20 Questions

Good Leadership Questions to Ask

Navigate leadership discussions with strategic questions that help you understand leadership principles, practices, and challenges while gathering valuable insights for your own leadership development.

1

What's your approach to building and maintaining trust within your team?

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Why this works

Reveals their trust-building philosophy while helping you understand how they establish and maintain trust in leadership relationships.

2

What's your approach to making difficult decisions and handling tough choices?

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Why this works

Shows their decision-making process while revealing how they approach complex decisions and navigate difficult choices.

3

What's your approach to developing and mentoring other leaders?

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Why this works

Demonstrates their development focus while revealing how they identify, develop, and mentor emerging leaders.

4

What's your approach to handling conflict and resolving disputes within your team?

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Why this works

Shows their conflict resolution skills while revealing how they manage disputes and maintain team harmony.

5

What's your approach to communicating vision and strategy to your team?

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Why this works

Demonstrates their communication skills while revealing how they share vision and strategy with their team.

6

What's your approach to handling failure and learning from mistakes?

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Why this works

Shows their growth mindset while revealing how they handle setbacks and use them as learning opportunities.

7

What's your approach to working with different types of personalities and work styles?

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Why this works

Demonstrates their adaptability while revealing how they work with diverse personalities and adapt their leadership style.

8

What's your approach to handling the pressure and responsibility of leadership?

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Why this works

Shows their resilience while revealing how they manage the intense pressure and responsibility of leadership roles.

9

What's your approach to working with different types of teams and organizational structures?

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Why this works

Demonstrates their versatility while revealing how they work with various team structures and organizational models.

10

What's your approach to working with different types of stakeholders and partners?

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Why this works

Shows their relationship management while revealing how they work with various stakeholders and build partnerships.

11

What's your approach to working with different types of change and transformation?

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Why this works

Demonstrates their change management while revealing how they lead and manage organizational change and transformation.

12

What's your approach to working with different types of performance and results?

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Why this works

Shows their results focus while revealing how they drive performance and achieve results through their team.

13

What's your approach to working with different types of innovation and creativity?

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Why this works

Demonstrates their innovation focus while revealing how they foster creativity and drive innovation within their team.

14

What's your approach to working with different types of ethics and values?

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Why this works

Shows their values while revealing how they integrate ethics and values into their leadership approach.

15

What's your approach to working with different types of feedback and performance management?

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Why this works

Demonstrates their feedback skills while revealing how they provide feedback and manage performance within their team.

16

What's your approach to working with different types of delegation and empowerment?

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Why this works

Shows their empowerment focus while revealing how they delegate responsibilities and empower their team members.

17

What's your approach to working with different types of crisis and emergency situations?

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Why this works

Demonstrates their crisis management while revealing how they handle emergencies and crisis situations.

18

What's your approach to working with different types of diversity and inclusion?

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Why this works

Shows their inclusion focus while revealing how they promote diversity and create inclusive team environments.

19

What's the most rewarding aspect of leadership for you?

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Why this works

Focuses on positive aspects while revealing what they find most fulfilling about their leadership role and journey.

20

What's the most important thing for aspiring leaders to know about leadership?

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Why this works

Provides key guidance while revealing what they consider most critical for success in leadership and team management.

Mastering Leadership Conversations

Expert tips and techniques for getting the most out of these questions.

Best Practices

Show Understanding of Leadership

Demonstrate knowledge of leadership principles, practices, and challenges. This shows you understand the complexities of leadership.

Focus on Development and Growth

Ask about their approach to developing others and growing as a leader. This shows you value continuous improvement and development.

Understand the Role

Ask about the challenges and responsibilities of leadership. This helps you understand the role and assess if it's right for you.

Question Sequences

The Trust Builder

1
What's your approach to building and maintaining trust within your team?
2
What's your approach to making difficult decisions and handling tough choices?
3
What's your approach to developing and mentoring other leaders?

The Challenge Handler

1
What's your approach to handling conflict and resolving disputes within your team?
2
What's your approach to handling failure and learning from mistakes?
3
What's your approach to handling the pressure and responsibility of leadership?

Common Pitfalls

Don't Focus Only on Success Stories

While success is inspiring, also ask about challenges and failures. These experiences often provide the most valuable lessons.

Avoid Generic Questions

Don't ask questions that don't reveal their specific approach and experience. Ask about their unique methods and strategies.

Don't Ignore the Personal Side

Remember that leadership is deeply personal. Ask about their motivation, values, and personal approach to leadership.

Conversation Templates

The Trust Builder

1
Step 1: Start with: "What's your approach to building and maintaining trust within your team?"
2
Step 2: Follow with: "What's your approach to making difficult decisions and handling tough choices?"
3
Step 3: Deepen with: "What's your approach to developing and mentoring other leaders?"

The Challenge Handler

1
Step 1: Begin with: "What's your approach to handling conflict and resolving disputes within your team?"
2
Step 2: Explore with: "What's your approach to handling failure and learning from mistakes?"
3
Step 3: Connect with: "What's your approach to handling the pressure and responsibility of leadership?"

Further Reading

"The Leadership Challenge" by James Kouzes and Barry Posner
"Good to Great" by Jim Collins
"The 7 Habits of Highly Effective People" by Stephen Covey

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