How to choose a leadership coach

Leaders typically have no shortage of subject matter experts. They're surrounded by employees, board members, and peers who understand their industry. What's often missing is an unbiased outside perspective—a thought partner who can ask difficult questions freely, without agenda or judgment.

“I find my most powerful coaching happens when I’m working with someone outside my own career background,” shares Christine Guthrie, PCC, Executive Leadership Coach, Founder of Authentic Ascent, and Faculty at Georgetown Leadership Coaching Program. “I’m more naturally curious. I’m not projecting what I think they ‘should’ do but helping discover answers that belong to them, not me.”

When a coach doesn't know the intricacies of your industry or the politics of your organization, something valuable happens: you're forced to articulate your assumptions, clarify your thinking, and explain your goals fully. This process of slowing down, simplifying, and reflecting often surfaces insights that can be hidden when surrounded by those who share your context and assumptions.

A coach's outsider status isn't a limitation—it's a strategic advantage that creates space for breakthrough thinking.

After deciding you want a leadership coach, the next questions are often about how and when to start. A useful next question is “Am I ready to be coached?”

As we explored in the first section, coaching isn’t about advice or quick answers. It’s about making space to reflect and grow in ways that can be hard to access alone. While coaching doesn’t necessarily involve homework, it helps if you are in a place to examine and question and, most importantly, be open to change and growth.

You may be ready for coaching if:

• You’re asking questions about who you are and what really matters now
• You’re open to feedback, even when it’s uncomfortable
• You’re more focused on growing than on fixing
• You want a space that’s fully yours, without judgment or agenda

If you’re considering coaching, how many of these feel true?

• I have a goal, question, or transition I want to explore
• I’m open to feedback and self-reflection
• I’m willing to be challenged in service of my growth
• I don’t expect answers; I want a thought partner to help me find my own
• I want to be accountable for the work, inside and outside the sessions

If you checked any of these, you’re in a good place to begin coaching. If you checked most, you’re primed for growth.

Whether you're selecting a coach for yourself or evaluating options for your organization, focus on these critical factors:

Chemistry and trust. Coaching is an inherently personal relationship. The foundation is psychological safety—can you be open with this person? Will they challenge you constructively? Have exploratory conversations with two or three coaches to help choose the best for you. If you’re in HR or professional development choosing coaches for employees, ask them to have a couple conversations with potential coaches and choose the best for themselves.

Coaching philosophy and methodology. Different coaches bring different frameworks and approaches. Ask about their process: How do they structure sessions? What methodologies inform their practice? Can you align on goals and what success looks like?

Powerful questions. During initial conversations, notice whether the coach asks insightful questions about you and your needs, goals, and challenges. Great coaches focus on helping you discover your own answers.

It's natural to gravitate toward coaches who share your background or industry. But remember: coaching addresses universal leadership challenges—how you communicate, how you motivate yourself and others, how you set and hold expectations—not the technical details of finance, tech or law.

While it may feel harder to evaluate who asks great questions or listens with true insight, these are the competencies that distinguish exceptional coaches. If you're investing in developing your leadership capacity, it's worth evaluating what truly matters.