat on Tuesday, September 15, 2026 at The Island in Spooner, Wisconsin. One registration covers the full day — all 20 sessions across the Leadership, Sales & Marketing, and Builder tracks, including this one. In person is $495 (working lunch included); attending live online is $250. Seats are limited.

This session is one of twenty.

One registration covers the whole day — every track, every workshop, the working lunch, and your written 90-day roadmap. Sept 15, 2026 · The Island, Spooner WI.