5 Questions You Should Ask A New Boss Right Away

Your direct manager can make or break your job, so it's critical to get on the same page ASAP.
Establishing trust with a new boss is key to your future success.
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Establishing trust with a new boss is key to your future success.

The relationship you build with your direct manager is the most important one you can establish at work. That’s because their support — or lack thereof — can determine whether you languish in your role or grow in it to be the best you can be.

So when you start a new job, or your old boss quits or is moved to a different team, it’s critical to get up to speed on how your new boss manages so you can get a sense of where you fit in their plans.

Employees with new managers are typically wondering three things, according to Lara Hogan, a manager coach and author of “Resilient Management”:

  • “How does this manager view me? Do they appreciate my contributions, or am I at risk of them ignoring me or undervaluing my work?”

  • “Can I lean on my new manager for help? Will they invest in our relationship? Can I be honest with them about how I’m doing, and can I ask them for the things I need to do my job well?”

  • “With this new reporting relationship change, is my job at risk? I had a career plan with my previous manager — has all that work and relationship-building gone to waste?”

“We obviously can’t ask our new manager those questions outright,” Hogan added. “We haven’t developed a foundation of trust yet, and even if we felt that we could trust them, those kinds of questions can feel really awkward for the other person to answer. So, instead, we can try to get the same signal in a different way.“

Asking questions about how your boss leads and what they consider a priority is how you get those signals. Here are career experts’ suggestions for the most important questions you should ask your new boss and why.

A young job candidate is in an office shaking hands with the HR team during introductions.
Dimensions via Getty Images
A young job candidate is in an office shaking hands with the HR team during introductions.

1. “What work, project or priority is top-of-mind for you right now?”

This question is a way to get more information on the issues that weigh on your boss’ mind.

“Maybe they’re worried about a deadline or goal. Maybe their focus is unrelated to your team’s work. Maybe they’re still in sponge mode and gathering data,” Hogan said. “No matter what their answer is, by asking this question, you’ll gain a better sense of whether you’re working on solving problems that your new manager cares about. Plus, you’ll be better equipped to connect any future requests for your manager back to the things that they care about.”

2. “What goals would you like this position or team to achieve this year?”

Gregory Tall, a workshop facilitator who coaches managers and has over 15 years of experience in human resources, said this question is important to ask so that you understand exactly what your manager wants you to accomplish.

“Job descriptions are not specific, so you need to hear directly from your manager about the top priorities for your position,” he said. “In fact, it’s a good idea to make this a regular touchpoint of conversation as priorities can shift as things happen in the organization and the external environment. “

And if you can, try to score an early win with your boss, Tall suggested.

“It doesn’t have to be something big, but do something right off the bat to demonstrate that you are a proactive and reliable team member,” Tall said. “It could be as simple as taking the initiative to give your boss a status update on what’s happening in your role before they ask for it.”

“It’s easier to establish a new relationship than repair a damaged one.”

- career strategist Ana Goehner

3. “How would you like to communicate day-to-day and week-to-week?”

Gorick Ng, a career adviser at Harvard University and the author of “The Unspoken Rules: Secrets to Starting Your Career Off Right,” said this is a good question because “under-communication leads to ambiguity. Ambiguity leads to anxiety. Anxiety leads to micromanagement. Aligning communication style and communication frequency can help you avoid getting micromanaged!”

By clarifying how your boss likes to hear updates, you can learn, for example, if your boss prefers a recap email at the end of every week or something else, Ng said.

4. “What’s the best way to approach you with a question?”

“If you are a new hire or have a new manager, focus on communication and strive for mutual understanding,” said career strategist Ana Goehner. “It’s easier to establish a new relationship than repair a damaged one.“

That’s why Goehner recommends asking your new boss about how they prefer you come to them with questions, along with other communication-establishing questions like: “Can you describe your management style?” and “How do you like to provide feedback to a new employee?”

These questions are a chance for you to share your communication preferences. “You can discuss your needs, but be open to feedback,” she said. “Let your manager know you don’t check messages after work hours. If you like to have weekly one-on-one meetings, ask if they would be open to that.“

Sometimes, what a boss does can tell you more than what they say. Outside of what they tell you about how they communicate, you can also observe your new boss’ behavior to get a better idea of how they operate.

“Check any previous messages from your manager and watch for their communication style,” Goehner advised. “Do they write short sentences, or do they provide details? Does your manager reply to emails at certain times of the day? Do they seem more relaxed and approachable on Fridays?”

5. “Is there anything I can do to help you get up to speed on the team or the work?”

When your manager is new to an existing team, Hogan said asking this question signals that you are here to help your manager and want to learn about the kinds of work you might be doing with them going forward.

How they respond can also help you see what kind of boss they will be.

“They might have a specific request; they might express a vague question and expect you to come up with an idea about how to help; they might say, ‘Not now, thanks,‘” Hogan said. “No matter what they say, you can learn a lot from their answer and what it’s going to be like to work with them. If they say ‘Not now, thanks,’ don’t necessarily take this as a sign that they don’t trust you yet — they might truly be unsure of how you can help!”

Similarly, if the situation is reversed and you are a new person on your boss’ established team, Ng suggests asking, “Is there anyone that you’d suggest I speak to so that I can get up to speed?”

He said, “it gives you an opportunity to learn from someone who’s been in your shoes before, but it also allows you to build your network.”

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