Redefiners Podcast – Episode Summary
Transformation in Turbulent Times with Former Telstra CEO Andy Penn
Date: February 25, 2026
Hosts: Marla Oates (A), Dr. Tomas Chamorro-Premuzic (B)
Guest: Andy Penn (C), Former CEO, Telstra

Episode Overview

This episode of Redefiners features Andy Penn, the former CEO and Managing Director of Telstra, Australia’s leading telecom company. The conversation focuses on leading large-scale transformations during challenging times, drawing on Penn’s unconventional career path from CFO to CEO and highlighting his expertise in digital and business transformation, culture change, and cyber risk management. Listeners gain practical advice on leadership, overcoming organizational inertia, and navigating the complexities of AI and cybersecurity in today’s business landscape.

Key Discussion Points, Insights & Timestamps

1. Andy Penn's Unconventional Leadership Journey

• Andy left school at 15, started as a shipping clerk in London with a humble salary, and supplemented his income with a second job. He later completed his education through evening classes and ultimately built a career that led to C-suite roles in two major industries.

  • Quote [03:00]:

    "I dropped out of school when I was 15... My first job in London was as a shipping clerk... I had to get a second job to supplement my income... But I found motivation at work and then took myself back to evening classes." – Andy Penn

• His foundation in finance served him well but his curiosity drew him into broader management and strategy roles.

  • Quote [04:30]:

    "I've always then tried to push myself to move more into management and strategic roles... finance and accounting has always been a great and solid foundation." – Andy Penn

• Transitioning from CFO to CEO was a “bigger step than you anticipate,” especially regarding stakeholder management and organizational complexity.

  • Quote [05:31]:

    "Moving into the CEO role... is always a bigger step than you anticipate... being self-aware enough to know that you’ve got a lot to learn, even if you make the transition through that pathway, is super helpful." – Andy Penn

• Advice for CFOs aspiring to be CEOs: Leverage the holistic business perspective finance offers, but be ready for the expanded scope, especially stakeholder engagement.

2. Lessons from Leading in Multiple Industries [06:07]

• Andy highlighted both transferable leadership lessons and the necessity of quickly learning industry-specific details, especially given today’s deep specialization.
  • "How do you take what I know and what I've learned and then apply it in a new sector? But then how do I take the time to actually learn the new sector? ...the degree of specialization...is pretty important as well." – Andy Penn [07:21]

3. Transforming Telstra: Diagnosing and Tackling the Real Problem [07:42]

• Upon taking over as CEO of Telstra in 2015, Andy faced multiple crises—customer complaints, outages, regulatory issues—but traced them back to a core lack of business and digital transformation.

  • Quote [08:07]:

    "...fundamentally, the organization had not really tackled an upgrading and transformation of its core business..." – Andy Penn

• Telstra’s response to industry disruption had been to pursue adjacent opportunities instead of confronting transformation head-on. This diluted focus.

• The transformation needed wasn’t just digital, but a radical simplification of business operations.

4. Business Simplification: The Key to Digital Transformation [09:14]

• Digital transformation often fails because companies try to fix systems without confronting the underlying business complexity.

  • Quote [09:37]:

    "Most digital transformations fail because people believe the problem is the systems. It doesn’t originate in the systems, it originates in the complexity, in the way in which we’ve chosen to do business over many, many years." – Andy Penn

• Example: Telstra simplified its 1,800 customer plans down to just 20, leading to dramatic gains.

  • NPS up 20 points, costs down 40%, 90% fewer calls, 50% fewer complaints, market and profit gains.
  • Quote [10:20]:

    "We simplified... from 1,800 plans to 20... Our NPS went up 20 points, costs came down 40%, 90% reduction in calls... 50% reduction in complaints... win-win for everyone." – Andy Penn

5. Overcoming Resistance to Change and the Power of Agile [10:40]

• Resistance to change often materializes as the “withholding of resources”—money, people, or emotional energy—but not openly.

  • Quote [11:18]:

    "...resistance to change... actually the withholding of resources... By resources, I mean money... people... emotional energy." – Andy Penn

• Implementing Agile as a systematic approach to force resource alignment and break functional silos enabled transformation.

  • Quote [13:05]:

    "We implemented Agile... the Agile system effectively controls that process, it controls the allocation of resources..." – Andy Penn

6. Building the Right Culture and Senior Team [16:40]

• Culture isn’t a parallel project—it’s reflected in day-to-day actions and business decisions.
  • Quote [17:02]:

    "Culture is a function of the things that you do and say every single day. It’s not some abstract sort of concept... culture is a manifestation of how you do business." – Andy Penn

• Getting senior leadership right is about openness, trust, and consistently working on relationships—"culture is like a marriage."
  • Quote [18:34]:

    "It requires a lot of work. It requires a lot of openness or honesty, authenticity... culture's like a marriage. Got to keep the communication going." – Andy Penn & Marla Oates

7. AI Transformation: Lessons and Governance [19:11]

• AI’s promise is real, but relies on simplified digital foundations.

  • Quote [19:11]:

    "If you don't tackle [digital simplification]... it makes the job of leveraging AI much harder." – Andy Penn

• Companies expecting to build AI capability organically are likely mistaken; upskilling and/or outside help are needed.

• Ethical governance is critical: AI is literal (“it won’t check if the answer is right or ethical”) and must not be a black box; organizations must ensure explainability and test for ethical impacts.

  • Quote [20:40]:

    "AI is literal... you need to cater for that. And then secondly, AI can be a black box, or rather you cannot afford to let it be a black box." – Andy Penn

8. Cybersecurity Resilience for Business & Nation [21:48]

• As Telstra’s CEO, Andy was responsible for Australia’s critical national infrastructure, seeing firsthand the rise in cyber attacks.
• Cyber risk management, he argues, is like any other risk—there’s no silver bullet, and total elimination is a myth.
• Andy’s Four-Point Cybersecurity Plan:
  1. Inventory all digital assets—know exactly what you must protect.
  2. Prioritize asset protection—a differentiated approach based on sensitivity/importance.
     • Quote [24:17]:

       "Some things are more important than others... you could take a different approach to protecting sensitive data versus a Netflix account." – Andy Penn

  3. Crisis planning and simulation—prepare before a crisis hits; scenario testing must be visceral to be effective.
     • Quote [25:16]:

       "The worst possible time to develop a crisis response plan is in the middle of a crisis... the more visceral you can make that, the more the learnings stick." – Andy Penn

  4. Stay vigilant—what’s safe today may not be safe tomorrow. Monitor emerging threats like quantum computing.

9. Leadership Philosophy, Career Reflection & Advice [28:22]

• The move from financial services to leading in a technology-driven business was transformative.
  • Quote [28:34]:

    "The factor that's had the biggest impact on business... the last 40 years has been technology and it's the most underestimated in terms of potential impact." – Andy Penn

• For future leaders: focus on technology, as its significance will only grow.

Memorable Rapid-Fire Answers [29:49]

• Favorite way to decompress: Painting (the artistic kind).
• Language to be fluent in: Spanish (currently learning).
• Success in five words or less: “Making a positive contribution.”
• Favorite interview question:

  “Think of a time in your career when you were really happy...what was going on? Who were you working with? What were you working on?”
  Motivation is key and cannot be taught.

• Childhood nostalgia item: Camping holidays in the south of France with family.

Notable Quotes & Highlights (with Timestamps)

• "I've always been inspired to learn new things and learning new industries has been one aspect of that." – Andy Penn [06:21]
• "Do not fall into the trap of thinking a digital transformation is just changing your systems unless you do a major business simplification first." – Andy Penn [10:05]
• "If you say diversity is important, but your daily business decisions don’t support it, you’re sending a different message." – Andy Penn [17:32]
• "There is no internet without a telecommunications network... you basically are responsible for the network where most malicious cyber activity is actually going." – Andy Penn [22:25]
• “What is safe today may not be safe tomorrow... quantum computers are not that far away.” – Andy Penn [27:13]

Tangible Takeaways for Leaders

• Transformational change starts with business simplification, not tech fixes.
• Organizational resistance hides in resource allocation, not outspoken opposition—align resources through systems like Agile.
• Culture is daily practice, not side projects; it requires constant, open work—especially among senior teams.
• AI and cybersecurity strategies must be grounded in business fundamentals and ethics, not just technology.
• There’s no shame in unconventional paths—curiosity, resilience, and lifelong learning pay off.

For more insight-packed leadership dialogue, find all Redefiners and Leadership Lounge episodes on YouTube and your preferred podcast platforms.