Matt Shoup, an Entrepreneurs' Organization (EO) member from Colorado, is founder and CEO of He helps inspire and encourage CEOs and leaders around the world with life, love, and leadership advice.

Many entrepreneurs hope to grow a business that will one day run without them. As I grew mine, I was always intrigued when I met business owners who go on vacations and adventures, secure that their companies would run smoothly while they were away. My phone was always ringing with problems, questions from team members, and customer and vendors' calls. My role as CEO, president, founder, and "Fearless Leader" involved my taking on a few mundane tasks from each department. And I loved being the go-to-guy in my business, but it was also preventing me from living my dream, fostering leadership, and ultimately growing my company.

It took me a decade of trial-and-error to learn how to fulfill this dream and step out of the daily operations of my company. Earlier this year, I made the decision to relinquish oversight of day-to-day processes within M & E Painting, which I founded in 2005. While the growth was exhilarating, I was everything in the company: the closer, the strong arm, the problem solver, the marketing genius, the assistant to the finance manager, and ultimately the bottleneck that held us back from growing even faster.

Today, I am fully involved in the growth and daily operations of my new company, Here are the steps I recommend to others looking to ensure that their business can run without them, so that they too can make the transition that I have.

  1. Stop hovering and answering questions. You hire people for a reason, so let them do their jobs. When team members have specific roles and you move out of the way to let them fill them, you get a group of inspired and empowered team members. When you "hover" and watch over them, they tend to be less motivated and come to you with questions instead of figuring out things on their own. Now, to such questions, I often respond, "I trust your decision, which is why I hired you."
  2. Take a mini-vacation. There is no better way to see how the company runs without you than leaving it. Plan a vacation during which you are completely unavailable for one to four weeks. When you come back, evaluate where issues arose and unanswered questions linger. These bottlenecks will show you how you can and should empower your team.
  3. Become the grandparent. When team members are new to the organization, they are like "children"--they don't know what they don't know. You teach them the basics of their position through their "teenage" years. As they become trustworthy "adults" who are ready to bring new leadership and team members within the company, you have to give them room to do that. You now become the "grandparent"; they are old enough to make their own decisions and appreciate the repercussions of making the wrong ones.
  4. Delegate the role. Although I am the CEO and leader of the company, my job description did not match my title so I erased my role from the whiteboard and listed out my last year of activities. From there, I categorized and delegated everything. I realized that I was doing 10-15 percent of each one of my leader's roles. Changing this did not create more responsibility for my existing team--instead it gave them the opportunity to fully take on their responsibilities and roles.
  5. Let failure happen. As my leadership team ran things independently, I noticed them doing things I would not have done. Sometimes, they find better ways that produce more effective outcomes. When I first saw a small failure, I jumped in to help. However, I learned to embrace failure as an opportunity to coach and lead my team.
  6. Get rid of anything that can tie you to the company. When I left the company, I handed over the company vehicle to a sales team member, turned in all my company shirts and gear, threw away my business cards, and canceled my phone extension. In my case, the company has been part of my identity for a third of my life. This step is extremely difficult, but I believe it is crucial.
  7. Let yourself go and announce it. Once everything was in line for my exit, I made that known publicly. I posted on social media that I was "let go" from my company, which led to some interesting calls and messages. I also announced any promotions, new roles, and acknowledgments that needed to happen in the company. This created some wonderful free exposure, and got a lot of people talking about M & E Painting, as well as
  8. Avoid the "zone." My dominant personality can lead to me getting trapped in the zone of running things. These bad habits can linger. But as you stay away from the triggers, they will lose their hold on you. Understanding how you are wired and how you will get sucked back toward the business is important.

It wasn't easy for me to step away. It still isn't, but I believe this is the framework to create a machine that runs without you, while honoring who you are, what you stand for, and what you have built over the years.

To learn more about EO members' entrepreneurial experiences and insights, visit Overdrive, EO's global business blog.