Dear Dave,

I have a young employee who’s struggling financially. I don’t really see him outside work, but I’d like to introduce him to your plan because it helped me. As his boss, would it be inappropriate to approach him about this and try to help?

Les

Dave Says:

Dear Les,

My advice is to look at it this way. If you were in his shoes, would you want someone to care enough to try and help you? I think we both know the answer to that, but you have to be sure you approach this young man the right way.

If you come in as Mr. Know-It-All, you’re probably going to turn him off immediately. Just be genuine, and don’t get too deep into his business. Maybe you could share a book with him, and let him know about some of the problems you had before. It could just be a friendly gesture, and make sure he understands it’s not something you’re requiring of him as his boss. Then, if a wall goes up, you just back off. Just because he doesn’t jump at the idea immediately doesn’t mean a seed won’t take root.

Leaders in business who care about their team are real leaders. So, congratulations, Les. In my book, you’re a real leader!

—Dave