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For those who have never had a mentor before, it can be difficult to understand the subtleties of this unique relationship.

Busy professionals often expect early-career job seekers to understand the unwritten rules that dictate the interactions – such as preparation, follow-up, and how to best utilize their limited time – but there are few resources to help them navigate this dynamic. This often leads to nepotism, where only those with parents or other family connections can get the mentors and networks they need to succeed.

In an ideal world, every mentor would take the necessary time to help young people develop their networking skills and become a better mentee. Since we don’t live in a perfect world, however, I asked Bridget King, IBM’s talent acquisition manager for early professional hiring and a mentor to many promising young adults, to walk us through the first interaction, from preparation to follow-up.

Find similarities and points of interest

Whether it’s a formal business meeting or an informal coffee chat, it’s always important to arrive prepared.

“I really appreciate when someone has taken the time to do their research and identify common connectors or interest points,” Ms. King says. Her advice to mentees: “Check out their [mentor’s] LinkedIn profile, do a quick Google search on their company, and look for common connection points that could be conversation starters.”

Further, as you conduct your research, jot down any questions or topics you want to discuss, and refer to that list during the conversation. Look for volunteer, education and work experiences and prepare questions to understand why they did these experiences, how they helped and if there are similar experiences you could enroll in.

Be curious and explore

Mentees are always encouraged to prepare for meetings with mentors, but there is such a thing as overpreparing. When students arrive with a long list of questions, they tend to fall into a rigid script, turning what should be an informal and curious conversation into more of an interview.

Having some idea of the mentor’s past work experiences and educational background is encouraged, but it’s also important not to dig into more personal details.

“It’s a little uncomfortable when someone comes with too much information about you, so there definitely is a line,” says Ms. King. “Just stick to where they work, what they do, their education, volunteer experiences, those sorts of things.”

Talk about your future, ask about their past

If you’re struggling to come up with questions and conversation starters, there’s a few topics you can always fall back on. Mentors are encouraged to share information about their past, such as how they made important career decisions and how they got to where they are now. Mentees, on the other hand, are encouraged to discuss their future ambitions, what work experiences would be most interesting, and even share job postings at potential companies that might be a fit.

“I always ask, ‘You’re here now, but where do you see yourself? Where do you want to go in your career?’” says Ms. King. For mentors, be open to sharing specific activities that the mentee can do in order to start orienting themselves toward their future ambitions. The best role a mentor can play is to relate back to the young person, share how you were once in their shoes and share experiences and stepping stones that happened for you that can inspire their thinking.

Set goals and next steps

As your first conversation is ending, mentee’s should know that it’s very much okay and appreciated to be clear and explicit with the next steps, what your goals are and ask the mentor for help. The mentee should request a follow-up meeting, while the mentor should be open about their boundaries of the relationship moving forward and how the mentee can best approach.

“If they don’t hear from the mentee for a couple of months, they might forget who they are,” warns Ms. King. “If the first conversation went well and seems like a good fit, ask, ‘Would it be okay to meet again in a month or two?’ and actually go ahead and schedule that now.” It’s best to open your calendars during the actual meeting, find dates that work for both of you and send a calendar invite.

Following your initial conversation – a thank-you note 24 to 48 hours after the initial conversation referencing some of what was said to help refresh their memory in the future.

Just as scheduling the next meeting is often the responsibility of the mentee, Ms. King believes it’s important for mentors to encourage mentees to reach out when they need help.

“A lot of students don’t message the mentor first because they’re afraid of bothering them,” she says. “It’s important for the mentor to put it out there, ‘Hey, I’m here, if you need anything give me a call, don’t assume I’m too busy.’”

Dave Wilkin is a serial entrepreneur and founder of – an award winning virtual mentoring and career development technology.

This article supports Ten Thousand Coffees as part of national career month. In partnership with Canada’s major colleges and universities, Ten Thousand Coffees’ leading technology smart matches industry professionals to provide career mentoring and networking to students and recent grads. Ten Thousand Coffees is making virtual career conversations easy, find your school and sign-up for free today at

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