If You Don’t Know What Questions to Ask a New Leader, You’ll Hate Yourself Later
Optimize team management in minutes with ManageBetter. Start your free trial now and join Uber and Microsoft in boosting performance, gathering insights, and generating reviews—all AI-powered, no writing required.
They say “you only get one chance to make a first impression.” Also, it only takes about seven seconds for a person to make a judgement call about who you are and whether they can trust you. Therefore, your first meeting with a new leader can make or break your career. Make an amazing first impression and you’ve set yourself up for success.
But, hold on.
People also judge based on the quality of the interaction after the initial seven seconds. Appearances may catch your new manager’s eye, but the conversation is what he or she will remember long-term. Make sure you’re prepared to have meaningful discussions with your new boss at your first meeting together. In addition, take advantage of this time to ask pertinent questions. Ask questions that will help you:
Understand how to adjust your actions to create the ideal interactions between you and your manager
Understand what their expectations are of you
Reach your career goals by learning from his or her mistakes
The top 35 questions to ask a new leader
What do you believe are the characteristics and actions that you used to get to where you are today?
Looking back on your journey and knowing what you know now, what is one piece of advice you would have given yourself along the way?
Which is most important to your organization—mission, core values or vision?
How do you ensure your organization and its activities are aligned with your “core values”?
What is one characteristic that you believe every leader should possess?
What is the biggest challenge facing leaders today?
What is the one behavior or trait that you have seen derail more leaders’ careers than any other?
What are a few resources you would recommend to someone looking to gain insight into becoming a better leader?
What are you doing to ensure you continue to grow and develop as a leader?
What are your goals for me in the next month/year?
When do you do your head-down work?
How do you best like to communicate?
What can I do to assist you immediately?
What would you like to know about me?
How would you describe your leadership/management style?
What specific expectations do you have of me?
How do you prefer to hear about bad news?
What annoys you most in someone who reports to you?
What is your vision for our organization?
How can I best contribute to the vision?
What are your top personal values?
How do those values impact the way you lead?
How will you evaluate my performance?
Who are my most important stakeholders (in addition to you)?
What will you need to know about my area of responsibility on an ongoing basis?
How often should you and I meet to discuss performance and progress on my mission?
What kind of data or reports would you like to see?
What does success look like for our organization?
What does success look like for the part that I’m responsible for?
What barriers to success should I be aware of?
How would you like to receive feedback from me?
If there are a number of projects to be done, and management is hands-off, what should I prioritize?
What is your biggest source of stress at work?
Do you want to be copied on all emails of significance?
Is there anything in particular that I should know about you?
Next time you meet with a new manager, you’ll be sure to leave a lasting impression through great conversations.
Sharpen Your Leadership Edge: Join 3,000+ executives receiving weekly, actionable insights from industry experts. Subscribe free to The Thoughtful Leader and elevate your team's performance.
