How to Ask Your Mentor to Get You a Job (Without Making it Awkward)

In a mentor-mentee relationship, mentors provide valuable resources to their mentees. These resources, which may vary from offering advice to handle a difficult situation to introducing a mentee to a member of their network, enable and empower mentees to move forward in their careers. But many mentees have likely had a moment (or two) where they mulled over whether it’s a good idea to ask their mentor to help them find a job. When is it ok to show your colors to your mentor, and how can they help you? Here's a story of how one mentee landed a new job because of her mentor: 

Brooke Fallek is a PR assistant at luxury travel company Black Tomato. Her now-boss, Brendan Drewniany, was previously her mentor.

How did this relationship evolve from mentor to boss? Fallek met Drewniany at her first job out of college. They both worked at the same company in New York City, but were on different teams in 2016 and 2017. When the company launched a new Mentor-Mentee program, Drewniany was assigned to be Fallek’s mentor. 

Fallek learned tangible skills during the program, but it was the relationship she established with her mentor that carried the most weight. Drewniany, already successful in an industry Fallek had just started her career in, provided Fallek with valuable opportunities to create relationships with his clients and meet with journalists. 

When Drewniany left the company to work as an in-house PR Director for his client Black Tomato, Fallek told him she wanted to work with him. However, there wasn’t a position that was a fit for her at that time.

Over the next two years, Fallek and Drewniany maintained their mentor-mentee relationship. They also continued to explore options where they could work together. 

Some time later, Drewniany created a PR assistant role and promoted it on his personal LinkedIn account. It was the perfect fit for Fallek, who immediately reached out for the opportunity.

“I texted him asking if I could come in for an interview,” Fallek says. She recalls Drewniany streamlined the interview process to get her in the door. Some of the clients even remembered Fallek from a summer party a few years ago!

Today, Fallek has been working with her mentor for nearly a year. They’ve graduated to having a working relationship, rather than a mentorship, together. 

“He’s still a role model and teacher for me, but we have moved to a working relationship away from the mentor and mentee,” Fallek says. “I really enjoy working with him in this new role. I’m able to learn from him an applicable, daily way in a setting where he can now directly help my career and skills grow.”

Mentors, however helpful they may be, are not genies. They cannot give you exactly what you want when you want it — as illustrated in the story above. Knowing this makes toeing the line to ask them for a new job difficult. When you do decide to do it, what’s the best approach?

Career coach and mentor Carlota Zimmerman, J.D. says the best time to ask a mentor for career assistance is the moment you know what you want for your next steps. The connection you have with your mentor should be solid, not based on a random LinkedIn message sent five years after meeting together. Zimmerman advises approaching your mentor as prepared as possible. Know what you need, what you can bring to the table and how you believe your mentor can help you.

You mentor might not be able to make you a job offer, but they might know someone who can help. Lynn Juve, job search strategist and founder of Bespoke Professional, says mentors may be able to introduce you to someone in their network that can lend advice. 

Once you have the new job, you may find yourself easing into a working relationship with your mentor. Or, you may maintain the mentor and mentee relationship. No matter what comes next, don’t forget about the connection you have with your role model. Stay in touch, grab coffee together and regularly check-in on each other’s lives to see where you’re going next.