Briefing #31: How to Make AI Your Sparring Partner
Instead of merely asking AI to offer answers, ask it to challenge you instead.
Note: This briefing was originally published on LinkedIn on March 6, 2026. It has been migrated to our new home on Substack to create a complete archive. Multi-format features like video and audio commentary are available for all new briefings published from April 2026 onwards.
For the past two years, the dominant metaphor for AI in the enterprise has been AI as “co-pilot,” a comforting and brilliantly marketed concept. It suggests a helpful assistant, sitting at your side, ready to take over routine tasks and ease your day-to-day.
But I believe this metaphor, while well-intentioned, brings along with it an implicit bias that limits the way in which we think about the role that AI can play in our work. It encourages a master-servant relationship with technology.
We delegate our thinking, we passively accept the AI’s first answer, and we optimize for comfort and efficiency. This, as I’ve shared in the past, is a direct path to cognitive dependency and organizational fragility.
A far more powerful, albeit more challenging, model is to think of your AI not as a co-pilot, but as a sparring partner.
A co-pilot’s job is to make you comfortable. A sparring partner’s job is to make you better. A sparring partner challenges you, tests your defenses, and exposes your weaknesses in a safe environment, before you step into the real ring with a competitor or a customer.
This positions AI not just as an interface for delegation, but as a partner through which constructive dialogue is possible.
Instead of asking the AI, “What are the top 5 markets for us to enter?”, a leader in a “sparring partner” culture would say, “Our top market is Germany. Now, act as our biggest competitor and tell me why this is a terrible idea.” The goal of this interaction is not to get a faster answer. It’s to build a more robust strategy by subjecting it to rigorous, critical debate.
This is the “Socratic Dialogue” in a modern context. It’s an iterative process of questioning, challenging, and refining that uses AI’s immense knowledge base and capacity for analysis to sharpen our own human judgment.
Cultivating this culture requires a new kind of leadership. It means explicitly rewarding the employee who challenges the AI’s output, not the one who accepts it fastest. It means celebrating “productive friction” as a sign of a healthy, intelligent team. It means training your people not just on “how to prompt,” but on “how to question.”
The co-pilot model promises a smoother ride. The sparring partner model promises a stronger team. Choose wisely: do you want to build a business that’s merely efficient, or one that makes the best decisions?