How to Pick the Right Mentor

entrepreneur entrepreneurship mentor mentoring mentorship musician Mar 09, 2020

The 1st Month of My Son’s New Business Was One Year Ahead of Projections

One of my sons opened a business, and it is not every day that a musician starts a successful business. “Musician” and “business” don’t even sound good together, but he has done it. His opening was three times what he expected, and much better than others had experienced in the same industry. Yes, as a Serial Entrepreneur, I did help him some and so did his wife. However, what really made a difference was getting a mentor in his specific industry. The mentor also experienced fulfillment in being able to help a young person.


All of what my son and the mentor experienced can happen to anybody with ambition in any size organization. Read on if you want to be more successful or help someone be successful…


Mentees: How Do You Find or Pick a Mentor

  • Someone you can trust: Either from asking around or your personal intuition on this will be needed. When you ask the mentor, make sure you are clear with him what the confidentiality boundaries are.
  • Someone objective: You want someone who will give you the brutal truth. Assuming the mentor has your best interests at heart, you need to ask him to give it to you straight. Your ego will be bumped up a bit, but it is better to have high self-awareness than someone walking around that everybody can see thinks more highly of himself than is true. There is great power in servant leadership – another topic and greatly outlined in Jim Collins’ book Good to Great.
  • Someone who is wise: As a general rule, a wise person will listen more than he will talk. Older people tend to be wise because of the lessons from the many mistakes they have made in their careers and life in general. Humble people also tend to be wiser. Comparing their advice to the book of Proverbs would be enlightening.
  • Someone rising in his/her career: This area is another one for research and how he/she got there. If they stomped on and ran over others, don’t ask them. Do your research before asking. See if your personality, values, and other attributes are in pretty good alignment with the prospective mentor. If they cooperated with and helped others succeed and truly have God first, company second, themselves last, you may have found your mentor.
  • Not necessarily your boss: The reasons your boss is not necessarily the best choice is included in the above four criteria as well as those in the “How a Mentor Can Help You” section above.



I had one meeting with a mentor, and it saved three businesses in my career, never mind a bunch of money, blood, sweat, and tears. After business school, I called the school dean (I’ve always been pretty bold) to ask him a few questions about my business plan. He gave me some answers but asked me more very pointed questions. Upon hearing my answers, he said that he thought the school had taught me well.


Then he said something that collapsed my puffed out, prideful chest. “Charlie, now double the amount of capital you think you will need and triple the amount of time you think it will take to get started.”


I said, “Dean, are you sure? You said I’ve been conservative and was taught well.”


“Charlie, that’s my advice for you.”


“Thank you, Dean,” I said trying to sound excited.


I hung up and realized, I had just challenged the best mentor that I probably ever will have – the Dean of a top-ten business school. He also was head of the Xerox’s venture capital fund in its best years, he truly wanted me to succeed, he listened, he had had a meteoric career, he was as wise as they come, and so much more. I took his advice, and it saved my company. Mentors can really matter, so go find one or be a great one to others.


Charlie Haines

[email protected]


Per research, only 13% of employees are engaged at work. A personalized career plan may help you avoid this statistic and idols at work.