How to find and maintain the perfect mentoring relationship

A longtime mentor and mentee explains the art of building this unique, essential relationship

Building your career is a journey filled with challenges, excitement, and forks in the road. And journeys are easier with maps. In this column, job experts answer your questions and deliver advice to help you take the next step.

Question: I’m thinking about getting a mentor, but I have no clue where to start. What should I consider?

Answer: With a career of more than 15 years in technology, spanning engineering, sales, business, and program management, Guada Casuso has been both a mentee and a mentor. One key thing she’s learned: any mentoring relationship should be grounded in trust and respect between both parties, with mentees taking the communication lead. Here are her top tips and insights on how to both establish and nurture a mentoring relationship.

Know what you want

“A mentorship should start with a goal you’re trying to address,” said Casuso, currently the principal technical product manager in Intelligence Sales for Microsoft. For example, do you want to improve your coding skills? Are you interested in getting a job in artificial intelligence (AI)? Once you know what it is that you want to pursue or accomplish, you’ll be able to identify potential mentors who are successfully navigating the area you’re passionate about. The goal serves as the compass throughout your sessions and communications with your mentor.

Once you’ve crystallized your main goal, Casuso advises not to seek a carbon copy of yourself in a mentor. Instead, look for someone who represents your ideal professional destination.

“When you are exposed to a new scenario, want to learn something new, and need advice, that would be the perfect time to seek a mentor,” she said. “A mentor can guide, facilitate resources, and help you prioritize.”

Don’t be derailed by common misconceptions

Some people are reluctant to find a mentor because they believe only interns and younger employees should be mentees. But, you’re never too young or too old to seek a mentor.

“The most important thing you can do before you place limits is ask yourself, ‘what do I want to achieve?’ Let that guide you,” said Casuso. “We are all apprentices in some areas of our professional careers and life.”

Another common misconception is that people should have only one mentor. Different people can offer you guidance in different areas and help you pursue specific goals depending on where your focus is at a given time in your career.

“I have never had just one mentor. Look at people you respect and who are aligned with the different goals you have in life. By having more than one mentor, you are exposed to different perspectives. If you can find mentors who complement each other, that would be perfect,” she said.

Seek chemistry, build relationships

Casuso recommends that once you identify a mentor who is aligned with your goal, you reach out to him or her in email, LinkedIn, or other social channels.

“Express your goals, explain why you’d love their guidance as a mentor, and suggest a 30-minute chat over coffee,” she said.

At this first meeting, your objective is to communicate what you are trying to achieve, see if the mentor believes he or she can advise you, and determine if the two of you would work well together.

Casuso suggests that you seek someone you admire on the career side but who also can offer “holistic advice.” A person might be able to counsel you on coding or project management, but can he or she also offer advice on conquering time management? “Look for someone who is empathetic and a good listener,” Casuso said. “Seek chemistry. You need to feel that.”

You may find that a person is not a good fit or simply doesn’t have the time to spare. If that’s the case, Casuso suggests that you ask if he or she can recommend other potential mentors. Also, keep in touch by checking in periodically (every six months or annually) and sharing what you’ve been up to in your career. This will help you establish a relationship. If mentorship didn’t work out initially because of bad timing, the person may reach out when the time is better because you kept in contact in a meaningful way.

Set the rhythm

Mentees should take the lead on their new mentoring relationship, Casuso said. During your 30-minute chat, first agree on the goal that you plan to tackle together. Then, agree on a cadence that works best for both of you. Casuso believes that once a month is perfect; however, each scenario varies.

“If I’m new in a role and I need guidance as I ramp up, I may need to meet with my mentor once a week until I get the hang of things. Then we can level out to once a month,” she said.

Ultimately, as the mentee, don’t be afraid to guide the conversation, find out what works best for your mentor, and set up all meetings. It shows your mentor that you appreciate his or her time and respect his or her guidance, Casuso said. Communicating openly about the obstacles you face, how you learned to overcome them, and your subsequent growth gives mentors insight into what you’re made of. This can motivate them to vouch for you when new opportunities arise.

While the agreed-upon mentorship may finish once the goal has been successfully reached, the relationship doesn’t have to end.

“Keep in touch. Let them know how you’ve grown and about your career-based successes along the way,” she said. All mentors want to see that their guidance has led to great strides in their mentees’ careers.

Of course, Casuso feels there’s one true test of a successful mentorship.

“The proof is when the mentee becomes the mentor, which feeds the cycle. And that’s simply magic.”