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Advice / Succeeding at Work / Changing Jobs

6 Questions to Ask if You Want Your New Boss to Like You (and Spoiler, You Do!)

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Starting a new job is all about making a good first impression. You have this amazing opportunity to start over—to build strong relationships and set your new career in the right direction—so don’t just enter your new office prepared to do the bare minimum or the same old routine you did before.

This also means asking a lot of questions as soon as you get started. You may worry about being annoying, but asking questions is actually a great way to quickly understand the inner workings of your new company and also get on your boss’ good side. (Plus, science says it actually makes you sound smart.)

While there are no bad questions, there are some that will boost your reputation better than others. For example, these six are worth asking in the first few days and weeks if you want to get ahead.


1. “How Are You Doing?”

First off, this shouldn’t be a one-time question. In fact, you should be asking this regularly of your new boss, if not daily. (And hopefully, they’re asking the same of you.)

Why? Your boss is probably very busy, very stressed, or in some instances feels ignored or underappreciated, so making them feel noticed is an instant plus for you. And, it gives them a chance to open up. This could lead to more transparency and even more opportunity for you to get involved.

Look, I’m aware that not every boss is going to take this kind of question and immediately become your confidante. But at the very least it’s a nice thing to ask, and that’ll help you build rapport.


2. “What Can I Take Off Your Plate?”

Their answer might be nothing. You’re just beginning to get ramped up, so it’s possible they’ll let you know when they’re ready to hand stuff off to you.

But maybe they just haven’t thought about it, or they’re currently working on something that could use an extra set of hands. By asking rather than waiting for them, you make it easier for them to delegate—and shine a spotlight on your work ethic.


3. “Who (Besides You) Should I Meet With in My First Week/Month?”

Networking in a new job is crucial. You should be meeting with not just your new teammates, but other teams and executives (if possible) to get a better sense of your company’s goals and initiatives and how they tie back to your role.

Getting your boss’ weigh-in on who you should interact with shows you respect their opinion, but also are proactive about collaborating with other teams.


4. “What Are Your Goals for Me in the Next Month/Year?”

Thinking long-term shows you’re driven and ready to hit the ground running from day one. It also helps you best set and align your priorities.

It’s possible your boss doesn’t know yet, or maybe their sole goal is to get you onboarded. In that case, turn it on them: “What are your goals for the next several months?” This way, if nothing else you can set your own goals and actions by figuring out how you can contribute to theirs.


5. “When Do You Do Your Heads-Down Work?”

This shows respect for their time and how they like to work. It’ll also help you work efficiently.

Use their answer to organize your schedule accordingly. Ensure you’re not communicating with them when they’re in this mode, and that you give them enough lead time with projects so you’re not waiting around for them to get back to you.


6. “How Do You Best Like to Communicate?”

Like the above question, this can help you avoid miscommunication or conflict and immediately put you and your boss on the same page. They may prefer email for certain things and in person for others. They may hate meetings. Take note.

Also, get their insight into other folks on your team (and other teams you might work with) and their communication styles so you’re effectively interacting on all sides (that said, you can also ask these people individually).

You can follow this up with more specific questions, depending on the conversation and your needs: How much notice do you prefer when requesting time off? Which emails do you want to be CC’d on? What projects would you like regular updates on, how often, and how? are some good places to start.



Looking for more ways to impress your boss? Here are eight questions you should be asking of any boss—new or old—and that’ll help you better manage up.