Dodge a Bullet: 29 ?s to Ask Your New Employer and Yourself Before You Say “Yes” to a Job Offer

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 twenty-nine 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.

If you enjoyed this post, you might find other helpful posts on intriguing topics in the career and professional development sections of this blog or in my book Solutions: 411: Workplace Answers 911: Revelations for Workplace Challenges and Firefights

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4 thoughts on “Dodge a Bullet: 29 ?s to Ask Your New Employer and Yourself Before You Say “Yes” to a Job Offer

  1. Hi, LeeLani, thanks so much! I appreciate you & Susan, Cheryl, Joe, Dee, Wendy, Dan and the others who take the time to cheer me on; merry Christmas!

  2. These are outstanding questions to ask. I still remember my interview for an internship position and asking about what would be my immediate priorities and the interviewer–who would be my immediate supervisor if I got the position, said, “Everything.” I didn’t get the position, but given that answer, I don’t regret not having been selected. I lost quite a bit of respect for the person, who I knew through a professional association, after that.

    1. Susan, great comment (on this and other posts). Your answer says accurately that interviews are two-way. Lynne
      p.s. Am struggling with the post I’m writing for tomorrow or Friday, about what to do when senior management lies.

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