Helping People Rediscover The Joy of Genuine Connection in a Disconnected World
Cheryl Dillon brings warmth, humor, and genuine insight to every stage, screen, and conversation she’s part of.
What Audiences are Saying
Cheryl’s talk on the Power of Genuine Connection was one of the most fun and interactive presentations we’ve had at Rotary. She has a rare ability to speak straight to the heart – her humor, authenticity, and practical wisdom left me with a new perspective on how I show up in my conversations. I’d recommend her to any group looking for a speaker who helps people truly connect while having fun doing it.
I’ll be honest, when Cheryl started leading us through some of the exercises, I wasn’t sure what to expect. It felt a little outside my comfort zone at first. But once we got into it, the value became crystal clear. Two months later, I’m still using what I learned that day in my conversations.Cheryl has a gift for making practical, meaningful skills genuinely accessible, and even fun. I’d recommend her to any group that wants to walk away with tools they’ll actually use.
Cheryl’s presentation was fabulous – engaging, practical, and honestly a lot of fun. She gave us real tools for going beyond surface-level chatter and building genuine connections, from how to ask better questions and remember the details that matter, to how to gracefully exit a conversation with someone who can’t stop talking about themselves.
I made a new connection right away during the exercises. If your organization is looking for a speaker who is warm, funny, and genuinely changes how people interact with each other – invite Cheryl.
Cheryl’s presentation was both inspiring and immediately practical. She walked us through several techniques for remembering names and personal details – the kind of tools that actually change how you show up in a conversation.
I left with specific strategies I’m already putting to use.
Bringing Connection to Life
Connection Experiences
Many events bring people into the same room, but meaningful interaction rarely happens on its own. Guests stay with people they already know, exchange a few polite words, and leave without ever connecting with anyone new.
Cheryl changes that – designing and facilitating experiences that turn a room full of strangers into a room full of people who actually talked to each other, laughed together, and left feeling genuinely energized.
The result is a more memorable event – one that keeps guests engaged and leaves a lasting positive impression of the host, organization, or brand behind it.
These experiences work especially well for:
- Conferences and professional gatherings
- Networking events
- Corporate retreats and team gatherings
- Community gatherings
- Business or brand launches
- Member-based organizations
- Parties and social events
Podcast Interviews & Conversations
As a speaker on genuine connection and friendship, Cheryl enjoys thoughtful conversations about how we build meaningful relationships – with ourselves and with others – during life’s many transitions.
Her warm, relatable storytelling and practical insights resonate with audiences navigating changing priorities, evolving identities, and the question many midlife women quietly ask themselves, “What’s next?”
Topics often explored include:
- Why real friendship in midlife is harder than most women expect – and what actually changes everything.
- The connection between how you treat yourself and the quality of your relationships with others.
- What it actually takes to build genuine friendships as an adult – and why good intentions alone don’t cut it.
- How to navigate life’s biggest transitions without losing yourself in the process.
- What a truly Funderful midlife looks and feels like – and how to start living it now.
Featured Conversations
The Midsters
Carlsbad Chamber of Commerce: People, Purpose and Impact
Connected Hearts in Carlsbad: Creating Deep Friendships in Midlife
Reinvention Real Talk
Radiantly Rooted with Rachel
The Secret to Deeper Connection in Midlife, Starting with You
Her Comeback
Not Your Mother’s Midlife Crisis
Key Points in the Divorce Process Through Mediation & Coaching
