4 Tips for Developing & Maintaining Healthy Mentorship Relationships

Ajay Mentor Post
Ajay Pattani
March 1, 2016

Over the years, I’ve been fortunate enough to have both formal and informal mentors in my life. In addition to these meaningful relationships, I’ve also been involved in more structured mentorship programs, like my connections with 1871, the shared office space in Chicago, and the Entrepreneurs’ Organization (EO).

When I reflect on all of my mentorship relationships, from unofficial to official, from being a mentee to a mentor, and so on, I can’t help but think about how invaluable they are to my success as an entrepreneur and as an individual. It’s an incredible way of acquiring insights into your own goals and business practices, building your professional network, and gaining all kinds of experience.

I recall years ago thinking that experience is often overrated. Looking back, I realize that I thought that because I didn’t have much experience.


The 4 key points of successful mentorship relationships

For the past two and a half years, I’ve been a member of a fantastic organization called the Entrepreneurs’ Organization (EO). It’s a dynamic, global network of around 10,000 business owners in 43 countries that enables entrepreneurs to learn and grow from each other, leading to greater business success and an enriched personal life. The non-profit organization’s stated mission is to “engage leading entrepreneurs to learn and grow,” and that’s one of the values that drew me to it in the first place.

Recently, I took a board position to lead the EO mentorship program. Once I began the position, I realized that there were a few challenges that had to be addressed in order to curate and foster valuable, healthy mentorship relationships. Each of these challenges aligned with one of four key points of mentorship.

1) Think about compatibility

Pairings must be based on requisite strengths and weaknesses of both the mentors and the mentees. For mentorship relationships to be fruitful and lasting, it’s always recommended that one mentee’s area that he or she wants to improve in aligns with a mentor’s point of strength.

Of course, mentors can have weaknesses, too. Nobody’s perfect. Not even the guy who founded Perfect Search.

2) Quality over quantity

In the EO mentorship program, it felt like the number of pairings was sometimes the primary focus. While obviously matching up everyone who wants to participate is very important in a huge organization like EO, the quality of the relationships should matter as much as the quantity of mentorships, if not more.

Otherwise, if the main goal is pairing up as many people as possible, other aspects of the relationships (like aligning strengths and weaknesses!) will surely suffer. Still, I felt that having a specific goal for number of pairings is vital, as it provides a measurable benchmark to aim for. However, the focus of the program should shift from number of pairings to total value gained from the pairings.   

3) Match up mentor & mentee demand

EO had a relationship with another organization, the World Presidents’ Organization (WPO), whose members were more seasoned CEOs. Though this was a powerful partnership, we quickly realized that there were not enough WPO mentors to fulfill the demand from prospective EO mentees.

This was a mismatch issue; while EO members who got the opportunity to be mentored by WPO members were happy, it wasn’t the best set-up simply because there was a supply and demand discrepancy. If you’re running a mentorship program, this is a common challenge you’ll likely face at some point.

4) Like any relationship, communication is key

While mentorship relationships are clearly different from friendships, family ties, or romantic relationships, they’re still relationships. This means that regular communication is necessary to keep the connection healthy and fulfilling.

Some things to communicate about within a mentor/mentee relationship: how often you’d like to communicate (whether by email, phone, or text), how often you’d like to meet in person, how to incorporate each other in professional networking and events, and so on.

In EO, we had a different kind of communication challenge. There was little feedback requested from current pairings to support the value of the mentorship program. Still, because EO is a facilitator of these relationships, it was the organization’s duty to communicate with the pairings to maintain a healthy program. Now, this is a goal.


Mentorship is a two-way street

After engaging in a number of cherished mentorship relationships in my life and then going on to help facilitate a mentorship program, one thing became clear to me. There’s a popular underlying assumption that the mentee gains the value and that the mentor offers the value in any given mentorship relationship.

I think this assumption is often incorrect. The value of giving can often outweigh the value of receiving. Here are a few examples of how being a mentor is equally as rewarding as being a mentee:

  • Mentors and mentees develop strong bonds that often extend into lifelong friendships.  
  • Similar to fulfillment in entrepreneurship, mentorship can lead to the extremely rewarding creation of new jobs and employment growth.
  • Mentorship is an advanced form of leadership and thusly will improve this skill set.  

The EO program’s strategy to increase the number of mentors isn’t just to satisfy demand. It’s intended to emphasize the value of being a mentor as an extensive entrepreneurial experience, as well as highlight the importance of impacting another business owner’s success.  


Go forth and mentor!

I’ll conclude with what I’ve learned throughout my years in entrepreneurship and mentorship. First and foremost, if you have ever thought about being a mentor, just do it. It’s a fantastically rewarding experience that will provide you with so much more than you ever expected.

Secondly, if you find yourself wanting a mentor, don’t be afraid to ask. You can reach out to people you admire or join a mentorship program like at EO.

Finally, I’ll end on two quotes that speak to the value of mentorship more eloquently than I ever could.

“Only a life lived for others is a life worthwhile.” –Albert Einstein

“The greatest good you can do for another is not just share your riches, but reveal to them their own.” –Benjamin Disraeli


Do you have any stories of how a mentorship relationship furthered your career? What about tips for maintaining mentor/mentee connections? Tweet us at @Perfect_Search or reach out to Ajay at @AjayPattani. We look forward to hearing your thoughts!

Don’t forget to check out other posts by Ajay. Discover his 4 pillars of happiness, the importance of “the human element,” and international words of wisdom

Ajay Pattani
CEO & Founder

Ajay Pattani is a lifelong resident of Chicagoland and is fiercely passionate about his white wine. If he could be a spokesperson for any product, it would have to be white wine. Ajay says if he could be good at one thing, it would be reading minds. If you could read his now, he’d most likely be thinking about white wine.

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