What Winning CEOs Can Learn From Head Coaches

The question that terrifies BOTH every successful executive and head coach

What if your greatest advantage is becoming your biggest liability?

Every company and championship team faces the same paradox -

The strategy that won last season is the blueprint every opponent studies in the off-season.

Your greatest strengths become predictable.

What made you elite threatens to make you obsolete.

Technology executives face an identical challenge. But with a critical difference in industry —your cycles aren't seasons, they're continuous.

CEOs that achieve significant success are simultaneously the hunter and the hunted. Innovations that drove your company to success are RIGHT now being reverse-engineered by competitors.

But one of the lessons I learned over 25 in the NFL, college football and Premier League  – that will surprise you is this …

… for the very best leaders – that’s actually when they get most excited.

This excitement comes from recognizing the challenge that follows success – a challenge that, if mishandled, becomes the trap that destroys even great companies.

The Trap That Destroys Great Companies

When any team, such the Philadelphia Eagles win the Super Bowl or a Paris Saint-Germain, win the Champions League, they now face a problem.

Every other team is analyzing their tactics, studying their patterns, and developing specific tactics to beat them or copy them

Imitation is the sincerest form of flattery.

Imagine you’re Paris Saint-Germain coach Luis Enrique now, or you're Nick Sirianni at the Eagles - the temptation now is either to abandon their successful approach entirely or to double down on what worked.

The truth is both responses are strategic mistakes.

You see the same dynamic working with technology or data companies during transitions.

The usual instincts are to either:

1. Completely reinvent themselves (perhaps to show doubters they can do it a different way) or
2. Defensively protect legacy (fear of change).

Both paths typically lead to failure.

Elite Leaders Are Just Built Different

I’ll never forget being called to a hotel function room - only two days after winning a championship by the Head Coach. You can imagine how sharp both of us felt after two days of celebrating.

He had one topic he wanted to discuss.

How to plan to win next year.

I’ve had this very same conversation with a CEO at the end of the year too - how to plan to win for next year. What to change, what not to change.

It’s About More Than Winning

You see, elite leaders aren’t interested in winning. They want to dominate. They want consistent repeated success.

Success milestones, trophies or awards are NOT an end in themselves. They are a quantitative and qualitative assessment of the strategies, work, operation and processes of the organization.  

CII

The best organizations, sport or business, implement the mindset I refer to as – CII. Continuous Iterative Improvement. The key to Continuous Iterative Improvement is maintaining core tactical or strategic principles while continuously developing new expressions of those principles.

The result?

Sustained championship-level performance despite continuous adaptation.

The Trap

Many companies, technology and otherwise, fall into an "adaptation trap." Changing everything in response to market pressure or a sudden change in fortune - losing their competitive identity in the process. Or they commit the opposite error: protecting their legacy approach so fiercely that they become irrelevant.

And it’s completely understandable.

From an emotional perspective. But not from a pragmatic reality. 

I've witnessed this across every elite environment Premier League football to special operations, Fortune 500.

Same pattern every time.

Systems Advantage

One thing I learned early in in my Phd, there are fundamental principles that apply whether you're optimizing factory production lines or organizational strategy

Sustainable excellence must respect complexity in elite organizations.

One event has multiple influences, many out of your control and unless you accurately identify the source you can jump to the wrong conclusions. Easily. 

Therefore, your fundamental principles remain constant, WHILE your methods, tactics, and expressions continuously evolve.

This is why I use the phrase ‘Take the emotion out” to remind people to analyze the event in the cold. 

There’s no difference between winning and losing

There’s one other fundamental assumption often overlooked. You can underperform and still be successful. Many organizations win in spite of themselves.

Similar to ‘survivor bias’:

• Some organizations and teams I’ve been involved with won while performing poorly
• Some teams and companies had record years but actually on analysis performed poorly

The difference though ALWAYS becomes apparent the following year. And it always stems from leadership – the best leaders ruthlessly assess performance, separate from result – and emotion.

Your Performance Only

If you want to improve you must ruthlessly analyze and improve on both winning and losing in the very same way.

Your standard is your standard.

There’s no difference between winning and losing – in elite performance.

You learn equally from both.

Myth of Losing

Working across sports, business military reveals a consistent pattern: sustainable excellence requires the same approach to outcome.

Those who say you only win from losing are clearly mistaken.

Think about how your favorite winning team approaches this challenge. They maintain their core philosophy—perhaps defensive excellence or high-tempo offense—while constantly adapting their specific tactics based on opponent analysis, player development, and evolving competition.

Only As Much As Is Necessary

In a day and age when people think doing as much as possible is smart – the opposite is key. Make as much change as is necessary to improve.  

In fact, one of my old teams, Liverpool FC, did it exceptionally well – even after changing managers.

Arne Slot replaced Jurgen Klopp, one of Liverpool’s most popular and transformative managers. Rather than coming in with a whole series of his own new ideas, he kept the style Klopp had implemented and made minor adjustments.

The result?

Going further than Klopp had done, surprising everyone and winning the Premier League – in his FIRST season.

Arne Slot doesn’t get enough credit for is how little he changed while still evolving key areas.

The same principle applies to technology leadership. Your core mission, values, and strategic approach provide stability, while your products, processes, and tactical approaches must continuously evolve.

Building Adaptive Excellence

The key is developing principled models. Systems that enable rapid tactical adaptation without compromising principles or identity.

This requires integrated approaches that I've seen work identically across elite organizations:

1. Beat Yourself

Elite teams constantly analyze their own performance – from the opposition perspective. Essentially asking – How would we beat us?

How would we overtake our market position?

It requires ‘performance safety’ (not psychological safety, more on that another time) where tendencies, strategies analysis sessions resemble almost intelligence briefings.

Pull apart your own capabilities!

The outcome, by the way, is not just practical but truth-telling, humbling and most of all very motivating.

2. Nine Most Hated Words

Championship teams practice to have multiple tactical variations so they can adjust seamlessly.

This means being very clear that a mindset of ‘Because this is how it has always been done’ will not survive your organization. Nothing is beyond challenging.

It’s human instinct to become possessive, insecure but it leads to fast failure.

3. Sacred Cows

There are no ‘sacred cows.’ Nothing is beyond challenge. And no one.

This was one of the core rules I was exposed to in a special operations community. Technology leaders need similar capabilities—the ability to test new approaches quickly without disrupting core operations.

4. Holistic Performance

This final stage is where most organizations fail, and I've seen it frequently.

New capabilities developed in isolation rather than in context with existing strengths and then fail when applied. Harvard Business Review called this, what has been known in elite sport and special operations for a long time, "ambidextrous innovation"—the ability to exploit existing capabilities while simultaneously exploring new ones.

5. Always Drive In Both Lanes

I use an embarrassingly less-sexy term – “Driving the freeway in both lanes”. Slow lane for development and implementation, fast lane for execution and ingraining. But most critically of all – You, the truck, the organization never stop improving. Keep switching lanes – and always moving forward.  

6. Enhance Don’t Eliminate

Elite teams ensure that new tactics enhance rather than replace their core competencies. This reductionist approach might work in lower level organizations, but not in high performance settings where the application is already refined.

And Remember CII

A continuous improvement methodology provides a structure for adaptation while still maintaining the performance excellence you’ve’ achieved.

Just as sports teams have a core game plan they have perfected, but adjust slightly for each opponent, technology leaders must continuously adapt their strategic approach based on market conditions while maintaining operational excellence.

Rather than abandoning successful approaches, championship organizations develop new capabilities that complement and enhance their proven strengths – creating new synergies. These new innovations must be integrated seamlessly with existing operations rather than creating internal competition or confusion.

The companies or organizations or departments that thrive are those that treat their core principles as non-negotiable but understand methods are constantly evolving.

Because, to win, they have to.

References:

1. Reeves, M., & Deimler, M. (2011). Adaptability: The new competitive advantage. Harvard Business Review, 89(7), 134-141.
2. O'Reilly III, C. A., & Tushman, M. L. (2013). Organizational ambidexterity: Past, present, and future. Academy of Management Perspectives, 27(4), 324-338.