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Learning through leadership

  • SIMA
- Posted: August 1, 2015
By Jon Crandall

Employees aren’t the only people in your organization who can benefit from having a mentor to guide them and help them grow. As owner of my company, I have experienced firsthand the powerful impact of mentoring relationships. I have been fortunate enough to experience both roles as a mentor and as a mentee. I believe it has not only changed me and my company for the better but also has allowed me to share my experiences with others. 

An early start 
When I was 18 and in high school, a close friend asked me to start cutting the grass at his home along with a few properties the family owned. He said his brother, Jim, owned a painting company and would pay for the service. I met Jim when I went to pick up my check; during these visits, I would talk to him about business and my plans for the future. He would challenge me by not always giving the advice I was seeking but instead asking more questions to help guide me to a solution on my own. As time went on I noticed he was away quite often and I asked where Jim was going so frequently. 

His administrator said Jim had joined a group and was traveling all over the world. She said he attended meetings once a month where he couldn’t talk about what happened and was being trained to speak in a particular way during the group’s meetings. I jokingly thought to myself that he had joined a cult. It wasn’t a cult - It was the Entrepreneurs Organization (EO).   

EO members agree not to do business with one another and keep what is said within meetings 100% confidential. This allows members to let their guard down and become completely transparent. With nothing to lose, members can learn from one another’s experiences.

As time passed, Jim, who had become a mentor, started inviting me to local Boston chapter learning events. My business did not qualify for EO (you must have annual revenues greater than $1 million) but I was able to attend as a guest. As I experienced the quality of the members and the experts they brought in to speak, I quickly realized the value of the organization and, more importantly, the value of the way it conducts business. I was hooked and made it a personal goal to build my business to at least qualify as a member before I graduated school.   

Surround yourself with greatness
Business philosopher Jim Rohn said: “You’re the average of the five people you spend the most time with.” Enhancing the caliber of people around you will enhance you. Enhancing the people within your organization will enhance the organization. I believe this works, which is why I am attracted to mentorship programs, forums, and organizations that are selective in how they recruit members.   

While EO was initially out of my reach, I jumped at the opportunity to join its sister organization (Accelerator) when it started in Boston in 2007. Accelerator’s purpose is to help push smaller businesses through a ceiling of complexity to eventually qualify as EO members. Within one year, I had surpassed the qualifying $1 million mark, and I was asked to help run the Accelerator program. The next year I was asked to chair the Accelerator program in Boston. I wanted to make an impact and thought one of the best ways to do so would be to start a mentorship program utilizing the resources of Boston EO chapter members. I learned who the most influential long-term leaders within the chapter were and asked them to help. After some persistence, each embraced the challenge. We started with eight seasoned business owners, and the program was an instant success. Several years later, I am still a member and continue to see the fruits of that labor. Many Accelerators have surpassed the $1 million mark, and many of the early mentors have started coaching and consulting businesses.  

After my term as Accelerator chair, I became the president of EO Boston. The chapter president oversees the entire chapter, including the Accelerator program. Having looked up to many of the board members who had much larger businesses than mine and knowing they would be looking for me to lead them and the organization forward, it was an honor to serve. I had many ideas, and in the beginning I remember feeling unsure that the board would take me seriously since they were running organizations with revenues upward of tens of millions of dollars. I remember thinking, “Why should they listen to me when they are more successful than me?” After about two months of head trash, I realized even leaders need leaders.  

Many returns
My desire to pay it forward drove me to become involved, but I did not expect to get back what received. In many ways I found out that I got back tenfold what I had put in. The experience helped me learn about myself, and my ability to emotionally mature was worth a second college education. It allowed me to build the confidence that enables me to operate the business I have today. That experience also showed me the amazing outcomes a team can produce when a group of top performers are aligned well and are passionate about what they do.  

I’ve learned that big or small, pharmaceutical or snowplowing, most businesses struggle with the same basic problems around the same basic topics (money, people, strategy and sales). Find someone who has been where you are going. Ask for a monthly or weekly breakfast, and you may be amazed at what action items and information you take away. People naturally want to help and will. SIMA has excellent resources such as the Snow & Ice Symposium and excellent staff that can connect you to members who may be interested in being a mentor. I hope this article has inspired you to seek out a mentor or find a program near you that may have mentorship programs. It may change your life! 

  • You get back as much or more than you contribute in a mentoring relationship. When mentoring and giving advice, it typically makes you re-evaluate the topic and realize that you may need to reset an initiative in your own business.
  • Your time is valuable, so when offering it, select someone who is a good fit and who is willing and able to be coached.  
  • Have your mentee set the meeting time and place, and arrange the logistics. If the mentee values the relationship and is driven to succeed, they will be happy to take this on.
  • Ask for a topic 48 hours ahead of time so you have time to think of relevant information or experiences to share. I always ask: “What is keeping you up at night?”
  • Sharing stories seems to be the easiest way for people to relate and retain information. Do not give advice based on opinion but rather share a personal experience from a similar scenario.
Jonathan Crandall is chief visionary of JC Grounds Management in Danvers, MA. Contact him at
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