How to talk to your boss (when the questions get tricky)

Tricky boss questions

Here are ways you can respond to tough questions professionally so you don't damage the relationship with your boss.

Landing a job doesn't mean your days of navigating difficult questions are over. You should be prepared to handle uncomfortable queries, an especially tricky feat when it’s coming from your boss.

You may face one or more of these awkward questions at some point in your career. Here are ways you can respond to them professionally and keep the relationship with your boss intact.

1. "Are you looking for a new job?"

  • If you're putting yourself back on the job market, tell the truth. Chances are that your boss has a good reason for asking, so a denial will only make you look bad. But don't overshare. This question isn't an invitation to air all your complaints about the position or the company. When responding, keep the focus on you and your career.

Keep the answer short and to the point:

  • "I'm interested in exploring positions in a different industry."
  • "I'm thinking about relocating to another city."
  • "A former colleague contacted me about an exciting opportunity, and I feel I should look into it."
  • "I'm looking for a position with more flexibility."
  • "I don't feel I'm making much progress here."

Be polite and emphasize that you're committed to performing your current job to the best of your ability.

2. "Have you heard the latest about Jamie?"
Co-workers who spread rumors are difficult enough to deal with, but having a boss who engages in office gossip is a potential landmine. You don’t want to sound disapproving or like a Goody Two-shoes. Your best option is to offer a noncommittal response such as, "I really haven't heard," and then either change the topic or try to leave the conversation. Maintain an attitude of polite disinterest. Once your boss realizes you're not a gossiper, he or she will drop the subject.

3. "How would you rate my performance as a manager?"
This question is particularly tricky because you might not know your boss's motivation. Has upper management requested that he or she seek feedback from employees; is the person just fishing for compliments; or is he or she genuinely interested in constructive criticism?

To remain on safe ground, lead with positive feedback. Then choose one aspect of the person’s managerial style that could use some work, and make it actionable. For example, "The next time there's a new project, I'd like a little more guidance so I don't go in the wrong direction."

4. "How would you rate your performance during Q1?"
Balance is key. Outline what you did well, and reference tangible results such as exceeding goals or meeting tight deadlines. Then discuss a few ways you might do better next time. To show you're serious about self-improvement, ask your boss for an assessment — and any tips for Q2.

5. "Can you take on this project (that no one else will do)?"
You may feel pressure to say yes to every request in order to maintain a good relationship with your boss. While it's occasionally necessary to "take one for the team," you need to be honest about how Project X will affect your present workload and whether it's within the scope of your job description.

If you're genuinely reluctant to lead this project, tell your manager that you simply don't have the bandwidth to do it justice and get all of your regular assignments done on time. But also think about what may happen if you agree: If leading Project X will win you points with the boss and prove your leadership skills, it might be worth the extra work to say yes — this time.

Robert Half is the world's first and largest specialized staffing firm with a global network of more than 400 staffing and consulting locations worldwide. For more information about our professional services, visit roberthalf.com. For additional career advice, read our blog at blog.roberthalf.com or follow us on social media at roberthalf.com/follow-us.