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Questions to ask your boss

Few jobs — even the “dream” ones — are perfect. Once we find a job, it’s easy to settle into a “good enough” mindset. Yet the COVID-19 pandemic gave employees an opportunity to rethink their career goals, and many quit in what is known as the Great Resignation. With so many jobs available, you don’t have to put up with a horrible boss or a discriminatory work environment. It might be time to ask your boss some uncomfortable questions. The answers may make you fall more in love with your job or leave you searching for a new position. 


Questions For Your Current Employer

Even if you like your job, you may still need to ask some uncomfortable questions. Here are five to get you started. 


1. Can We Evaluate My Compensation?

Women ask for raises just as often as men but are less likely to get them. Why? One of the main reasons is the type of job women hold. Service and care industries are full of women, and many of those positions are public sector jobs that often follow distinct pay raise schedules. Here’s how you can negotiate a raise, even when it’s not on the schedule:

  • Stop apologizing: Your contributions are valid, your needs are real, and your presence at the company is worth it. 
  • Research salaries: If you think your salary is low, research what others with the same training and experience are earning. Go to the meeting with your boss armed with numbers.
  • Outline your contributions: Chances are good that your boss already knows how valuable you are. Lay it all out for them. 
  • Negotiate more time off: If you can’t earn more, negotiate working less. 

If you haven’t received a raise in a year or more, it’s time to schedule that meeting. If your boss refuses, it may be time to walk away and find a higher-paying job. Your financial success could be the best revenge. 


2. Can We Discuss Opportunities for Growth in the Company?

Men apply for a job when they meet only 60% of the qualifications, but women apply only if they meet 100% of them, according to a Hewlett Packard report. Even if you’re not completely qualified, ask your boss about filling an open position in the company. It shows your desire to contribute and grow your skills.


3. Can We Make That Meeting an Email?

Hybrid employees — those who work a portion of their time from home — report longer work days. Ask if your boss would be willing to hit the high notes in a quick email, with an in-person follow-up if needed. That will free up time for you to get more work done.


4. Are Sick Days Available for Family Illness?

Although long-term leave for employees and their families is protected under the Family and Medical Leave Act, the law is much less clear when it comes to your toddler’s sniffles. Children are walking Petri dishes, and if an illness spreads to you or your other kids, you may need to take time off to care for them.


5. Will You Pay for Training?

Most workers are eager to increase their skills. After all, upgraded skills and pay increases go hand in hand. Training may cost serious dollars, but many W-2 employees can’t write those expenses off on their taxes. Sit down with your boss to talk about training opportunities and who’s going to pay for them.


Questions for a Job Interview

Whether you’re part of the Great Resignation or are just looking to see what’s available, you’ll want to ask these five questions in an interview.


1. Is Working From Home a Possibility?

In 2020, nearly 71% of workers headed home because of the coronavirus pandemic. About 54% of those workers found that they preferred being in their jammies all day. If this sounds like you, you’ll want to make sure that remote or hybrid work is an option — now or in the future. Fully remote work allows employees to work from anywhere, so you may want to find a real estate agent and reserve a moving POD to relocate to a lower cost-of-living area. 


2. How Much Vacation Time Is Given and Used?

Even if a company has a copious vacation and personal leave allowance, it may not be normal to take what’s given. This question allows you to peek into the company culture. If your boss expects you to be available 24/7 with no breaks or vacation, you might want to continue the job search.


3. Are You Committed to Diversity, Equity, and Inclusion?

Businesses can no longer afford to turn a blind eye to discrimination, bias, and prejudice in the workplace. Also, ask about specific programs, written materials, efforts to create a diverse workplace, and cultural norms that reflect that commitment. Starting this conversation is good information for your potential boss too. It signals that you are an aware and engaged employee.


4. What’s Your Policy on Politics?

These days, it seems like every year is an election year. Ask how the company handles political conversations, posters, and other topics surrounding elections. The question isn’t about surrounding yourself with people just like you. It’s about a workplace that creates a space that doesn’t feel like a war zone. 


5. Why Do You Think This Company Is a Good Fit for Me?

Your credentials likely caught the eye of someone in HR. So, ask your boss what specifically stood out and how they see your skills as a match for the company’s needs. The answer will outline your potential trajectory in the company.


What If It Doesn’t Go Well?

These conversations are worth having, but they aren’t easy. So, for a less awkward meeting:

  • Identify your strengths, then plan how to present them.
  • Find a good time with few distractions, no big deadlines, or after a big success.
  • Keep an open mind. The goal isn’t just to get your questions answered. It’s to understand more about the company.
  • Recognize if you’re looking for trouble.  If you expect the worst, you’re already sunk.
  • Just do it. Chances are good you’ll survive the conversation.

On the whole, these 10 questions to ask your boss aren’t without risks, but arming yourself with the knowledge you need to make smart career choices is the key to success.