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Unlock Your Potential: 5 Brilliant Questions to Ask the Boss 

Are you ever at a loss for words when speaking with your manager or leadership? Do you covet a leadership position but need help standing out from the crowd? Asking the right questions is often the key to unlocking your leadership potential.

Here are our Top 5 thoughtful questions to ask the boss to help shine bright.

What is the big-picture objective this quarter?

You want to demonstrate that you know the sauce and can articulate your manager's short- and long-term objectives. Seeking to understand or make meaning of how your work contributes to the complete, overarching story or idea shows you are future-focused and want to be closer to the business and its mission. Good leaders make the business their business and often look beyond their immediate tasks. By asking your boss questions about the 'big picture,' you can:

  • Better understand the outcomes you need to aim for. 

  • Show your commitment to helping the company reach their goals. 

  • Create a positive and successful working environment.

  • Optimize how your work contributes to the organization’s goals.

In addition to helping you achieve success, having a deep understanding of the 'big picture' can help foster a positive, forward-thinking environment. For example, proactively asking your boss questions about their vision for the company and how you can work to make that vision a reality shows your thoughtfulness and your dedication to the organization's overall success.

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Which would you choose if I were to improve any skill between now and our next one-on-one meeting?

The age-old adage “knowledge is power” rings true in many aspects of life, especially in the professional world. As an employee, staying up-to-date on technical skills and trends in your field is not only important, it is vital to gaining power and influence in an organization. Google's' 20% rule’ encourages their team members to allocate time to dedicated training and learning.

Bringing your boss into the conversation and discussing your development can be advantageous if you hope to grow within an organization or expand skills in areas core to the business. Your manager may have better visibility into opportunities or business needs and usually appreciate their opinion being considered. It also shows you are willing to learn and grow; good leaders will remember that and can help you create common goals that benefit both you and the organization.

Here are a few best practices for professional development you can consider or discuss during your next one-on-one:

  • Focusing on just one skill and stating a learning objective. Don't take too many classes in different areas or attempt to learn without a target outcome. Instead, work with your manager to identify a skill to develop and a desired learning outcome.

  • Managing workloads and education while staying positive and engaged. It's essential to look at the positives in any situation you find yourself in, even if it doesn't turn out as you expected.

  • Trying different learning modalities. Ask your manager what methods, resources, publications, etc., have worked for them. Talk about more modern mediums for learning, like podcasts and audiobooks and ask if you can take advantage of any company programs or resources. Most teams have a budget for training and up-skilling, so it’s worth inquiring how to take advantage of free training. 

  • Improving networking skills and connections. Your manager has likely interacted with all sorts of leaders and departments in your organization and most likely worked at other jobs throughout their career. Ask them if anyone who may be able to help inspire or add to your career development journey comes to mind. Discuss any apprehensions about networking and the best ways to engage a coworker for lunch or a coffee chat.

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How will my role evolve over the next six to twelve months?

Inquiring about how your role may change can jumpstart the conversation about your career trajectory. Be open to an honest dialogue about the expectations you and your manager have for your position. Focus the discussion on the value you currently bring to the team, and be prepared to speak to how your future ideas and contributions could translate to future business value.

When asking a challenging question, use these body language essentials:

  1. Mirror their actions

  2. Nod your head

  3. Plant your feet

  4. Remember to smile

  5. Keep an open posture

A clear vision of your future job scope can open up possibilities. Knowing what your boss expects from you allows you to make the necessary changes in your role or performance to meet the company's needs, AND it helps you avoid any surprises down the road. Your boss will also likely be impressed by your interest in furthering your career. This gives you a valuable chance to develop your professional profile and build meaningful relationships.

What advice do you have for me at this point in my career?

Asking your boss for their advice is a strategic move that can set up a successful conversation. Not only does it demonstrate that you are a self-sufficient worker who is open to feedback, but it also gives you a chance to gain valuable insight.

“People who succeed in giving feedback make sure the individual receiving it knows what he needs to improve.” - Dr. Travis Bradberry.

Asking your boss what advice they would give you is an act of courage and commitment. It shows you respect their opinion and position and value their mentorship. This vital question can seem intimidating, but it can be the start of a great working relationship and help you reach your goals. Everyone wants to find a balance between gaining criticism and offering support, and asking your boss for advice is a great way to ensure both.

What's the best way to collaborate with you?

Communication is vital to professional success, and asking for advice helps foster better working relationships. For example, they may prefer meetings on a specific day or time allotted for updates. Conversations become smoother and more productive when you know their preferences.

Grow your team with 21 Empathy Builders Icebreaker Cards. This digital download contains fun warm-up games and team-building activities to help colleagues get to know each other better. In addition, each card includes a question prompt to explore preferred ways of working, communicating, and collaborating. Choose a card and start exploring people's working styles and preferences. Perfect for new hires, groups of any size, and all work environments.

Unlocking your potential and taking on a leadership role doesn't need to be an intimidating process. Asking thoughtful questions can be the first step to unlocking your leadership potential. Contemplating each can help you understand what is expected from the team and what you must do to succeed. 

Check out article 7 Reasons Team-building Activities will Transform your Organization.