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Questioning the curious incident of the $100K raise

Dear J.T. & Dale: I’ve worked for the owner of a company for 11 years. I am the executive vice president. I am ready to leave. He has been dangling stock ownership in the company to me for the last five years. He always talks about “When we sell,” but I don’t see him retiring, even though he is 65 and already had one heart attack. I think he sensed I had reached my limit because this week he told me he found an investor to buy out part of the company. He also gave me a $100,000 raise. Yes, $100,000. But I don’t think I want to stay. I don’t trust him. Something doesn’t feel right. Any thoughts? – George

DALE: Five years of “dangling” stock options? You’re very patient. Early in my career I worked at a consulting firm whose owner told me that he planned to retire in five years and wanted me to replace him. A year later he told me the same thing – he planned to retire in five years. So, that clock wasn’t moving. I soon left and lost track of him. Ten years later, he still hadn’t retired. Was he lying to me? I believe he believed it. My point is that you can’t count on the entrepreneur to depart; that requires him to part with someone he loves: himself, CEO.

J.T.: I agree something is up. From an HR standpoint, I think the raise is to keep you in place while the investor checks out the company. Your leaving, as second-in-command, could be a warning sign that could make the investor pass. My question is, What will happen when the investor does invest? If you get a chance to meet the investor, I would be honest about what’s been promised to you. That way, during negotiating, the investor can bring it up if your boss appears to be cutting you out. Also, I see two upsides here. First, you might really like the new owner and he or she may want to keep you on. Second, I’d take the raise and bank it all in the event the company is sold and you choose not to stick around. At your executive level, a job search takes an average of 9-18 months. The higher you climb, the fewer jobs that fit your criteria. So having money to live on while you find the right opportunity is key.

Dear J.T. & Dale: My co-worker has been spending a ton of money lately – new clothes, car, jewelry, a trip to Hawaii. She’s single, so it’s not money from a significant other. And, she hasn’t inherited cash (that I know of). I have to assume she got a raise or has a side hustle. Is it wrong to ask her where the additional funds are coming from? She’s never brought it up. But frankly, I’m dying to know as I’d like to make more money too! – Chelsea

J.T.: I think it depends on how close you are. Have you shared personal information before? If so, then you might be able to say: “You know I really admire that new outfit. I’ve noticed you’ve been investing more in yourself lately. I’d love to do the same. I just don’t have the cash. What’s your secret?” That way, you are focused more on the activity and less on where the money is coming from. She may reveal where she gets the extra dough, or not, but at least you won’t sound too nosy! And, if she doesn’t reveal anything, don’t ask again. Instead, I’d focus on ways you can make more money with a side hustle. She’s inspiring you to think bigger, but it’s up to you to make it happen!

DALE: That’s good advice. Not only does that suggested approach focus on the activity more than the money; it comes across as upbeat and admiring rather than suspicious or judgmental. I suspect she’ll be eager to share her story, but if not, you’ll have phrased it in a way that will be easy for her to deflect. Thus, no downside.

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.