The Billion-Dollar Question Every CEO Must Answer

Hey friend,

Last week, I had a conversation with a CEO who is proud of the generational wealth he has created for his team by growing and scaling a company to just over a billion dollars in sales in under 10 years. However, the pressure of potentially losing it all keeps him up all night—sound familiar?

I asked him the billion-dollar question: is your team keeping up, staying ahead, and ready for anything?

(We all know the answer.)

The Problem

When you build something incredible, it creates expected conditions. The pattern of success, the feeling of comfort—this can lead to a lack of urgency, unity and complacency. Pressure is what forges diamonds. Without the pressure to perform, sometimes we don't. The tension points you're feeling—old vs. new perspectives and me vs. we—are natural and expected with explosive growth. Here are some signs this is happening:

• Resistance to Change: Team members are sticking to old methods rather than exploring new, innovative solutions. When new teammates come on board, they are met with an us vs. them mentality.
• Communication Breakdowns: Increased misunderstandings and lack of alignment in goals and strategies. We often judge behavior as intent.
• Decreased Morale: A noticeable drop in team enthusiasm and engagement. People are not locked in.

Humans have an immunity to change, but it is also the way out. Phones update their software periodically just to optimize performance, but especially when something is wrong. When was the last time your team updated its "software" versus just running the same play in the wrong game?

The Wrong Games

1. The Blame Game (Us vs. Them): It's easy for teams to fall into finger-pointing when challenges arise. This creates division and erodes trust. To remedy this, foster a culture of radical honesty and collective accountability. Encourage your team to voice concerns openly and take shared responsibility for outcomes.
2. The Fame Game (Success Blind Spots): Success can create blind spots. Kodak, Blockbuster, and many more companies were successful but didn't pivot fast enough. What got you here will not get you there, which brings us to …
3. The Lame Game (Not Meeting the Moment with Growth): Every situation requires growth and adaptation. Not being able to see the forest through the trees. Not being able to read the room. Looking at things happening to us vs. for us.

Speaking of Games

Who’s watching the Olympics? Confession time: not me, at least not a lot this time, but do you remember The Redeem Team?

The Redeem Team Story

In the early 2000s, the U.S. men's basketball team, known as the Dream Team, was synonymous with excellence. However, after their stunning defeat in the 2004 Athens Olympics, it became clear talent alone wasn't enough. Complacency had set in—just like the CEO noticed in his company above.

The 2004 loss was a wake-up call, sparking a need for change. Enter the Redeem Team, assembled for the 2008 Beijing Olympics, led by Kobe Bryant, Dwayne Wade, and LeBron James.

Recruiting the best is only part of the game. Forming an actual team that feels like they are all in the boat together, rowing in the same direction, is another challenge.

The team did okay, but struggled until Kobe inspired them all in an elevator (yes, read that again). Teammates saw Kobe heading to the gym at 4 a.m., while they were returning from a late-night event and still recovering. This stark contrast was a wake-up call. Kobe's dedication inspired the team to adopt his relentless mindset. They realized success required more than talent; it demanded discipline, preparation, a commitment to playing your role and a refusal to settle.

How is your team reading this moment?

This shift led to the Redeem Team's success. They won gold in Beijing, restoring pride to American basketball. Kobe’s influence taught them greatness requires constant effort and teamwork. Under Coach Mike Krzyzewski, they focused on chemistry and accountability, ultimately defeating formidable opponents like Spain to reclaim their top spot.

Simone Biles: The Redemption Tour

Okay, I lied a little... I have watched the Olympics, but mainly just Simone Biles. Why? She’s updating the software on what winning means and takes.

"Overcoming adversity takes time. Resilience is not about how quickly you bounce back—it’s about how fully you recover. You can’t judge people’s strength when they fall. Their fortitude is visible when they rise again." — Adam Grant

In the 2020 Tokyo Olympics, the U.S. women's gymnastics team won silver instead of gold, and Biles withdrew from several events due to mental health concerns. At the time, this was not a popular move.

Biles and her teammates, including Sunisa Lee and Jordan Chiles, decided to return for the 2024 Paris Olympics, calling it the "Redemption Tour." They faced numerous challenges—mental health struggles, setbacks, injuries, and even criticism from former teammate MyKayla Skinner about their work ethic.

In Paris, Biles returned to form, showcasing exceptional skills. The team’s collective effort and mutual support led them to gold. Their victory was a powerful redemption from Tokyo, highlighting the importance of resilience and mental health. She is now the most decorated woman gymnast of all time, with a record number of gold medals.

Winning and success come with a cost.

Their win not only redeemed the Tokyo performance, but emphasized the idea that mental fitness is just as important as physical fitness when preparing to compete at this level. Their win carried deep personal significance for Biles and her teammates and silenced critics. It illustrated the alternative paths available to success, and that the old “push yourself no matter what” mentality isn’t the only way. So many good lessons here…

The Legacy

These redemption stories are a testament to resilience, self-awareness, and courage. It shows true strength lies in rising after a fall and that playing the right game means bringing the heart, preparation, and adaptability.

These Olympic stories remind us it’s never too late to change the game and come out stronger.

Bringing It Back to SHIFT

At SHIFT, we help teams break out of complacency, adopt the right mindset, and perform at their best. Ready to take your team to the next level?

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Best,

Joe

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