Professional Development

3 questions you should always ask your new boss

Written by Eric Titner

Regardless of the industry you’re in, whenever you start a new job your mission is clear—make a great initial impression and reinforce the notion that you’re indeed the right person for the job. You want to demonstrate that you’re a great fit into the existing climate and culture, a seamless addition to the team, and an obvious asset to the company’s short- and long-term success.

Today’s job market is ultra-competitive and volatile—to say the least—and the level of available talent vying for the very same positions that you are has never been higher, which means that organizations from lean startups to giant international conglomerates have plenty of options when hiring and recruiting—and for making staffing changes if things aren’t working out as well as planned. Beyond this, we all know the power of first impressions, and the one you make when starting a new job can stick and become hard-wired in the brains of your colleagues—which means that your opportunities for growth and longevity at your new company can be expanded or restricted from day one.

Hopefully, by now, we’ve convinced you that these initial goals when starting a new job are absolutely mission-critical. If you agree, then chief among your new job to-dos should be to create a positive working relationship with your new boss. When your boss likes you, you’ll enjoy work and collaboration more, open up new doors to opportunities and challenges, and set yourself up for greater levels of professional success. Your level of workplace satisfaction will increase as your stress levels and anxiety lower. Conversely, having a contentious, adversarial, or downright awful relationship with your boss can be disastrous to your health, happiness, and well-being, and may make your new job more of a “quick visit” than an “extended stay” along your career journey.

Sometimes, getting your boss to like you is easier said than done. The truth is, not all bosses are created equal—some are a breeze to get along with while others can be more difficult nuts to crack, to say the least. Depending on the type you find yourself with, which largely comes down to luck and careful sleuthing during the interview and hiring process, your approach should be tailored accordingly. That said, there are a few tried and true strategies for getting your boss to like you—including asking them the following 3 questions.

What can I do to help you?

This one seems kind of obvious, right? Well, you’d be surprised by how few new hires take the initiative to ask this simple, straightforward, and incredibly powerful question—and you may be surprised by how far it can go toward getting your boss to really like working with you. Too often, new hires are so eager to not make a misstep that they just quietly wait for their bosses to feed them tasks, which at best sets you up as a willing subordinate. But those who want to take things to the next level go above and beyond and assert themselves as a proactive and self-driven colleague who’s constantly thinking about how they can support their bosses and make their lives easier. What boss isn’t going to like someone like that?

What are your goals for our team?

Asking your boss this question is a subtle yet effective way to show them that you’re determined to be a committed and supportive team player and that their priorities and vision are important to you. It also gets you both in sync and on the same page and provides a roadmap for on-the-job success if you plan effectively to help your boss achieve these goals.

How do you like to work with your team members?

This question lets your boss know that you are interested in their preferred management style, which will really help reinforce the notion that you’re aware that their needs and chosen work habits are important priorities. The main takeaway will be that you are determined to support them as a manager and a team member. It’ll also help you set a solid foundation for a good work relationship—once you know how they like to communicate, collaborate, and delegate, then all you’ll need to do is meet them on their own terms and keep up the good work.

If you’re serious about your new job and making a great lasting impression, getting on your boss’s good side should be a key goal. Consider asking your boss the 3 questions mentioned here during your first week and you’ll be setting yourself up to build a great working relationship.

About the author

Eric Titner

Eric is a NYC-based editor and writer, with years of experience in career-focused content development across a wide range of industries.