Questions to Ask if You Want to Win Over Your New Boss

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 without a game plan or the same old routine you did before.

This 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’s’ good side.

While there are no bad questions, there are some that will boost your reputation better than others. For example, here are four that 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, even more opportunity for you to get involved, and it’s the number one strategy for managing up.

We are aware that not every boss is going to take this kind of question and immediately become your new best friend. But at the very least it’s a nice thing to ask and that will help you build rapport.

2. “What Can I Take Off Your Plate?”

Their answer might be nothing (you’re new to the job, so it’s possible they’ll let you know when they’re ready to hand stuff off to you.) Or maybe 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. Even when you aren’t asking this question directly, you need to be asking yourself this question. If this is top of mind when it comes to your boss, not only is this a leadership perspective, but you can be sure you’re headed in the right direction.

3. “Who 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’s insight on who you should interact with shows you respect their opinion but also are proactive about collaborating.

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

Looking for more ways to impress your boss? Our award-winning coaches at the Ignite Your Potential Centers offer a complimentary 25-minute phone session to help. We are the #1 career coaches in San Francisco and Los Angeles, let us show you how we earned that praise.

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