5 Career Questions You May Be Too Embarrassed to Ask

Finding a job is no day at the beach. It’s even tougher when you’re faced with difficult or embarrassing career quandaries.

We asked five job seekers to share their job-related questions. Then we asked seasoned career coaches, Michael Cushman and Ayn Fox, to weigh in with some expert advice.

1. Q: I left my last job on pretty bad terms. In fact, my boss was a jerk and I threw a major hissy fit. How can I approach this issue when interviewers ask me why I left, or if they can contact my previous employer?

MC: This is a growth moment. Fix the problem. Phone the person you had words with, and apologize for how you handled it. No matter what the circumstances, your behavior was inexcusable. That’s it. Ask for nothing in return. Be an adult. Learn from this and grow. It’s very unlikely your previous employer will hold a grudge after a sincere apology. He or she might even feel guilty, because relationships are systems. He or she probably had a part in the bad termination, too.

AF: It’s important to get references from people with credibility, who strongly believe in you.


2. My friend says I should pursue a degree in computer science to make myself more marketable, but I hate computers. I’m mostly interested in art. Should I take the practical route?

MC: Follow your natural talents. Do what comes easily and joyfully to you, then become great at it; no one will be able to out-compete you. Achieving greatness is its own reward, and greatness is always rewarded financially.

AF: Although I agree that you should follow the path of ease and joy, most of today’s jobs require some basic computer skills. (This is true even for artists.) I do NOT recommend going to school for computer science. I do suggest that you learn how to operate the new technologies that will allow you to communicate with others. I recommend that you find an instructor who understands how you think and learn. You may want to seek counsel from a fellow artist who is tech-savvy and willing to help you.


3. I don’t know how to respond when job posts ask me to include my “salary requirements.” Should I tell them how much I used to earn at my last job? Or should I use this opportunity to ask for what I deserve?

MC: It doesn’t matter what you think you deserve or how much you made in the past. You get paid based on the value your job creates, your ability to perform the job, and the rates of your competitors. Your best strategy is to research the current market salary range for the job, and request a figure that’s on the high side of that range. But, be willing to negotiate. Most likely you will end up with the salary you deserve.

The one exception is when you are not qualified for the job and everyone knows it. In that case, it’s wise to ask for the bottom of the range. If the company is willing to interview you despite your shortcomings, it’s because they are looking for a bargain. So go low in exchange for the opportunity.

AF: If you are starting on the low side — it is helpful if you ask the employer what you might need to accomplish or demonstrate in order to be eligible for a higher salary.


4. I haven’t had a paid job in ages. I’ve been a stay-at-home mom for the last 10 years (which is plenty of work, believe me!). Now that I’m headed back into the workforce, what are some strategies that can help me succeed?

MC: Plan to close the gap between where you are now and what you want. Often this means going back to school, volunteering, and finding a mentor. Build a support network. Surround yourself with like-minded people. If you have negative people trying to hold you back, it’s time to reevaluate these relationships. True friends want you to have a great life and help you get there.

AF: Stay-at-home moms have the opportunity to gain clarity about what they want by channeling the hopes they develop for their children. Pay attention to which activities you encourage your child to do, to which behaviors you think are important. You can also learn about yourself by trying different volunteer roles, part-time work, etc.

Don’t forget that it’s important to create an infrastructure in your home so that the homemaking and childcare demands don’t become overwhelming when you are working. Finally, familiarize yourself with the technologies that will be needed in today’s workplace: PDA’s, computers, and applicable software programs.


5. I’m out of work, and I’m thinking of contacting a headhunter. Is that a good idea?

MC: Headhunters are effective for employed individuals, whose skills are in high demand. If that’s not the case, you are better off taking steps to increase your skills. Once you’re in high demand, headhunters will vie to represent you, and employers will seek you out — instead of the reverse.

AF: Headhunters are primarily interested in people who have the specific credentials and experience that their clients are interested in. A good way to gain the attention of a headhunter is to give presentations at conferences, and write articles related to your field. Headhunters are not typically interested in career changers. Still, they may be a good resource to learn about the trends in your field. You could contact a headhunter to find out what employers are looking for. You do not want to depend on a headhunter or job sites to get you a job.

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