Debra Chantry-Taylor:
Clarity Through Chaos
After a devastating business failure, Debra found herself unemployed, bankrupt, and pleading for government assistance in a pinstripe suit. But that wasn’t the end of her story—it was the start of something deeper.
Bio
Certified EOS Implementer | Family Business Advisor | Visionary Entrepreneur
I don’t just teach EOS. I live & breathe it. I use it in all three of my own businesses & have helped 100+ Kiwi & Aussie companies implement it too. I work with entrepreneurs & family business owners to build companies that are scalable, sustainable & ultimately saleable — whether they plan to grow, pass it on, or step away.
Many business owners reach a point where the business feels stuck. The team isn’t aligned, the vision is fuzzy, & they’re working harder than ever without the same results. That’s where I come in.
I work with leadership teams to:
- Get clear on their vision using simple, powerful language
- Create traction through focus, rhythm & accountability
- Build healthy, functional teams who actually enjoy working together
I specialize in private & family-owned businesses where the personal often collides with the professional. These environments are complex, emotional & deeply personal. I use EOS tools alongside the Harvard 3-Circle Family Business Model to help teams make better decisions, with less drama & more clarity. I bring calm, curiosity & structure to messy dynamics.
My style is direct, practical & no-nonsense. But I’m also empathetic, fun & people-focused. I’m not a consultant who tells you what to do. I’m a facilitator, coach & teacher who asks the right questions so you & your team find your own best answers. I’ll challenge you kindly, hold space for tough conversations, & help you make real progress.
Outside of work, I love nature, fast cars, electric bikes, photography & travel. I’ve won trophies in horse riding, go-karting, dog agility & tennis. I speak three languages (not fluently, but fearlessly) & I’m always learning something new.
My 3 uniques:
1. No fluff. Just real-world leadership experience
I’ve built businesses, led 220-person teams, survived failures & created wins. I get straight to the point & help you move forward fast.
2. Certified EOS Implementer with high-challenge, high-support energy
I bring clarity, energy & momentum. I’ll support you, but I won’t let you hide. I ask the tough stuff because I care.
3. Specialist in family & multi-owner business dynamics
I help navigate emotional complexity with practical tools. You’ll gain structure, better communication & stronger relationships.
This is why my clients get real results! 💖
Topics
- How to come back after total business failure
- What forced clarity breaks can teach entrepreneurs
- The emotional toll of entrepreneurship—and how to survive it
- Merging businesses: what no one tells you
- Navigating grief while running a business
- How personal loss reshaped my business philosophy
- Why market validation sometimes fails (even when you know better)
- Learning to let go: business identity and ego
- Self-worth after failure: rebuilding belief in yourself
- Creating entrepreneurial spaces that support the whole human
Guiding Questions
- Can you take us to the moment you found out about the tax debt?
- What was it like walking into Work and Income New Zealand in your suit that day?
- What limiting beliefs did this experience reinforce—and how did you move past them?
- How did you emotionally process letting your team go?
- What did you learn from the first business collapse that you took into your second venture?
- How did the deaths of your brother and mother shift your priorities in business?
- What exactly changed in your business model after that “forced clarity break”?
- Why do you think entrepreneurs often struggle to let go—even when something clearly isn’t working?
- Can you talk about the role grief played in your clarity and decision-making?
- What advice would you give to someone who’s hit rock bottom but isn’t ready to give up?