25 Questions to Ask an Executive Coach Before, During, and After Your Partnership

Choosing the right executive coach is more than a logistical decision—it’s a strategic one. Coaching can catalyze deep self-awareness, shift leadership styles, and unlock hidden potential. But to get the most from the coaching process, you need to start with the right questions.

Whether you're preparing for your first coaching engagement or midway through one, this guide equips you with powerful questions to ask an executive coach—and yourself—so your coaching sessions are focused, impactful, and transformative.

Part 1: Questions to Ask Before Hiring an Executive Coach

Before you commit to a coaching engagement, it's essential to evaluate the coach’s experience, coaching style, and fit with your leadership development goals.

These questions help you clarify expectations, understand the executive coaching approach, and ensure a values-based match with your coach.

1. What is your background and experience in coaching leaders like me?

This helps you assess whether the coach has relevant experience with similar roles, challenges, or industries—including C-suite leaders, founders, or high-potential managers.

2. Do you hold any certifications from the International Coach Federation or similar organizations?

Credentials like ICF certification reflect a coach’s commitment to ethical standards, continuous learning, and a strong coaching methodology.

3. What’s your coaching philosophy, and how does it influence your methodology?

Understanding their coaching philosophy (e.g., transformational, performance-based, neuroscience-informed) ensures alignment with how you want to grow.

4. Can you walk me through your typical coaching structure (frequency, duration, format)?

This gives you clarity on logistics and consistency, helping you set expectations for the cadence and rhythm of coaching sessions.

5. Can you share success stories or testimonials—without breaching confidentiality?

A good coach can provide anonymous examples that highlight real outcomes, past experiences, and coaching results tied to leadership skills or business impact.

Part 2: Questions to Ask During the First Coaching Sessions

Early sessions are where the foundation for effective coaching is built. Here’s where coachee and coach align on goals, success metrics, and the partnership dynamic.

6. What are the short- and long-term goals we’re working toward?

This helps both coach and coachee get clear on direction—and it creates a shared commitment to outcomes.

7. How will we track progress—qualitatively or quantitatively?

Good coaching includes reflection points or metrics (even if soft) to measure change and reinforce professional development.

8. How do you tailor the coaching experience to fit each client’s leadership style and personality?

Every leader is different. This question reveals how adaptive the coach is to your communication style, pace, and mindset.

9. What’s expected of me between coaching sessions?

Some coaching processes include fieldwork, journaling, or on-the-job experiments. Knowing this helps you plan your engagement and accountability.

10. Can I bring real-time business issues or decision-making dilemmas into our sessions?

If your work is dynamic, this ensures your coach can pivot with you and stay relevant to your evolving challenges.

Part 3: Questions to Ask Yourself Before and During Coaching

Some of the most important questions aren’t for your coach—but for yourself. Effective coaching starts with the courage to reflect honestly and show up fully.

11. What patterns in my leadership or communication am I ready to shift?

This invites self-awareness about how you show up—and what might be holding you back from greater influence or clarity with your team members.

12. Am I open to being challenged or seeing blind spots I haven’t yet considered?

Coaching requires vulnerability. This question prepares you to receive feedback with curiosity rather than defensiveness.

13. What would a breakthrough look like for me—not just professionally, but in my personal life too?

Great coaching impacts the whole person. Reflecting here helps you define meaningful change beyond your LinkedIn profile.

14. Where am I holding back, playing small, or staying in my comfort zone?

Growth often begins where comfort ends. This prompts you to name your resistance—and move through it.

15. How willing am I to show up with honesty, vulnerability, and self-responsibility?

Effective coaching requires full participation. If you’re not all in, the results will reflect it.

Part 4: Questions to Ask Midway or Later in the Coaching Engagement

As your coaching journey progresses, reflection and recalibration become key. These questions ensure you’re still on track and making the most of your investment.

16. How have I grown since we began this coaching engagement?

This invites both coach and coachee to name tangible shifts in mindset, behavior, or results.

17. What new skills have I developed or sharpened?

Coaching often leads to upgrades in communication, presence, or emotional intelligence—naming them reinforces progress.

18. Are there blind spots or patterns I still haven’t recognized?

A leadership coach can help you uncover recurring ways of being that are invisible to you but impactful to others.

19. Is there anything I’m avoiding, resisting, or not fully owning?

This helps surface avoidance patterns that may be stalling your growth.

20. How can I continue integrating what I’ve learned beyond the coaching partnership?

As the coaching engagement nears its end, it’s important to build a sustainable action plan for continued leadership development.

Part 5: Specialized Questions by Coaching Goal

Your coaching questions should reflect your specific challenges and intentions. Here are goal-based prompts to guide deeper dialogue:

21. Career Transitions: How can I reposition myself confidently after a career change or professional pivot, especially on platforms like LinkedIn?

A career coach can help clarify your narrative and articulate your evolution with authenticity and strategic framing.

22. New Leadership Roles: What leadership skills and mindset shifts are essential for success at this level?

Transitioning into a higher role often means rethinking time, communication, and authority.

23. Imposter Syndrome: How do I shift my self-perception and mentor others through similar challenges?

This opens a space to explore self-worth and influence, especially when stepping into visible roles.

24. Team Dynamics: How can I improve psychological safety and effective communication within my team members?

Culture starts with leadership. Coaching can support more trust, empathy, and accountability within your group.

25. Burnout Recovery: How do I create a rhythm that balances drive with well-being and sustainable professional development?

Preventing burnout isn’t about slowing down—it’s about aligning ambition with energy, values, and boundaries.

Asking powerful, timely questions isn't just a coaching technique—it’s part of the transformation. It’s how good leaders become great ones.

The right coaching starts with the right questions. At Macula Executive Coaching, we help you lead each conversation with clarity and purpose — so you get more than insights: you get momentum. Ready to make your next move count? Let’s talk.

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