We’re experts in the coaching relationship. We know what makes a great coach and how to find one.

Mentoring relationships can be a little harder to pin down. People often use the term too broadly, calling anyone a mentor if they offer a bit of advice to someone on their way up. I see mentorship as a deeper, long-term relationship between two people. Even if it doesn’t start out that way, it becomes so from time spent together and mutual care for each other.

The relationship with a mentor is a meaningful one.

We reached out to our clients to get deeper insight into how having a mentor can impact people’s lives. A couple of stories stuck with us and showed the power of effective mentoring relationships.

Here’s what we learned.

A good mentor sticks with you through setbacks and tears, ups and downs

When Jaime Picozzi asked John, a wealth manager, out for lunch, she was hoping to get some professional mentoring. She wasn’t anticipating a five-year (and still going) mentoring relationship that would change the way she saw herself in the world.

Right before the COVID-19 crisis began, Jaime was in a difficult spot. A client wasn’t paying a large bill, and cash was tight.

“I remember getting on the phone with John, and I think I got ‘Hello’ out before I started crying,” says Jaime. “I just sat and cried on the phone the whole time. He talked, and one of the last things he said before we got off the phone was, ‘Do you remember that young woman from five years ago? Look at you now.’”

That was a powerful moment for Jaime because she did remember herself five years earlier. She was anxious about their lunch meeting, uneasy in a suit and heels, and uncomfortable in her own skin.

“That’s what I’ve been most pleasantly surprised by,” says Jaime now. “I never expected to have a confidante, someone who could put all the pieces together and teach me so much. He taught me how to build relationships, and now I can pick up the phone and call someone with no hesitation. I know how to bring people together.”

Jaime’s ability to be vulnerable with her mentor John, knowing he was there for her even if things weren’t going well, allowed her to move into a period of real growth.

Effective mentoring relationships can open doors to major career opportunities

When Keith Leaphart met Gerry Lenfest, Keith was working through a dual degree in medicine and business while running his own commercial cleaning company. Gerry, who was the CEO of Suburban Cable at the time, said to Keith, “Sit down. Something’s different about you. Why are you here dumping my wastebasket?”

From that point on, Gerry and Keith had a mutual respect for each other and developed a close personal and professional relationship. “He was someone I would go to for anything and everything,” says Keith.

After Keith finished medical school, he borrowed money from Gerry to purchase his first business. “You come out of medical school with debt, not with the ability to buy a business,” says Keith. “Gerry opened up so many doors for me.”

In 2007, when Keith was considering a run for Congress, Gerry’s office was one of his first stops. Gerry happily agreed to support Keith’s campaign. He also told Keith that he was thinking of changing the focus of his Lenfest Foundation to help inner city and underprivileged kids. “I want to help people who look like you,” he told Keith.

Keith ended up deciding not to pursue a congressional run, and he became the Lenfest Foundation’s executive on loan to the City of Philadelphia. There, he helped develop and implement Philadelphia’s ex-offender reintegration strategy. He eventually became Chair of the Lenfest Foundation Board, a position he still holds today.

Keith also credits his relationship with Gerry as the inspiration for his newest venture, Philanthropi, a platform that uses corporate good to empower individual giving. “Gerry gave me that exposure to big philanthropy.”

Good mentoring relationships offer encouragement as well as a few painful (but perhaps necessary) truths.

Jaime Picozzi got so much value from her mentoring relationship with John that she sought out a second mentor. Sometimes Jaime talks with her mentors two or three times a week. And sometimes they talk every six months.

Most importantly, when they do talk, they never shy away from the hard truths. “They’ve never lied to me, and they’ve never been afraid of me,” says Jaime. “I want somebody to tell me if I’m an idiot, if I’m failing, if I can’t do what I think I can do.”

While hearing that type of feedback might be useful, it’s not always easy.

Another client told us that she’d never cried so much from another person telling her such raw truths. She knew the feedback from her mentor came from a place of encouragement, but she sometimes had her feelings hurt.

Looking back, she sees those tough conversations as the ones that made her grow. She’s grateful that her mentor cared enough to say, “let’s fix this.”

Not all mentoring relationships form organically

While many mentoring relationships start organically (like Keith’s relationship with Gerry Lenfest), some require an ask. Jaime’s relationships with both of her mentors began with her specifically requesting their mentorship.

She gets different types of guidance from each, and both mentors are personally invested in her success. When Jaime asked her mentor Beverly, who built her career in tech at a time when there were few other women around, why she made the time to mentor, Beverly said, “I made a promise to myself when I took my first C suite role that when I got to a position where I could help others, I would send the elevator back down. And you are helping me hold that promise to myself.”

Some people want to mentor as much as others want to be mentored, but haven’t found the right mentee. Connections that don’t occur organically can still turn into deeply meaningful relationships.

A good mentor isn’t always the one who can give the most time

Like Jaime, Keith was hungry for additional mentoring relationships. After deciding not to run for Congress, he reached out to David Cohen, a top executive at Comcast. Recognizing that Cohen was extremely busy, he asked for 15 minutes of his time, once a quarter.

When Gerry was alive (he passed away in August 2018), they didn’t have weekly coffees or lunches. Keith respected all the demands on Gerry’s time. “There was no specific cadence to it. He was very called upon, but whenever I called on him, he was available.”

The mentoring Keith has received has made him a vocal advocate for mentoring others. He sees the amount of time a mentor can give as directly connected to their level of leadership. Those at the very top are so called upon that they may only be able to carve out a few minutes. Fortunately, they’re so efficient with their time and have such useful guidance that those are powerful minutes.

“With super busy, super successful people, you only have their mind for 15 minutes,” says Keith. “Even as close as Gerry and I were, it didn’t take long to get where we wanted to go. If you want someone who is uber successful to mentor you, don’t be offended when you walk in and they’re doing three things while they talk to you. Trust me, they’re getting everything you said.”

Final thoughts

Building or leading a business shouldn’t be done in isolation. You need to surround yourself with others who can support and guide you on the path to success. Many successful entrepreneurs can point to dozens of people that helped guide them along the way—mentors, coaches, advisors, advocates, consultants, maybe even friends and family.

If you’re wondering how to find a mentor of your own, download our free ebook. We share six tips that will help you build a strong mentor relationship.