Securing a mentorship is an invaluable resource, but it can also take time to find someone willing to invest in your career. But finding a mentor is only half the battle. The mentor-mentee relationship is a two-way street; the only way it works is if both parties continue to find value and fulfillment. One of the quickest ways to sour the relationship as a mentee is to overstep boundaries or appear ill-prepared.

There are several ways the relationship can unravel over time. To avoid experiencing a “pre-mature breakup”, stand clear of these pitfalls:

1. Don’t expect a roadmap.

It’s not a mentor’s job to hold your hand and walk you through every step needed to advance your career. Every person is unique with their own set of strengths and resources. You shouldn’t believe you will reap the same accomplishments by specifically following in your mentor’s shoes.

Questions to ask: To gain insights into your mentor’s journey, try asking, “If you were to start over, how would you get to where you are today?” This will give you an idea of what they would do differently in today’s environment.

2. Stay away from requesting a new job opportunity.

You should never treat your mentor like they are your own personal job board. Your mentor often has  wonderful career-focused wisdom to share and they want to these lessons. Some of those lessons may naturally lead to a job opportunity, but if you’re only looking for a mentor to land you a job, you’re wasting the connection – and may lose your mentor. If they feel you are only trying to use them for their connections, they will most likely walk away from this agreement.

How to approach the situation: If you’re looking for a new gig, ask your mentor what it takes to land a role in a specific department or industry. If you both are employed at the same organization and you’re looking for a promotion, ask them to give you examples of what it takes to rise in the company based on what they’ve seen and done. Mentors can also walk you through what skillsets can help you get to that new opportunity and can coach you through developing an improvement plan.

3. Avoid inquiring about handouts.

Your mentor is giving you their time and their battle-tested advice already, so don’t push it. If you’re looking for new connections, referrals, or anything else, make sure these are offered voluntarily rather than asked for, or you risk putting an unnecessary strain on a critical relationship.

How to approach the situation: When you first enter a mentor-mentee relationship, focus your effort by investing in the present. This includes actively listening during meetings and putting advice into action. If they feel you should turn to someone else who can provide better advice on a specific topic, they’ll connect you to them.

4. Don’t show up unprepared.

There is a famous saying that the most precious resource is time. For your mentor, this is most likely one resource that is probably in high demand. When you come into a meeting without an agenda or a generalized direction of where you want the conversation to go, you’re essentially wasting your mentor’s time. During the conversation, it’s also wise bring pen and paper to reference their advice over the months and years to come.

How to be prepared: Before the meeting, make a list of items you would like to accomplish, including following up on previous discussions and a list of specific questions to ask.

5. Avoid general or vague questions.

Most likely your mentor will not know enough about your current situation or have enough prior knowledge to give you helpful advice. Asking questions like “What advice do you have for me?” without context will not be helpful and can be a time-waster.

How to ask for advice: Before meeting with your mentor, figure out the specific goals you are looking to accomplish. Develop targeted questions intended to achieve your set goals.

6. Don’t let your ego get in the way.

When speaking to your mentor, remember that this isn’t the time to paint the best image of yourself. To make the relationship work, be honest and open about the problems, anxieties or fears you are currently facing in your career. Being candid with your mentor will allow them to relate to your problems and identify specific items to help you grow.

How to approach the situation: Open up to your mentor by sharing the struggles you are currently facing in your career. Ask your mentor their thoughts on the matter and what advice they have to help you navigate the situation.  

The key to maintaining a mentorship

When nurturing the relationship with your mentor, it’s important to be intentional with your approach by taking a step back to examine how your actions can be received by the other person and if those results are the ones you want. By doing so, you’ll have greater success learning the skills and approaches needed to land your dream job while also avoid alienating the person who’s rooting for your achievement.


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Brandon Osgood is a strategic communications and digital marketing professional based out of Raleigh, NC. Beyond being a passionate storyteller, Brandon is an avid classical musician with dreams of one day playing at Carnegie Hall. Interested in connecting? Email him at