9 Questions to Ask Your New Boss

By Mark Swartz

So you’ve got a new boss. Naturally you want to make a great first impression. There’s an impulse to rush out and demonstrate your worthiness.

Resist that urge. If you really want to show your value, first find out what’s on their mind.

Here are 9 relevant questions you could ask them early on. Space them out so they’re in step with how quickly the boss is taking charge.

When You Are Introduced to The New Boss

Normally a fresh manager takes a couple of weeks to get the lay of the land. If they’re new to the employer or division, they’ll need to learn about the projects, priorities, systems and people.

During this opening period you can offer to be of assistance. Appropriate questions you could ask include:

1. When would you like to have our first meeting?

After initial introductions, it might take the new boss time to schedule a detailed meeting with each direct report.

You can take initiative here. Let them know you’re available for a get-together at their convenience. Mention that meanwhile you’ll be working busily on existing assignments (name the top few).

2. Is there some way I can assist you immediately?

Proposing to lend a hand gives you a chance to get on their radar. It’s also an opening to prove your dependability. Make sure you can deliver on whatever you promise, or risk looking unreliable.

At The First In-Depth Discussion

The new boss must find out what each of their direct reports is working on. Also what your plans, strengths and aspirations are. You’ll need to prepare for what is essentially a two-way interview. These are some of the questions to pose in that session:

3. What would you like to know about me?

Be prepared to briefly highlight your employment history, and tenure with this employer. Focus on the scope of your role and the work you’re doing. Try to be concise and positive.

4. How would you describe your management style?

Every boss has their own way of dealing with staff. Understanding their approach will aid you in modelling your behaviours to meet their needs more effectively.

5. What specific expectations do you have of me?

As the boss settles in, they’ll start determining objectives for the team. At that point they may want your input on how to direct your efforts. Or they may simply tell you what they want done.

If the leader hasn’t given this much thought, your question will prompt discussion. You should to suss out details of what you should be working on. Inquire about which projects to prioritize. Also get deadlines and specific deliverables.

6. How do you prefer to hear about bad news?

At some juncture something will go wrong at work. When this happens communicating is essential. Some bosses want to know about foul-ups right away to give input. Others would rather wait till solutions have been developed.

7. What annoys you most in someone who reports to you?

This question is related to “How would you describe your management style?” You are seeking to ensure that you avoid irritating the boss unnecessarily.

Two More Important Questions to Ask

New bosses want to see that you’re competent and reliable. Two additional questions can help you here.

8. When do you want to meet next?

Be proactive in getting together again. Confirm that you aren’t going to hide yourself away.

9. Want to grab lunch?

Ask this a few times and see how it’s received. Some bosses want to prevent the appearance of favouritism or of getting too close to those they supervise. Others will welcome the opportunity to bond.

Adults may come to believe that asking questions is a sign of weakness. Yet by making a few basic inquiries you can put your new boss at ease and get on their good side from day one.