No matter where you are in your career path, a terrific mentor can help you take on bigger roles, gain insight into technical challenges, and become a better leader. Being a mentor, too, is an important career move — and not only because it looks good on your CV and flatters your ego.
Mentoring can help you hire quality staff, create knowledge on your current team, keep employees from leaving, and boost everyone’s job satisfaction. It is a learning opportunity — for mentor and mentee — unlike any other. But how do you establish a mentorship, and do it well once you get there? And how do you encourage and enable the people on your teams to do it, too?
Asking someone to be your mentor or offering to be someone’s mentor can be more awkward than asking someone out on a date. That social anxiety about dating has spawned an industry of advice columnists, books, and sitcoms to help people navigate it. How about mentoring?
I asked skilled mentors for pointers on how they initiate a mentorship, what they talk about, and whether there’s an app to help connect mentors and mentees.
This is what they told me.
Mentoring opportunities are everywhere if you look and listen
The first step is finding someone interested in joining you on the mentorship journey. Most experts I spoke to insist that mentorship opportunities are everywhere: on your team, in your company, in other departments (because crossover skills are great), in your social world, maybe even at your local bar.
But asking someone in a role you hope someday to hold to spend their valuable time helping you get there, or suggesting you know enough to help someone else achieve their goals, can be awkward.
“Most people are receptive to being asked to mentor,” says Richard Bird, chief customer information officer at Ping Identity. It’s flattering. Much harder, he says, is offering to be someone’s mentor. This can feel like hubris and raises feelings of imposter syndrome. Before you jump in with an offer to mentor, Bird suggests keeping your ears open for people who are signaling that they are looking for one.
“They might say they want to grow or develop,” he says. “Or, one of the biggest phrases I hear is, ‘I have been working but still haven’t figured X out.’ This will often be more about how to navigate organizational or interpersonal dynamics than any type of technical challenge.”
If it seems difficult to find someone, you might be overthinking it, suggests Nicole Gavel, head of business development and strategic partnerships at Waymo.
“A lot of folks find it intimidating to get involved in structured mentoring relationship,” she says. “But I think successful mentoring, both from the experience of the mentee and the mentor, can be quite informal. Think about all the potential mentors in your network and cultivate those so that you can call on them when you are faced with a challenge.”
This is a very targeted approach to mentoring, rather than an ongoing formal meeting with clearly defined roles. In fact, there could be some role switching, with one person mentoring on one topic and being mentored on another.
Gavel suggests that when faced with something difficult — whether it’s a technical challenge, a struggle to get stakeholder buy-in, or a career move — scan your network for people you know who might have gone through something similar. “Ask that person: ‘I know you worked a deal like this or did this kind of integration. What was your experience on that? Did you learn anything that could be helpful for me?’” she says.
The same goes for being a mentor. “I’ve largely approached this by saying to people, if I could ever be helpful for you just get in touch,” Gavel says.
“Finding a mentor is a lot like dating,” says Colleen Tartow, PhD, director of engineering at Starburst Data. “That’s one reason I’m part of a community called Plato. This is a leadership mentoring group where businesses bring aspiring engineering leaders and Plato matches me with mentees based on things they are interested in — such as diverse teams, data, and startups.”
The Plato mentoring experience is a bit more like speed dating in that it allows Tartow to work mentoring into a busy schedule and is also an easy way to set up mentoring opportunities for an entire team. “I reserve a half hour a week and mentor whoever they set me up with,” she says. “I have found some amazing relationships this way.”
Chronus, eMentorConnect, MentorcliQ, and MentorCloud are a few other options for online mentoring programs that match individuals or teams with a mentor or mentee.
Define what you will get out of it
Once you have found a mentor or mentee, the next step is making sure the time you spend is productive for both of you.
“I like to start by setting goals and expectations for the mentorship,” says Tartow. This is like setting up an operating agreement before you start, and she suggests covering everything from goals, expectations, and availability at the outset. Are you available only at your meetings or are you there for your mentee all the time? What is the purpose of this mentorship?
“You are saying, ‘We’re going to have coffee once every other week,’ or simply, ‘We’re part of this mentoring program,’” she explains.
Creating this sort of clarity is a leadership skill, says Tartow. “This is leading by example. You are asking your mentee to be clear about what they want to get out of the relationship. Do they want to get promoted? Do they want a new job? Do they want more direct reports? Are they looking to have more strategic influence? Are they looking to help with execution in a challenging environment?”
Of course, the goals can change over time but starting with clear definitions of your goals and roles sets the tone. It also helps you know when — or if — the mentoring relationship is over.
“This is also a lot like therapy,” she says. “When they achieve their goal — get the job or whatever it was — then you know, my job here is done.”
Look for a mentee who can teach you
Mentorship and sponsorship are, according to many sources, powerful tools for creating a diverse workplace and for promoting diversity of thought.
“Mentoring is the only corporate related activity that allows us to make choices about who we impact and who impacts us,” says Bird. “I encourage people — and I do this myself — to ask to be mentored or to mentor people who are as different from you as possible.” That way, he says, “you both have the opportunity to learn about different experiences, pathways, and challenges, which helps create a more diverse workforce.”
Mark Schlesinger, senior technical fellow of Broadridge Financial Solutions, suggests that to capture this opportunity — even if your mentee is very junior to you — you should work some “reverse mentoring” into your interactions. Your mentee can, he says, “provide valuable insight on topics that can help from an overall diversity and inclusion perspective. These might include insight into generational preferences the company may not be aware of and can help you shape your culture as the workforce changes over time.”
Mentoring as a form of recruiting
Reaching out into your community and offering mentoring to students, job seekers, and other industries is a very effective way to not only recruit talent but also to increase the job satisfaction of your current team.
“In our business there is more demand for skilled talent than is available,” says Isabel Dewey, senior vice president of people at ReliaQuest. “So, our mentoring starts in the community.”
One of the company’s outreach mentoring programs sends junior team members to the local university to mentor.
“We call it RQ labs,” she explains. “We have a screening process to make sure the mentees have acumen for cybersecurity. Then we give them exposure to what we do and align them with our tech teams, where they learn more about us, how we operate, and how we solve business needs.”
Those mentoring relationships feed the company’s internship program and “oftentimes those internships become full time,” she says.
The program has no problem finding internal mentors because this is an opportunity to help team members grow their careers and is baked into their day, not added to their plate.
“These mentors are only two or three years out of college,” she says. “So, it gives them one of their first opportunities to be formal mentors and guides. It was not that long ago that they were in this person’s shoes, and it is a great opportunity for people who may be focused on answering tickets to grow some leadership skills.”
Practice the art of listening
Several of the experts I spoke to warned against offering advice to a mentee who isn’t ready to hear it. One trick to making sure you aren’t monologuing just to tick mentoring off on a check box somewhere in your own career path is to learn to listen instead of to teach.
“There’s a lot of value in having a mentor to act as a sounding board and help you look at things in a different way,” says Heather Natour, head of engineering for seller and B2B at Opendoor. “Being a mentor can be more about listening and empathizing than providing advice and life experiences.”
When people are asking for advice, it’s often because they have a specific problem to work through, they can’t see themselves in the next role, or they feel trapped in a situation or not ready for a challenge.
“A mentor can provide validation of the challenge and point them in the right direction,” says Natour. “I help the person see what they can do to move toward a goal. Giving the person a safe space to sort through their unrefined thoughts and emotions is sometimes more productive than advice.”
Natour also recommends skip-level mentoring — where the mentee’s manager reports to the mentor —because it gives both the mentor and the mentee insight into the workplace, their role, and specific situations that are hard to achieve otherwise.
“Skip-level managers often have the dual advantage of having more context about the details of a situation and also have more experience for the mentee to learn from,” she says. “I have had skip-level managers help me navigate difficult situations with my direct manager, act as sponsors, and help me understand my own role in leveling up the organization or team. In my role as a skip-level manager, I’ve found that I often provide a different perspective on an issue someone is having. Or I might share feedback that’s unique because of my own interpretation of the situation. Rather than trying to solve all their problems, I view my role as helping peers work together, which builds more trust amongst the team.”