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Smart Questions to Ask Your New Boss

Andrew Langat
May 11, 2023

Starting a new job can be exciting and nerve-wracking. You're eager to get started and create an impression that would, hopefully, create a good rapport with your new manager or boss.

How do you go about it?

One way to do that is to come prepared with some smart questions to ask during your first or subsequent meetings, such as when doing a performance evaluation.

But, first, you need to take time and understand your new manager and learn what they prefer and don't. This way you can help to manage up.

When a new manager joins an organization or a company, they would like to implement their leadership style as quickly as possible and ensure they're on the same page as their employees. Their management style may allow open communication with employees.

Asking your manager questions is crucial for building a solid professional relationship with them and gaining knowledge about your role. These actively help you recognize areas of improvement and opportunities for professional growth.

Please do not neglect the value of your manager's experience and the valuable insight it provides for your career trajectory. Make sure to take advantage of this resource to ensure your success.

This article will explore some intelligent questions you can ask your new boss.

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17 Smart Questions to ask your New Boss.

Asking the right questions is key to advancing your career. Inquire about new hire expectations, set goals, and learn from successful managers to gain insights for a fulfilling professional journey. Here are a few questions to ask:

1. Who inspires you?

Asking your boss about their personal life and biggest inspirations can reveal much about their personality and motivations. You might also discover new leaders to admire and learn from. Knowing their favorite author, business professional, or entertainer can produce many helpful materials.

It is advisable to ask this question once you have established a good rapport with your boss to get the best response.

2. How can you assist me in working towards my personal goals and objectives?

Your boss could be someone you aspire to become in the future. Seeking their advice on achieving your goals can help establish them as your mentor. A mentor can help you navigate your path to achieving your personal and professional goals more smoothly.

Additionally, public speaking, asking for guidance on your goals can help establish a professional relationship throughout your career.

3. How can we establish an ideal workflow?

Individual personality traits necessitate distinct approaches to the boss-employee relationship. Certain managers may favor team meetings and constant collaboration, while others are more flexible and hands-off. You can devise a workflow that optimizes your abilities by recognizing the disparities in how you and your supervisor function most effectively.

4. Can you share with me your career aspirations?

Asking your boss about their personal goals can offer valuable insight into their work philosophy and methods. They may be working towards a promotion or have plans to start their own business. Understanding their short and long-term objectives can assist you in performing your job to the best of your abilities.

5. Would you happen to have any book or media recommendations?

This can be an excellent inquiry to learn about your boss's path to success. Many executives tend to be avid readers as it enhances their performance. Reading regularly sparks fresh ideas, improves memory, and alleviates stress, which is advantageous in cultivating a rewarding career. 

Education can improve your leadership skills and assist you with carving out a slot in your field.

6. Can you give me some guidance on setting performance goals?

To ensure you add the most value to the organization, it's best to ask your boss for specific objectives to set. Employee evaluations are an excellent opportunity to track your progress and adjust your targets accordingly. You can also schedule informal meetings periodically to ensure you're on track to achieving your goals.

7. What do you find most fulfilling about your job?

A company comprises different personalities, professions, and work styles collaborating toward a common goal. Discovering your manager's definition and passion for their job can provide valuable insight into their personality and driving forces. This can contribute to a clearer vision for the company and assist you in performing your job to the best of your abilities.

8. What accomplishments are you most proud of in your career?

Your manager's past achievements can provide valuable insight into their leadership style. Additionally, it can inspire you to take steps toward advancing your own career further. It is beneficial to know their areas of expertise and how they have gained or utilized them.

9. What do you expect from me as an employee in this position?

To ensure that we have a clear understanding of our roles and responsibilities, it's essential to establish specific expectations. This will help us set achievable performance goals and work towards bringing the most value to the organization. Can you please let me know what your expectations are for me in this role?

10. If you had a sudden influx of cash for the company, how would you allocate it?

This question can reveal your boss's definition of success and's priorities and values. Many professional and personal projects require financial investment to succeed. When money is not a limitation, it offers a glimpse into the company's and industry's direction. Typically, the response will provide insight into the boss's vision for the company's future.

11. Can you suggest the most effective way to share my feedback or ideas?

Understanding how to approach your manager with concerns can improve your communication style, teamwork, and positive company culture. Your manager's preferred method of contact, whether an open-door policy or email communication, can be influenced by their personality and leadership style.

Knowing this can help establish a functional working relationship that yields positive results. And when you receive feedback, you can work on a few areas that need polishing.

12. How can I be a team player and add value to the organization?

This question will enable you to clarify your role, align with your boss on expectations, and strategically prioritize tasks and efforts. Managers often fail to clearly and explicitly articulate their top priorities, how they see team members fitting in, and what they most need from them. Understanding this quickly will help you deliver where it matters most.

13. What would you do if you were in my shoes?

Posing this question can assist your manager in comprehending your viewpoint and demonstrate that you esteem their proficiency. It also fosters a constructive bond between you and can enhance your comprehension of how your manager perceives, senses, and behaves, irrespective of the validity or sagacity of their counsel.

14. I am eager to enhance my potential. Can you offer any advice?

According to Hermina Ibarra, Author of Act Like a Leader, influential leaders excel at coaching and mentoring their team members; one way to encourage your boss to take on this role is by requesting an evaluation of your potential development. This entails focusing on your current performance and what you can accomplish in the future.

In today's world, where reskilling and upskilling are essential for career advancement, it's crucial to broaden your horizons and be receptive to reimagining your skills. Additionally, asking this question will clarify the promotion and advancement criteria, allowing you to be pragmatic and objective in your career goals.

15. How can I elevate my performance?

Asking this question early in your role can prompt your boss to provide valuable guidance on bridging the gap between your current performance and expectations. While many managers avoid conflict and strive to maintain positive morale, seeking constructive feedback can help you identify improvement areas and progress toward your objectives. 

16. What advice can I get in my current position?

While you may have your own goals, gaining an outside perspective from someone already in your current position is always helpful. They can provide clarity and direction and give you actionable steps to take. This is especially true if they are only a step or two ahead of you in their career.

For instance, getting there can seem challenging if you're starting in an entry-level position and aspire to be a CEO someday. But someone in a position closer to yours can offer visible short-term goals to work toward.

17. What is your work-life balance?

This can be an excellent question to ask for your own career good. By revealing their work-life balance, your boss can give you vital tips that you incorporate. Moreover, it passes the message that you understand about work and life boundaries.

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How do you ask your boss questions?

A new boss has a higher level of experience as compared to yourself. They might even have occupied your position at a particular time, so asking them questions can help you gain insight into some aspects and your professional development.

Here are a few tips on asking your boss questions:

1. Ask your questions directly and politely.

Being direct and polite is the best way to ask your boss questions. You can request a one-on-one meeting with your boss or send an email that briefly outlines the reason for the discussion and the length your boss expects it to take.

If you join a new team, you may want to build rapport with your new boss, so you must be precise and polite to build a functional relationship moving the team forward.

2. Prepare your questions.

Planning forward and preparing the key questions you want to discuss is a good idea to make the most of your meeting. Gather examples and data beforehand if you have concerns about your work environment. These will help you best use your time during the meeting.

3. Attempt the tasks first.

Attempt to accomplish the task independently before seeking assistance. These will enhance the efficiency of your time with your boss and provide a basis for asking pertinent questions regarding day-to-day work. If you encounter difficulties finishing a task during work hours, it is necessary to request help. Your boss possesses a wealth of knowledge regarding your assignment and can supply valuable advice on tackling it.

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Why is it essential to ask questions to your new boss?

The best way to showcase value is by understanding what your boss values—their clear expectations, what matters to them, and their preferences, such as communication and boss management style.

Here are some importance of asking essential questions:

  • You achieve clarity on your role and those of your boss, especially if it's a new job.
  • You build rapport with your boss to help you perform your daily work better.
  • You align on your mutual career goals.
  • You get to understand each other's working preferences and styles.
  • You gain clarity on your boss's perspective and experience.
Inspiring, isn’t it ? Let’s go further and try one of the most comprehensive coaching experience with us.

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How Highrise Can Help You Get Connect to Your Boss

In summary, asking smart questions to your new boss can effectively establish a positive and productive working relationship. By demonstrating a genuine interest in your new role and a desire to learn and grow, you can set yourself up for success in your new position. However, knowing how to ask the right questions is essential to ensure you get the information you need to thrive in your new job.

This is where Highrise coaching comes in. It offers accessible and affordable online executive coaching to help professionals at all levels develop the communication skills necessary to ask the right questions and build strong relationships with their superiors. With Highrise coaching, you can take your career to the next level by mastering the art of effective communication and achieving your professional goals.

Join us today to learn this, plus more.

Andrew Langat
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Andrew Langat is an experienced content specialist in Leadership, Productivity, Education, Fintech, and Research. He is an avid reader and loves swimming as a hobby. He believes that quality content should be actionable and helpful.