From Overseeing to Orchestrating: An AI Readiness Workshop for Leaders
Jory Des Jardins
AI Advisor | Human Agency Architecture
A working diagnostic for AI readiness, with a plan for team adoption.
AI is changing what management means — not just what tools your team uses, but who decides what, and who's still accountable when it matters. Most leaders are adopting AI faster than they're redesigning the decisions underneath it, and the gap doesn't show up right away. It shows up later, in decisions nobody remembers choosing to hand off, and in managers who can't tell if their team is more capable or just more automated.
This workshop gives you a working diagnostic — not a lecture — to find out where your own team stands. You'll assess two critical layers of AI readiness: who holds decision rights on your team today, and whether your managers have shifted from overseeing execution to orchestrating a mix of people and AI. Then you'll build a real readiness plan for your organization, with live feedback in the room, not a template you fill out alone later.
You'll leave with a specific, prioritized read on where to act first — not a framework to file away.
What you’ll learn
You'll learn to see your team's AI readiness clearly — and lead as an orchestrator, not just an overseer, from day one.
Map which decisions your team has already ceded to AI, deliberately or not
Use a decision rights framework to see where judgment is eroding by default
Score your managers against five concrete orchestration indicators
Spot the gap between AI adoption mandates and manager capability to govern them
Leave the room with a prioritized, written plan — not a framework to file away
Identify the one or two gaps worth closing first, not everything at once
Share your readiness read with the group and get real critique in the room
Hear how other operators are solving the same problem
Take home a repeatable method for assessing decision rights and manager readiness
Apply it to a new team, function, or reorg without needing to hire it out
Understand what the other layers of readiness — beyond today — actually require
Workshop agenda
Framing (20 min)
Why AI adoption breaks without decision architecture — and why the gap shows up later than you'd expect.
Diagnostic walkthrough (60 min)
Self-assess your team against two critical readiness layers: decision rights and manager capability.
Working session (60 min)
Small-group breakouts — plot your own team's readiness and identify the top 1-2 gaps to close first.
Share + live critique (25 min)
Volunteers share their readiness read and get direct feedback in real time.
Close (15 min)
What full transformation requires beyond today's session — an honest look.
Learn directly from Jory
Jory Des Jardins
AI Transformation Advisor | Frontier Tech Executive | 30+ Companies
Who this workshop is for
Chief of Staff or Function Leader steering AI adoption across a team or org. Wants a concrete plan, not another concept.
VP of People or Head of Talent responsible for managers capable of leading through this shift and needing a way to assess readiness.
Independent or Smaller-Company Operator who wants senior-level guidance sized to a single session.
What's included
Live diagnostic session
You'll actively assess your own team's readiness in real time, guided live by Jory.
Written readiness plan you leave with
Walk out with a prioritized, specific plan for your organization — not a framework to file away.
Direct feedback from Jory
Share your readiness read with the group and get real critique in the room, not generic advice.
A room of senior operators
Work alongside other Chiefs of Staff, People leaders, and function heads solving the same problem.
Credit toward the Founding Cohort
Your workshop fee applies toward tuition if you enroll in the full four-week cohort afterward.
Certificate of completion
Share your new skills with your employer, or use it to support expense reimbursement requests.
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