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5 tricky questions your boss will ask (and how to answer them)

Landing a job doesn't mean your days of navigating difficult questions are over. You should be prepared to handle sticky queries if and when your boss lobs them your way.

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 so you don't damage the relationship with your boss.

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. And 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."

If your boss presses for details, be polite and reiterate the reason you just gave. Then, emphasize that you're committed to doing your 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 nightmare. The trick is declining to participate without sounding like a scold or Goody Two-shoes. Your best option is to give a noncommittal response such as, "I really haven't heard," and then either change the topic or leave the conversation. Maintain an attitude of polite disinterest. Once your boss realizes you're not a gossiper, he 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 she seek feedback from employees, or is she genuinely interested in constructive criticism? Maybe she's just fishing for compliments. If the latter, an honest critique could hurt the relationship with your boss.

To stay on safe ground, lead with positive feedback. If she presses for ways on how she could improve, there's no need to make a laundry list. Choose one aspect of her managerial style that could use some work, and make it actionable. For example, you could tell her, "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 Q3?"
Balance is the key when it comes to this sticky question. Start by outlining 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 his assessment — and any tips for Q4.

5. "Can you take on this project (that no one else will do)?"
You may feel that you have 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.

Sticky questions can catch you off guard. And depending on how you answer them, you could risk jeopardizing an otherwise healthy relationship with your boss. Tact, honesty and careful wording are strategies that will serve you well in smoothing over potentially awkward situations.

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.


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The non-tech skills needed to succeed in IT

Workers with information technology skills are some of today’s most in-demand workers. In fact, employers are having a hard time finding people with the right IT skills to fill open positions. While technical skills are naturally important to employers seeking qualified IT candidates, that’s not all it takes to get a job or be successful in an IT role.

Here, IT experts share the nontechnical skills they believe are needed to succeed in IT:

Analytical skills

“I think it’s critical that IT professionals must be analytical in nature — the ability to look at trends and problems with an eye on cultivating a solution that can speak to an overarching trend rather than a particular, nuanced issue is critical.” – Richie Lauridsen, director of operations, SEOhaus


“The most important non-technical skill for IT professionals in my experience is empathy. With empathy comes understanding of the clients’ and/or end-users’ problems. This breeds an ‘ownership’ of the problem, which, in turn, breeds clarity in delivering communication of the problem and its resolution.” – Yehuda Cagen, director of client services, Xvand Technology Corporation

Communication skills

“After 30 years in this industry, which began as a programmer, the skill that helped elevate my career most is that of communication. Learning to be succinct and communicate clearly to your intended audience is absolutely essential for continued success in this business. Communication skills should be developed early and attention paid to detail that is expressed in emails, presentations, phone conversations, meetings and so on. I often coach our younger staff members on communication and why understanding the context of communication is critical.” – Kevin Carlson, vice president and chief security officer, Optaros Inc.

Presentation skills

“Presentation skills make the difference between your ideas being implemented in the real world and them never seeing the light of day. When an IT professional complains that no one in the business understands them, they often have their own faulty presentation skills to blame. To have effective presentation skills, an IT professional must understand how to communicate clearly to a non-technical audience, to be comfortable with the tools and techniques of speaking to a group and have the ability to create a business ‘value proposition’ for their audience. The key to learning to present is practice, practice, practice — to your IT peers, to friendly colleagues and even to the mirror.” – Jon Eberly, CEO, Clock Four

Ability to listen

“The ability to listen to the needs of those you support can directly determine the types of products and projects you are assigned to. And while everyone in IT may want the latest and greatest, it does not mean it is necessarily the right fit. Listening to staff needs will also affect your judgment(s) concerning specific products or methods required to fulfill those needs. Lastly, listening will help to foster relationships within the department. Working and listening so closely with one another establishes a sense of trust, reaffirms their faith in your abilities and aids in ensuring all IT personnel meet or exceed expectations.” — Sean Harris, network administrator, City of Palm Bay, Fla.

Business sense

“Today’s IT professional needs to be sure they possess the ‘soft skills’ that can help them really merchandise their work — and worth — to the organization. They need great people skills, the ability to anticipate questions, and most importantly, a good business sense. I’d recommend IT professionals get really smart about return on investment and showing how their work impacts the bottom line. They should also make sure they’re absolutely clear about the organization’s business goals as a whole and find ways to show how their work contributes to those goals. In today’s market, it is not enough to have great IT skills and knowledge, it is equally important to position yourself as a strategic business person.” – Peter Nordberg, CEO, InSite


“I believe that entrepreneurship is the most important non-technical skill IT professionals should possess. Entrepreneurship is more of a mindset than a skill, a perspective that can transform problems into opportunities and opportunities into innovation. In the world of IT, innovation large and small can be viewed as ‘career currency’ that increases the value of the IT professional to their organization.” – Ara H. Bagdasarian, CEO, Omnilert