When you’ve been working as an executive as long as I have, you are often approached to be a mentor. Behind closed doors, my friends and I swap stories about mentees that have gotten those requests all wrong. There are a few fatal conditions that are death to a successful mentor-mentee relationship. Let me pull back the curtain to share a few harsh truths with you. (I promise they’ll make you stronger).

Here’s why you’re having trouble:

1. You ask me questions you could Google – Let’s say an advertising VP agrees to meet with you. Her time is not free. At $300 an hour, her commute and lunch with you are the equivalent of $450. Do you really think you should ask her what degree you need to get into advertising? What a copy editor does? How many employees her company has? No. If you don’t come to the meeting prepared with thoughtful well-researched questions, you waste everybody’s time and time is money. If you invest some time reviewing articles, blogs and YouTube videos, you will be able to come up with great questions that yield invaluable information. Research your mentor using company bios and LinkedIn. Do your homework and your time together will be well spent.

2. You want a hook up – Sometimes, it’s clear that you want access, not information. You want to meet someone I know or you want a leg up on an opportunity I have the inside track on. I know you’re trying to use me. I see you a mile away and I don’t like it. Be upfront about what you want in the relationship. Honesty is the best policy. Be clear about your intentions and bring value to the relationship.

3. You don’t tend the garden – Every relationship needs maintenance behaviors to grow and deepen. Send a birthday card, a thank you note, some flowers or at least a kind email. These gestures go a long way in forging a real relationship. What you water grows.

4. You know every damn thing – I am not a genius and I don’t have the answer to every question, but I’ve lived a little more life than you. Sometimes, you have taken those blog posts about confidence a little too far and act like you are an expert at everything. I don’t want to spend our time together discussing an article you read or a podcast you heard about being a CEO. I actually am a CEO. Listen more than you talk.

5. You think I’m your Mama – You have baby bird syndrome. A baby bird sits in the nest expecting the Mama bird to come feed them. This behavior is wholly inappropriate in a mentor-mentee relationship. I am not your Mama. Do your research. Investigate the profession you are interested in. Ask me actionable questions, not general ‘what should I do with my life’ questions. I have no idea what you should do with your life. I met you 2 weeks ago.

6. You have an innie and I have an outie – Sometimes, more often than we would like to admit, we are just too different. Maybe one is a staunch Republican and the other a raving liberal. One is a fast-talking, F-bomb dropping Yankee and the other a genteel Southern lady. One hates technology and the other lives their entire life ‘doing it for the Gram’. It doesn’t mean one is wrong and the other right, but it does make a mentor relationship challenging. Don’t take it personally. You can’t force every relationship. Know when to take the ‘L’ and move on. If you decide to stick it out, understand that it’s up to you to manage these differences. You’re the one seeking advice. Swallow your pride and get the goods.

7. You go all ‘Single White Female’ on me – Be careful not to get too dependent. The idea that one person with one perspective can “direct” your career is outdated. You need the perspectives of several people. I’m not an expert in every subject. If you build your tribe of support around your career development, it will prevent from becoming over-reliant on me to be your muse. Even Jesus rolled with 10 people. I can’t meet with you once a week or talk to you every couple days. Don’t show up to my office uninvited. Don’t hover around me if we happen to be at the same event. Make sure your requests for my time are reasonable and you focus our time together on my areas of expertise so we can be successful. Admiration is nice. Stalking is just weird.

8. What got me here won’t get you there – This one isn’t really your fault. Sometimes an industry has changed so much, that the path I took 25 years ago isn’t as directly applicable to your career as we both would like. Maybe I got into my industry because it was the family business or because my parents pulled some strings. I got here, but I can’t necessarily help you blueprint a path. This is hard for me to admit, so you will have to ask good questions and listen carefully for steps you can execute to make sure I’m the right advisor for you.

9. You forget I’m breathing my own rare air – I’m busy. Maybe I no longer have a secretary. Downsizing has me doing the work of 2 people. Technology creates a round the clock expectation of responsiveness. I’m never off. I don’t have time to see my own friends and family. You forget I am a real person with my own challenges; both professional and personal. It’s lonely at the top and you approach our relationship selfishly never once asking me how I’m doing or what you can do to support me. Time is my most precious resource. I want to help you, but it costs me time and focus on other priorities. Never forget that. Be appreciative.

A successful mentor-mentee relationship is possible, but you have to work at it. Mentors are like mates; you may have to kiss a couple frogs, but don’t give up. In the event that you don’t have a mentor, don’t despair. If you can’t learn from someone in person, don’t underestimate your ability to learn from afar. There is more information available than ever before online both written and video-based on WatchHerWork.com. Take ownership of your career and get the info you need.

Make it easy for me to help and maybe, just maybe, I will.




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