Engaging Dennis Kennedy
Then something stopped fitting the model.
My current work centers on how we exercise judgment, manage risk, and make consequential choices when technology has made it extraordinarily easy to make things happen.
Acceleration is becoming abundant. Direction is becoming more valuable.
There are exactly two ways to work with me.
- The Prudent AI Keynote
It’s not another talk about what AI will do next. I’m interested in what we do when prediction is unreliable, experimentation is cheap, and organizations can move extraordinarily quickly.
The goal is better judgment while meaningful choices remain, not just caution..
Prudent AI treats AI adoption as an architecture and risk-management challenge rather than a prompting problem. We establish the discipline of Semantic Stewardship: deciding where AI can act, where human judgment must remain, and how risk is calibrated as a portfolio so your organization can use AI more boldly without surrendering accountability, context, or meaning.
The Terms: I deliver the framework, answer the hard questions, and then I leave. There are no ongoing advisory loops, implementation programs, or software sales.
The Fee: $50,000 plus travel and expenses. - One Meeting Before Consulting
There is a meeting in the life of an important project when everyone finally realizes something has been missed. I’m interested in the meeting before that one. Nothing has to be going wrong. Things might be going very well.
Then something stopped fitting the model.
The earlier meeting has less certainty but more optionality. The later meeting has more certainty but fewer choices. Don’t wait until you can explain exactly what’s happening. Not knowing quite what to make of it yet may be the reason to call.
I accelerate your velocity (speed + direction) to your first usable starting point while the situation is still movable. I don’t run the implementation, and I don’t become your transformation program.
And I don’t do autopsies.
One Meeting Before is especially well-suited to private equity and venture firms investing in legal services and legal technology. Before you commit capital, I help pressure-test the premise, the value-creation thesis, and the assumptions about current AI capabilities that may be driving the deal. Is the category itself sound? Is this really an efficiency play, or is there a more durable productization opportunity?
The Terms: We interrogate the problem together before you commit to a solution. We isolate the problem worth solving, identify the decisions that matter, establish the architecture for thinking about them, and then I leave.
The Fee: $101,000 plus travel and expenses.
Contact
For speaking inquiries or to discuss an engagement, contact me when something stops fitting the model or something weird is happening in your most important project.
To start a discussion, send a brief note answering these four questions:
1. What consequential decision, transition, or project is becoming difficult to read?
2. Who will be in the room?
3. Why is this critical now?
4. What is the cost of getting the framing or decision wrong?
If the problem is one I should be working on with you, we will be talking.
