Listen actively: Encourage your team members to share their thoughts and ideas and take the time to truly listen to and understand their perspectives.


The number one leadership initiative in any organization today is improved coaching. Coaching empowers employees, empowerment drives engagement, and engagement drives performance. At its core, coaching is about transformation. Leading distributed teams requires transforming how we coach and changing our play calls and playbooks to get things done. As a part of our interview series called “Moving From Command & Control to Coaching & Collaboration; How Leaders and Managers Can Become Better Coaches,” we had the pleasure to interview 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 to explore a critical inflection point in how we define leadership. Our readers would like to get to know you better. What was a defining moment that shaped who you are as a leader?

As a teenager, I had a knack for starting businesses and turning a profit no matter the obstacles. These early experiences sparked my passion for leadership. They taught me valuable lessons about perseverance, adaptability, and the power of a positive attitude. From running my lemonade stand to managing a team of employees, I learned that true leadership is about inspiring others to reach their full potential and working together to achieve a common goal.

One defining moment was when I started a small online retail business during high school. I faced many challenges, from sourcing products to building a website and marketing, but I never gave up. I put all my effort into making it a success, which paid off. This experience taught me the importance of hard work and determination to succeed as a leader.

Those early experiences helped me to develop the skills and mindset I needed to become the leader I am today, and I am grateful for the opportunities that allowed me to learn and grow. I am excited to continue exploring the defining moments that shape leadership and sharing my insights with others.

John C. Maxwell is credited with saying, “A leader is someone who knows the way, goes the way, and shows the way.” How do you embody that quote as a leader?

As a leader, I think of myself as a GPS for my team. I know the destination we’re headed towards, and I constantly update and adjust the route based on any obstacles or detours that may arise. But more importantly, I make sure to lead by example and pave the way for my team, and actively guide and show them the way. After all, a true leader isn’t just someone who knows the way but ensures the entire team arrives at the destination safely and successfully.

How do you define the differences between a leader as a manager and a leader as a coach?

A leader as a manager is like a conductor of an orchestra. They have a clear vision of the final product and guide their team through the performance, ensuring everyone is playing their part in harmony. They are responsible for the project’s overall success and have the power to make decisions and delegate tasks.

On the other hand, a leader as a coach is like a personal trainer. They work one-on-one with their team members, helping them to develop their skills and reach their full potential. They are more focused on the individual’s growth and development rather than the project’s overall success. They inspire and motivate their team members to be their best selves.

In summary, a leader as a manager is like a conductor, directing the performance, while a leader as a coach is like a personal trainer, helping individuals reach their full potential. Both are important, but they have different roles and responsibilities. A good leader knows how to switch between the two and use the right approach at the right time.

We started our conversation by noting that improved coaching is the number one leadership initiative in any organization today. What are some essential skills and competencies that leaders must have now to be better coaches?

Being a great coach is not just about having a whistle and a stopwatch. It’s about having a toolbox full of essential skills and competencies that allow you to connect with your team, build trust, and drive results. The most important skills for leaders now are the ability to communicate effectively, listen actively, provide constructive feedback, and lead by example. Additionally, leaders must have a deep understanding of their team’s strengths and weaknesses and be able to provide the support and resources they need to succeed. To be a great coach, you must also be able to build a culture of accountability and ownership and inspire and motivate your team to reach their full potential. In short, being a great coach is about being a great leader and having the right tools and skills to guide your team to success.

We’re all familiar with the adage, “You catch more flies with honey than with vinegar.” How are you inspiring — rather than mandating — leaders to invest in upskilling and reskilling?

As a leader, I think of myself as a beekeeper rather than a fly swatter. Instead of mandating upskilling and reskilling, I prefer to attract my team with the sweet nectar of opportunity and growth. By creating an environment where learning and development are encouraged and celebrated, I can inspire my leaders to invest in themselves and their skills. I firmly believe that when you give people the tools and resources they need to succeed, they will naturally want to take advantage of them. So, instead of pouring vinegar on my team, I’m all about spreading honey and watching them soar to new heights.

Let’s get more specific. How do you coach someone to do their best work? How can leaders coach for peak performance in our current context? What are your “Top 5 Ways That Leaders and Managers Can Be Effective Coaches?”

As a leader, I believe that coaching for peak performance is about creating an environment where individuals feel supported, motivated, and empowered to do their best work. Here are my top 5 ways that leaders and managers can be effective coaches:

  1. Lead by example: Show your team members that you are committed to doing your best work by consistently meeting and exceeding expectations.
  2. Listen actively: Encourage your team members to share their thoughts and ideas and take the time to truly listen to and understand their perspectives.
  3. Provide regular feedback: Give your team members regular feedback on their positive and constructive performance to help them stay on track and improve.
  4. Encourage growth and development: Help your team members identify areas where they can improve and provide opportunities for them to learn and grow.
  5. Create a positive and supportive work environment: Create a culture of positivity and support where your team members feel encouraged and motivated to do their best work.

In the current context, I believe creating a culture of positivity and support is more important than ever. When individuals feel supported and motivated, they are more likely to do their best work, even in the face of adversity. As a leader, I create an environment where my team members feel empowered to do their best work and reach their full potential.

We’re leading and coaching in increasingly diverse organizations. And one aspect of workforce diversity on the rise is generational diversity. What advice would you offer about how to effectively coach a multi-generational workforce? And how do you activate the collective potential of a multi-generational workforce?

As a leader in a diverse organization, I understand the importance of effectively coaching a multi-generational workforce. My advice would be to approach each generation with an open mind and a willingness to learn. Each generation brings its unique perspective and set of skills, and it’s important to tap into those strengths to activate the team’s collective potential.

One key strategy is to establish a culture of mutual respect and understanding. This can be achieved through regular team-building activities and open communication channels where all team members feel comfortable sharing their thoughts and ideas.

Another important aspect of coaching a multi-generational workforce is providing learning and development opportunities. This can include training programs, mentoring, and cross-generational learning opportunities. By providing these opportunities, we can ensure that all team members are equipped with the skills and knowledge they need to succeed in their roles.

Finally, it’s important to remember that while there may be differences between generations, we are all working towards the same goal. By embracing diversity and utilizing the strengths of all team members, we can achieve great things together.

You’re referring to emotional intelligence, in a sense. What are two steps every leader can take to demonstrate a higher level of emotional intelligence?

Ah, the age-old question of how to demonstrate emotional intelligence as a leader. Allow me to share my two cents or my two steps.

Step one: Practice active listening. This means truly hearing and understanding the perspectives and emotions of those around you rather than just waiting for your turn to speak. It’s a small step, but it can make a big impact in building trust and fostering a positive work environment.

Step two: Lead by example. Show your team that it’s okay to express and manage emotions healthily. Share your vulnerabilities and emotions when appropriate and encourage open communication. Remember, as the leader, you set the tone for the team’s emotional intelligence.

So there you have it, folks. Two simple steps to elevate your emotional intelligence as a leader. Give them a try and watch as your team flourishes under your empathetic and understanding guidance.

Words matter. And we’re collectively creating a new leadership language right now. What are the most important words for leaders to use now?

Words truly matter, and as leaders, it’s our responsibility to use them wisely. In these times, the most important words for leaders are those that inspire hope and unity. Words like ‘empowerment,’ ‘inclusion,’ and ‘transparency’ are crucial for fostering community and trust among our teams. Additionally, words like ‘adaptability,’ ‘resilience,’ and ‘innovation’ are essential for navigating the ever-changing landscape of the current world. But perhaps the most important word for leaders to use now is ‘listen.’ As we collectively create a new leadership language, we must listen to the needs and perspectives of our teams and communities and use our words to empower and uplift them.

I keep inspiring quotes on my desk. What’s your favorite “Life Lesson Quote,” and why does it mean so much to you?

My favorite “Life Lesson Quote” is one that I’ve always kept close to my heart: “The greatest glory in living lies not in never falling, but in rising every time we fall.” It speaks to the resilience and determination that I believe are crucial in leadership. Life is full of challenges and obstacles, but it’s not about avoiding them altogether; it’s about overcoming them and coming out stronger on the other side. This quote reminds me to always keep pushing forward, never give up, and always strive for greatness, even in the face of adversity. It’s a powerful reminder that failure is not the end but rather an opportunity to learn and grow. And that, to me, is the true essence of leadership.

Our readers often like to continue the conversation. What’s the best way for readers to connect with you and to stay current on what you’re discovering?

The best way to connect with me and stay current on my latest discoveries is to follow me on my social media channels. Whether it’s LinkedIn, Instagram, or Facebook, I promise to keep you entertained and informed with my witty musings and exciting new findings. And if you’re looking for a more in-depth experience, be sure to check out my website, where you’ll find a plethora of content and resources to keep your brain buzzing. So don’t be shy. Let’s connect and let the conversation flow!

Thank you for sharing your insights. We appreciate the gift of your time and wish you continued success and good health.