4 Trap Questions Your Boss Asks You all the Time

The interview process is already difficult enough without tricky interview questions. High-stress scenarios don’t always lead to the most prepared or ideal situation for the interviewee, however, it isn’t impossible. But what happens once you get past the interview phase? Do you need to keep your defense up once you have already landed the job?

More frequently, employers and managers are working to gauge the interest of their employees in the work that they do. This isn’t always the most ethical approach in business, but keeping tabs on employee interest can help management weed people out over time.

Here are 4 trap questions your boss may ask you, and various ways to tackle them.

This type of question can be extremely difficult. We all want to say “yes” to this question. We are trained to go above and beyond in our work often, so having the capability of wowing management by taking on extra work can be an adrenaline rush. However, there is a fine line between working on an extra project here and there because of your expertise and being thrown into every issue other people don’t want to deal with. This can become especially harmful if it isn’t a task within the realm of your contracted job position. However, will saying “no” hurt your career, or damage your relationship with your boss?

When I began my career a decade ago, I was a “yes” person. Essentially, anytime someone asked me if I could take on a project, create HTML, do some editing, or take on a task, I said “yes.” Often, I knew nothing about that task and allowed it to build my strength in the industry I was working, as well as my character and work ethic. As a career professional, it isn’t always the best idea to take on extra projects. Of course, if it is something in your wheelhouse or a task that belongs within your department, it is definitely worth considering. Often, those experiences can truly help you get a leg up with your company and/or management. But successful people aren’t always “yes” people.

It can be easy to become overwhelmed with work and additional projects, so you want to be honest in your answer by considering your current workload. Would taking on another project create a kink in the flow of your other work, take away any work boundaries, or leave you feeling exhausted? Have you been asked in the past to complete miscellaneous projects that didn’t benefit your portfolio, or weren’t considered by your boss when it came time for a raise? Is this a “one-and-done” or “once in a while” opportunity that could help pivot your career? Honestly explore your options.

If you need more time to decide than to just answer in a pinch, let your boss know that you need to evaluate your workflow and availability and that you can let them know in fifteen minutes or so if you’ll have the bandwidth to tackle it. That way, there is a level of comfort knowing you are still dedicated to the task, even if it isn’t entirely in your realm of responsibility. Your superior can rest assured knowing they have a dedicated team, regardless of how you respond to their query.

Remember to be kind to yourself. And, no matter what your answer is, be sure to respond with gratitude that you were considered to complete the project. (Even if it was simply a project no one else wanted to take on.)

Other options include:

In all of these instances, your boss is essentially asking for a review without asking for a review. This could be for many reasons. They may be fishing for compliments, trying to get feedback on their work, or trying to decide if they’d like to keep you in their department. One of these reasons has nothing to do with your job eligibility, but perhaps could be about an impending performance review your boss or supervisor may be dealing with in their own position.

Regardless of what this question is asked, it is always important to approach it carefully and with kindness. The strategy here is constructive criticism to remind them that you are paying attention, that you are a valuable cog in the wheel of your department and that you are growth-minded. Begin with any top-of-mind positive feedback you may have on the project or person. In a given circumstance where it applies, you can choose one trait, action item, or work effort that you believe could use some work.

Remember, however, to make the negative item small and actionable for them. Provide feedback on a different way to approach it if you have any suggestions, and remember to fight off any condescension or judgment in your voice.

This question is asked regularly by management in a variety of work settings and can be very unsettling. Being asked to comment on your colleague’s work in a professional setting without a formal review or set meeting can be daunting, especially if you harbor any irritation for the person in question. (Work relationships can be multi-faceted and a little tough, we know.)

Your answer to this question will depend entirely on the dynamic between you and your boss. Are you close to your colleagues, or do you socialize outside of work? If you’re more casual with your boss, you may have open discussions often about the work you and your coworkers do.

Often, this type of question is asked to gauge the compatibility of a team or group. In most professional settings, if you are asked this question you want to tread lightly. Like most others, it can also be used to weed people out, and your response – depending on the intent behind the question – could honestly be used against you. If you have positive feedback, go at it. If you have any negative feedback, make sure to have ideas handy for how to improve in the future. Consider approaching your coworkers with any ideas during a project, to better avoid scrutiny once all is said and done.

Remember, unless you’re willing to defend your stance and work directly with your colleagues on a solution, office gossip is not something you want to partake in. Not only will it distract you from your work, but it could create tension within the workspace that does not need to exist, and even damage working relationships.

Sometimes, your boss just knows. And sometimes, they happen to notice a social media post, more activity on LinkedIn, or other behavior that signals their employee is looking for another job. Our first bit of advice? Never let your job search inhibit your current work. If you’re distracted at work by applications, resume tweaks, or other items, you will draw attention to yourself. Be tactful in your approach, and respectful of your coworkers.

That said, this question is likely to fluster you. The ball feels like it’s in your manager’s court when they corner you with questions like this, but it isn’t. Here are some reasonable (short and sweet) responses to get you through the conversation with minimal incident.

If you are actively seeking other work, you have your reasons. Reassure your boss that you are not engaging in job-seeking activities during work hours, and be as honest as you’d like. If you’d rather not open up that conversation, craft a response to keep in your back pocket that will work with your particular relationship or dynamic. After all, you want to be a part of something and make a difference. And wanting more from yourself or your job is a fair response.

At the end of the day, your responses to questions your boss asks will vary depending on your relationship. But many of these persistent questions stick with you, and could drastically change your relationships or experiences within your work environment. Check out our best career advice here and then head over to find your next high-earning job at The Ladders job board.

— Meredith Schneider

--