A two-day executive engagement that reverses the order of AI strategy. Instead of starting with what AI can do, you start with where you’ve chosen to play and how you’ve chosen to win — then stress-test every initiative against those choices.
of AI projects fail — nearly double the failure rate of traditional IT efforts.
RAND, 2024
of CEOs report investing in AI tools before fully grasping their value.
IBM, 2025
of executives say AI has had no measurable impact on productivity or employment in three years.
National Bureau of Economic Research
The pattern is consistent: leadership adopts an “AI-first strategy,” then back-fills use cases. The result looks strategic but isn’t reinforcing how the organization has chosen to win. Teams burn cycles. Customers feel the drop in quality. The board asks where the return is. This workshop reverses the order.
Built for a CEO plus 3–6 direct reports at an organization with at least two active AI or automation initiatives — especially where one or more of these is true:
Not a fit? If your team is shopping for AI tools or still building basic AI literacy, a foundational Intuition Building Sprint is the better starting point.
A completed check for each major AI initiative in flight, anchored to the Strategy Choice Cascade.
Every initiative plotted on the Autonomy Decision Matrix — placed in Hold, Question, Assist, or Automate.
A sequenced plan: which initiatives to accelerate, slow, repurpose, or stop — and in what order.
Surfaced through a structured pre-mortem, with mitigation owners assigned.
A one-page story suitable for board, investor, and all-hands communication.
A working session to review traction, drift, and the next quarter’s choices.
Each day runs roughly 9am–4pm with breaks. On-site or off-site — in-person preferred.
The engagement is designed so the two days in the room are the easy part — fit is confirmed up front, and the thinking continues long after the session ends.
Confirms fit and surfaces the initiatives the workshop will focus on.
A short pre-read goes to every participant before the session.
Facilitated personally by Stefanie Hutka. Roughly 9am–4pm each day, on-site or off-site.
Delivered within 10 business days: roadmap, risk register, and executive narrative.
A review session on execution, traction, and drift.
Author of Designing Automated Futures (Rosenfeld Media). UX practitioner, UC Berkeley instructor, and Bay Area startup mentor with two decades designing and shipping emerging-technology products — from augmented reality systems at DAQRI to generative AI workflows at scale. She has facilitated versions of this material with enterprise leadership teams across financial services, insurance, design tooling, and robotics.
Format: two consecutive days, on-site or off-site, for 5–8 senior leaders. Investment is available on request. The next step is a 30-minute scoping call to confirm fit.