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How can I help my clueless boss improve her business?

Dear J.T. & Dale: I work at a retail shop that just opened a few months ago. The owner is the wife of a very rich guy. This shop is clearly just a hobby for her, but I absolutely love it and want to see it be successful. Meanwhile, she is pretty clueless about the retail business and is making some key mistakes. I would like to put together a proposal to step up and run it, but I don’t want to insult her. Any suggestions? – Heather

J.T.: I would put the plan together and then ask if you could meet with her to discuss an idea. I would let her know how grateful you are that she started the business. Then, tell her you are so into it that you put together some ideas based on your past experience in retail. I wouldn’t highlight any mistakes she’s made; instead, present alternative ideas that show her other ways of doing it without implying her ways are wrong. Then, I would simply tell her you’d like the chance to take on a more substantial role to grow the business. Be sure to include how she can leverage her strengths. For example, if she is really good at spotting trends and buying merchandise, you can tell her you want her to be able to focus on that while you’ll handle the rest. That way, she’ll see you as more of a much-needed partner that will free her up to do the parts she enjoys most. This will keep her interested in the business, which you need because if she gets bored or frustrated, she might just decide to shut it down.

DALE: Terrific advice – that I wouldn’t implement all at once. Rather, I’d suggest stretching it over weeks, maybe months. Pick one idea that would have the biggest impact and make your suggestion. Offer to do whatever extra work is involved. Let it succeed. Then do it again with another idea. At no point would I suggest that you are “stepping up” to “run it.” I suspect that the whole point of the endeavor is to give her something to call hers, something to run. Do not let yourself seem to be taking that away from her. This is simply the politics of an organization: You keep doing more of the work and the boss keeps getting all the credit. Said another way, you take over everything but the credit. That’s how you become indispensable.

Dear J.T. & Dale: My co-worker got invited to speak at a conference. She can’t stop talking about it. The company is paying for her to go. All she does is mention all the things she’s going to do in her free time. I’m pretty annoyed. Is it OK to tell her that she needs to stop bragging? – Jason

J.T.: Personally, I would let it slide. But if you feel you must get her to stop, then be tactful. Ask her to coffee and then say: “This is really tough to bring up. I know you are excited about the trip, but you may not realize that you are talking about it a lot. I’m so happy for your success, but it’s also hard to hear all that you’ll be doing while the rest of us will be left behind. Do you think maybe you could hold off on talking about it until you return? Then you and I can grab lunch and you can tell me all about it.” You’re still offering a way for her to share her excitement while showing what a kind and caring co-worker you are. If she is emotionally intelligent, she’ll realize she needs to get humble.

DALE: That runs the risk of hurting the relationship. So, before resorting to a Big Conversation, I’d try the light approach: Next time she brings it up, say, with a grin: “Stop! You’re making me too jealous. Let’s talk about ____ instead.” You make a joke of it and change the subject. Let her be happy and let yourself be happy for her.

Jeanine “J.T.” Tanner O’Donnell is a career coach and the founder of the leading career site Dale Dauten is founder of The Innovators’ Lab and author of a novel about H.R., “The Weary Optimist.” Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 628 Virginia Dr., Orlando, FL 32803.