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Boss’ feelings will survive employee’s departure

DEAR J.T. & Dale: I know I’m worth more than what I currently make, but the one thing holding me back is fear of hurting my boss’s feelings. He’s a great guy; unfortunately, there’s not much upward mobility here. – Becca

J.T.: If there is no room to grow, then you need to start a job search. If your boss can’t create more opportunity for you, then he will have to accept that you will move on. Business owners understand this. He may be sad or disappointed, but he will be OK. This is your life and your career. I would start looking for a new opportunity.

Dale: It says good things about you, Becca, that you’re worried about the guy. And it also says good things about him. But here’s how to look at it: If your boss is the commendable person you know him to be, then he will want what’s best for you, and upon your finding another job, his disappointment will be swamped by his satisfaction at seeing you thrive. If that isn’t his reaction, then he isn’t the man you thought he was. So, either way, you can conclude that you need to go ahead and look for another job.

J.T.: When you find the right opportunity, you can do your best to make the transition as easy as possible. Try to help him find your replacement. The more you show him how much you appreciate him, the easier it will be for him to accept. All that said, keep in mind that if he had to let you go because the business was failing, he would. That would be hard on him, but that’s life too. There are going to be tough situations like this throughout your career. It’s best to deal with them. Sticking around would only make you start to resent him and the job. That would really ruin the relationship!

Dale: One more thing. As you look for that better opportunity, never forget how important it is to work for someone you admire. Most people look for the salary and title, maybe the commute; however, it’s the excellence of management that determines how quickly you will evolve and whether you will look back in anger at our advice to leave your old job.

Dear J.T. & Dale: I applied for a new job recently. A couple days after, I could see that the hiring manager checked out my LinkedIn profile. But I haven’t heard anything. Can I reach out to him and ask what he thinks of me as a candidate for the job? – Johan

Dale: Even though anyone familiar with the workings of LinkedIn would know that it’s possible to see who’s looked at your profile, there’s still something that feels to me a bit stalker-ish. Am I just being old-school here, J.T.?

J.T.: No, you’re not alone in that feeling. That’s why I wouldn’t blatantly mention that you know he checked out your profile. Instead, I’d ask him to connect, sending a message with something like: “We’ve never met, but I came across your profile while researching ___ company. I just applied to the ___ position and would love the opportunity to connect and get your perspective on what I can do to earn the opportunity to interview.” If he accepts, you could start up a conversation. If he doesn’t, then I’d assume he has decided you aren’t a fit for the role. Even if you don’t hear back, I wouldn’t give up. I’d focus on trying to connect with other employees so you can build your network and hopefully meet the hiring manager in person someday. Getting a job means putting yourself in the path of the employer. That can take several tries, but with patience and persistence, you can do it.

Dale: Let’s repeat that gem in your last response: Getting a job means putting yourself in the path of the employer. That’s a radically different approach to a job search, one that puts you ahead of opportunities, not running behind trying to jump on the bus. Bang.

Jeanine “J.T.” Tanner O’Donnell is a professional development specialist and the founder of the consulting firm jtodonnell. Dale Dauten resolves employment and other business disputes as a mediator with Please visit them at, where you can send questions via email, or write to them in care of King Features Syndicate, 300 W. 57th St., 15th Floor, New York, NY 10019.