The Price of Winning: Can You Be a Great Leader and Still Be Liked?

Balancing ambition, relationships, and leadership intensity

"Has your intensity come at the expense of being perceived as nice?" the narrator asked Michael Jordan in the Netflix special Last Dance.

Michael Jordan's answer speaks to all leaders and high achievers who face this challenge...

"Winning has a price,
Leadership has a price,
I pulled people along when they didn't want to be pulled,
I challenged people when they didn't want to be challenged.

I earned that right.
You ask all my teammates, and they'd say, 'He never asked anyone to do anything that he didn't do.'

If you joined the team, you had to play at a standard that I played the game, and I wasn't going to take anything less.

Now, if I had to get on you a little bit, then I did that.

People say 'he wasn't nice.'
They never won anything.

I wanted to win, but I wanted them to win and to be a part of that as well.

That's how I played the game."

His approach won the Chicago Bulls Six National Championships.

The C-Suite Challenge

So many CEOs and executives are criticized for being intense, competitive and 'not nice'. Women leaders, especially, face the challenge of intensity earning the label of "bitch.”

Yet often, success in business requires a toughness to push yourself and others that’s not as ‘nice’ as we wish we could be. Compounding the issue, long hours, intense pressure, and physical drain cause even some of the nicest executives to speak bluntly or lose their temper. Nice people can be rude under duress.

I don’t want to excuse jerks or flagrant behavior of extreme criticism, cruelty, and personal attacks.

But it is difficult to always be considered nice when you push people beyond their comfort zone. When you push outside of normal social norms. When you have to hire and fire people for the good of the business. When you have to provide feedback that may not be well received, even if it's wrapped in compliments.

Being the best requires doing more, better and faster than the competition. As a leader, it also requires making tough decisions that will have negative consequences on some people.

Being a leader can be really, really hard. And often very lonely.

How to balance the drive and the relationships

While Michael Jordan highlights the challenge and risks of leadership, he also models several core values for navigating the delicate balance of pushing people while staying connected - so they will stay on the team and perform well.

1. Set a Standard—But Lead by Example - People will accept high expectations if they see you holding yourself to the same (or higher) standards. Michael Jordan’s teammates respected his work ethic and his results.

2. Push with Purpose—Make It About the Team, Not Just You - People respond better when they know you’re pushing them for their growth, not just your success. Intensity should feel like a force that elevates people, not one that destroys them. Michael Jordan wanted the TEAM to win. He needed the TEAM to win.

3. Build Trust First, Then Challenge - People accept being pushed when they believe you genuinely care about them. Invest in relationships outside of high-stakes situations—acknowledge efforts, support their career growth, and have real conversations.

4. Control Your Delivery—Be Direct, Not Demeaning - Intensity doesn’t have to mean harshness. There’s a difference between challenging someone and breaking them down. The best leaders push hard on the work, not the person. It’s critical that you take care of yourself (sleep, exercise, centering) so you have control of your emotions and approach in the toughest times.

5. Know When to Dial It Down - Winning requires drive, but sustainable success requires emotional intelligence. If your intensity is always on, you’ll burn out relationships. Pick your moments—push when stakes are high, but create space for connection.

You can be a fierce competitor and a respected leader if people believe you’re pushing them with them, not at them. The best leaders make others feel challenged and supported.

The Parenting Challenge

As an intense, driven person, I struggle with challenging my kids and observing the trade-offs. Studying more than others reduces time with friends. Working on academics together sometimes comes at the cost of more fun activities we could enjoy together. It’s all a yin and yang, but my kids often say “why do we have to work so hard - other kids don’t.”

Pushing my kids beyond their comfort zone puts pressure on our relationship. I feel viscerally MJ’s words “Winning has a price, leadership has a price.” But I also see rays of sunshine in the pride of accomplishment, the satisfaction of a job well-done and the progress toward successful independence.

The leadership principles from work continue to spill over to parenting leadership at home.

Advice? How do you navigate this all?

-> How do you balance the leadership challenges of pushing hard vs. being “nice”? Real-world advice would be much appreciated!

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Unrelated, One More Speaking With Clarity Class - March 20th

I’ve written a few times about Speaking with Clarity and a Precision Q+A class I took and set up for my clients. The two sessions were over-capacity, so we added one more session for March 20th. The session covers how to ask higher-value questions and match them with clear, concise answers. It is a powerful tool for communicating more effectively with executives, customers, and significant others : ) For more information or to register click here

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Carilu Dietrich is a former CMO, most notably the head of marketing that took Atlassian public. She currently advises CEOs and CMOs of high-growth tech companies. Carilu helps leaders operationalize the chaos of scale, see around corners, and improve marketing and company performance.

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