How to be a Bada$$ CEO in 2025

“I just want to be a Badass CEO.”

That was not the usual response when I ask someone about their goals. It was, however, intriguing, and deserved time to unpack the true intent.

There are several meanings you could assign to the label. It could be the idea of being ruthless, a bully, or a troublemaker. It could also mean being confident, independent, committed to excellence, and driven by values such as honor, responsibility, compassion, and selflessness.

Jim Taylor, Ph.D. penned an article in Psychology Today back in 2010 that offers this important insight:

“A badass does what needs to be done, no matter how difficult it is, without complaint or need for fanfare. A badass doesn't take the path of least resistance.”

The person sitting across from me had a definition that was closer to Taylor’s interpretation of strength. For him, a badass CEO develops and grows a legendary company … and in the process secure his own reputation for being one of the best at what he does.

For him, being bad wasn’t just being good. It was being great—even legendary—over time. Knowing that some will find badass to be offensive or confusing, let's use legendary as the benchmark.

Names like Steve Jobs, Jack Welch, Norman Brinker, Jeff Bezos, and Reed Hastings were mentioned as examples. The response would have been equally positive if Bob Iger, Indra Nooyi, Jamie Dimon, Satya Nadella, Bill McDermott, or Debra Cafaro were used.

Some—like Jack Welch and Steve Jobs—are known for being demanding, ruthless, and occasionally egotistical. They moved quickly, offered blunt criticism, had high expectations, and were viewed as leading led through intimidation.

Others, like Indra Nooyi and Satya Nadella, are known for inclusion, championing innovation, and empathy. Bill McDermott is inspirational and philanthropic while delivering sector-leading growth.

Debra Cafaro might be less recognizable than other names mentioned. She is, to use my prospects definition, probably the baddest of the bunch. Ms. Cafaro led the turnround of Ventas. Her company has experienced a record-breaking 2,373 percent return over the past 17 years. She balances strategic dealmaking and a focus on results with generosity of spirit and a commitment to building a great team.

Translating Style and Talent to today.

Would a legendary performer from past generations still be legendary today?

The question sparks endless debate that can apply to anything. Would athletic stars of the past be dominant in the way their respective games are played today?  Could today’s stars have been successful in the past?

No one knows for sure. A safe assumption is that exceptional talent would still succeed given access to today’s training, nutritional science, and improved competition.

The same can be said of the legendary CEOs of previous generations.

Jack Welch was named “Manager of the Century” and “The CEO’s CEO” by Fortune and Forbes respectively. His relentless focus on execution and results would still be a strength today. His volatile style would not.

Welch, on the other hand, would have received feedback and coaching about altering his style for today’s workforce early in his career. Assuming he was motivated and capable of changing his style, he would likely be equally effective. The same is true for Jobs since he did alter his style over time without losing the authenticity that made him effective.

Here is the takeaway: Legendary CEOs are both right for their organization and right for their time. Being legendary requires mastering mindset and skillset within the context of the current environment.

How do you become one of those legendary names?

First, let’s talk about what you don’t do.

You don’ t make the mistakes of those named as some of the worst to do the job. This illustrious group:

• Failed to breakout of their own paradigm to explore other opportunities (Whitmore at Kodak).

• Antagonized both workers and investors while leading the company toward massive losses (Fiorina at HP).

• Allow your emotions to drive decisions (Scully at Apple).

• Create a culture that believed in winning at any cost (Lay at Enron).

• Risk more than you can afford to lose (Jiulin at China Aviation Oil).

• Disrespect your customers (Ratner at Ratners Group).

What Bezos said.

Jeff Bezos offered this sage guidance: “The best entrepreneurs are missionaries not mercenaries.”

This doesn’t mean that you can avoid being tough minded, focused, results driven, and even calculating when necessary. The mercenary does these things for the singular purpose of increasing shareholder value. It is a transactional approach that can make you (and your investors) wealthy.

Missionaries are no less focused on results. They just achieve them while also striving for (and achieving) more.

Where the world is headed.

The legendary CEOs of the next 10 years will be those that lead organizations that are built to flourish not just thrive.

Thriving companies deliver amazing growth and results. In the process, they create value for customers, investors, and to some degree associates through job opportunities.

There is nothing wrong with thriving. It is a wonderful goal considering that many businesses struggle to survive much less be a market leader. Fewer than 30 percent of S&P index companies beat the overall index average in 2024. There is a lot of good but not great performance out there.

Flourishing companies achieve amazing results and growth, too. They accomplish this while also making associates, the community, their industry, and even the broader society better. They will tell you that their commitment to a purpose broader than themselves is a strategic weapon that makes them stand out in the marketplace.

It is, to be sure, harder work. Isn’t that the stuff that legends achieve?

Yes, but how?

Gary Wojtaszek (Wojo) is another name you might not know. He led the team that grew Cyrus One into one of the top data center companies in the world. Today, he’s the founder of RecNation, and that company is doing what everyone who knows Gary would expect – growing and flourishing.

If you are looking for a road map of where to invest your energy and efforts as a CEO, Gary’s guidance is an excellent staring point. He told me that his work as CEO of Cyrus One could be placed into four basic areas:

1. Leading the vision and strategy.

2. Aligning resources and ensuring accountability for execution.

3. Building and empowering a high-performing team.

4. Protecting and enhancing the culture.

What else do you need to know for 2025?

Your organization—like the entire world—exists at the center of a Vin diagram. Its components are:

• Intense unpredictability.

• Extreme complexity.

• On-going uncertainty.

• Constant change.

You should expect the cost of money to remain relatively high in the coming year compared to pre-COVID era standards. Geopolitical concerns will disrupt supply chains. The global economy will stress your ability to grow internationally. Natural disasters seem to occur on a weekly basis. The approach taken to addressing undocumented immigrants could stress your workforce, customers, or both. There will be a continued shortage of qualified staff.

Effective use of AI and other new technology will create a competitive advantage. The only question is whether it will be for you or your competitors.

In that space, the CEO (and every other leader) must grow and flourish in every area of their leadership toolbox to help their teams more from where they are now to where you need them to be.

Now for the real challenge.

There will be winners and losers regardless of the environment. That means disruption and the challenges of life in that Vin diagram are not the real problem. That is just the water in which we swim. When people drown, it is not the water’s fault.

Your true competitors know how to create a vision and strategy. They are about as good as you at aligning resources and ensuring accountability. Being better in those areas is important, but it isn’t a difference maker.

You have a nimble culture problem.

Protecting and enhancing the culture becomes the difference that creates lasting leverage and value.

It is more important than having the best talent on your team. Enron is a classic example of incredibly talented people failing because of a corrupt culture.

Culture is also a key factor in recruiting superior talent. Almost half of applicants listed culture as one of the deciding factors in choosing a job, and 15 percent declined a job offer because of the culture.

Think of your culture this way.

Culture has, unfortunately, been somewhat hijacked to be code word for how we treat people.

That is part of it, but your culture must become much more to become the CEO of a legendary organization today.

Start with the basics. Your culture must be:

• Customer obsessed.

• Results focused.

• People centric.

• Values aligned.

Then move to the culture accelerators that allow you to respond to any challenge while flawlessly executing:

• Change ready.

• Data led and process driven.

Finally, there are culture Game Changers that allow you to make being nimble a strategic advantage:

• Collaboration enabled.

• Future seeking.

The legendary leaders will take their culture to new levels that become the catalyst for being nimble and remaining relevant. To accomplish that, they will rethink their leadership mindset, commitment to talent development, and strategy.

Most important, they will create an organization full of missionaries not mercenaries.

That’s how you become a legendary, badass CEO.

Randy Pennington is an award-winning author, speaker, and leading authority on helping organizations deliver positive results in a world of uncertainty, complexity, and change. He is a leading thinker and conversation generator on helping organizations flourish. To learn more or to engage Randy for your organization, visit www.penningtongroup.com, email info@penningtongroup.com, or call 972–980–9857 (U.S.).