Embrace failure. Failure is an inevitable part of innovation and experimentation. Don’t be afraid to take risks and try new things, even if they don’t work out. Instead, learn from your mistakes and use them to inform your future decision-making.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Chris Kille.

Meet the dynamic and visionary entrepreneur behind two successful companies — a payment processing firm and a virtual assistant agency. From a young age, this CEO had an entrepreneurial spirit that drove them to experiment with various business ventures. His passion and determination paid off, as they have now successfully led their team to become a global leader in both payment processing and virtual assistant services. With a sharp mind and a relentless drive to succeed, this CEO has built a reputation for being a highly skilled and effective leader who is always pushing the limits and finding innovative solutions. Whether it’s developing new technology for payment processing or expanding the services offered by their virtual assistant agency, this CEO is constantly seeking new and exciting challenges. With a strong work ethic and a commitment to excellence, this CEO is a true inspiration and a force to be reckoned with in the business world.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

I am currently in the middle of a very exciting project, personally and professionally. I am writing my first book, a collection of my leadership philosophies and strategies that have helped me throughout my career. I am thrilled about this project, as it has been a lifelong dream of mine to share my experiences and insights with others. I believe that my book will be a valuable resource for anyone looking to improve their leadership skills and achieve success in their personal and professional lives. I am also planning a leadership retreat for young professionals, which I am extremely passionate about. I believe that investing in the development of future leaders is crucial for the growth and success of any organization or community. So, I am excited to be able to provide a platform for young professionals to learn, grow, and connect. Overall, I am grateful for the opportunity to pursue my passions and positively impact the world.

We all get by with a little help from our friends. Who is the leader that has influenced you the most, and how?

I firmly believe that we all get by with a little help from our friends, and I’m lucky enough to have the greatest one of all — my wife, Kristen. She’s not just a friend but a true leader in her own right. Her unwavering support and encouragement have been my constant source of inspiration. From handling difficult situations with grace and poise to always putting others before herself, she’s taught me much about leadership. I’m grateful for her guidance and support; I couldn’t have achieved half of what I have without her. She’s not just my friend but my role model and I couldn’t be more thankful for her influence on my life.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

As a leader, I think of myself as a bit of a risk-taker. I believe that to truly succeed, you have to be willing to take a few chances and make a few mistakes along the way. That being said, I can’t deny that there have been a few times when I’ve made a decision that didn’t quite pan out the way I had hoped. But, as the old saying goes, sometimes our biggest mistakes lead to our biggest discoveries.

One of my biggest mistakes as a leader came when I decided to invest heavily in a new product line that I was convinced would be a surefire hit. Unfortunately, it turned out to be a complete flop, and we lost a lot of money in the process. But, instead of dwelling on the failure, I decided to take a step back and take a hard look at what went wrong.

Through that experience, I discovered the importance of truly understanding our target market and doing thorough market research before making any big investments. It was a valuable lesson that ultimately helped us become a more successful and profitable company. So, in a way, that mistake ended up being one of the best things that ever happened to me as a leader. It taught me that failure is an inevitable part of the journey to success and that how you handle those failures defines you as a leader.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

Over time, my definition of leadership has evolved from simply being in charge to truly leading by example and empowering others to reach their full potential. I now understand that being a leader means being a servant to those around me, working to understand and support their needs and goals, and fostering a culture of collaboration and growth.

In the past, I may have focused solely on achieving my objectives and making decisions without considering the perspectives of my team. However, now I understand that true leadership involves actively listening to and valuing the input of those around me and making decisions that consider the entire team’s needs and goals.

Being a leader now also means embracing change and being adaptable. The world is constantly evolving, and leaders must be able to pivot and adjust their strategies to meet new challenges and opportunities. It also means being transparent and accountable for my actions and decisions.

Overall, my definition of leadership has evolved from a top-down approach to a more collaborative and empowering one. It is about leading by example and creating an environment where everyone can thrive and reach their full potential.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

As a leader, I have realized that success is not only about what we start but also about what we stop. One legacy leadership behavior that I have stopped is micromanaging my team. I used to believe that by closely monitoring every step and decision my team made, I could ensure that everything was done correctly and efficiently. However, I soon discovered that this approach stifled my team’s creativity and autonomy and hindered their growth and development.

I realized that instead of micromanaging, I needed to trust my team and give them the space and resources to make their own decisions and take ownership of their work. By doing so, I have seen a significant improvement in my team’s productivity and morale and their ability to adapt to new challenges and opportunities.

Stopping this legacy behavior has benefited my team and myself as a leader. I have been able to focus on more strategic tasks and have more time to develop my leadership skills. It is a powerful reminder that being a leader is not just about starting new initiatives but also about being willing to stop old ones that are no longer valuable or relevant.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

One lasting leadership behavior I have started cultivating is the ability to truly listen to my team members and understand their perspectives. I believe that effective leadership is not just about giving orders and expecting them to be followed but about fostering a sense of collaboration and mutual respect. By truly listening to my team members and considering their ideas and suggestions, I can build trust and create a more cohesive and productive team. Additionally, this behavior allows me to identify potential issues and challenges early on and take proactive steps to address them before they become major problems. Overall, I believe that this is a valuable and relevant leadership behavior that will help me to lead my team to success in the long term.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

  1. Embrace change and experimentation. Instead of clinging to past playbooks and patterns, try experimenting with new strategies and approaches. This can help you stay on top of the latest trends and technologies and also help you stay ahead of the competition.
  2. Stay flexible and adaptable. As a leader, adapting to changing circumstances and shifting priorities is important. This means being open to new ideas and perspectives and willing to change course when necessary.
  3. Cultivate a culture of innovation. Encourage your team to think outside the box and come up with new and creative solutions. This can help foster innovation and experimentation within your organization and help you stay ahead of the curve.
  4. Stay connected to your customers. Make sure you are in tune with your customer’s needs and wants. This will help you stay relevant and responsive to their changing needs and also help you stay ahead of the competition.
  5. Embrace failure. Failure is an inevitable part of innovation and experimentation. Don’t be afraid to take risks and try new things, even if they don’t work out. Instead, learn from your mistakes and use them to inform your future decision-making.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

The most important piece of advice I would offer new and emerging leaders is to lead by example. Show your team that you are willing to put in the hard work and dedication you expect from them. This will earn their respect and inspire them to do their best work.

Another important piece of advice is always to communicate clearly and effectively. Ensure that your team knows what is expected of them and that they understand the goals and objectives of the organization. This will help to ensure that everyone is on the same page and working towards the same goal.

Finally, it is crucial to be open and approachable. Encourage your team to share their ideas and concerns, and take the time to listen to them. This will foster a sense of trust and collaboration, which is essential for any successful team.

In short, lead by example, communicate effectively, and be approachable and open to feedback. Remember that as a leader, your role is to empower and inspire your team to reach their full potential.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

  1. Emotional Intelligence: Effective leaders possess high emotional intelligence, meaning they can understand and manage their emotions and those of their team members. A great example of this is the CEO of a company I once worked for, who would always take the time to listen to our concerns and address them with empathy and understanding.
  2. Visionary: A leader with a clear vision for the future and who can communicate it effectively to their team is essential for success. I remember working for a manager who always had a clear vision for the company, and it was contagious- we all wanted to be part of it.
  3. Decisiveness: Effective leaders can make difficult decisions quickly and with confidence. I once worked for a leader who, when faced with a tough decision, would always weigh the options carefully, but once a decision was made, they would move forward with it without hesitation.
  4. Adaptability: Leaders who adapt to change and new circumstances are crucial for success in today’s fast-paced business world. I have seen this firsthand in my current role as a leader who, when faced with a new challenge, can quickly pivot and develop a new strategy.
  5. Empowerment: Effective leaders empower their team members to take ownership of their work and make decisions. A manager I once worked for would always give us the autonomy to make decisions, and it made us all feel valued and invested in the company’s success.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

As a leader, I strive to embody John Wooden’s quote by approaching each day with a clear mindset and strong purpose. I believe that every day presents an opportunity to create something great, and I am constantly looking for ways to make the most of that opportunity.

One example of this is my coaching style. I believe in setting high expectations for my team and pushing them to reach their full potential. I am always looking for ways to improve their skills and help them become better players and people.

Another example is in my approach to work. I strive to be organized and efficient to make the most of each day and accomplish as much as possible. I also believe in taking time to reflect on my progress and set new goals to continue improving and growing as a leader.

Ultimately, I believe true leadership is about making the most of each day, and I am committed to doing just that, whether as a coach or a professional. By making each day my masterpiece, I believe I can help others do the same and make a meaningful impact.

What is the legacy you aspire to leave as a leader?

As a leader, I aspire to leave a legacy of excellence and integrity. I believe true leadership is about achieving great results and fostering an organization’s culture of excellence and integrity. I strive to lead by example, always striving to do my best and to hold myself and others to the highest standards of excellence. At the same time, I believe that integrity is the foundation of true leadership, and I am committed to always acting with integrity and honesty in all of my actions and decisions. Ultimately, I hope to be remembered as a leader who inspired others to reach their full potential and helped create a culture of excellence and integrity that will continue to inspire others for years.

How can our readers connect with you to continue the conversation?

As a leader, I am always open to connecting with my readers and continuing the conversation. One of the easiest ways to connect with me is through my social media channels. You can find me on Twitter, Instagram, Facebook, and LinkedIn. On these platforms, I share insights, updates, and thoughts on various topics related to my field of expertise. I also engage with my followers and respond to their comments and queries.

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!