In this episode, we explore what makes a coaching question truly powerful and why lists of powerful questions are useless.

I see powerful questions as an emergent outcome of a coach’s presence, listening, relational attunement, and capacity to stay with uncertainty. Powerful questions do not come from performance or preparation; they arise when the right internal and relational conditions are in place.

Much of the difficulty coaches experience with asking impactful questions has little to do with not knowing what to ask, and much more to do with how they listen, how attached they are to outcomes, and how comfortable they are with ambiguity, discomfort, and vulnerability, both their own and the client’s.

In this episode, I explore:

• What defines a powerful question and how it differs from content-deepening or information-gathering questions
• How trust, relational presence, and generative listening create the conditions for impactful questions to emerge
• The role of timing, attunement, and emotional readiness in whether a question lands or falls flat
• How noticing what is not being said (somatic cues, emotional shifts, gaps, or contradictions) can lead to deeper inquiry
• Practical ways to work with frames of reference, assumptions, and systemic patterns in a client’s thinking
• Why powerful questions are closely linked to the coach’s own tolerance for ambiguity, complexity, and not knowing.

If you find yourself searching for the “right” question, worrying about sounding “insightful enough”, or feeling pressure to perform as a coach, this episode offers a grounded, relational, and psychologically informed way to rethink what powerful questions really are and where they come from.

Coming up next:

In the next episode, we shift to a more practical focus on laser coaching: how to work effectively and with depth in short, focused conversations, particularly relevant for leaders and coaches working within tight time constraints.

Enjoy Other Free Materials:

• Free Coaching Course for People Leaders: upthinkcoaching.podia.com/basic-coaching-skills-for-new-leaders
• Mock ICF Credentialing Exam (PCC, MCC) from UpThink Coaching: podia.com/mock-icf-credentialing-exam-pcc-mcc
• PCC Marker Demo: upthinkcoaching.podia.com/pcc-marker-demo-session

Next ICF-Accredited Coach Training Programs (designed for coaches who want to work at depth):

• ACC Path: https://upthinkcoaching.com/coach-training-development/become-a-coach/
• PCC Path: https://upthinkcoaching.com/coach-training-development/the-path-to-excellence-for-certified-coaches/

In this episode, let’s explore one of the most common questions that comes up in coach training and mentor coaching: how to establish clear and meaningful measures of success for a coaching session.

Rather than treating measures of success as a technical requirement or a box to tick during contracting, let’s look at them as a relational practice that serves the client first. Measures of success are not there to help the coach manage the session; they help the client clarify what would make the conversation truly useful, satisfying, or complete for them.

Much of the difficulty coaches experience with measures of success has little to do with not knowing how to ask the question, and much more to do with presence, listening, and the ability to stay with uncertainty. Working with measures of success often mirrors a coach’s own relationship with uncertainty, time, and results.

In this episode, I explore:

• Common patterns that make measures of success feel elusive or “hard to get”
• How presence, deep listening, and curiosity allow success criteria to emerge naturally
• Different ways clients define success, including internal shifts, emotional resolution, learning, clarity, or a felt sense of completion
• Practical ways to recognize and co-create measures of success using the client’s own language

If you find yourself unsure whether you are “doing contracting right,” or if measures of success sometimes feel awkward, forced, or overly formal, this episode offers a grounded and relational way to think about them.

Coming up next:

In the next episode, we shift to a very practical focus on the art of asking powerful questions by looking at what makes a question impactful, deep, and capable of opening something new in the client’s thinking.

Enjoy Other Free Materials:

• Free Coaching Course for People Leaders: upthinkcoaching.podia.com/basic-coaching-skills-for-new-leaders
• Mock ICF Credentialing Exam (PCC, MCC) from UpThink Coaching: podia.com/mock-icf-credentialing-exam-pcc-mcc
• PCC Marker Demo: upthinkcoaching.podia.com/pcc-marker-demo-session

Next ICF-Accredited Coach Training Programs (designed for coaches who want to work at depth):

• ACC Path: https://upthinkcoaching.com/coach-training-development/become-a-coach/
• PCC Path: https://upthinkcoaching.com/coach-training-development/the-path-to-excellence-for-certified-coaches/

This final episode of the year is a reflective exploration of unlearning.

In this final episode of the year, I spend some time with the idea of unlearning as making space for something new to emerge in our coaching. I look at unlearning not as erasing old patterns, but as creating the conditions for new responses to emerge.

Much of what coaches struggle with in training, mentoring, and supervision is not a lack of knowledge, but difficulty letting go of control, performance, over-reliance on technique, or the need to be helpful in familiar ways. This episode looks closely at how those patterns form, what keeps them in place, and what helps loosen them safely.

In this episode, I explore:

• Why unlearning is a necessary part of developing presence, listening, and relational responsiveness
• The difference between knowing something cognitively and being able to embody it
• What experienced coaches often need to unlearn as they move toward greater mastery
• Qualities that support an unlearning mindset

The episode closes with a set of reflective questions you can use to look back on the past year not in terms of what you’ve learned, but what you’ve let go of, softened, or stopped doing in your coaching.

If you’re ending the year in a reflective mood and thinking about how you want to grow next not just in skills, but in how you are as a coach, this episode offers a gentle place to pause before the new year begins.

Coming up next: We start the new year with a practical focus on how to define clear and meaningful measures of success for a coaching session, especially when clients bring topics that feel big, vague, or abstract.

Enjoy Other Free Materials:

• Free Coaching Course for People Leaders: upthinkcoaching.podia.com/basic-coaching-skills-for-new-leaders
• Mock ICF Credentialing Exam (PCC, MCC) from UpThink Coaching: podia.com/mock-icf-credentialing-exam-pcc-mcc
• PCC Marker Demo: upthinkcoaching.podia.com/pcc-marker-demo-session

Next ICF-Accredited Coach Training Programs (designed for coaches who want to work at depth): Spring of 2026, exact dates TBC Check out our website