The boss who made vague promises seems ready to sell, retire

Dear JT & Dale: I have been working for my boss for 10 years. It’s a small business and he always said that when he retires I would be rewarded, especially if he sold the business. However, he has been very ill recently and has been out a lot, and I have a feeling he might be selling and retiring. I’m afraid I won’t get what I was promised. Is it OK to bring it up? -Carmen

JT: I think there is nothing wrong with asking him how he is feeling and whether or not he is considering selling the business. However, I don’t think you should inquire about what you will receive right away. Considering everything that is going on, it is possible that he has nothing to give you. I would focus more on assessing the actual situation of the company. Then you can, at some point, discuss your exit strategy. I imagine if you talk to him about it that way, he’ll talk about rewarding you.

DALE: You want to be sensitive to the health situation, but I hope you can find an opening to negotiate something in writing. After all, it’s easy to offer to share the hypothetical proceeds of a future pink sale. This owner tied you up for 10 years and now it would be easy for him to stiffen you up and just say, “Sorry, that didn’t work.” It is true whether he is ill or not. Let this therefore serve as a warning to other employees with owners offering vague promises. Early in my career I was vice president of a consulting firm and the owner kept telling me he wanted to retire and sell the business to me. Concretely, he made me sit down one day and told me he wanted to retire in five years. Well, two years go by and he talks about it again, and he tells me he wants… you guessed it… retire in five years. Then, when he knew I was thinking of leaving, he suggested that I put the transition in writing. He drafted a deal that provided for when he would retire and how I owed him a fortune, which essentially meant that all the profits would come back to him for a decade or more after he left. I was grateful – grateful that I discovered the real story and that I was able to move on.

Dear JT & Dale: I have been going to my first in-person interview in over two years. I don’t know what to wear. I will bring a mask, but I don’t know how people dress these days. I can’t imagine a super dressy outfit is always required, but the company is in the fintech realm so it could go both ways. Suggestions? —Xavier

JT: The easiest way is to ask the person who organized your interview. Send an email asking what the dress code is. I agree that it’s highly unlikely that it’s super formal, but you don’t want to go there and miss the mark. No one will blame you for asking. In fact, it shows that you are focusing on a successful interview by asking the question. However, if you’re not comfortable doing it, you can always check out their social media and see what people are wearing in the photos taken in the office.

DALE: Two thoughts: One, unless you show up in a tuxedo, you can’t really dress too much. If you’re wearing a suit and he’s wearing jeans, you can take the tie off and say, “I’m so glad you are wearing a casual outfit.” They will love you for the respect you have shown them. Second, as part of your preparation, you will probably want to visit the offices before the day of the interview to make sure you know where they are, where you will park, etc. While you’re at it, walk around the area and get a feel for the styles, or you can play private investigator and watch employees come and go as they start or leave. Understand this and you will eliminate a small distraction.

Jeanine “JT” Tanner O’Donnell is a career coach and founder of the leading career site Dale Dauten is the founder of The Innovators’ Lab and the author of an HR novel, “The Weary Optimist”. Please visit them at, where you can email questions, or write to them at King Features Syndicate, 628 Virginia Dr., Orlando, FL 32803. (c) 2021 by King Features Syndicate, Inc.

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