Work Relationships

Just hired? Here are 8 questions you should ask your new boss

Written by Kate Lopaze

The first days at a new job can be a total whirlwind. You’re meeting people, doing piles of onboarding paperwork, and making all sorts of notes for yourself. Soon, you’ll be a seasoned veteran in your new role, but for now, things can feel busy and even a little overwhelming, no matter how great your new team is. And if you’re working remotely in a new job, doing all of this over Zoom or Teams can make things seem even more complicated.

Chances are, your new boss will set up some check-in time, and ask if you have any questions. And the answer to that should always be a resounding, “Yes, thanks! I’d love to touch base on a few questions I have.” But with so much going on, it can be easy to lose track of the bigger questions you want answered, in the minutiae of your new day-to-day. Here are 8 questions to keep in your back pocket, so you don’t have to feel put on the spot.

1. What’s your preferred method of communication?

Every manager is different. Some are big on email, texts, and instant messaging to keep things moving. Others prefer calls or face time. Much of your new job will be managing your relationship with your boss, as much as managing your daily responsibilities, so it’s important to make sure that your relationship starts off in a way that works for both of you. Asking your boss their favorite communication format not only saves you time and energy later on but also tells your boss that you’re looking for good, efficient communication.

Sometimes, you might find that what they say is their preferred method isn’t actually the most productive way to approach them, but that’s the knowledge that you develop over time and experience together.

2. Who should I get to know outside of our team?

Teamwork is so essential, but it’s not just your immediate team members who will influence your work and your career. Just about every job involves reaching out to people beyond your immediate circle—and those are the people you should be getting to know soon after you start. Your boss knows which people in the company would be assets for your work and your success. One of the quickest ways to feel comfortable at a new job is to feel connected and supported, so getting a “cheat sheet” of people you should meet will help you start building that network.

And in a work world where more and more people are working remotely or not gathering in offices like they once did, you can’t necessarily count on old standbys like coffee machine small talk to help you meet colleagues.

3. How will my performance be evaluated and what benchmarks should I keep in mind?

Unless you’re in a very intense new work culture, you’ll likely have some breathing room before you’re part of the performance evaluation cycle. Still, you want to hit the ground running, and make sure you’re hitting the milestones that show you’re successfully settling in. It also helps you track your own progress, and make sure you’re meeting expectations.

4. What are your expectations for my first six months/year/etc. here?

You may have a rough idea of what your goals are for your first months at the new job, but it’s best to get your new boss on record and understand what they expect of you. For one thing, it helps you align their expectations with yours. And for another, it can help you modulate your own expectations. It might be that your personal goals are too aggressive or not realistic, so getting a brief rundown of expectations from your boss can help you fine-tine how you see your role—at least to start.

5. What would your ideal workflow be?

Going back to boss management, everyone has their own work style. If a boss is hands-off, it’s not going to be productive for either of you if you’re constantly checking in or expecting guidance. If your boss is on the micro-manage-y end of things, if you’re not checking in enough, it may be seen as a lack of collaboration or not being productive enough. The ideal is finding out how your boss works best and then finding ways to do things that work for both of you.

6. What are the company’s biggest priorities right now?

One of the biggest adjustments in any new job is adapting to the company’s culture, and figuring out where you fit in the larger scheme of the organization. Asking your boss about the company’s current values and priorities can help you understand how those priorities may affect your own work and goals.

7. What can I do to grow in this role?

Even when you’re the new kid, don’t stop thinking about your career growth and development. You don’t necessarily want to seem like you’re trying to move up too fast when you’ve barely started, but your boss gets that professional development is a long-term goal. Asking what the likely growth opportunities are for this role—and the steps you can take, like training—is a good way to make sure that you’re staying on track, and won’t get stagnant in your job.

8. What could I be doing better?

Everyone wants their new boss to think they’re a superstar, and asking what you could do better might seem like a bit of weakness. It’s not! In reality, asking this question shows you’re interested in fine-tuning things to make sure you’re always doing your best work. Asking for constructive feedback can also help your boss communicate better with you, instead of having to criticize things that aren’t 100%. It opens a dialogue about how to keep growing and improving.

Asking smart questions in your early days can help you and your boss get to know each other and establish good, open communication. The better you work together from day one, the more likely you are to feel supported and comfortable in your work. So even as things get busy with forms and new people and a new to-do list, the time and dialogue you put in now can really help you get started in the right way.

About the author

Kate Lopaze

Kate Lopaze is a writer, editor, and digital publishing professional based in New York City. A graduate of the University of Connecticut and Emerson College with degrees in English and publishing, she is passionate about books, baseball, and pop culture (though not necessarily in that order), and lives in Brooklyn with her dog.