60 seconds with Jill O’Reilly & Caoilfhionn Buckley

Monday 1 September 2025

Meet Jill O’Reilly & Caoilfhionn Buckley – creating space for curious leaders with their Leadership Book Club.

Tell us about yourselves!

We’re leadership coaches who are passionate about helping leaders show up authentically, grow with confidence, and lead well. We’re also both Women in Business members and our passion for all things leadership – and a shared love of Brené Brown – sparked a friendship and collaboration.

Together, we’ve created the Leadership Book Club – a space for curious leaders to connect, explore big ideas, and put learning into practice.

Give us a brief overview of your career journey so far.

Jill is the founder of O’Reilly People Management, specialising in leadership coaching and development. Her career has been rooted in people strategy and supporting leaders through complexity and change. She runs workshops and coaching programmes that equip leaders to build confidence, lead with impact, and handle difficult conversations effectively.

Caoilfhionn is the founder of Dare to Unlearn, a leadership practice that helps leaders build human skills, resilience, and adaptability to thrive in an AI-driven world. She cares deeply about why people resist change and works with leaders across industries to help them lead with courage and impact.

What brings us together is a shared belief that leadership is about courage, connection, and growth - and that learning doesn’t have to be lonely.

Describe yourselves in 3 words.

Jill: Curious, Supportive, Driven

Caoilfhionn: Thoughtful, Energetic, Grounded

What is one skill that helps you most in your role?

For both of us – listening deeply.

Leadership conversations often hinge on what isn’t being said as much as what is.

What advice do you have for women in your sector/industry/type of role?

Leadership doesn’t mean having all the answers.

It’s about creating the conditions for others to thrive - and being brave enough to show up as yourself.

Are there any exciting plans in the year ahead in your organisation that you can share with us?

Yes! Our Leadership Book Club kicks off this September with The Power of Wonder by Monica C. Parker. We’ll be meeting online, so anyone (female or male) can join from anywhere, and we can’t wait to see where this community grows.

Who has been your biggest career inspiration and why?

We’re both very inspired by Brené Brown – for her courage, vulnerability, and practical wisdom about leadership and life.

If you had to pick your soundtrack song to get you through the working day, what would it be?

When writing this we realised we have more in common than we thought! We both love Motown classics 🎶 – with Aretha Franklin always on the playlist!

What’s your favourite break-time drink?

Jill: A strong coffee ☕ (always!)

Caoilfhionn: Matcha 🍵 (she was drinking it long before the hype!)

How can fellow members keep up to date with you and your organisation?

Connect with Caoilfhionn on LinkedIn & Instagram: @daretodu

Connect with Jill on LinkedIn & Instagram: @jill_oreilly_executive_coach

Want to join our Leadership Book Club?

Here is the link to our WhatsApp group where all the details live.

Monday 1 September 2025