IS YOUR PROBLEM WICKED OR MERELY TAME?
Most organizations mistake complicated problems (Tame) for complex ones (Wicked). Tame problems have known solutions and expert consensus. Wicked problems have competing stakeholder realities and no stopping rule.
Dennis Kennedy will tell you which one you’re facing, before you waste resources solving the wrong problem.
KEYNOTE SPEAKING #1: The Holmesian Leap
Not a traditional presentation. A structured provocation using the NeoHolmesian Method to expose the difference between problems you can solve and problems you must first learn to see correctly.
The Holmesian Leap reframes your challenge from a “Kind Problem” (missing information) to a “Wicked Problem” (bandwidth crisis, stakeholder conflicts, no clear stopping rule). You will leave with a new lens for examining your most critical challenges, not with answers, but with the questions your current framework cannot generate.
Format: 60-90 minutes, followed by structured dialogue
Ideal venues: Corporate law department retreats, law firm leadership summits, board meetings (trustees/directors), executive strategy sessions, and trade association annual meetings where attendees have decision-making authority over organizational challenges.
Example: Dennis Kennedy’s keynote to the National Association of Women Judges (October 2025) reframed the SRL crisis from an “information gap” to a “bandwidth gap,” demonstrating how AI can augment human capacity rather than replace judgment.
Fee: $35,000 (Plus travel/expenses)
KEYNOTE SPEAKING #2: Taking Charge of the AI Control Plane
TAKING CHARGE OF THE AI CONTROL PLANE: From Prompting Problem to Architecture Problem
This keynote event moves your organization from the performance of “AI efficiency theater” to the mastery of AI as a complex, volatile system.
The Strategic Alignment. I provide a forensic keynote that transforms your AI challenge from a Prompting Problem into an Architecture Problem. I identify the hidden AI traps and “Drift Vectors.” These are the specific points where the machine will quietly deviate from your institutional rules. I provide the framework to convert these hidden risks into managed, defensible assets.
The Map. I help you locate your organization’s Control Plane. By mapping the exact boundaries between AI automation and required human judgment, I help you establish the structural walls you need to protect your fiduciary and proprietary value.
The Artifact. After the session, I provide a customized “Decision Compass.” This load-bearing tool allows Boards and Executive Leadership to navigate high-stakes AI integration with clear eyes and practical judgment. It is designed to transition leadership from passive oversight to active Systems Stewardship.
Fee: $55,000 (Plus travel/expenses)
PRELIMINARY INQUEST: Diagnostic Biopsy
A time-bounded forensic examination of a decision or system where the cost of being wrong exceeds the cost of investigation.
Fee: Beginning at $50,000
Deliverable: A diagnostic brief that provides:
- Stakeholder conflict mapping (who believes what, and why)
- Problem classification (Wicked vs. Tame, with evidence)
- If Wicked: Investigative framework and recommended approach
- If Tame: Referral to specialist facilitators with rationale
You receive strategic clarity on the true nature of your challenge, the most valuable investment before committing resources to solutions.
Timeline: 2-4 weeks
What this is: Diagnostic investigation. Clarity on whether your problem is what you think it is.
What this is not: Implementation. KIPL does not execute solutions, manage projects, or provide ongoing advisory services. We investigate problems and map approaches. Execution is referred to specialist partners.
SELECTIVE INVESTIGATIONS
In the Holmesian tradition, I occasionally accept exceptional investigations: complex challenges where the difficulty is not finding answers but identifying the correct questions. I accept only cases where the problem is genuinely Wicked and the cost of being wrong significantly outweighs the cost of investigation. These are diagnostic inquests, not implementation projects.
REFERRALS FOR TAME PROBLEMS
KIPL does not accept work on Tame problems, challenges with clear solutions, established best practices, or straightforward implementation paths.
Tame problems include:
- Vendor selection and technology procurement
- Standard implementation of known systems
- Process optimization with established methodologies
- Training and change management for defined solutions
For these challenges, we refer to our network of expert facilitators who specialize in efficient execution.
FILTER: THE COST OF BEING WRONG
KIPL accepts engagements where the cost of being wrong significantly outweighs the cost of investigation.
If uncertain whether your problem qualifies, submit an inquest description here. I provide an initial Wicked vs. Tame assessment at no charge.