How to Use Challenging Coaching Questions Effectively?

How to Use Challenging Coaching Questions Effectively?

Talyaa Vardar, MA, FCPC, MCC
Talyaa Vardar, MA, FCPC, MCC
Executive Coach, Psychologist & Art Therapist

This blog explores the art of using challenging coaching questions with intention and safely, and constructively during a coaching session. We will also explore how these powerful coaching questions can help your clients, use them and potential situations to avoid. 

A challenging coaching question is a stretching coaching question and therefore they are powerful. These questions might evoke awareness and create an emotional reaction. These types of coaching questions are mostly open-ended. 

Challenging questions are said to serve many ICF Core Competencies along with other benefits like: 

  • Promotes an alternate thought process. 
  • Creates awareness.
  • Catalyzes learning, growth and change.
  • Provides different perspectives. 
  • Helps to reflect. 

Best place to use challenging coaching questions: 

It is highly likely and possible that you have already used these types of coaching questions in your coaching sessions, even if it was not intentional. 

Here are some situations where you are making use of challenging coaching questions; however, it is best to use your judgment as a coach and decide: 

  • To get a client out of the “stuck” mindset 
  • To help to find meaning and purpose 
  • If the client is unaware of their core values

How to make use of challenging coaching questions?

  • Discuss with your client beforehand and ask for permission to ask such powerful questions. These questions might trigger some of the vulnerable areas that the person might have consciously or unconsciously. Sometimes, you might include it in the coaching agreement if you have one as part of your style. 
  • It is essential to make the foundation of trust before you step into challenging coaching questions. 
  • Make use of silence when you use a challenging coaching question.
  • Ask with purpose; make sure to know how the question will benefit your client. 
  • Check-in with the client; you don’t want to make them too uncomfortable. 
  • Know when to retreat, observe verbal and nonverbal signals and know when to take a step back. 
  • Be creative; challenging coaching questions can also be a part of homework for the client. 

Keep in mind that the client might not always answer your question, and that’s okay. 

Some examples of challenging coaching questions: 

  • If you were given an option to change who you are and be reborn as someone else, who would you choose and why? 
  • Why is this important for you?
  • Who are you becoming?
  • Who will you become when you achieve this goal?
  • What three qualities will help you accomplish this goal? What else?
  • If tomorrow was your last day on earth, what are the three things you would like to do before it happens? Who would you like to reach out to? 
  • What questions are you scared of if someone asks you? 
  • Is there any question you wish you knew the answer to? How would it affect your life/situation? 
  • What kind of a person do you want to be remembered as after you pass away? 

Keep in mind that the question is just a tool to use to get your client to reach their desired outcome. It’s not about the question but the answer you receive, 

We hope this blog contributes to your coaching practice and helps you and your client step out of their comfort zone and make it challenging. If you want to learn more about how you can do that safely and constructively, email us now to get more information about our programs; reach us at

Social Share