How to ACTUALLY Implement Zero Trust | Enterprise Tech Playbook

Episode Summary

In this masterclass episode of Enterprise Tech Playbook, host Matt Ashby sits down with Matthew Hackling, Director of Cyber Shield and 25-year cybersecurity veteran, to demystify Zero Trust implementation. They dive deep into the practical realities of transforming enterprise networks from traditional castle-and-moat architectures to modern Zero Trust frameworks.

Matthew shares his real-world experience leading a Zero Trust transformation at an oil and gas company, revealing the critical prerequisites, common pitfalls, and pragmatic strategies that make the difference between success and failure. The conversation covers everything from the business case for Zero Trust to specific technical implementations, with a focus on knowledge workers and gradual, low-impact rollouts.

Key topics include the importance of CMDB data quality, identity governance, microsegmentation strategies, and the shift from VPN appliances to Zero Trust Network Access (ZTNA) solutions. Matthew emphasizes that perfection is the enemy of progress and provides actionable advice for CISOs and IT leaders looking to make Zero Trust a reality in their organizations.

Video Chapters

00:00 - Introduction: The Zero Trust Challenge

Making Zero Trust a reality - moving from theory to implementation

00:28 - Welcome & Guest Introduction

Meet Matthew Hackling, 25-year cybersecurity veteran and Director of Cyber Shield

01:26 - Forging a Leader's Philosophy

"Be honest, do your best, deliver value, you are only as good as your last job"

04:34 - The Business Case: Why an Oil & Gas Giant Invested

Life safety drivers and critical infrastructure protection as catalysts for transformation

11:45 - The Playbook: A Gradual, Low-Impact Rollout

First three tangible steps for implementing Zero Trust without disrupting operations

23:07 - Your First 3 Steps (The Action Plan)

Start with visibility of flows between users and applications

Replace VPN appliances with ZTNA solutions

Focus on crown jewel applications first

33:19 - Lessons from the Field: The #1 Mistake to Avoid

Why "boiling the ocean" kills Zero Trust initiatives and how to avoid it

36:33 - The Future: Advice for the Next Generation of Leaders

Essential skills and certifications for aspiring Zero Trust architects

51:55 - Cybersecurity for Good & Your Next Step

Cyber Shield's mission to protect nonprofits and community organizations

Key Takeaways

✅ Prerequisites for Success:

Quality CMDB (Configuration Management Database) data

Identity Governance Administration solution for crown jewel apps

Clear strategy with defined outcomes

✅ Implementation Strategy:

Start with knowledge worker use cases

Focus on crown jewel applications first

Use monitor mode before enforcement

Drive security ownership to application teams

✅ Technology Stack:

Zero Trust Network Access (ZTNA) to replace VPNs

Microsegmentation for lateral movement prevention

Identity-driven security policies

Security Service Edge (SSE) solutions

✅ Common Pitfalls:

Trying to protect every application equally

Lack of organizational buy-in

Poor CMDB data quality

Treating it as purely a technology problem

Resources Mentioned

Forrester Zero Trust Strategist Certification

Microsoft Cyber Security Reference Architecture

Entra ID Conditional Access Policies

Security Service Edge (SSE) vendors

Connect with Matthew Hackling

LinkedIn: https://www.linkedin.com/in/mhackling/

Website: cybershieldnonprofit.com

About Enterprise Tech Playbook

Empowering IT professionals with actionable wisdom and a collaborative community, making their next stride in enterprise tech one that truly leads with impact.

Subscribe for more deep dives into enterprise technology, cybersecurity, and IT leadership.

#ZeroTrust #Cybersecurity #EnterpriseTech #ZTNA #Microsegmentation #ITSecurity #CISO #NetworkSecurity #CloudSecurity #DigitalTransformation