The Most Impactful Mentor and Mentee Relationships

A great deal has been written about mentoring in books, podcasts, TED Talks, and beyond. While there are best practices and practical ways to approach mentoring, I have found that the strongest mentoring and mentee relationships are rooted in the personal connection between the two individuals. This week, I’m sharing three mentoring experiences that I’ve had in my career, including how they came to fruition, the engagement model, and the short and long-term benefits that have been gained. 

Serving as a Mentor 

Something really special happened to me on Veteran’s Day 2022. I’ve always appreciated the sacrifices that military members and their families have made for our country. Our active duty military and veterans are the reason why America is the land of the free and home of the brave.  My gratitude for serving in the Armed Forces grew even deeper when I started dating my boyfriend, now husband, and heard his story of attending the Naval Academy and his five years of service afterward. So bringing it back to this past Veteran’s Day and the email I received from LinkedIn:

You have the skills to help a veteran build a fulfilling career. That’s why we’ve partnered with the nonprofit American Corporate Partners (ACP) for Veterans Day to offer a unique, customized mentoring opportunity to professionals like you.

As a mentor, you’ll share invaluable career advice with your Veteran Protégé to help them break into the tech field. This is a year-long opportunity with a time commitment of approximately one hour per month and can be entirely virtual.

I was intrigued and it felt like this opportunity to give back to someone who served came at just the right time. I decided to check out the ACP and learn more about how I could help a former military member enter into a career as a civilian. Very quickly I was matched with my protege and each of us jumped into this relationship with both feet. Our first conversation was a get-to-know-you chat where we talked about our work experiences, hopes for the future, families, and how we could learn from each other. I could tell from this first meeting that spending time together was going to positively impact both of us.

Then we moved into the next phase where we dove into my protege’s resume and cover letter. This was some of the most fun work so far. We reviewed his resume line-by-line and translated the 25 years of military service and achievements into corporate language. We made sure the words were authentic and his own, but talked about how some bullets points such as – I built consensus in our military decision making across my battalion and execute those orders can be translated into civilian speak such as – I will be able to work across cross-functional teams and divisions to drive toward team decisions making for company success. We spoke about evolving language from being tactical-based to outcome-oriented. Within just one update the resume evolved to be one where someone who is glancing at a resume for 10 or 20 seconds would put this one in the yes pile.

The third session had us doing mock interviews. I played the role of the interviewer and peppered my protege with questions about the 25 years of military service and how they could serve him well in civilian life. We brainstormed on the lessons he learned in the military, his biggest successes, and what are his strengths. After each question and answer, we went back through the answers and crisped them up. I could bring the background of someone who has been in tech for 25 years and has interviewed hundreds of people. So I let him know how various phrases landed on me or asked for clarification about a military termination I didn’t understand. We kept refining until I could grasp and appreciate the details in non-military terminology, but still his own story.

Now we are at the stage where my protege has several interviews under his belt and it is likely to be moving toward an offer or two. I’m excited about this next chapter for him and what that will mean for his life. I feel very grateful LinkedIn connected us and I have an opportunity to contribute to the next chapter in my protege’s life.  

Peers as Mentors

Oftentimes when people think about mentors, they assume the relationship needs to be with an executive who has two decades more experience than us and can impart deep wisdom in every interaction. Those types of mentors are wonderful, but I’ve also had peers who I have considered mentors as well. Peers have a way of seeing your blindspots daily and when they are generous to point those out, they can be life-changing. When you have a great colleague that you interact with regularly, the relationship does not need to be formal. Often it was when my peer and I had our 1:1s that she would share a perspective and it was a growth opportunity for me. I also knew the spirit that she shared feedback was to be candid and to help me improve; there was no other motive.

Our conversations were wide-ranging – how would we partner for success, what projects were underway that we could brainstorm about, and any challenges between our two teams we needed to iron out and beyond. My peer did not have a selfish bone in her body. She was willing to give advice freely. She was driven and hard-charging, however, she wanted the best outcome for us and our organization, which I found refreshing and unique. Since my peer had a few years more experience them me at our company, she was able to guide me, especially in my early days, about what approach might work with certain people or not. This was invaluable as I was learning the lay of the land. 

I will always look fondly back on the partnership and take the lessons that I’ve learned throughout my career, especially the skills around being brutally honest but doing it in a way that cares deeply about the individual getting the feedback. 

Finding a Mentor

I might be atypical in my approach to identifying mentors throughout my career, but I’ve never approached someone and formally asked them to be my mentor. It has always happened much more organically for me. Of those relationships, each was with colleagues at the same company and generally in the same office. There was no need to set up formal sessions and do monthly Zoom calls, but the interactions, whether they were coffees, lunches, or 1:1s, happened naturally when the time and setting were right. There were absolutely times when I reached out and asked for a few minutes of someone’s time and we could jump on a quick call or meet in person if that was an option.

What I’ve always found valuable from my mentors is being able to give them actual situations and talk through the pros and cons of one approach versus another. It was never about telling me how to do my job, but instead having another individual provide their insight that might be different than mine about a specific situation. I’ve often found mentors outside of my department to be very helpful since they can have a more objective view of the challenge I’m facing without knowing the exact details of the situation. As I’ve advanced in my career, it has become clear that most challenges can be tackled in many ways as opposed to only one approach. Mentors help you open the aperture and see a wider view of people or a situation. They can also probe and ask you questions you might have not thought of, so you can arrive at the decision yourself not being told to do a, b, then c. 

The best mentor and mentee relationships came down to chemistry. When there is an opportunity for both of you to be honest with one another that leads to growth and gaining new perspectives. I’ve found being mentored and providing mentorship to be one of the most gratifying aspects of my career and benefits each party for years to come.

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