Why Every CEO Needs a 'Team of Rivals'

Leading a company is a tough job. It’s even tougher when you feel like you’re in an echo chamber, potentially surrounded by others who consistently default to agreeing with you. Groupthink sets in, biased decisions are made, and you’re left questioning if you’ve considered all the risks.

Many CEOs today rely heavily on their executive teams for advice and decision-making. However, these teams often come with their own set of challenges—internal politics, favoritism, subject matter bias, and a tendency to protect their departments over the organization's overall well-being.

Others have found the allure of AI. While tools like ChatGPT can process vast amounts of data and offer insights quickly and in a confined space, they often revert to the mean, providing average solutions based on existing information. It lacks the creativity, innovative thinking, and nuanced understanding that those who break new ground bring to the table.

But there’s a better way to navigate these challenges—by assembling a "team of rivals."

Imagine having a small, trusted group of advisors who aren’t afraid to push back. Their sole purpose is only to push back and challenge you on major decisions, either building confidence in your output or helping build a new plan. This isn’t about creating conflict; it’s about fostering healthy, constructive debate and making sure your decisions are the best for your organization.

The goal is simple: make better decisions by challenging assumptions and uncovering blind spots.

Here’s how you can build your own 'team of rivals' and start making smarter, more confident decisions:

Start Small and Go Fractional

To get started, you don’t need to overhaul your entire leadership organization. Nor do you need an actual team.

Begin with one objective, external advisors. These could be fractional Chief of Staffs or, for this specific use case, Challenger Officers—roles designed to provide you with unfiltered feedback without the internal politics while still having access to gain a full understanding of your business model and organization.

By starting small, you can gradually build a culture of constructive feedback without overwhelming your team or putting yourself in unchartered waters.

Engage Future Leaders

The concept of a "team of rivals" comes from Abraham Lincoln's unique approach during his presidency. Instead of surrounding himself with like-minded individuals, Lincoln deliberately included his political opponents in his cabinet. This strategy not only helped him build rapport across different factions but also ensured he had access to a wide range of perspectives and ideas, which was crucial for making well-rounded decisions during a turbulent time in American history.

In the context of your organization, developing a team of rivals serves a similar purpose—and more. You want individuals from different business units, backgrounds, and levels of experience to shed light on your unknown unknowns. Additionally, this team can act as a gateway for succession planning. Those who can engage with you at this level are the ones who will drive your organization forward in the future.

These are individuals (4-5 employees) who aren’t part of the executive team but show great promise and a fresh perspective. Involving them not only brings new ideas to the table but also prepares them for future leadership roles.

Maintain Momentum and Confidentiality

It’s essential to keep the discussions within your 'team of rivals' confidential. Trust is key. Engage them in both significant and minor decisions to keep the team active and discussions relevant. Regular engagement ensures that all viewpoints are considered, and your decisions are well-rounded and robust.


By creating a 'team of rivals,' you’re not just protecting your decisions from bias—you’re also fostering a culture of transparency and trust within your organization. This approach helps you lead with confidence, knowing that every angle has been considered.

In the end, a CEO’s true strength isn’t measured by making decisions in isolation but by the courage to invite challenge and the wisdom to act on it. Embrace the diverse voices around you, and watch your company grow.

To get a more tactical approach to running a ‘team of rivals’ or to discuss the concept further, reach out to setup a call.

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The Elephant in the Room: How a Chief of Staff Can Unite Your Organization

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