Nathan Tanner

A Tale of Two Mentors: How Informal Mentoring Can Change Your Career

This article was originally published on LinkedIn. 

Many years ago I boarded a red-eye flight bound for New York City. I was about to start a Wall Street internship and couldn’t wait to get started. At the end of my first day, I learned that all interns would be assigned a formal mentor to provide guidance during the internship.

The next day I briefly met mine, a senior investment banker with a distinguished pedigree. I was excited to learn from his experiences and felt lucky to have someone of his caliber as a mentor. During our quick discussion, he committed to reach out a few times during my internship to check on my progress and answer questions.

Weeks went by, but I didn’t hear from him. Near the midpoint of my internship I sent an email to request time on his calendar. Still no word. Disappointed, I decided not to follow up. I told myself he was busy and probably had better things to do than spend time with an intern. I didn’t think I’d hear from him again.

But surprisingly, he sent an email during the last week of my internship, asking if I was available to meet for lunch that day. We went to an incredible steakhouse in Midtown. The food was amazing, but the experience was awkward. I could tell our lunch had more to do with his need to check some box than a desire to spend time with me. He didn’t really want to be there.

Fortunately, the mentoring I desperately needed came from another – Colin Cropper. Colin and I met a year before my internship when he hosted a group of college students in New York. I had just declared to major in finance and dreamed of landing a job on Wall Street, but I didn’t have a clue how to get there.

Colin was a gracious host and stayed well after the scheduled time to talk to students individually. I shared my goals with him and he kindly agreed to meet one-on-one the next day. He encouraged me to pursue my dreams. When I expressed concern about getting into banking from a “non-core” school (i.e. not an Ivy League), he assured me that if I hustled things would work out.


I was fortunate to get an internship in New York, and despite Colin’s busy work schedule and personal commitments, he always made time for me. When the company I worked for imploded the following year, becoming the largest bankruptcy in history, he was the first person I called. I was freaking out, but Colin helped me calm my nerves and create an action plan for moving forward. I’ll always be grateful for his mentorship.

What I’ve learned, from this experience and others, is that the best mentoring relationships develop organically. Formal mentoring programs can be effective, but if the relationship feels forced or the mentor lacks a desire to participate, the program’s goals will likely go unachieved. Informal mentoring, where the mentee proactively seeks out a mentor for career advice and guidance, is almost always more rewarding to both the mentee and mentor.

As you seek out a mentor, identify people in your profession whom you respect and schedule time to ask for their advice. If the discussion goes well and you sense a mutual connection, ask if they’d be willing to chat more in the future. There’s no need to explicitly ask whether they’ll be your mentor, and doing so can be awkward, adding unnecessary pressure to the relationship. Take things one meeting at a time and don’t force it. Additionally, seek a mentor who can give you candid feedback and is willing to invest in your long-term success. These two factors will be critical to your professional development.

Adam Grant’s recent post about mentorship outlines four steps to be an effective mentor. I’ve tried to tackle the other end of the spectrum. Here are four steps mentees can take to make the most of a mentoring relationship:

1) Be Proactive. As the mentee, you are responsible for driving the relationship. Don’t wait for someone else to take the lead. Show initiative and be bold.

2) Be Clear. What do you want from the relationship? Avoid ambiguity by clearly articulating your goals and how the mentor can help you.

3) Be Flexible. Adapt to your mentor’s time constraints. The person you want as your mentor will likely be busy. You may need to adjust your schedule to get on their calendar.

4) Be Engaging. View the relationship as one of reciprocal learning and development. Come prepared for meetings and look for ways to help your mentor. This may include sharing relevant articles or introducing them to people they’d find interesting. Mentoring is not a one-way relationship.

Achieving long-term career success takes help from others. As LinkedIn Chairman Reid Hoffman has said, “No matter how brilliant your mind or strategy, if you’re playing a solo game, you’ll always lose out to a team.”

I’m grateful to Colin for mentoring me during a pivotal point in my career and always carving out time when I asked for help. As you seek out mentors, remember to be proactive, clear, flexible, and engaging. The right mentor can help you accomplish your goals by providing you with perspective, support, and advice. But it’s up to you to make it happen.

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