Lessons in leadership from Carlo Ancelotti for startup founders

What makes a founder an effective startup leader? My starting point is that founders should aspire to be empathetic leaders, a subtle, personal approach to leadership, not the populist bravado or hustling style. Set empathy as a cultural value, the behaviours that create psychological safety instill togetherness. The best leaders listen, and show sensitivity to feelings and needs.

Founders willing to set their ego aside, show their own vulnerability and are humble, authentic and sincere, grow as leaders and become better versions of themselves at work and in life, creating a healthy foundation for startup growth. You have an opportunity to create a meaningful, positive, and thriving environment which will create increased social connection and inclusion.

Being an empathetic leader starts with the simple truth that leadership is about people. When you demonstrate these behaviours, your people will be engaged. They’ll give their best effort. They’ll be more innovative. The evidence tells us that performance improves. 

In your startup, draw a narrative arc from impossible to possible, and show people the way. Create a balanced, egalitarian environment helmed by a caring, thoughtful leader, one who considers more than just the bottom line. Measure your impact on the lives you touch, creating human experiences to achieve something extraordinary together, not an unending drive for purely financial success. Don’t leave people behind, mentally and physically worn out by the lack of emotional engagement and a binary focus on what success looks like. 

There are many lessons for founders to be drawn from great sports team leaders. Richie McCaw, the All Blacks captain for 110 games, was a stand out leader on the field during their years of domination. Known for his sheer doggedness, he wasn't the loudest speaker, but he was always the first to the breakdown and the last to give up. He played through a broken foot to win the 2011 World Cup. He led from the front and by example.

Another notable sporting leader is Carlo Ancellotti, currently manager of Brazil. He’s just ahead of Rinus Michels in my book, the ‘father of total football’ who transformed how modern football is played and inspired Johann Cruyff, whose own tactical innovations inspired Pep Guardiola. Arrigo Sacchi, who developed the concepts of high press and zonal marking, was also a great leader, but it's the leadership style of Ancellotti and his success that marks him out for me.

Ancelotti is regarded as one of the greatest football managers of all time. He has won the UEFA Champions League a record five times, and is also the only manager to win league titles in each of Europe’s top five leagues. As a player, Ancelotti won two European Cups with AC Milan, making him one of just seven people to have won the European Cup/Champions League as both a player and a manager.

In 2009, Ancelotti became the manager of Chelsea and won the domestic double of Premier League and FA Cup in his first season. In 2011, he became the manager of PSG, and won their first Ligue 1 title in twenty years Following this success Ancelotti became the manager of Real Madrid. In his first season, he led Real to their tenth Champions League title and a Copa del Rey. He left Madrid in May 2025 and was appointed as coach of a national team for the first time when he took on the position with Brazil.

In addition to Ancelotti's tactical prowess and adaptability, he has drawn praise for his kindness, good humour, and his calm, balanced approach as a manager. His ability to motivate players and cultivate a good relationship with them, and foster a united, winning team environment are strong leadership qualities.

During Ancelotti's first season with Bayern Munich, he was admired for the freedom he gave the players to express themselves and the confidence instilled in them. During his second spell at Real, he won praise for his balanced approach, adaptability, and man–management during the club's run to a Liga–Champions League double. His ability to develop a strong relationship with his players and his willingness to consult them on tactical decisions were singled out as reasons for the team's success and unity. 

There are two very readable books offering auto-biographical insight into Ancelotti the man and the manager: The Dream (2025) and Quiet Leadership: Winning Hearts, Minds and Matches (2017). Here's what I’ve taken from both to identify lessons in leadership for startup founders.

1. Leaders are there to help people grow. Ancelotti treats players as adults. He builds trust, listens, and understands personalities rather than imposing his own rigid authority. This makes stars and squad players alike feel respected, and willing to give more for him for the team.

Ancellotti shows the role of a leader is about building strong, personal relationships based on trust with individuals, engaged in both their emotional and professional development to help them grow. Empathy, active listening, and clear language can transform a frenzied interaction into a therapeutic one. In high-pressure scenarios, these skills are even more critical.

2. Calm authority Ancelotti leads with composure. In high-pressure moments, he rarely over reacts or loses control which stabilises teams during such moments. His calmness spreads confidence, especially in knockout matches and finals.

This trait comes from his self-awareness. Effective leadership starts with you, cultivating your personal impact and presence - how you show up and what you convey both emotionally and energetically. Leadership is not about you, it’s about those you lead. It’s knowing when to step into a situation, and when to step aside. Learn to lead yourself, and always position yourself calmly in a place and headspace where you can help. For a leader to act with authority, they do not have to be loud or forceful.

3. Emotional intelligence He knows when to protect players, when to challenge them, and when to step back. This emotional awareness helps him manage egos, dressing-room tensions, and generational differences. A team is a collection of diverse personalities and it’s essential to connect emotionally at a personal, individual level.

It’s about doing the right things, it’s not a popularity contest, trying to improve players and the team. Ancelotti emphasises that understanding and managing emotions is crucial to effective leadership. He sees emotional intelligence as a vital component in fostering teamwork, and maintaining a positive atmosphere. Ancelotti's approach is rooted in patience, and the ability to listen.This allows him to connect with his players on a personal level, which enhances their performance on the pitch.

4. Adaptability over ideology Unlike dogmatic coaches, Ancelotti adapts to the players he has rather than forcing them into a fixed system. This is shown by his track record of success in different football cultures and environments. This flexibility shows humility and pragmatism, key leadership traits in elite environments. There is no single Ancelotti system, but there is an Ancelotti way.

Leaders need to be flexible, adapt to and also anticipate. Leadership is not a one-size-fits-all role, great leaders are those who understand what is needed in the moment and can then provide direction as to what will make a difference. Ancelotti's success stems from his willingness to adapt his methods and tactics, ensuring that his approach is always relevant.

5. Clear, simple communication Ancelotti is renowned as a good communicator. His instructions are uncluttered. Players often say they know exactly what is expected of them, which reduces anxiety and improves execution on the pitch.

An effective leader listens to and respects front-line employees’ opinions, direct experience and feedback. The reality is that often, front-line employees have the solutions to organisational problems, and we need to give them a stronger voice. Next time you watch a football match keep an eye on the interaction of players with the manager on the touchline - a manager who listens to feedback will be more successful in any walk of life.

6. Trust and empowerment Ancelotti empowers leaders within the team (captains, experienced players) and trusts them to take responsibility on the pitch. This shared leadership strengthens team cohesion. Consensus based decision making is powerful.

Leadership is about having the right people in place so that you can guide them in their decision making and direction, and let them manage the detail themselves of what needs to be done. Show them the way, then let go. Give folks the opportunity to show what they can do and give them responsibility.

7. Credibility through experience Having succeeded across leagues and cultures, Ancelotti carries natural authority, gravitas earned from repeated success. Players believe in him because his track record proves he understands what it takes to win.

You evolve as a leader. To become a great leader, you need to challenge yourself and embrace the responsibility every day. Being a leader is not a sprint, it’s an event that helps you become better with every challenge you overcome. Experience and resilience shape you.

8. Human-first philosophy Above all, Ancelotti sees footballers as people, not just assets. This human centric approach builds loyalty, and loyal teams tend to perform better. There is no downtime in a leadership role. Football matches are frequently frantic and fraught, so Ancelotti has to be ‘always present’ and ‘always a leader’ with players dependent upon him, keeping the human connection alive above the noise.

Ancelotti believes it is imperative that you are mentally two steps ahead because when necessary, everyone will be looking to you for a response, with decisive decision making creating a clear sense of direction. Ancelotti has coached some of the world’s biggest football stars, and he speaks privately to them, listens carefully, and treats them as people first.

9. A leader’s morality matters as much as their competency. Ancellotti is renowned for his honesty with players. He shows us that the moral aspect of leadership is as important as any aspect of competency. You must lead by example and work with high integrity. It’s not just about getting the job done but embracing the moral imperative of doing the right thing even when it may mean an unpopular decision.

Know thyself. The greatest tragedy for a founder is believing the only perspective that matters is their own. An empathetic leader has self-awareness, understanding that their thoughts and opinions aren’t gospel. They have an empathetic mindset that causes them to seek and gain a better perspective by listening to everyone at all levels. Doing so helps them grow their leadership skills to be the best for their team and customers.

10. Leaders are dealers in hope Leading by example oversimplifies the underlying reality. Yes, you have to stand at the front but it's about ensuring you create followers by reaching into the hearts and minds of your people. Positive mindsets can be built in adversity, a leader is a dealer in hope. Ancelotti’s teams don’t win every game, but he creates the conditions to shape a winning mindset in his players and an expectation of winning. 

The popular perception of effective leadership is defined by confidence and assertiveness. This is a narrow view as it diminishes the complexity of leadership and is an outdated view. Applying greater force to a problem doesn’t always result in a breakthrough. When all you have is a hammer, every problem begins to look like a nail. It’s about building togetherness in a team at the individual level, creating unity of belief and purpose.

Summary Ancelotti’s strengths as a leader come from emotional intelligence, calm confidence, adaptability, and respect for people — qualities that work far beyond football. So startup founders, it’s time to drop the hustle and adopt a leadership style based on these qualities of a stand out winner. 

The stereotypical view of a successful startup leader as driving and pushing the team relentlessly is done. Press pause on the ideology that more hours worked means greater achievement. This has passed its sell by date, hustling is now a redundant myth.  

Leadership that focuses on charisma, dominance, or big motivational speeches is ineffective, Ancelotti’s approach is rooted in respect, listening, and calm authority. He shows that leadership is not about being the loudest voice in the room but about understanding the people you lead. mastered the balance between empathy and authority. Respect is not given automatically just because of a title, it has to be earned every day.

Ancelotti believes that football is played by human beings, not cogs in a machine or data points on a graph, and human beings require an emotional connection with their work.  It’s no coincidence that football’s growing obsession with a particular style of play has coincided with a focus on data, but sport operates in the humanities rather than the hard sciences. The iconoclastic Austrian philosopher of science and author of Against Method, Paul Feyerabend, makes the counterargument: The only principle that does not inhibit progress is: anything goes.

Ancelotti would probably support this. His career teaches us that leadership is a blend of technical mastery and human connection. By focusing on relationships, Ancelotti has developed a sustainable leadership model that delivers both results and respect. 

His legacy highlights the impact of empathetic leadership and communication. His success is built on the understanding that great coaching is not just about systems, data and strategy, but about trust, connection, and emotional intelligence. His calm, measured, and personalised approach continues to set a standard in elite football management, one startup founders would do well to replicate.