Use a Team of Rivals

The Problem with Making Big Decisions Alone

When you're facing a major decision—whether it's choosing an enterprise software solution, launching a strategic initiative, or restructuring your team—there's a dangerous trap: your own perspective. No matter how experienced you are, you have blind spots. You favor certain types of solutions. You overlook risks that don't naturally occur to you.

Most of us try to compensate by seeking advice, but here's what usually happens: you get polite feedback that doesn't challenge your assumptions, or you get input from people who all think similarly. You end up with validation, not genuine scrutiny.

Lincoln's Secret: Surrounding Himself with People Who Disagreed

Abraham Lincoln had a radically different approach. He deliberately filled his cabinet with rivals and critics—people who had competed against him, who disagreed with his methods, and who weren't afraid to challenge him directly. His Secretary of State, William Seward, had been his chief rival for the Republican nomination. His Secretary of the Treasury, Salmon Chase, actively undermined him while serving in his cabinet.

Why would Lincoln do this? Because he understood that rigorous debate and diverse perspectives led to better decisions. He wanted his ideas stress-tested by people who naturally saw their weaknesses, not cheerleaders who'd rubber-stamp whatever he proposed.

Now you can apply this same approach to your decisions using AI—by creating a custom ChatGPT that simulates a "Team of Rivals" advisory council.

How to Create Your Own Team of Rivals Custom GPT

Here's how to build a custom GPT that gives you the kind of rigorous, multi-perspective analysis Lincoln valued. This takes about 5-10 minutes to set up, and you can use it repeatedly for any major decision.

The configuration document creates six distinct advisors, each with different personalities, priorities, and ways of thinking. They'll challenge each other—and challenge you—to ensure you've considered all angles.

What Makes This Approach Powerful

Unlike asking ChatGPT a straightforward question, this custom GPT is specifically instructed to generate authentic disagreement. You're not getting six variations of the same perspective—you're getting genuinely different ways of looking at your problem.

The advisors include a data-driven strategist, a pessimistic risk manager, an ethics-focused advocate, a blunt pragmatist, an optimistic visionary, and someone focused on historical precedent. Each one looks for what the others might miss.

How to Use It for Real Decisions

When you open your Team of Rivals GPT, describe your decision or challenge in specific detail. The more context you provide, the better analysis you'll get. Include relevant constraints, stakeholders, resources, and your preliminary thinking.

The whole process typically takes one conversation of 15-30 minutes, depending on the complexity of your decision. You can ask follow-up questions, introduce new information, or ask specific advisors to elaborate on their concerns.

Real Scenarios Where This Works

This approach is particularly valuable for decisions where multiple factors compete: choosing between enterprise software platforms (cost vs. features vs. implementation complexity), deciding whether to pursue a strategic partnership (opportunity vs. risk vs. resource commitment), or planning organizational restructuring (efficiency vs. employee impact vs. cultural change).

It's less useful for straightforward technical questions or situations where there's a clearly right answer. Use it when you need genuine strategic thinking, not just information.

The Bottom Line

Ready to create your Team of Rivals? Download the complete configuration instructions here: Team of Rivals Custom GPT Configuration

Want to learn more? Check out Practical AI for Humans for more practical guides on using AI effectively.