I have a friend, Jeremy, who has always impressed me with his skill as an entrepreneur. No matter the venture, he almost always Steve-Strauss--in-article-Medium.pngmade money and the venture did well.  So I was surprised when he told me about one of his failures - that his mentor relationship had turned sour.


Now, maybe you are thinking that a guy with Jeremy’s skills did not need a mentor. You would be wrong. Jeremy always had more than his share of free advisors, most of whom gave him, not only valuable advice, but connections as well.

But for whatever reason, this time Jeremy blew it. Jeremy had created a board of advisors for one of his ventures, using his mentors’ knowledge and connections to help grow his business. In return, Jeremy offered them free weekend trips and other gestures of gratitude. The advisors never expected to be hit up for money, and that is where Jeremy went wrong. At his most recent board retreat, he had approached one of them and asked for a significant loan. The guy was incensed, feeling that he had been played, duped. He was interested in helping not investing, he said. He left the event that day, and Jeremy’s board meeting crumbled when he had to explain what happened to everyone else.


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It’s a good lesson for anyone who gets involved in a mentor – mentee relationship. Not long ago, I wrote an article entitled 5 Ways to Find a Mentor, and in it I shared some strategies for finding people who might be willing to mentor you. But Jeremy’s story is a reminder that finding a mentor is only part of the story. You must handle that relationship intelligently if it is to bear fruit.


Here’s how:



Be clear: Of course, this was Jeremy’s fatal flaw. What he thought the relationship was about was very different than what the mentor thought was going on. So it is vital from the get-go to set some ground rules with mentors and be clear about what you expect, and what it is they expect.


Set reasonable exFeb 26 pull quote.pngpectations: As part of the discussion above, let me further suggest that you find out what the mentor hopes to gain from the relationship. Is it merely to mentor you in the traditional sense, or are other things – like connections, experiences, and finances – going to be involved? You better know.


Make it easy: Jeremy almost hit this part out of the park, until his fatal error. The important thing is that a mentor is doing you a favor, and it is therefore incumbent upon you to make it as easy as possible on them. Work around their schedule. Take them out to lunch. Say yes.


Make plans: Mentor-mentee relationships fade away most often because the mentee fails to take responsibility for keeping it going. Mentors usually are busy folks and helping you for free is not at the top of the list of things you think about. As a mentee, the relationship is likely far more important to you than to the mentor.  As such, be sure to keep it going:

  • Take responsibility for scheduling lunches or dinners or other entertainment
  • Drop your mentor an email with a quick update
  • Call just to say hello


Show your appreciation: A mentor becomes a mentor because he or she thinks they can make a difference; so first of all, it is your job to show them that their time and efforts are paying off. Share your successes and lessons learned with your mentor.  Also be sure to share your appreciation in tangible ways – send a holiday present. Drop a thank you card in the mail.


Give back: What can you do to make things easier or better for your mentor? Do that.


And Jeremy? You can bet he won’t make the same mistake twice.


How do you maintain a relationship with your mentor or mentee? Share your story below.

About Steve Strauss


Steven D. Strauss is one of the world's leading experts on small business and is a lawyer, writer, and speaker. The senior small business columnist for USA Today, his Ask an Expert column is one of the most highly-syndicated business columns in the country. He is the best-selling author of 17 books, including his latest,The Small Business Bible, now out in a completely updated third edition. You can listen to his weekly podcast, Small Business Success, visit his new website TheSelfEmployed, and follow him on Twitter. © Steven D. Strauss

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