27 Focused Questions to Boost Your Clients' Confidence! | By Delaney Tosh CPCC, PCC

Woman shatters concrete to illustrate 27 Questions to Boost Confidence


When you have a client stepping into a new leadership role or taking on new challenges, they may doubt their capabilities or feel their confidence flag. Clients can also get confused about how to be more confident. This isn't surprising. First, there are several dimensions to confidence. Second, there are several myths about how to become confident. Fortunately there is a fresh abundance of research from several angles, such as neuroscience and psychology, to point us in a direction more likely to actually enhance confidence.

A Few Fun Facts From the Research About Confidence:

Things that POSITIVELY Impact our Confidence:

  • Connection to our foundational values
  • Ability to disarm our inner critic and engage our inner sage
  • Externalizing failures
  • Engaging a growth mindset
  • Taking calculated risks
  • Embracing failure as part of the journey
  • Working towards mastery versus perfection
  • Being in action

This is great news for coaches as it's typically the foundation of our work with clients!

And things that NEGATIVELY Impact our Confidence:

  • Pessimistic outlook
  • Listening to our inner-critic and letting self-doubt lead the way
  • Perfectionism
  • Poor self-awareness (about our values, our beliefs, our habits)
  • Over-reliance on external praise
  • Internalizing failures
  • Risk avoidance

This is also great news as we also work with our clients to reframe and find new, more positive approaches in these areas!

Here are 27 Questions to Boost Your Clients' Confidence!

The following questions can help clients explore and accept themselves, help them develop their internal compass and master their leadership presence. Some of these questions are better suited as enquiries for clients to consider over time, and some are great to explore in conversation and can be tweaked as needed as you dance in the moment with your client.


  1. What is the vision you hold for yourself?
  2. What is the vision you hold for this new role/project/challenge?

Inner Resources (Critic & Sage)

  1. Who are you when you give yourself full permission?
  2. What inner critic messages are you listening to and letting hold you small?
  3. What does your inner sage know to be true?
  4. What would be different if you chose to listen to/believe/honour your inner sage?

Beliefs and Values

  1. If you were to let go of X belief, what might be possible?
  2. What new perspectives could you explore/stand in/engage in?
  3. How will you amplify your core value of X today?
  4. Which values can you draw on as you meet this challenge?

Strengths and a Success Mindset

  1. If you absolutely believed that all of life was organized around your success, what would your decision/action be?
  2. Where do you hesitate?
  3. What strengths can you draw on?
  4. What is it to have a growth mindset?
  5. What can you trust about yourself (regardless of external praise)?
  6. How would you grow if this succeeded?

Taking Risks, Learning from Mistakes

  1. What feels like a risk here?
  2. What is a calculated risk you could take?
  3. What if you failed?
  4. What if this plan failed?
  5. How would you grow if this failed?
  6. What is your set-back plan?
  7. What do you want to learn here?
  8. What are you willing to learn?

Thinking Self as Capable and Reframing

  1. What are you most pleased with about your contribution?
  2. How can you reframe this?
  3. What will you take from this going forward?

In Conclusion

Confidence is linked to being able to quickly assess, learn from and move past failures, to leaning into mastery rather than perfectionism, and to fostering a positive self-concept of our capabilities even when challenged.

These above questions are only a few examples that can support clients in boosting their confidence. As you work with clients on confidence enhancement, keep in mind that the research points to confidence being strongly linked to doing. The best doing is being in action - then learning from the outcomes.

The research also shows that whatever you put your attention on grows, so consider how you can help your client focus their thinking on:

  • Their values
  • Their strengths
  • Their wins
  • Their learning
  • Envisioning successes
  • Thinking of self as capable

This is the basis of your roadmap for helping your clients enhance confidence.

If you liked this article on confidence and leadership, you may also like:

Delaney Tosh Headshot

Contributing Author:

Delaney Tosh, CPCC, PCC, coaches women who want to radiate with confidence and thrive as leaders. She helps her clients navigate the hurdles unique to women in leadership and also delivers the Resilience at Work® Toolkit and Resilience at Work® Leader Scale, helping leaders and teams create optimal performance through resilience. She is co-creator of the Phoenix-Hearted Woman retreats and webinars, designed to help women build resilience and strengthen their foundation for being heard and making a difference in the world. Connect with Delaney at SquarePeg Leadership or on LinkedIn.

Learn more about Delaney & see all their articles here >>

Image of Client Confidently Shattering Concrete by Sergey Nivens via Shutterstock


  1. Amal

    Beautiful articles, I questions make you think deeper and explore the beauty and the strength of people and what makes them unique and special...I love it

    • Emma-Louise

      Dear Amal, I am so glad you liked this article. I am sure Delaney will love to hear this too 🙂 Thank-you for taking the time to comment. Warmly, Emma-Louise

  2. Richard Andrew Forde

    Fantastic read, this will help me with a couple of my clients who go to opposite ends of the spectrum when giving presentations. If their confidence is a little low, they either shrink into themselves and go quiet or become too abrasive. This is great thank you.

    • Michela Phillips

      Glad to hear, Laurie! I hope you find ways to implement some of these questions into your practice 🙂
      - Kindly, Michela


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