Questions worth pondering

A great question can function like a compass. I recently hosted two workshop experiments. One on learning about product leadership, and a similar one on learning about leadership. My learning journeys about product and leadership both started with me at some point asking myself good questions about what makes a good product manager and leader. I recently published a whole post on good questions to ask yourself about leadership. More generally, I think all of us are wondering: what makes my life worth living? How might I find out what my purpose is in life? How can I feel more happy with my life? The answers to those questions can function like a compass to your life.

As coaches, we help our clients uncover their answers with powerful questions. I thought it would be an excellent idea to listen to a bunch of my fellow coaches, and find out what powerful questions they are asking to get people to explore what they want in life. What questions help their clients create powerful insights into building a life that feels fully alive, thriving and impactful to them. Here is what they said:

Raanah Amjadi, Ayurvedic Wellness/Life Coach & Founder of Lili Jade

Raanah Amjadi is a holistic wellness coach who helps people learn how to listen to their gut and lead balanced, nourished, and vital lives.

As a wellness coach, my clients often come to me wanting to prioritize their well-being and strike a better balance between the many facets of their life. The very first question I ask is: “How do you define your well-being?” The amount of people who are completely stumped by this question is both equal parts amusing and alarming. How can we prioritize something if we don’t know what it looks like, or more importantly, what it feels like? Our conversation then moves to discussing joy as I believe joy is one of the greatest data points we have. Joy is our embodied expression of alignment with ourselves and with the world around us. I have found we often disregard joy because it doesn’t feel “productive” in a world that demands we constantly consume or produce to be of value to society. If we can look beyond the absolutes to the qualities of the experiences and environments that bring us joy, we may find clues to our unique definition of well-being and discover ways to honor it.

You can find out more about Raanah and the work she is doing at:

Eli Blair, PCC, CPCC, MA

Eli Blair is an executive coach with over 10 years/3500 hours of 1:1 and group coaching experience working with leaders from Amazon, Workday, Asana, Helix, AAA, Abbott Pharmaceutical to startups.  Eli is on faculty with the University of California at San Diego developing and teaching coursework in Leadership and Team Dynamics as well as Diversity, Equity, Inclusion and Belonging.

As a coach who has worked both in the private and corporate environments I typically work with the concepts of story vs. truth.  Often, our “saboteur” or negative voices are telling us a story.  Usually, 90% of the time clients are not living in the truth. Often clients come to sessions with thoughts of “I am not enough”, fear of failure, fear of other people’s thoughts and so much more self limiting mindsets.  I often use the metaphor of two chairs, one is story and one is truth, and ask my clients to describe what is in the story chair and the truth chair. I then ask what their resonant choice is.  “You have the choice…do you want to sit in the story chair or the truth chair?”  To bring it more alive, I might incorporate the use of metaphor, various perspectives and resonant choices they create.

This does not come easily for many, so we continue to discuss “Conscientious Consciousness”.   What is this? Basically, this is the idea that people need to be more mindful of their thoughts and to be in the moment. The “conscientious” part means, that for most, we have to force ourselves, literally, in the moment, to step back and ask “what is the story I am telling myself in this moment.” The acronym for F.E.A.R. is False Evidence Appearing Real.  A powerful question I have recently begun asking is “What is it that you do not want me to know?” 

Of course, once we get to the truth we move forward to uncover any rocks that might be in the way and then create the sessions takeaway. Integrating these concepts into my coaching has helped clients to step back and get honest about communication, goals, strategy and relationships.  

You can find out more about Eli at

Gabe Kwakyi, Life/Leadership Coach & Founder of The Musing Mind

Gabe Kwakyi is a writer, coach & entrepreneur with 10 years of life and leadership coaching experience. Gabe is deeply passionate about empowering others.

The art of asking good questions is simple, but devilishly so. The trick is to not get caught up in trying to ask a good question, and to just keep it simple.

We can feel the need to add more words, context, or complexity to really make a question intelligent; however, most powerful questions are short questions. As coaches, we are trained to ask questions that are 7 or fewer words, for maximum impact. The more words, the more the impact and expansiveness of the question is diluted.

The power of a question can also be enhanced or dampened, depending on the first word. Beginning a question with the word, “what” is generally the best way to invite more insights from someone else. Other good open-ended question starters include “how,” “who,” or “where.” “Why” can be a good one as well, but starting with “why” requires a measure of trust to minimize the likelihood that the receiver will feel antagonized, and go on the defensive.

Some of my favorite coaching questions to open up a discussion:

  • What, if solved, would bring you relief?
  • What’s it like for you right now?
  • How are you living up to your values?

The question follow-up is just as important as the initial question itself. Relationship guru coach, Esther Perel, for instance, simply says “say more” to prompt a client to continue expanding. Other examples include “why is that important to you?” “tell me more” or “open that up more.” Let’s also not forget the purpose of asking questions, either, which is to invite another person’s insights and wisdom to come forward. In Coach the Person, Not the Problem, Marcia Reynolds details the technique of “reflective inquiry,” in which a coach reflects what a client says back to the client. This act, when properly used, can be the right spark that yields more insight for a client than even a short, open-ended question could.

Gabe Kwakyi writes The Musing Mind. He also works as a Life and Leadership Coach

And last, but not least, here is my take on powerful questions to ask:

I typically phrase my questions in the moment, depending on what is present in my conversation with my client at that point in time. Having said that, here is one that I particularly like:

“Imagine you look back at your life as a 90 year old. What piece of advice would you give yourself as a gift to help you live your best life today? What might wise old you say to you today?”
Then I would let them talk and ask deepening questions around “What about this is important to you”. “What does this mean to you?” “What else comes to your mind”.
Usually my client will then speak to something that really matters to them. It’s a great place to deepen their insights about values they hold. It allows them to turn these values into resources they can use as a way to find choices in their life that feel right to them.

Another scenario that can often work is asking the client “Can you think of an experience where you are so engaged in doing something that you completely lose track of time?” Another flavor of this question could be “Can you think of an experience that left you completely in awe?” And then again deepening their insight into those moments by asking the “What about this is important to you?” “What does this mean to you?” questions. I watch which words bring a huge smile to their face when they speak and ask more about what that means to them. It’s a great way to find values and perspectives that help a client understand what brings them joy. Once a client is aware, they can use these seeds of joy to intentionally grow them to a lot more joy in their life. Any moment they spend engaged with that joyful energy is one that adds to happiness in their life.

In sincerely hope that you enjoyed reading about this topic from a number of different viewpoints. I always think life is so much richer, when we collaborate and listen to each other’s wisdom. If one of these perspectives speaks to you, feel free to reach out to Raanah Amjadi, Eli Blair or Gabe Kwakyi directly. A way to get in touch with me can be found below.

Photo by Jamie Street on Unsplash

If you would like to explore my questions more: reach out for a free discovery session with me. I coach, speak, do workshops and blog about #leadership, #product leadership, #innovation, the #importance of creating a culture of belonging and how to succeed with your #hybrid or #remote teams.

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