For Powerful Conversations: Bring Your Inner Coach

Written by Jamie M. Killorin

When was the last time somebody asked you a powerful question?

What do you think? How do you feel? These are two favorites of retired Duke University Head Basketball Coach ‘K’ Mike Krzyzewski, arguably one of the most accomplished coaches of our time, that he shared this summer at the AICPA ENGAGE 22 Conference.

The essence of coaching is asking powerful questions. We deepen the learning and forward the action with coaching. Coaching provides fundraisers, gift planners, or consultants tools to have more meaningful conversations and learn with donors, colleagues, and clients.  

Powerful questions are short, succinct, and provocative, asking What? When?  How?  We avoid “Why” because this can put a client on the defensive and ask for an explanation. Coaching is forward-looking, and a “why” question is directed toward the past. Master certified coach Alex Verlek (2021) shares Rule #1 of his golden rules “coaching is about exploration, not about explanation.”

Exploration for the donor sends them to new places with new perspectives. Powerful questions are naturally curious – not for your curiosity as the coach, but to move the donor forward to deepen their learning and see new possibilities. Another great question from Coach K is, “What do you see?” Initiates reflection about observations and calls upon the imagination for learning.

Master certified coach L.A. Reding asks, “What’s important about that?” spoken with genuine curiosity and a desire to have people operate from what really matters. One of my favorites to invite imagination and playful exploration is, “If you could do anything, what would you do?”

Coaches should avoid closed-end questions answerable with a simple “yes or no” because these will stop the exploration. Closed questions have already concluded the topic. Although, it’s okay to ask permission to explore a new topic, such as “May we talk about…?”

Don’t be a Fixer

Foundational to coaching is the belief that people are naturally creative, resourceful, and whole (Kimsey-House, Kimsey-House, Sandahl, & Whitworth, 2018). Consultants and advisors want to give advice, offer solutions, etc. ….and be a fixer. Being a fixer is not coaching. Fixing for a client assumes a contrary view that they cannot arrive at good answers.

Questions that lead to or imply a preferred outcome come from the fixer. Stay in the moment with your client and stay with your powerful questions. Self-management for the inclined fixer is an area that takes practice for the new coach. If you remember that your client is not broken, it gets easier not to be a fixer.

Coaching and consulting require different and complementary skills. Sometimes a client will ask you for your specialized advice, which is to be expected, but that is not coaching.

Listen for the Giggle

One of the most challenging and essential coaching skills is listening. My training with the Coaches Training Institute (CTI) teaches that there are three levels of listening. Most of the time, we go about our day focused on our lives. This is Level I – Internal Listening – we gather information to accomplish our needs and are self-focused.

When you try to coach at Level I – you listen but are already formulating your next question. Internal listening is concerned with showing the donor that you are an expert. Level I is where the fixer stays – gathering information to solve the problem or offer a solution.

While the coach must move beyond Level I, the donor should stay in Level I. We want our donors to be self-focused, imagine the future, process the conversation, and understand their circumstances and opportunities.

Level II is Focused Listening. There is no voice thinking of your next question in your head, but you are keenly focused on the client. This is the place where you notice what they say and what they don’t say. Listen for values, dreams, vision, and emotions.

Infants start to laugh or giggle at around three or four months. Laughter indicates pleasure. In my practice, I coach clients over the telephone so that I can listen more intentionally. Did you know that you can ‘hear’ a smile? When I hear the audible giggle, I know we are headed in the right direction. The smile or laughter signals resonance for the client.

A coach can also hear tears. Emotion can be expected from a client in coaching. Coaching is not therapy, but it can be therapeutic to talk with someone you know is listening.

Global Listening or Level III builds on focused listening to encompass action, inaction, and interaction. This is the space where the coach’s intuition comes in. Coaches develop a sixth sense where they become aware of the subtle shifts in the environment and the client. Coaches will shift between Level II and Level III in the coaching dance with the client.

At Level III, the coach will probably encounter the donor’s saboteur. A saboteur expresses dissonance, and it is their job to keep things the same. We don’t demonize the saboteur because it is the voice that speaks up in all of us to stop change. The tricky thing about a saboteur is that its resistance is based on a small piece of truth that can be stretched into a powerful argument for the status quo. However, we want to call out the saboteur and let the donor know we see it. It is not the coach’s role to confront the saboteur but let the donor speak back to the voice of resistance.

Why Am I Talking?

A learned skill of a coach is the effective use of silence. Executive coach and trainer, Ken Oakley, shared the acronym WAIT for Why Am I Talking? A reminder of the negotiation adage, He (she) who speaks first loses. Allow your donor to feel the resonance of the coaching conversation – or the dissonance – don’t impede the learning with another question or suggestion. WAIT is terrific advice for the fundraiser and consultant alike. Your donor will notice that you gave them the moment of space.

Sometimes a powerful question will not land as you intended, and the donor will give you silence in return. Take that as an opportunity to re-group and move ahead with another approach. In your trusting conversation with the donor, the learning is reciprocal.

Training and Practice

While powerful questions are at the heart of coaching, there are many other skills to be an effective coach. Coaching is a profession requiring training, more than 100 hours of practice, supervision, and evaluation to become certified. The International Coaching Federation (ICF) is the source for learning about coach training. Take the opportunity to explore learning opportunities to enhance your coaching skills.

For the gift planner or advisor who does not seek to be a professional coach, the learned coaching skills can be invaluable for having more intentional and meaningful conversations. You will help your donors move forward in action by asking better questions and listening deeper.

Try a new powerful question today with a donor, client, or colleague. See how it lands. Listen and WAIT. And tomorrow, try another. With coaching conversations, your donors will see new possibilities for their future and the impact of their philanthropy.

Kimsey-House, H., Kimsey-House, K., Sandahl, P., & Whitworth, L. (2018). Co-Active Coaching (4th ed.). Boston, MA: Nicholas Brealey Publishing.
Verlek van Tienhoven, A. (2021). Golden Rules for Coaching, The Netherlands: Coaching Works International. Retrieved from


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