Is It a Team Mistake or a Leadership Failure? The Answer Is…

When a project goes off the rails or a client is left unhappy, it’s natural to look for the cause. Was it a breakdown in execution? A member of the team dropping the ball? Or is it something more?

It’s a question every person in a position of authority has to face. On a recent episode of Beyond The Grind, hosts Korede, Allen, and Tosin had a candid conversation about the painful, expensive, and necessary lessons that come from mistakes in business. They landed on a truth that might be hard for some to swallow.

Ultimately, the responsibility for a team’s fumble doesn’t just land at the leader’s feet — it starts there. This isn't about playing the blame game. It's about understanding the core of leadership failure and using it as the ultimate tool for growth.

"There are mistakes that cost money and then there are mistakes that cost time. And I can definitely tell you that I've done both."

— Korede

The Expensive "Continuing Education" of an Entrepreneur

Hosts Korede and Tosin call them “expensive lessons” or “continuing education,” and Allen shared a powerful story that perfectly illustrates the concept. Thrilled by a $1 million investment commitment, he got ahead of himself and started staffing up his team before the money was actually in the bank.

He was making moves, but the capital wasn’t there to back them up. The deal fell through, his company’s burn rate skyrocketed, and he had to make the painful decision to let go of the very people he’d just enthusiastically hired. It was a moment that cost him money, time, and a dose of humility.

While easy to frame as a financial misstep, it was truly a leadership failure in managing risk and expectations. Allen jumped the gun, and the consequences rippled outward. This is the kind of "tuition" that entrepreneurship demands—gritty, real-world lessons that no textbook can teach you. They're tough, but they forge better leaders.

"You didn't create the infrastructure and the trust to keep them successful."

— Tosin

Your Team’s Success Is a Test of Your Leadership

The central debate of the episode was whether a mishap is a team failure or a leadership failure. The verdict from the guys was unanimous: it’s always the leader.

As Tosin points out, a leader can’t separate themselves from their team’s output. Think about it: You are the one who hired the team. You are the one who designed the processes. You are the one who nurtured the culture. If your team doesn’t feel empowered to challenge a bad idea or if there aren’t enough checks and balances, that infrastructure is on you.

Tosin shared his own challenges with scaling his firm. As his company grows, he can no longer be the sole point of contact for every client, a shift that some long-time clients resist. The friction that arises isn’t the client’s fault for being resistant to change, nor is it his team’s fault for stepping into new roles. It’s a leadership challenge that requires empathy, clear communication, and a strategic transition plan.

If your team is failing, it's a direct reflection of your leadership. Have you guided them correctly? Have you explained the "why" behind the "what"? Do they have the tools and autonomy to succeed? If they continue to miss the mark and you keep them in that role, that’s not their failure—it’s yours for not making a change.

Taking this kind of radical ownership isn't about self-flagellation. It’s about recognizing that you hold the power to fix the root cause. You can change the system, improve the process, offer better training, or make the tough call to find a better fit for the role. That is the leader's burden and their greatest opportunity.

These lessons, whether they cost time or money, are what separate a manager from a true leader. The journey is full of them, and embracing the responsibility is the only way to move forward.

For the full, unfiltered conversation and more personal stories from the crew, watch the complete episode on YouTube. And for more real talk on business and life, make sure you’re subscribed to the Beyond The Grind newsletter.