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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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Skills spotlight: Customer service and 12 related jobs

In a world where every customer interaction is caught on camera, video, microphone or social media, it takes a special group of people to work in customer service. Rarely do they hear from satisfied customers who enjoy the products and services that company offers; instead, customer service workers tend to interact with those who have a problem.

But that gives workers in customer service a very special set of skills that can be used in a variety of other occupations. Every organization wants its users, clients and customers to have a good experience and continue to buy from them. And those workers who are able to change a disgruntled customer’s mind or help solve a problem hold a unique set of skills that can be used in a variety of other occupations.

Read on to learn about the skills workers in customer service hold and the related jobs you can consider applying those skills in.

Important qualities in customer service
The Bureau of Labor Statistics notes what skills workers need to perform their jobs exceptionally. For workers in customer service and the following related positions, here are the skills you’ll need:

  • Communication skills
  • Interpersonal skills
  • Listening skills
  • Patience
  • Problem-solving skills
  • Ability to multitask
  • Decision-making skills
  • Empathy
  • Organizational skills
  • Compassion
  • Time-management skills
  • Analytical skills
  • Instructional skills
  • Speaking skills
  • Critical-thinking skills
  • Emotional stability
  • Writing skills
  • Detail-oriented
  • Self-confidence
  • Stamina

To apply those skills, consider any of these 12 jobs that demand exceptional customer service:

1. Bill and account collectors* try to recover payment on overdue bills. They negotiate repayment plans with debtors and help them find solutions to make paying their overdue bills easier. Listening to the debtor and paying attention to his or her concerns can help the collector negotiate a solution.

2. Police, fire, and ambulance dispatchers, also called 9-1-1 operators or public safety telecommunicators, answer emergency and nonemergency calls. Dispatchers must stay calm while collecting vital information from callers to determine the severity of a situation and the location of those who need help. They then give the appropriate first-responder agencies information about the call. Dispatchers keep detailed records about the calls that they take. They use computers to log important facts, such as the nature of the incident and the name and location of the caller.

3. Receptionists perform administrative tasks, such as answering phones, receiving visitors and providing general information about their organization to the public and customers. Receptionists are often the first employee of an organization to have contact with a customer or client. They are responsible for making a good first impression for the organization, which can affect the organization’s success.

4. Social and human service assistants help people get through difficult times or get additional support. They help other workers, such as social workers, and they help clients find benefits or community services. They may follow up with clients to ensure that they are receiving the services and that the services are meeting their needs.

5. Training and development specialists create, administer and deliver training programs for businesses and organizations. To do this, they must first assess the needs of an organization. Once those needs are determined, specialists develop custom training programs that take place in a classroom, computer laboratory, or training facility.

6. Substance abuse and behavioral disorder counselors advise people who suffer from alcoholism, drug addiction, eating disorders or other behavioral problems. They provide treatment and support to help the client recover from addiction or modify problem behaviors. Furthermore, they help clients rebuild professional relationships and, if necessary, reestablish their career. They also help clients improve their personal relationships and find ways to discuss their addiction or other problem with family and friends.

7. Probation officers and correctional treatment specialists work with offenders who are given probation instead of jail time, who are still in prison, or who have been released from prison. They work with and monitor offenders to prevent them from committing new crimes, and create rehabilitation plans for them to follow when they are no longer in prison.

8. Computer network support specialists, also called technical support specialists, usually work in their organization’s IT department. They help IT staff analyze, troubleshoot and evaluate computer network problems. They play an important role in the daily upkeep of their organization’s networks by finding solutions to problems as they occur. Solving an IT problem in a timely manner is important because organizations depend on their computer systems.

9. Waiters and waitresses take orders and serve food and beverages to customers in dining establishments. They are responsible for ensuring that customers have a satisfying dining experience. The specific duties of servers vary considerably with the establishment in which they work.

10. Public relations specialists create and maintain a favorable public image for the organization they represent. They design media releases to shape public perception of their organization and to increase awareness of its work and goals. They also respond to information requests from the media and help clients communicate effectively with the public.

11. Wholesale and manufacturing sales representatives sell goods for wholesalers or manufacturers to businesses, government agencies and other organizations. They contact customers, explain product features, answer any questions that their customers may have and negotiate prices.

12. Retail sales workers include both those who sell retail merchandise, such as clothing, furniture and cars, (called retail salespersons) and those who sell spare and replacement parts and equipment, especially car parts (called parts salespersons). Both types of workers help customers find the products they want and process customers’ payments.

*All job titles and descriptions are from the Bureau of Labor Statistics’ Occupational Outlook Handbook.