Questions to Ask New Leadership

Questions to Ask New Leadership

Strategic questions to understand new leadership's vision, priorities, and approach while building rapport and demonstrating your value.

1

What's your vision for the team and organization?

Reveals their strategic direction and helps you understand how to align your work with their goals and priorities.

2

What are your top priorities for the first 90 days?

Shows their immediate focus areas and helps you understand what they value most in the short term.

3

How do you like to communicate and receive updates?

Establishes communication preferences and ensures you can effectively share information and stay connected.

4

What's your approach to decision-making and problem-solving?

Reveals their leadership style and helps you understand how to present ideas and get decisions made.

5

What are your expectations for team performance and collaboration?

Clarifies performance standards and helps you understand how to contribute effectively to team success.

6

How do you handle feedback and performance discussions?

Shows their approach to development and helps you understand how to receive and give feedback effectively.

7

What are your thoughts on the current challenges facing our team?

Reveals their understanding of team dynamics and helps you understand their perspective on existing issues.

8

How do you like to recognize and reward good work?

Shows their approach to motivation and helps you understand how to get recognition for your contributions.

9

What are your expectations for professional development and growth?

Clarifies their approach to career development and helps you understand opportunities for advancement.

10

How do you handle conflicts and difficult situations?

Reveals their conflict resolution style and helps you understand how to navigate challenging situations.

11

What are your thoughts on work-life balance and flexibility?

Shows their approach to employee well-being and helps you understand their policies on work arrangements.

12

How do you like to approach change and innovation?

Reveals their attitude toward change and helps you understand how to present new ideas and improvements.

13

What are your expectations for meeting participation and preparation?

Clarifies meeting expectations and helps you understand how to contribute effectively to team discussions.

14

How do you like to handle deadlines and project management?

Shows their approach to project oversight and helps you understand how to manage your work effectively.

15

What are your thoughts on the current team structure and roles?

Reveals their perspective on team organization and helps you understand potential changes or improvements.

16

How do you like to approach risk-taking and experimentation?

Shows their attitude toward innovation and helps you understand how to present new ideas and approaches.

17

What are your expectations for cross-functional collaboration?

Clarifies their approach to teamwork and helps you understand how to work effectively with other departments.

18

How do you like to handle mistakes and learning opportunities?

Reveals their approach to failure and helps you understand how to handle setbacks and learn from them.

19

What are your thoughts on the current company culture and values?

Shows their perspective on organizational culture and helps you understand how to align with company values.

20

How can I best support you and the team's success?

Demonstrates your commitment to team success and helps you understand how to contribute most effectively.

Want to learn more?

Best Practices for Engaging with New Leadership

Best Practices

Be Proactive and Engaged

Take initiative to introduce yourself and show interest in their vision and priorities. Demonstrate your value and commitment.

Listen Actively and Take Notes

Pay attention to their responses and take notes so you can follow up on their priorities and expectations.

Show Your Value

Highlight your skills, experience, and contributions while asking questions that demonstrate your understanding of the business.

Question Sequences

The Vision and Priorities Sequence

1
What's your vision for the team and organization?
2
What are your top priorities for the first 90 days?
3
What are your thoughts on the current challenges facing our team?
4
How can I best support you and the team's success?

The Working Style Sequence

1
How do you like to communicate and receive updates?
2
What's your approach to decision-making and problem-solving?
3
What are your expectations for team performance and collaboration?
4
How do you like to handle feedback and performance discussions?

Common Pitfalls

Don't Focus Only on Your Needs

Balance questions about your development with questions about how you can support the team and organization.

Avoid Negative Questions

Don't ask questions that criticize previous leadership or focus on problems. Focus on positive opportunities and growth.

Don't Overwhelm Them

Space out your questions and don't ask too many at once. Give them time to respond and show genuine interest in their answers.

Conversation Templates

The Leadership Introduction

1
Step 1: Start with: "What's your vision for the team and organization?"
2
Step 2: Follow with: "What are your top priorities for the first 90 days?"
3
Step 3: Deepen with: "How can I best support you and the team's success?"
4
Step 4: Connect with: "I'm excited to contribute to these goals and help drive our success."

Further Reading

"The First 90 Days" by Michael Watkins
"Crucial Conversations" by Kerry Patterson
"The Leadership Challenge" by James Kouzes
Harvard Business Review on leadership transitions