Saying Yes or No: How Coaching Questions Help You Break Free from Societal Expectations

Have you ever said “yes” to something that didn’t sit right in your gut, just because you thought you were supposed to?

Maybe it was a job that looked good on paper. A relationship that checked all the boxes. A move, a degree, a lifestyle, all chosen because it’s what “success” is supposed to look like.

We’ve all been there. And coaching is one of the most effective ways to figure out why and what to do about it.

The Pressure to Please: Why We Say Yes When We Should Say No

In a world dominated by social media feeds, cultural conditioning, and “shoulds,” it’s easy to lose sight of our own voice.

The American Psychological Association has documented how social comparison is linked to anxiety, poor self-esteem, and identity confusion, especially among young adults and women navigating life transitions. The pressure to conform is real, subtle, and deeply ingrained.

“People spend years pursuing a life that sounds good, instead of one that feels good. Coaching helps strip away the noise.”
— Lucy Avina, MBA, Operations Coordinator at the International Coaching Group

The Coaching Approach: Asking Better Questions

Unlike advice-giving or mentoring, coaching starts with one powerful principle: the answers are already within you. The coach’s role? To help you find them by asking the right questions.

According to Vogt, Brown & Isaacs (2003) and coaching research published by PositivePsychology.com, powerful coaching questions are those that:

  • Invite reflection and self-awareness
  • Surface hidden assumptions
  • Stimulate forward movement
  • Help people listen to their inner wisdom

And most importantly, they help you distinguish between your true desires and the ones society planted.

Coaching Questions That Get to the Truth

If you're facing a decision, or doubting one you've already made, here are some coaching questions that can clarify whether your “yes” is really yours:

  • “What about this feels aligned with who you truly are?”
  • “If no one else had an opinion, what would you choose?”
  • “What belief is driving your ‘yes’ right now?”
  • “What would change if you gave yourself full permission to say no?”
  • “What are you afraid would happen if you stopped trying to please others?”
  • “What does success look like, on your terms?”
“The power of coaching is not in giving people answers. It’s in asking the one question that changes everything.”
— Yedda Stancil, PCC, Executive Coach

Yes, No, and Maybe: Relearning How to Decide

One of the most transformative things coaching teaches is that you don’t always need to explain your “no.” You don’t need a spreadsheet of pros and cons. You need to trust the part of you that knows. That’s often buried under years of conditioning.

In her book Essentialism, Greg McKeown writes, “If you don’t prioritize your life, someone else will.” Coaches help clients not just prioritize, but get honest about whose priorities they’ve been living.

This work is especially powerful for:

  • People navigating identity shifts (e.g., divorce, career change, coming out)
  • Professionals stuck in roles that no longer align with their values
  • Young adults overwhelmed by societal pressure to succeed early
  • Parents and caregivers re-evaluating their purpose

Coaching Helps You Hear Your Own Voice Again

Saying yes to the right things means first saying no to what’s not yours. Through coaching, clients often realize they’re making life choices based on:

  • Family expectations
  • Fear of judgment
  • Old definitions of worth
  • Outdated beliefs about success or gender roles

Unraveling those threads isn’t easy, but it’s the first step to building a life that’s yours.

Final Thoughts: Permission to Choose Differently

What if the only permission you needed to change your life… was your own?

Coaching reminds us that our most authentic “yes” often lives just beyond the fear of disappointing others. It’s in the quiet clarity that comes after asking, “Whose life am I really living?” And once you know that answer, everything changes.

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