Coaching Questions You Should Always Ask

Powerful Thought-provoking Coaching Questions You Should Always Ask Your Clients

Great coaching practice starts with asking the right questions. You need to understand how your clients think, what they are struggling with to be truly able to help and impact their development.

Questioning is a great tool that helps you build trust and rapport with your clients, spurs learning, and exchange of stories and experiences.

There are 3 benefits that you get from asking the right questions:

  1. It helps you uncover problems or challenges that your client is facing, but they are not really aware of them
  2. It provokes an “a-ha” moment that leads to improvement and growth
  3. It helps you learn more about the client and helps you adjust the coaching program to their specific needs

The ability and skill to ask the right, effective, thought-provoking questions is the main characteristic of a great coach.

We have talked with over 20 coaches from different backgrounds and ways of coaching, and we asked them about their favorite questions and why they ask them. We grouped the questions into 3 categories:

  • Personal development questions
  • Business coaching questions
  • Questions that can fall under both categories – personal and business

We hope that the questions that we list below will help you hone in your question asking skills and develop your coaching skills even further.

Personal coaching questions

Henna Inam UpCoach

Henna Inam

Henna helps leaders thrive in disruption as an Executive Coach, Board Director, Author and Speaker.

How can you step into your most inspired and purposeful self in this challenging time?

joshua gross

Jordan Gross

Author of “What Happens in Tomorrow World?” Publishing Spring 2021, BenBella Books, Matt Holt Books

Why do you think there is a gap between who you are and who you could be?

Why do you think you are holding on to your past and not using it to redefine your future?

Moe Carrick

Best-Selling Author, Consultant, Relentless Optimist, and Bee Keeper // Is your organization fit for human life?

What is the story you are telling yourself about this?

Melissa G Wilson

President of Networlding, a turnkey book-creation firm and a 5-Time Bestselling Author

What’s the best question you have ever been asked and why?

Alex Salkever

Experienced Product, CMO and Product Marketing Executive, Award-Winning Author and Writer, Father, Coach, Sometime Futurist

How does it make you feel?

Sanjiv Sidhu

Sanjiv Sidhu is a software entrepreneur known for founding i2 Technologies, a supply chain management software company, and o9 Solutions, a Dallas, Texas-based company that offers a decision management platform for multinational corporations.

When did you notice it first?

Angela M. Odom

CEO at The Better U Project I Serving Women Leaders, experienced coach, author, and public speaker

And then what happened? And now what?

Todd Herman

Author of bestseller book “Alter Ego Effect”

If a good friend was faced with the same (problem/challenge/situation/decision), what advice would you give them?

Todd Herman with this question can get his clients to disassociate from their own feelings or emotions and think more clearly.

Christian Roach

Exercise Specialist, Fitness Educator and Author of Becoming Superhuman

What evidence do you have to form that belief?

Who can you seek out that has the opposing belief?

What would the best version of you do in this situation?

Rather than focusing on material things you want. What traits do you need to acquire to become the person you want to become?

What would be the worst-case consequences of not doing X?

What would be the best case consequences of doing X?

If you could build a team of five people from any point in history (dead or living) to help you achieve your potential, who would be on it and why?

Christian Roach has a set of questions that he goes through to understand the client better, what their beliefs, what led them to have those beliefs and to discover if those beliefs are limiting and what can be done to change those beliefs.

Business coaching questions

Nina Cooke

Nina Cooke

Nina Cooke is a Business Growth Mentor, helping entrepreneurs to release their deep inner blocks so they become motivated action-takers to significantly growing their income, impact and downtime.

She hosts Entrepreneur’s Inner Game Podcast, and has been featured in Forbes, and on BBC Radio.

How’s this last month been for you?

Nina Cooke uses this question to get her clients to focus on what’s going well and what needs to change in order to create significant momentum in their business growth.
Anke Herrmann

Anke Herrmann

Passion business coach & online tech mentor. Podcast host and author.

What was your biggest insight or takeaway today?

What was most valuable for you today?

Anke loves these questions because they get her clients to reflect and become a lot more conscious about what they got from their session. It also helps her see what did and didn’t “sink in”.

Erik Luhrs

Erik Luhrs is known as the Bruce Lee of Revenue Generation, and is the creator of Revenue Kung-Fu.

Why are you?

Erik knows that the success of a business is driven by the Founder’s vision and energy for the company. The more closely the Founder can get to his/her core self, the more they will tap into their passion and unlimited potential. This question opens a huge loop inside their mind and forces them to go beyond the standard “who are you?” and “why are you here?” questions into the void, where the answers become more feeling and less logical.

Michael Roderick

Michael Roderick is the CEO of Small Pond Enterprises which helps thoughtful givers become thought leaders by making their brands referable, their messaging memorable, and their ideas unforgettable.

What are the feeders, funders, and fillers in your business?
Which activities feed you new opportunities, prospect conversations, and press?
Which activities fund the business?
And Most importantly which things neither feed or fund and are just filler?

Michael always asks his clients these 4 questions, because many times they are spreading themselves too thin and not asking which activities are relevant to their goals. These questions help them nail down which things to focus on and which things to potentially get rid of or dial down.
Cloris Kylie

Cloris Kylie

Cloris Kylie, MBA, is the bestselling author of Beyond Influencer Marketing and host of “Beyond Influencer Marketing” podcast. She helps service entrepreneurs grow their business by building long-lasting connections with influencers.

How is this (project/task) helping you move your business forward?

Cloris Kylie asks this question because one of the most important keys to success in business is focus. It’s very easy to get distracted by “shiny objects” and unnecessary commitments. “If we know how to manage our time so that everything we do is aligned with our end goals, we will be successful. So, anytime I say yes to a project, I asked myself that same question!”

Personal and business-related questions

Kristin Swanson

Kristin Swanson is a coach and consultant who helps service-based entrepreneurs create consistent revenue by expanding their reach.

What would you do if you knew you could not fail?

Kristin Swanson asks these questions because they get straight to the heart of what they really want to manifest in their life or business.

Jerry Phillips

Consultant, Author, Speaker at NineRuns. Jerry help companies who want to improve their sales team revenue and profit

What does success look like 12 months from now?

Danny Iny

Danny Iny is a leading voice in the world of online courses. He has been featured or contributed to publications including the Harvard Business Review, Entrepreneur, Inc., Forbes, and Business Insider, has spoken at places like Yale University and Google, and is the author of books including Teach and Grow Rich, Leveraged Learning, and most recently Teach Your Gift.

What are we solving for?

Danny Iny aks this question so he can focus the conversation on the core of what they are trying to accomplish, rather than staying in the weeds of details that often don’t matter.

Rennie Gabriel

Rennie Gabriel is a CLU and CFP who donates 100% of his coaching and program profits to a charity that saves two lives at a time ( His award-winning, best-selling, book Wealth On Any Income has been translated into eight languages.

What are at least three results you want to produce out of our conversation? Which is the most important one if you could only achieve just one?

Rennie Gabriel’s goal with aksing these coaching questions is to prioritize clients’ goals and focus on the most important ones.

Michael Zipursky

Michael Zipursky is CEO of Consulting Success®. He has advised organizations like Financial Times, Dow Jones, RBC, Omron, Sumitomo and helped Panasonic launch new products into global markets, but more importantly, he’s helped over 400 consultants from around the world in over 50 industries add six and seven figures to their annual revenues.

WHY are you doing what you’re doing?

Michael Zipursky loves this question because, when people start doing something new they venture into uncharted territory. That can bring fear, anxiety, and overwhelm. That resistance is what holds people back from moving forward and taking the action that will create the result they want. When they are clear on WHY they are doing what they’re doing it can jump-start them to push past the resistance, to take the necessary actions that create the results they want.


There you have it, more than 20 different questions and approaches that our participants use to spark conversation with their clients. Find out more about their main problems and help them find the right solution that will bring them closer to their end goals.

Whether you are just starting with your coaching career, or you are a veteran in the business and you would like to provide your clients with the best coaching experience, check out our group coaching platform.

Picture of David Henzel
David Henzel
I’m CEO of UpCoach and a serial entrepreneur. I’m passionate about helping entrepreneurs and executives to find success and harmony in business and in life.
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