20 Essential Questions to Ask Your New Boss to Set You Up for Success

by Jason Evanish, CEO Get Lighthouse, Inc.

Congratulations! You landed a new job. 

It’s always exciting on your first day. All that hope and excitement. There are endless possibilities and every reason to believe this will be a great long term fit for you, even if you have questions for your new boss.

But then reality can set in.

Maybe there’s a conflict with others on your team, or even struggles with your boss.

No matter the reason, a great new job can sour much faster than you expected. 

An Ounce of Prevention is Worth a Pound of Cure.

The best way to avoid this scenario is to come in prepared from day 1.  By having a solid plan and the right questions to ask your new boss coming into your new role, you can set yourself up for success, while avoiding major pitfalls.

Yet, on Day 1 you know so little. You may have learned a few things in your interviews, but those are usually mostly you talking to them, not them answering your questions.

That’s why it’s important to come into your new job prepared to ask your new boss all the things you don’t know yet that can help you navigate your new role and find success from the start.

Today’s post helps set you up with a strong foundation to build on with your new manager. We give you the key questions to ask your new boss during your first weeks together.  We also explain why each type of question is important, and give you a few different ways to ask, so you can find the perfect question that fits your personality and situation. 

Table of contents: Your Key Questions to Ask Your New Boss

What questions to ask your new boss

Questions for Your New Boss About Their Management Style and Expectations

Understanding your manager’s preferences and work style early on will make it a lot easier to work with them. You’ll avoid misunderstandings in the future, and get a better idea of what your manager is like. 

Specifically, asking your new boss about communication norms, feedback styles, pet peeves and general preferences are the kinds of things that can often be told to you, so you don’t have to learn them with experience. 

Now, you still may learn some new or different things over time, but you’ll start on the right foot, and at least avoid the biggest possible mistakes and problems. 

Here are some great questions to ask your new boss about their management style and expectations:

  • How would you describe your management style? What approaches do you find most effective?
  • What are your preferred forms of communication? When do you prefer an email, a phone call, a chat message, or walking up to your desk/office?
  • How do you prefer I approach you for feedback?
  • If I have feedback or a suggestion, when or how would you like to hear about it?
  • Do you see yourself as more hands-on or hands-off? How often and in what format would you like project updates from me?

With answers to these and similar questions, you will know how to communicate and better work with your boss. You’ll know their management style, and how you can get what you need from them.

And even if it turns out some of the things they do are different than what they said in answers to these, that in and of itself is helpful to know. 

Yet, management and communication styles are only one part of your work relationship. 

Further Reading:

To learn more about management styles and getting feedback, read more here:

Questions to ask your boss about their priorities and goals

Questions to Ask Your New Boss About Their Priorities and Goals

Gaining insight into what your new manager cares about most is crucial. It shows you where to focus your time and energy to have the biggest impact (you do want to be a successful hire who is recognized, and maybe even promoted, right?)

Understanding their top priorities and objectives allows you to tailor your work accordingly. This ensures you're contributing to the initiatives that matter most to them.

Discussing their goals also provides valuable perspective into how they think and what they value. Are they focused on just one or two things? Or do they have a wide range of interests and priorities? This information can help you frame your communication and collaborate more effectively.

Additionally, if you directly help your new boss accomplish their most important goals, they will remember it. When promotion opportunities or raises come up down the line, you want to be top of mind as someone who contributed to their success.

Here are some key questions to ask your new manager to uncover their priorities:

  • What are your top priorities or goals right now? How do you see my work relating to those goals?
  • How are you and our team measured? What does success look like for us? 
  • What is the most important thing I can accomplish in my first 90 days to help us with our team’s / your goals? 
  • Of the work for me we’ve discussed so far, which are most important to our goals? How do they tie to them? 

With the answers to these questions, you will know what direction to take and what tasks to focus on.

Further reading:

If you want to help your team with their goals, or are thinking about your own growth, then these posts can help you: 

Team meeting in the office

Questions for Your New Boss About Team Dynamics and Collaboration

Getting advice from your new manager about team dynamics is priceless. As the leader who oversees your team, they have a unique and valuable perspective on the unwritten norms and personalities on your team.

Tapping into their knowledge can help you navigate your new relationships, avoid any cultural faux pas, and integrate as seamlessly as possible into your new environment. Knowing what not to do, as well as what to do, can help you build great relationships with your coworkers much faster than you would have otherwise.

For example, your new team may have very different habits around working hours or responding to after-hours messages. One employee may be known as easygoing while another has a more direct communication style. Acting accordingly will make you feel like a long standing member of the team quickly.

Here are some savvy questions to ask your new boss to help you thrive with the new team:

  • How would you describe the culture of your team? What makes it different than other teams?
  • What is the team culture around work schedules, and after hours?
    • What hours does everyone keep? Does it vary, or is everyone consistent?
    • What is the culture around sending messages after hours? (some teams will be very work-life balance, and others will be any-time always on)
    • If there’s an after hours emergency, what is the contact protocol?
  • What advice do you have about working with others on the team?
    • Who is easy to work with?
    • Who is hard to work with? What advice do you have for working with them?
    • What pitfalls should I avoid working with others on the team?
  • What rituals or habits do you and the team have for fun, or to celebrate?
  • What other routines and habits do you and the team have to work better together?

Asking your new manager these questions gives you a roadmap for integrating smoothly into your new team. You’ll be ready to confidently work with your peers and start directly getting to know them, too. 

For more on learning about building great relationships check out these posts:

Final Word - Asking your new boss the right questions makes all the difference

Asking smart questions of your new manager early on helps you get started on the right foot. It will help you understand their work style, priorities, and team dynamics. 

Best of all, focusing your efforts accordingly will make a great first impression and set you up to contribute the best way you can.

Asking good questions not only gives you insights into your manager's expectations, but shows you're committed to their success. Taking a thoughtful approach helps build a strong foundation for your relationship as well as the trust needed to thrive in your new role.

Only the beginning…

While today’s post is focused on questions for your new boss, that's just one important piece. So don’t stop there. 

Fostering strong peer relationships is also key when you’re starting with a new team. 

To accomplish this, schedule one-on-ones with your coworkers to learn about their roles and preferred collaboration styles, too. Discover how you can support each other in your work, and build rapport with them.

Developing a 90-day plan is another important activity. Outline your objectives for the first 3 months and break these down into weekly goals and milestones to hit. Track your progress to stay on target for a successful ramp-up.

If you need additional guidance for starting your new role on the right foot, start with these posts: 

And if you want to help a new manager on your team grow, or invest in yourself, then consider one of our training programs:

Tight on time, but dreaming of becoming a great manager? Our courses, crafted with leaders like you in mind, are tailored for leaders with busy schedules. 

Spend just 15 minutes a day and watch your management skills soar. 

Curious to learn more? Click here and step into your potential today.

Jason Evanish

Jason Evanish

As the founder and CEO of Get Lighthouse, Inc, Jason and the Lighthouse team have helped managers grow their leadership skills in dozens of countries around the world. They’ve worked with a variety of companies from non-profits to high growth startups, and government organizations to well known, publicly traded companies. Jason has also been featured in publications including NPR, the Wall Street Journal, and Fast Company.

Read more

Browse topics

Follow us:

Note: We do not accept guest posts, so please do not email us.

Get Your Free 1 on 1 ebook

Get Your Free 1 on 1 ebook

Want to Level up Your Leadership Skills?

Learn how great leaders use their 1 on 1s to bring out their teams best with for our FREE 📗 e-book: “10 Steps To Having Amazing 1 on 1s With Your Team”

Plus: Join 23,000+ managers learning weekly:

Share via
Copy link