From Entrepreneur to CEO – Great Leaders Create More Leaders

From Entrepreneur to CEO – Great Leaders Create More Leaders

I wrote this post years ago for the Infusionsoft blog and it is now posted on Medium. I’m sharing this again because I repeat this story often with early stage CEOs who are on their own leadership journey.


You become a leader as soon as you hire employees or contractors to make your business go. Whether you have three team members or twenty employees, you need to move from entrepreneur to being more intentional about your role as the most senior leader of the team. This takes continuous learning, feedback and personal growth.

As founders grow to become CEOs of bigger businesses, they realize that creating their next level of leaders is one of their most important priorities.

I have been leading, managing and developing people in fast-growing software companies for over 25 years. It’s an honor as a leader to help other people do great things, so here are my most important beliefs about leadership that I try to live up to every day.

The main job of a leader is to create capable leaders

To change the world for the better, we need to create more leaders faster.

Business owners, executives, managers, parents, teachers and community leaders have many responsibilities and lead very busy lives, but their most important function of a leader is to help great people do great things.

The world is full of smart people and big problems to solve, but we have a shortage of people who take full responsibility for those big challenges and aspire to solve them.

Nobody is born a leader — it’s not a finite natural resource. Leaders are developed through their own experiences and support from others.

For example, at Infusionsoft, we realized that our acceleration from startup to global business meant that we could only grow as fast as our capable leaders can help us do so. As a result, we intentionally developed and recruited leaders internally and externally. I spend 50 percent of my time nurturing my team, my peers, our partners and myself to be able to handle the opportunities and challenges expanding in front of us.

We knew that if we don’t grow ourselves as leaders, we stopped growing as a company.

Show people the game and how they can win it

Leaders shouldn’t tell people exactly what to do or how to do it. Leaders do need to define and frame what the game is, what success looks like, what the standards are and why all that is so important.

As a leader, you don’t have to have all the answers to these questions; you just have to make sure it gets figured out, and then share the vision and plan clearly and consistently with the team.

Framing the game helps people see and understand what they are responsible for and how they can think differently to solve big problems. I trust that someone can figure out a better solution than I can, but only when they see the entire problem and have ownership of the solution and the results.

I spend a lot of time with teams at white boards thinking through new challenges and agreeing on how to frame the problem and solution. Most people want to see the biggest picture possible and know the real facts (warts and all) so they can make a real difference. This takes openness and trust, but it unleashes incredible energy and commitment from talented people. Who wouldn’t want more of that?

Help people believe they can do big things

Leadership doesn’t stop after you help a team member frame the game, take responsibility and be accountable for the results. Big new challenges bring out all the typical anxieties everyone experiences when they sign up for big jobs that stretch their skills and challenge the beliefs they have about themselves.

I believe that the biggest challenge to growing leaders fast enough is not imparting knowledge or skills, but helping people through the common head game that plays out when they are challenged to change and move beyond their comfort zone. Fear slows us down and limits creativity and growth. An anxious leader will multiply the fear and limit the potential of any team.

It’s important for a leader to be involved enough to confidently say, “It’s a big job, and I know you can do it” so you can keep team members positive and confident while they handle big tasks with clear accountability. Helping people believe they can do big things is a continuous job of a leader.

Ask questions and delegate the answers

I have found that the best way to help leaders understand their problems and create better solutions is to give them all the questions. I don’t tell them my version of the answer; I ask all the questions that pertain to their area of responsibility and let them sort out the answers.

When a leader takes a new role, I offer to send them a few questions that they should be thinking about when developing their plans and figuring out solutions. I take twenty minutes and brainstorm fifty questions and then email the list to them.

It can be intimidating at first to get a list of all the big and small questions that others expect them to answer, but it quickly empowers them to know that they’re in charge and they don’t have to have all the answers right away. Figuring it out is an important part of their job.

Your job is to create a leader who can continually figure out all the questions and sort through the answers — without your continued help. The faster you delegate all the questions and hold them accountable to the results, the faster you will create self-sufficient leaders that do amazing things.

Be the best example of constant personal growth

Most importantly, leaders need to demonstrate how they are continual learners and growers themselves. How can you ask someone to change and grow when you aren’t a shining example of openness, vulnerability and change? I’m still working on this, but I am getting better every year. It doesn’t stop when you get a big title.

Growing is more than just reading great books and learning new skills. When was the last time you were outside your comfort zone, learned that you are not always right and overcame a big personal issue? Did you share that story with your peers and your team? Openly sharing your own challenges and how you are facing them shows people it’s OK to ask for help and that they don’t have to be perfect.

I find that the most senior and successful leaders continually challenge themselves and work on their own head game to keep growing. This is the real game being played at the highest levels. Nobody sees what’s going on behind the curtain because of most leaders are good at looking like they are fearless, smart and don’t make mistakes, even when that’s not the case.

I’ve been trying to be a better husband, father, leader, manager and advisor every day for more than 20 years. I still learn new things, make mistakes and struggle to stay positive sometimes. I feel like I’m starting to get good at it and there is still plenty to learn.