How we build teams who ask the hard questions.
The Hard QuestionsGoverning How Your People Use AI
Your people already use AI at work. Some of that use was approved. Some was not. Fear will not govern it, and a policy no one reads will not either. Controls will: a plan, a named owner, and a way to see drift before it costs you. Jack P. Flaherty spent two decades in digital risk and compliance, including Big Four director roles, implementing, managing and auditing every wave from ERP and cyber to electronic medical records and blockchain. He shows boards and leaders how to put controls around how their own people use AI, so the firm gets what it set out to get, and can stand behind every decision along the way.
Keynote Takeaways
- Go slow to go fast. The preventive control: plan, name an accountable owner for each tool, and build the governance before the first use.
- Mind the drift. The monitoring control: notice when people, tools and results slide from what was approved, and know what to do next.
- Spot the ripple. The detective control, with the front line as the sensor: the people closest to the work see it first, and the signal has a fast path to the person who decides.
- Gain a one-page owner map of how your people use AI today, built on the NIST AI RMF and ISO/IEC 42001.
Audience: Boards, C-suite teams, managing partners, PE and VC sponsors, and leaders in healthcare and financial services.
Format: Keynote 45 to 60 minBoard briefing 90 min
Version 1Boards & C-Suite
Boards approve AI plans. Only 22.6% have audited where AI is used, NACD found. Jack, a former PwC Director who led C-suite risk executives’ discussions twice a year for five years, helps directors set clear owners, ask for reporting they can read, and plan their own AI education. The question is not whether to use AI. It is who answers.
Source: NACD, 2025 Public Company Board Practices and Oversight Survey, July 2025.
Leave with: A named owner for your workforce’s AI use, and three lines of board reporting to ask for.
Version 2Professional Services
Clients send firms mixed signals on AI. The Thomson Reuters Institute found 40% of firms have been told by different clients both to use AI and not to. For managing partners, and the PE and VC firms rolling up practices, Jack shows how to set one staff AI rule, name the partner who owns it, and lead the client conversation instead of waiting for it.
Source: Thomson Reuters Institute, 2026 AI in Professional Services Report, February 2026.
Leave with: A one-page staff AI rule, an owner by name, and a script for the client AI conversation.
Version 3Regulated Industries: Healthcare & Financial Services
In banking, capital markets, fintech and healthcare, a fair first question from any examiner is simple. Who approved this tool, and who watches it? Jack’s career runs through both fields, from Morgan Stanley’s derivatives trading desk to California’s first statewide Health Information Exchange, with Big Four director roles in between. He helps leaders answer with records, not reassurance.
Source: IBM, Cost of a Data Breach Report 2026 (research by Ponemon Institute), July 2026: 92% of organizations that reported an AI-related breach lacked proper AI access controls.
Leave with: A view of who approved each AI tool your people use, and who watches it, in a form an examiner can read.
