How To Transform Your Mentor Relationships Into Lifelong Friendships


A version of this article previously appeared on Forbes.

Note: This is Part III of a series exploring the power of mentorships. Access Part I HERE and Part II HERE.

My relationship with my friend and mentor, Bob Wood, has matured over time. When we first connected, I was in listening mode most of the time, much like a dutiful student. However, as we established mutual trust, the balance of our exchanges shifted to the point that I am now a respectful but outspoken contributor to our friendship.

This transition from a unilateral, teacher/student paradigm is essential to sustaining a mentor relationship over the long term. In our case, this evolution has resulted in a rapport which enriches both of our lives, which should be the ultimate goal of any mentor/mentee combination.

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Stages Of A Typical Mentor Relationship

Most mentoring relationships encompass the following stages. Of these, stages 2 and 3 often occur simultaneously.

1. Setting the ground rules

2. Keeping it fun

3. Making it a two-way street

4. Ending on a high note

The article Don’t Do Tequila Shots With Your Mentor explores how a protégé can keep the mentor interactions fresh and engaging during stage two. This post focuses on how you can enhance the strength of your mentor relationships by making them bilateral exchanges.

Making It A Two-way Street

In addition to ensuring that the relationship remains rewarding for both parties, it is also important for the mentee to assert themselves and challenge the mentor all the while being careful to maintain a warm and healthy rapport.

The mentee should not begin to question the mentor’s feedback until adequate trust has been established. If done too early and without the proper level of deference, your mentor may misinterpret your dissension as disrespect and lose interest in the relationship.

Be Challenging – An important aspect of a mentor’s role is to expand your worldview by challenging your assumptions. In turn, you should question such challenges in a lively and spirited debate. If you find yourself in agreement with your mentor all of the time, seek a new mentor. In the words of former US President Lyndon B. Johnson, “If two men agree on everything, you may be sure that one of them is doing the thinking.”

By respectfully challenging your mentor in a fact-based debate, you will be forced to intellectually confront your beliefs, which may cause you to shift your worldview. Such exchanges will also inform your mentor in an intellectually stimulating manner.

Be Giving – Find meaningful ways in which you can enrich the life of your mentor. In my case, Bob and I share a passion for music. Although his depth of musical knowledge makes it challenging, I have marginally expanded his musical universe by sharing artists, songs, song origins, live performances, etc., that he had not previously uncovered.

Young people can bring value to their mentor by apprising them of trends, tools and technologies commonly understood by Millennials, but which may be foreign to someone who is not a digital native.

Be No Clone – At the outset of an intimate mentor relationship, it is tempting for the protégé to become a clone of the person they admire and respect. Avoid such tendencies by discarding opinions that you find errant.

Your goal isn’t to become an exact replica of your mentor (an outcome that no self-aware mentor would want for you). Rather, your responsibility is to internalize the experiences and opinions of each mentor with whom you engage. In this way, you will become a composite of your influencers over time, rather than a mirror image of a particular individual.

As Bob once told me, “No one has all the answers. Gain insights from everyone you meet, but filter each word of advice through the prism of your unique worldview and values.” 

Although challenging, your ultimate goal with each of your mentor relationships is to ensure that your mentor benefits from your interactions nearly as much as you do. In my case, Bob has noted that he has learned as much from me as I have from him. Although he is being overly kind, this is exactly the sentiment you want to hear from your mentors.

Again quoting Bob, “Any long-term relationship built on a hierarchical power imbalance is doomed to fail.” Thus, at the appropriate time in your mentor relationship, respectfully tear down the hierarchy and emerge as a dutiful yet opinionated collaborator.

Want to read more about managing mentor relationships? Check out Part I of this series HERE and Part II HERE.

Follow my startup-oriented Twitter feed here: @johngreathouse. I promise I will never Tweet aboutpeople too cool for a mentor or that killer burrito I just ate.

Image: Flickr Ambernectar 13

John Greathouse

John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara’s Faculty where he teaches several entrepreneurial courses.

Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.

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