Dodging a bullet: 27 questions to ask your potential new employer before you accept the job

Have you ever started a new job and regretted it within months? Wished you’d asked more questions before you’d excitedly said “yes” to the job offer?

Ever not been able to choose between two job offers because you didn’t know enough about either job?

Ever said, “If I’d known that, I’d never have taken that job”? Asking at least some of these 27 questions can help you avoid new-job remorse.

You need to know whether you’ll enjoy the job

During the interview, if the interviewer asks, “Do you have any questions?” ask: “What would my immediate priorities be?”

You’ll need to know you’ll be successful.

Neither you nor your new employer will be happy if you can’t meet your employer’s expectations. Ask:


— What will you want me to accomplish in my first thirty (sixty) days?

— What will tell you one month from now that you’ve hired the right candidate?

— What are challenges you expect the person in this position to face?

— How will you evaluate my performance?

— What is the biggest challenge facing this department right how?

As a secondary benefit, asking these questions shows the job interviewer you care about meeting employer expectations.

You can even ask, “Do you have any hesitancy in hiring me?” If your interviewer answers, you can address the interviewer’s unspoken concerns or at better prepare for future interviews.

What will it be like working for this manager?

Your manager has a large impact on your career. Can you trust and respect this manager? What’s his/her management style? Before you land a job with a hands-off manager unavailable when you need guidance, or a manager who expects daily briefings or other behaviors you consider micromanagement, ask:

— How often will you and I be communicating and what type of communication do you prefer — email, text, in person, or phone?

— Once I’m oriented and have won your trust, what decision-making responsibility will I have?

— What is your vision for the department?

What will your employer expect from you?

Will this job ask more of you than you’re prepared to give? Ask:

— How reachable will you want me to be on weekends or evenings?

— What’s a normal workday and workweek?

— How much business travel will I do?


What can you expect from this employer?

— What advancement opportunities exist for someone in this role?

— What professional development opportunities does this employer provide?

— Does the job include a work from home option?

— What is the corporate structure and where do I fall within it?

— How does the company determine salary ranges for remote workers and is it different for in-office or hybrid workers?

— How important is this position to the overall success of our company?

— What benefits does the benefits package include?


— Can I meet some members of my team before I start?

— What are the most important projects the team is working on?

Dodging a bullet

Better you uncover problems before you start a new job. Once you’ve received an offer, you can ask HR or the hiring manager:

— Is this a new position or how did this position come to be open?

— How did this company fare during the pandemic? What safety precautions have you put in place? What are some initiatives you’ve put in place post-pandemic to handle hybrid and remote work?

— What are the main reasons employees stay at or leave this company?

Questions to ask yourself

Most importantly, ask yourself:

— What about this job excites me?

— Can I picture myself doing this job and being happy doing it for at least two years?

When and how to ask questions


When you ask these questions, keep your tone positive and interested. Notice the effect of your questions and be careful not to grill or to touch a nerve. Word your questions to show you care about the job and meeting the employer’s expectations, and not just the compensation and benefit package. Finally, if you don’t like the answers, breathe a sigh of relief. You’ve dodged a bullet.

Lynne Curry writes a weekly column on workplace issues. She is president of Communication Works Inc. Send your questions to her at

Lynne Curry | Alaska Workplace

Lynne Curry writes a weekly column on workplace issues. She is author of “Navigating Conflict,” “Managing for Accountability,” “Beating the Workplace Bully" and “Solutions,” and Submit questions at or follow her on, or @lynnecurry10 on X/Twitter.