Mentor-Mentee Relationships: Best Practices for Both Sides

Mentor-Mentee Relationships: Best Practices for Both Sides

Peter Drucker spent his life “strengthening organizations to strengthen society”, and he served as a legendary mentor for many successful individuals. As a mentor, he had an unerring instinct for guiding others to greatness, and his legacy lives on today in the Drucker Institute. On the flip side, Drs. Vineet Chopra and Sanjay Saint focused on what makes a great mentee in a recent article for the Harvard Business Review.

No matter which side of a mentorship relationship you’re on, Stout breaks it down here with 5 tips on excelling in either role.

  A Great Mentor: 

Guides Discovery – Mentees are thirsty for knowledge, but the best mentors will teach them how to fish instead of giving them a fish. In other words, good mentors ask questions and help their mentees find answers through thought as much as they dispense actual advice.

Is Fully Engaged – Accepting the role of mentor is a serious commitment. Someone has honored you with respect and admiration, making you their choice for wisdom and guidance. Regularly schedule time with your mentee, and when you are together, be fully present and focused on their needs.

Listens More Than Talks – Drucker often said his greatest strength as a consultant, “is to  be ignorant and ask a few questions”. Don’t assume you know what your mentee needs, and come up with a standard prescription. Listen carefully to their goals, plans, dreams and questions – you may surprise yourself by what you learn. Only then is it time to talk.

Insists on Accountability – Some mentors fall into the trap of encouraging and applauding mentees for what they do – but not holding them accountable when they fail to follow through on promises or deliverables. True growth requires both praising the positive, and insisting on responsibility when things come up short.

Mentors the Whole Person – The strongest mentor-mentee relationships acknowledge that personal and professional lives are intertwined. Be there for your mentee not only during professional highlights and crises, but also for their challenges and successes in life.

  A Great Mentee:  

Knows What S/he Needs – “Mentor” is a very broad term. Drs. Chopra and Saint stress the importance of knowing what type of mentorship you need: coach, sponsor or connector. Coaches, they say, help with a particular issue, while sponsors help open doors to elite groups. The final type, connectors, are “multipliers” who help the mentee build a network. The length of the relationship is also a factor – does the mentee need short-term, situationally specific advice, or longer, more general guidance.

Researches Choices – Mentees need to seek mentors who align with both their professional goals, and their personal traits. The relationship is not unlike a marriage in some aspects, requiring trust and respect. The person who is at the very top of the field may not always be the best fit or choice.

Respects Their Mentor’s Time – Successful people are busy people. If a mentor has graciously chosen to share precious time with you, respect that by coming to meetings prepared, asking specific questions, and not monopolizing their attention.

Engages and Delivers – The best mentees return  the investment of energy to their mentors. Be the excited mind with fresh ideas and enthusiasm – your mentor can learn as much from you at times as you from them. Also be prepared, complete your part of tasks or projects with quality effort, and accept feedback as generously as it is given.

Addresses Problems Head On – Even relationship has its pitfalls, and the one between mentor and mentee is no different. Sometimes the problems are on your end: failure to deliver, monopolization, etc. Others can stem from your mentor: lack of attention, missing deadlines, idea theft. While the temptation to avoid the issue(s) may be strong, especially with someone you look up to, you must deal with things quickly and directly. Sometimes the relationship can be salvaged, sometimes not, but conflicts must always be addressed.


No matter which side of the relationship you are on, the most successful alliances require support, respect, clarity and patience. Not only does the partnership evolve over time, but so will each person in it. Learning is not a one-way street, either. Mentors can learn much about themselves, both from the process and from their mentees. It’s a rich and layered relationship, not so much about fast-tracking and teaching but discovery, legacy and trust.

Double Up: You can both HAVE a mentor and BE a mentor – we all have room for growth!

Still looking for your mentor match?

Opportunities to mentor or be mentored are all around. If you don’t have your own mentor, create one. Seek out thought leaders you admire and research them. Use people you admire around you  – your child’s teacher, your child, the barista or neighbor – and source inspiration from their #Stout attributes. Or harness the power of technology, and create a “virtual super mentor” by pulling the top characteristics from a handful of those you admire online. And if you are a success in something you do – whether it’s as an entrepreneurial adventurer or a power parent – be open to sharing your skills with others looking to level up in that role. And yes, you can both HAVE a mentor and BE a mentor; from starting exec to Fortune 500 CEO-we all have room for growth!

For even more insights on the power and possibilities of mentorship, check out these #Stout articles.