Want to Give Your Work Mentee Life Advice? Ask Madeleine

Dear Madeleine,

I am an experienced executive. A few years ago, my company created a mentoring program. I have really enjoyed mentoring young new hires and have done several six-month stints.

My first mentee and I have stayed in close touch and have become friendly. The kid is a rock star at work and has benefited from some introductions I’ve made and tips I’ve given him, which has been gratifying.

My problem is that I think he has been making some terrible decisions in his personal life.

He is in a long-term relationship with a young woman who appears selfish and volatile to the point of being unstable. The relationship seems to make him miserable. A few months ago he told me he was going to end things with her—but the next thing I knew, she was moving in to his condo.

At around the same time, he got a big promotion with a hefty raise. He had been telling me that he was saving up to take a sabbatical and travel the world; yet, right after he got his raise, he blew his savings on a very fancy new car. He had never mentioned any interest in cars or other status symbols. I suspect it was the girlfriend who convinced him to buy it.

I am having a hard time keeping myself from talking to him about how he says one thing and then does another and how I believe he is making big decisions he will regret.

My advice has always been centered around work, so it doesn’t feel right to chime in about his personal life. But I feel like I am watching a train wreck about to happen and don’t know how to stop it. Should I…

Say Something?


Dear Say Something?

Your instincts are right on the money. My short answer is to keep your mouth shut.

Friendly is a far cry from friends. With the age difference and the power imbalance, you do not have an equal, reciprocal relationship. Would you ask your mentee for advice about your big life decisions? It doesn’t sound like it. And it also doesn’t sound like he is asking for your advice on the choices he is making.

If you just can’t help yourself, you could ask for permission to share an observation. If given leave, point out that you have experienced him claiming to want one thing and then taking actions that are almost opposite from what he said he wanted. See where that leads. It may lead to your spilling all of your opinions, which would be a mistake that could very well ruin the relationship—so you would need to be prepared for that.

But I don’t see any upside for you in doing this. Ultimately, it just isn’t any of your business. It is true almost 100% of the time that no good deed goes unpunished. Young people have to find their own way and make their own mistakes. Your mentee may be creating train wrecks for himself, but they are his train wrecks and he will undoubtedly learn important things from them.

Maybe the two of you will become true friends over time and he will wise up enough to ask for your opinion on his personal choices. Until then, keep your counsel confined to professional work stuff and zip it on all other topics. And when the time comes when you want to say “I knew it”—don’t. Just nod your head and empathize.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

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