Photo by Olya Kobruseva
Getting a new boss can be exciting! Really, it's like a fresh start.
Use this opportunity to build a new professional relationship and even “fix” any of the hiccups you might have encountered by asking your new boss questions.
I remember getting a new boss. I was so impressed with the way he entered the organization. We were a team of 14 seasoned recruiters, and when the “new guy” came in as our manager, I was nervous and assumed he was coming to shake things up. There is a natural impulse when you’re new to want to showcase your amazingness, but you shouldn’t rush into showing your value.
Remember, your new boss is a human, too. They have their own nervous energy around starting a new job, being likable, and earning respect.
Table of Contents
- Why It's Important to Ask Questions Up Front
- Questions to Ask Your Boss When You're New
- Questions to Ask When Your Boss Is New
Instead of shaking things up immediately, my new manager started with many questions. I learned from that experience that whenever you’re building a new relationship, a great place to start is with questions. This is especially true when you’re getting to know a new boss and want to make a great first impression.
Why It's Important to Ask Questions Up Front
One of the ways to showcase your value to your new boss is to have a strong understanding of what matters most to them, their preferences such as communication style, and any other expectations they have. You can’t do that by making assumptions. Here are some other benefits of being proactive and getting to know your new boss by asking questions:
- 1. Get to Know Each Other's Work Styles + Preferences
- 2. Gain Clarity on Your Boss's Experience + Perspective
- 3. Build Friendly Rapport
- 4. Align on Your Mutual Career Goals
- 5. Achieve Clarity on Your Role and Your Boss's Role
Questions to Ask Your Boss When You're New
Congrats on your new job! Your first day in a new job means learning how to navigate a new work environment, colleagues, and, most importantly, a new boss! Each company, team, and manager will come with unique preferences, and the sooner you learn about those, the sooner you can become an asset.
As a new employee, we recommend that you take the initiative to learn about your new workplace. Here are some important questions to get answered, so you can start the new job on the right foot.
1. What is your definition of success for someone in my role?
Why You're Asking: It’s pretty hard to set and achieve goals if you’re unsure what success looks like to your boss. Is your boss focused on landing new clients, or is success more focused on retaining your current clients year over year?
Getting clarity on how your boss defines success helps you set SMART goals, share the progress of your goals in your 1:1 meetings, get specific help to eliminate challenges, and, hopefully, get recognition and rewards when you are successful.
2. How can I best feed my professional growth here at [COMPANY]?
Why You're Asking: It’s natural to want to progress in your career. By asking this question, you can learn what professional growth looks like at this new company and what your boss values.
For example, does growth mean learning new software skills and sharing that with your team? Or does your new boss really value executive education courses so you’ll look into formal continuing education courses?
3. What sort of guidance do you offer as a team leader?
Why You're Asking: This question helps you manage your own expectations around feedback. Is your new boss more hands-off when it comes to approaching a project, or do they prefer to guide you in deep detail? One style might seem disconnected and the other more like a micro-manager, but when you know what to expect, it’s easier not to assume your boss is either.
Another example might be that your boss offers 1:1 meetings but only when the employee requests them. If you know that ongoing feedback helps you be more successful in your role, you might request this right away. It’s a good idea to know your personal needs around guidance and feedback before you ask this question as well.
4. What are the biggest challenges in my role?
Why You're Asking: Even if you like surprises, you probably don’t like “bad” surprises. And if you know what challenges, obstacles, and issues, are already standing in your way, you can be more proactive about navigating them.
It’s also nice to see if your boss has insight into the challenges that come with your job and whether they can articulate them. One of the main reasons for a toxic workplace is your boss is too disconnected from your role.
5. Do you hold performance reviews or regular feedback?
Why You're Asking: Does regular feedback really matter? Yes, big time. 92% percent of employees want feedback more than just once a year. Recognition of great work, regular feedback, and support for your professional development all have been proven to increase employee engagement, work quality, and decrease employee turnover.
By asking this question, you’re setting yourself up to be more fulfilled in your new role and with regular feedback, you’ll also decrease burnout that comes from ambiguity around work responsibilities.
6. What does an ideal workflow look like?
Why You're Asking: A team is only as successful as its processes and workflows. With this question, you’ll gain clarity into the team’s overall organization, including any challenges with the current workflows and the characteristics that make a workflow successful.
For example, is an ideal workflow documented through video tutorials, so each person “owns” their individual part of the process, or does the team rely on assignments from the manager?
7. What recurring tasks are the most important?
Why You're Asking: We wish jobs were only made up of glamorous assignments, but the reality is that a lot of the important work gets completed in the recurring tasks. Can your boss clearly articulate what those weekly tasks are, why they matter, and how they get done?
Understanding why these tasks matter so much will also help you organize and prioritize your own daily to-do list.
8. If there was one thing you could have known about working here on your first day, what would it be?
Why You're Asking: Who wouldn’t want to benefit from this type of insight?! Not only do you get a sneak peek into what your boss has learned since their first day, but you get the opportunity to use that knowledge as a guide for navigating your first few weeks.
This might even say you time when it comes to learning about the company culture, policies, or overall work environment. The other nice thing about asking this question is that it can save you from overthinking stuff in the future.
For example, maybe you learn how much the team values regular feedback, so you make an effort to learn how to give effective feedback and then ensure you include that in your team meetings.
Questions to Ask When Your Boss Is New
Learning how to manage your boss is just as important as learning how to manage your own career. And getting a new boss often means relearning how you set goals and do work because everything that may have made you effective with your previous manager may not necessarily help you with your new one. This is because each manager will come with their unique style, preferences, and goals for the team.
Of course, there is no simple formula to guarantee you’ll get along and have a productive working relationship with your new boss—but you can improve your chances (and make progress toward this goal) by asking the right questions. Here are seven to consider:
1. What does your decision-making process usually look like?
Why You're Asking: In order for you to make progress at work, you’ll need to know how your boss prefers to make decisions. Are there certain times when your new boss wants you to call the shots, or do they always want the final word?
It’s also helpful to have insight into how they evaluate decisions, their timeline, and what information they find helpful to have upfront. You can make sure to provide this information whenever you need a decision to be made, which will save you time and the energy of chasing down an answer.
2. How would you describe your leadership style?
Why You're Asking: Numerous psychology studies have explored how a supervisor’s leadership style can negatively impact employees, so it’s natural for you to be curious about how your new boss operates.
Even more important, you want to ensure your new boss has taken the time to consider how they will lead the team. Will they lead by example? Do they prefer an authoritative approach? How they prefer to lead helps guide your actions moving forward.
3. What are the three most important things you need from me?
Why You're Asking: With this answer, you’ll be able to gain clarity about your role, align with your boss on expectations, and know which tasks to focus on first. Your efforts can be used where it matters most to your new boss.
This is also a good question to ask right away because many managers often fail to clearly articulate what their top priority is, how they see team members fitting in, and what they most need from them. Understanding what they see as the most important from you will help you deliver where it matters most.
4. What is your preferred collaboration style?
Why You're Asking: Communicating collaboration preferences up front prevents problems.
With so many of us working remote, hybrid, or in-office, it’s a valuable skill to be able to collaborate no matter where your desk is located. Even more valuable is making sure you’re flexible with adapting your collaboration style to meet the needs of your boss.
5. Are there any resources or insights I can share about the team to help you?
Why You're Asking: Remember your boss is the newbie around here, and you can help them greatly by offering to share what the current team dynamic is. Plus, when you ask this question, you learn what learning gaps your new boss still has and can build rapport by offering to support them as they learn the ropes.
6. What is your impression of the company culture here? Is there anything that stands out to you?
Why You're Asking: First impressions can be lasting impressions.
With this question, you can understand how your new boss views the culture. Culture ranges from how people dress and talk to leadership and reward structures. We all know that culture fit matters—you’ll be happier and more successful (as will your manager) if there’s a good match.
7. How do you avoid burnout when handling a large workload?
Why You’re Asking: Showing support means a lot to your employees.
As a manager, we hope you want to do right by your employees and support them through intense work periods, so they don’t get burned out. By asking this question, you’ll learn what steps your new boss might take to reduce your stress level and actions you can take to improve your own well-being.
