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So you think you want to be a CEO

  • SIMA
- Posted: January 9, 2018
By Jon Crandall, CSP

Do you really want a multimillion-dollar business, or just the rewards that come from it? Do you really want a multimillion-dollar business, or a small lifestyle business that is really a self-designed job with huge risk added to you and your family? If you are willing to take on the personal sacrifices and financial risks, then gear up to become the best you can be to steer your dream toward reality. Following are some traits that I believe characterize many of the successful CEOs I know.

You must love the business - not just what the business delivers. Read “The E-Myth” by Michael Gerber. He explains why most technicians go into business and how perception changes dramatically in Year One of business ownership.

This is a rare talent. True leaders ask questions to guide their employees into making their own decisions. After a decision is made, they can review the outcome and talk about what the employee learned and what he or she may change. A short video by Inno-Versity that explains “greatness” by Capt. David Marquet explains this very well. Leaders can be friendly, but, more importantly, need to hold the team accountable to get things done  whether it’s you as CEO or your trusted managers. If you turn this duty over to your managers, it’s still your responsibility to hold them accountable.

Leaders also are responsible for paying more attention to the future and the high-level view of the company’s direction. In his book “Good to Great,” Jim Collins uses an example of chopping a path through a rain forest without a compass. Clearing a straight path would be difficult, so the leader climbs a tree and yells to the team below which direction to chop. The high-level view is most important to focus the team on the right tasks that will ultimately lead to the desired long-term result.

A good friend and mentor Jim Kaloutas simply calls this “never, ever, ever, ever give up.” I relate best to this in a few ways. In my snow business we manage some medical facilities that have emergency rooms. Would it be OK if we decided to hold off on plowing until the end if it was snowing too much or too hard? A man who has four young children and a wife to support doesn’t care if equipment is broken down or if there’s too much snow when he’s having a heart attack. He needs the ambulance to make it up the hill to the hospital. It’s up to you to make sure he is able to walk his little girl down the aisle one day! Failure is not an option.

As another example, I was hiking in the mountains with a friend’s 10-year-old son, who had been asking me for a while to come along. I made him aware of the distance and that I believed it was reasonable, and he agreed to hike. About three-quarters of the way up he asked if we could turn back. I asked if he would feel fulfilled if we did not reach the summit, and he said he didn’t know. I asked if he would think it would be a cool story if he told his friends he made it three-quarters of the way to the top. He agreed that didn’t sound quite as cool. Of course, decisions must be made to alter a plan if needed; but at the end of the day, failing to follow through because it is convenient or it is too hard is not OK in business.

Deal-making ability

I find almost all entrepreneurs I meet have an amazing self-awareness and emotional maturity, not only about how they feel, but also how they affect the feelings of others. They also have the ability to see the perspective of the client, employee and or vendor, and usually are able to adapt to make a deal work for both parties. They usually have a high level of common sense. This ability can be strengthened through self-assessment profiling. I have studied deal makers and can spot them from a mile away. In the finance world they are known as relationship managers. These people are not only subject matter experts but are able to make deals with most people they encounter.

Support system
Employees, friends, family and mentors are all hugely important. These people make you look good, are who you work hard for and from whom you learn. In the early days I thought I could do it best - I had something to prove. As time went on I learned how much of a positive impact a great employee in the right role can have on the business. I learned how much a true friend can help lift my mood in times of doubt; how much a family can support you; how a great team can make all the difference; and how valuable it is to listen and learn from my mentors. I still have a lot to learn and something to prove; but I have a team, support and love to help get it done.

Desire to learn and humility to admit you’re wrong
If you think you know it all or don’t have any desire to better yourself, think again. Running or owning a business is all about change. A growing business is just like a growing child. It changes constantly. If you have never been in the space in which you are growing, you cannot perform well unless you do everything in your power to learn before, during and after you get to where you are going. Humility to say I made the wrong choice is required. You must take ownership and then learn from what went wrong and try again.

A few years back, I took a course called the Landmark Forum. I highly recommend it, and I fund any of my employees in full if they choose to take part. A key concept from this forum relates to what you know and what you “don’t know you don’t know.” Even with extensive mentoring, schooling and reading of about 20 business books a year, I learn all the time through missteps - the things “I didn’t know I didn’t know.” The key is to reduce those missteps to as few as possible; and when they do occur, recognize and learn from them.


If you aren’t willing to work long hours, not take a paycheck during tough times, miss birthdays and anniversaries, and put everything you own on the line knowing that it could all disappear in an instant, success will likely be elusive. Don’t get me wrong, it can get much better with an awesome, highly accountable management team; but those sacrifices never completely go away and you shouldn’t expect them to. Although the sacrifices are great, the reward can be, too; and it will be rightfully deserved for you and your family when it comes.

You have a decision to make - choose wisely. If you decide to build a true business, then own it and live the part. Do your best to value your support system. Life balance may not be attainable, but you can do everything in your power to be where you need to be for the people you love and for your business. My advice is to grow to a size that, at minimum, can sustain a strong management team that has your back and can help share some of the load. Once achieved, you may find the sky is the limit. I love talking with other entrepreneurs. Call my office and schedule a time to talk if you have questions. If I can share some experiences, I will gladly do so. Good luck!


Following are a few of Jon Crandall’s favorites on leadership and business development:

  • “The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About it” by Michael Gerber
  • “Turn This Ship Around! A True Story of Turning Followers into Leaders” by Capt. David Marquet
  • Inno-Versity Presents: “Greatness” (video) by Capt. David Marquet
  • “How to Win Friends and Influence People” by Dale Carnegie

Jon Crandall, CSP, is Chief Visionary, CEO, Landscaper, Snow & Ice Manager, Salt Truck Driver, and Building Janitor when needed for JC Grounds Management. He’s also a member of the SIMA board of directors. Contact him at or call 978-532-9368.

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