Jess Kyle

I help people handle hard conversations, be assertive, and set boundaries with confidence and values-based alignment.

5.0(2 Reviews)
Book a session

I'm the CEO of Human First and creator of the Say the Hard Things framework. I work with people who want to navigate difficult conversations with clarity and calm—the kind of confidence that comes from genuinely liking who you are. Self-acceptance isn't just nice to have; it's the foundation for handling interpersonal dynamics with grace.

My approach centers on the idea that when we accept ourselves, we can relax into listening, stay out of defensiveness, and bring the right energy to every interaction. That alignment shifts everything—not just in how we communicate, but in what becomes possible when we move toward greater connection and understanding.

United States
Public Speaking & Communication

Services

One-hour Call

Get guidance on a specific challenge related to interpersonal conflict, setting boundaries, asserting yourself, or cultivating nonjudgment.

1 hour$189
Say the Hard Things

Are you ready to stop avoiding setting boundaries, asserting yourself, and having the conversations you need to have? Say the Hard Things is more than just the right words: It's the work we must do internally to become the type of person who can navigate any interpersonal interaction in a way we can feel proud of - with clarity, compassion, and confidence. This is a 3-SESSION package. In the first session, I will send you a private link to book the other sessions.

1 hour$527
Discovery call

Let's learn a little bit about each other and determine whether my services are a good fit for your specific needs!

30 minFree

Endorsements

Lila Galipeau

Founder at Partnr Media

When my therapist told me to do an assertiveness training I didn't know where to look. I found Jess in a networking group I'm part of and am so glad I did! I feel so much more comfortable having hard conversations now with the frameworks she gave me. What I appreciated most was how BS free her approach is and how efficiently I was able to improve my skills and come to some major realizations with her guidance. Thank you, Jess!

Service provider

Reviews

Average rating5.0
Total reviews2All time
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Shannon Hill

Verified

4 weeks ago

Jess is one of those people that immediately makes you feel like you've known her for years, even if you just met. She has a gift in balancing directness with compassion, which was so helpful to set the space and tone of the work. She teaches how to engage more effectively by first helping you improve how you engage with yourself. Everyone should have a session or several with Jess, but you especially should if you're struggling with saying the things you know you need to say. Book it.

Afton Negrea

Verified

7 weeks ago

I loved my call with Jess. She made me feel instantly at ease and she listened closely. Her insights on setting boundaries in the workplace were really helpful as I navigate a difficult situation in my work. Book some time with her if you're also struggling with how to have difficult conversations—and perhaps how to feel truly human again.