St. Thomas Law Mentor Blog

Patrick O’Shaughnessy prepared this post for one of his mentor classes.  He graciously agreed to share it in the blog.

What makes a great Mentor                                            Patrick O’Shaughnessy

I have been fortunate to have several excellent business mentors that have formatively shaped, refined and guided my business career.  Webster dictionary defines a mentor as “a trusted counselor, guide or coach.”  Great mentors provide the critical foundation from which learning, introspection, challenges, growth, and opportunity arise.  In my experience, I have found that it’s absolutely imperative that a mentor be contextually situated within your personal or professional landscape.  Simply put, “beginners must start with models of those who have practiced the same art before them.”[1]  In sports parlance, a coach has witnessed the multitude of play options, time and time again, and knows which play is most likely to be successful.  In essence a mentor’s purpose is to help you achieve your goals and presumptively both student and mentor self-selected each other due to their collective belief that this particular mentor can best help the student achieve their goal.

Enumerated below are the personal & professional qualities, I believe are the prerequisites to, and hallmarks of great mentors. 

1. Personal Interest & Long Term Commitment- I firmly believe that the mentor and student should have, or develop a deep personal interest in working together and building a long-term relationship rooted deeply in friendship, trust and a long-term desire to be of service and benefit to each other.   The mentorship experience is certainly a two way street, with mentors often learning equally from their pupils.   Most people tend to think of mentors as being at a higher stature, or further along in their career.  Generally true, as one first starts their career as a business professional or lawyer, but inevitably over the long run the mentorship playing field balances out.  Interestingly, Bill Gates and Warren Buffet, consider themselves to be co-equal mentors in life & business with each party bringing unique and divergent skills and perspectives to the table.  This rings true to my own experience, where historically I was the fortunate pupil of a great investment banker (now a lifelong friend) who now relies on me for advice in the venture capital arena.  As I am an advocate of life-long mentoring relationships, mentors and students should self-select carefully if the relationship is to ensure.  It’s not to say that short-term mentorship opportunities are not valuable, but my preference is for the long run.
2. Deep experience- As noted above, a mentor generally should have deeply contextual experience in the business/legal area of personal interest to the student.  If you’re planning to practice securities law, all things being equal your mentor should be a securities legal expert.  Deep experience is required because the student is consistently looking for feedback on similar issues faced each day and how to best resolve them. 
3. Knowledge- A personal mentor must be a reliable source of specialized information and knowledge about relevant subject matters.  As the age-old adage states, “knowledge is power.”  A great mentor must be well equipped to provide the student with knowledge that can be put to practical use or effect.  Knowledge sharing in this regard must be additive to informed decision making.   Great mentors love to share their experiences, triumphs and more importantly war wound lessons.  Ideally, the best mentors are the “fishing buddy” types that always have a powerful parable to tell to the students benefit.
4. Wisdom- A great mentor has effectively, “been there and done that.”  Notably, this can be in either learning’s derived from success or failure, as both teach valuable pragmatic lessons.  Over their career, a mentor should have accumulated wisdom as the direct result of their extended historical experience that can in turn be conveyed to the student in the form of insight and understanding.
5. Patience- A mentor must be patient and recognize that often a student is learning some things for the first time and mastery will not be achieved immediately.  So goes the adage, “patience is a virtue.”  Working with a student is like cultivating a vineyard; as it takes careful preparation, appropriate tilling of the soil, etc.  Great results can happen over time, but as Steven Covey say’s, “success comes when preparation meets opportunity.”  The preparation part requires time and patience to be offered from the mentor to the pupil.
6. A Desire & Ability To Teach- A mentor must have a strong desire, motivation and proper purpose for sharing their insights, experiences and advice.  Not everyone is well suited to be a teacher.  A mentor should be a good listener, help the student articulate problems and explore solutions, and provide feedback.  A mentor should sparingly provide sage direct advice, but generally should teach the student how to come to the right conclusions via a process of solution exploration. 
7. Trial & Error Learning Incorporating Risk Elements: Parent’s often don’t let their children fail, choosing to bail them out from their poor choices/experiences rather than let them suffer through the pain.  I think it’s extremely important that a mentor purposefully let a student struggle to gain experience and learn from their mistakes.  In situations where protégés work directly for their mentors, the mentors are often not willing to allow, or encourage taking risks.  I believe this approach is fundamentally flawed because it insulates the protégé from real learning and facing the consequences.  I fortunately was a protégé of a mentor that while teaching me put our combined assets on the line.  The trial & error learning for me was along the following lines: be willing to risk, be absolutely accountable for mistakes, willingly accept potential diminishment of your reputation by family/friends/peers, learn to take more calculated risks, recognize that persistence allows transformation of bad outcomes into positive ones.  A mentor that does not accept a protégé taking risks clearly limits their learning opportunities.  An increase in the risk, with tangible outcomes on the line, generally improves the learning upside.    
8. Trust- A relationship of trust between mentor and student is absolutely imperative.  Only in an atmosphere of total trust can a student fully convey their needs, express their fears, reveal shortcomings, focus on strengths, and be able to receive direct, open and honest feedback.  Without this level of trust, students will hold back for fear of looking stupid, silly, uniformed, etc. 
9. Confidence Building- Great mentors put great faith and belief in their pupils, to facilitate confidence building and empowerment that encourages students to take risks, see new horizons, challenge themselves, etc.  Great mentors vocally praise accomplishments and achievements to bolster self-esteem and belief.  If done correctly, eventually the student becomes confident they can dance on the edge of the tree limb while managing and controlling the chaotic entrepreneurial process. 
10. Vision- Great mentors have vision across a two fold path.  First, great mentors fundamentally believe in their pupil’s future success and inspire the student to hold true to this vision.  Second, mentors are skilled at casting illumination on the path ahead, knowing the landscape, helping to navigate through obstacles and successfully leverage opportunities.
11. Actionably Supportive- A great mentor is wholly engaged in the mentorship process; ready to be active contributor, ask tough questions that get to the heart of the matter, provide critical input on vital issues like product pricing, etc. 
12. Challenging- Great mentors hold absolute accountability to what your plan is, whether you achieved it, why or why not.  They expect pupils to turn good intentions and ideas into real results.  The best mentors do this through the dialectical process of testing your assumptions and probing questions, thus allowing the pupil to arrive at the right conclusion via a process.  Great mentors are harder than your critics, but offer feedback in a non-threatening manner.