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Job Hunting and Career Planning — Q&A with the Career Coach

“Q&A with the Career Coach” is a series of articles featuring questions from readers and answers from 42-year Human Resources veteran and career coach Cliff Montgomery. Future questions can be submitted to him at his address below:

Q: I have a new boss, and in the early going it appears he only hires, rewards or promotes employees who tell him what he wants to hear and punishes those who don’t. How do you suggest I handle this?

A: Recently, one of my clients asked me a tough question … “What was one of my biggest career regrets?” For me the answer was simple; while being honest and open with people has been one of my strengths as a coach, during my corporate career, I wish I could have been just a little more political than I was.

As an HR executive for my entire career, I always believed that if you cared about your boss, it was your obligation to talk openly with them and tell them the truth, even if it wasn’t always positive. This wasn’t always the best idea.

Unfortunately, some bosses just don’t want to hear bad news and hire and reward only loyalists. I’ve also seen this type of boss conspire with some of their employees to punish or separate other employees who didn’t fit the profile.

This is a very challenging situation in that while most bosses will initially “tell” you they want to hear the truth, some really don’t, so you need to be careful how you phrase things in the early going.

I’d suggest you give it some time before you are truly open and honest with your boss and watch how he initially reacts to direct feedback. While it may feel right to be open and candid, I can tell you it might not be in your best long-term career interest.

Q: I am in the final interviews with a new company and believe I’m about to get an offer. In your experience, is there one thing I should look for before accepting to assure I’m making the right decision?

A: I have always felt that one of the key areas a candidate should evaluate before joining a new company is cultural fit. This can be done in several ways but the first is during your final interviews when they ask you if you have any questions, ask them to describe employees who are successful there and those who are not. With this information, you can compare your style to their responses to see how you compare.

Another idea would be to ask them about the company’s leadership style and how goals are set.

You might also try to look up any ex-employees of the firm you may know in your network and contact them to find out what it was like for them to work there and knowing you, how they feel you would fit in.
Lastly, it’s important to follow your gut. If you had issues relating to the people that interviewed you, that might be a clue that the environment’s not right for you.

Send your questions to Clifford E. Montgomery, CPC, executive and career coach in New Hope. He can be reached at 908-209-1642 or His website is