The Mistakes That Shaped Me

What happens when you’re running at 150 miles per hour but the people around you can’t keep up?In this candid conversation, AI advisor and CX leader Simon Kriss opens up about the career-defining mistake that blindsided him, moving too fast for his team and leaving them struggling in his wake.From the high-pressure world of airlines to advising organisations on the future of AI, Simon shares:How a “strategic misfit” conversation with his boss changed everythingWhy leaders need to go beyond the “Are you okay?” surface check-inHow to spot the quietest person in the room and why their voice matters mostThe strategies he uses now to keep teams aligned while still moving at speedIf you’ve ever wondered whether you’re bringing your team with you or just dragging them along, this episode is essential listening.About Simon Kriss:Simon is an AI advisor helping organisations navigate the fast-changing world of artificial intelligence. With decades of leadership experience in CX, he brings a unique blend of strategic insight and people-first thinking.Apply for your place at Ashton Media's Contact Centre 2026:

If inaction is a decision, how do you explain it? In this thoughtful and candid conversation, Rajan Kumar, CEO & Co - founder of The Lumery, shares the leadership misstep that shaped him most: not acting quickly enough, and more importantly, not explaining why.From transparency traps to communication preferences (are you yellow, green, blue, or red?), Rajan dives into the psychology behind trust, culture, and the misunderstood power of slowing down before speeding up.If you lead a team or want to, this episode is a goldmine of insight into leading better by being more human."Inaction is still a choice. But if you don’t explain why you’re choosing it, people will make up their own reasons."Marketing Tech Symposium | 9-10 September NSWMarketing Tech Retreat | 9-10 October VICThe Grey Podcast

Our host Thomas Haffenden sits down with Anna Jackson, Head of Creative Excellence at Telstra, for a raw and refreshingly honest conversation about trusting your gut, letting go of “the shoulds,” and taking the scenic route to a fulfilling career.Before leading Telstra’s creative vision, Anna was on a very different path, training as an architect in one of the toughest degrees you can do. But a brutally hard year working in London forced her to confront a truth: she was in the wrong profession. That so-called “mistake” became the first step into a whole new world of creativity, storytelling, and leadership.They discuss:How a chance encounter in a Kings Cross nightclub led her to advertisingWhy kids make the best critics (and sometimes the best boardroom consultants)The power of making decisions with your gut, even when it makes no sense on paperBuilding trust to take creative leaps in large organisationsWhy you should audit your life as often as your carThe leader who changed her career trajectory The role other people play in helping you find your place, and why job descriptions are often BSThis one’s for anyone who’s ever felt stuck, misaligned, or on the wrong path. Anna’s story is a powerful reminder that it’s never too late to pivot and that the best careers are often built on the boldest decisions.

Leadership Is a Muscle – And Tough Conversations Are the Workout with Stephanie Walters, Customer Experience Head for Contact Centres at EmiratesIn this episode, Stephanie reflects on a pivotal leadership mistake: avoiding the difficult conversations.With decades of experience managing global contact centre teams and millions of customer interactions each year, Steph knows that delivering great CX starts from the inside out. That means leaders have to create cultures of safety, accountability, and, yes, honest feedback.She shares how she learned (the hard way) that shying away from uncomfortable conversations can fracture trust and stall team performance. And why facing them, with empathy and courage, is the key to building teams that thrive.You’ll learn:Why leadership behaviour is the blueprint for team behaviourHow to build psychological safety without dodging the hard stuffThe difference between feedback that’s kind and feedback that’s just niceHow emotionally intelligent conversations become easier with practiceThis episode was recorded onsite at the Contact Centre Symposium. The leading conference for Senior Contact Centre leaders in NSW.Apply for your place for 2026 now: https://ashtonmedia.com.au/symposiums/contact-centre-symposium/

Work, Worth & the Grown-Up Gap Year with Samantha Ezra, Principal of CX Strategy at TelstraIn this honest and deeply reflective episode, I’m joined by Samantha Ezra, Principal of CX Strategy at Telstra, to talk about the trap so many of us fall into tying our worth to how hard we work.Samantha shares the story of pouring everything into her career, believing hard work would earn her equal treatment and recognition. But when she finally stepped into the room she’d worked so hard to reach, she was met not with respect, but a patronising, “Sweetheart, how old are you?”We dive into:The moment she realised work is not family, it’s businessThe emotional cost of putting all your eggs in one basketWhy working harder isn’t the same as working betterThe opportunities she missed while chasing validationTaking a “grown-up gap year” and reconnecting with herself through travelHer advice to everyone: Travel, travel, travel and get perspective beyond the jobThis episode is a must-listen for anyone who’s ever lost themselves in their work. It’s a reminder that life is bigger than your job title, and that sometimes the bravest thing you can do is step away to come back stronger.

In this episode, Tomas Haffenden sits down with Toby Ellis, Head of Customer Service at AMP, to explore a pivotal leadership lesson from early in his career and how it shaped the way he leads today. From building high-performing teams to driving innovation through grassroots engagement, Toby shares practical insights, career reflections, and the values that guide both his corporate and community work. Key Topics Discussed: The importance of setting clear expectations Fostering innovation through hackathons and frontline insights Why ambiguity can erode trust and slow progress Creating a culture of “freedom within boundaries” The story behind Deadly Rugby and its mission to create real social impact Resources Mentioned: Learn more about Deadly Rugby and how to get involved here https://www.deadlyrugby.com.au/The podcast is brought to you by Ashton Media, the organisers of ANZ’s leading events for senior leaders across the marketing, customer experience, HR and L&D industries. For more information on our events and how you can be involved, visit https://ashtonmedia.com.au/symposiums/ And to continue to conversation with your CX and contact centre community, follow our Customer Collective by Ashton Media page on LinkedIn here https://www.linkedin.com/showcase/am-customer-collective/

The cost of staying silent versus the power of speaking up with Jacquie Alley, Chief Operating Officer at The Media Store, and hosted by Tomas Haffenden. Jacquie Alley has worked in the advertising world for over 25 years with one main goal: to leave the industry a better place than when she found it. She’s passionate about people and purpose and has had a brilliantly successful career, but for years she made the mistake that so many of us make: staying small. That is until she realised that her voice mattered, and that she could use it to not only supercharge her career but move the needle for others too. In this candid conversation, we cover:What happens when you really listen to others, and yourselfThe cost of staying silent Vs the power of finally speaking upThat electric feeling when you find your passion and act on itThe work (and reward) of getting more women into leadershipWhy amplifying women's voices isn’t just important, it’s essential This podcast is brought to you by Ashton Media – the organisers of ANZ’s leading events for senior leaders across the marketing, customer experience, HR and L&D industries. For more information on our events, including the exciting Future Media Forum, and how you can be involved, visit https://ashtonmedia.com.au/symposiums/ And to continue to conversation with your marketing and advertising community, follow our MadTech Collective by Ashton Media page on LinkedIn here https://www.linkedin.com/showcase/am-madtech-collective/

Navigating leadership, motherhood and defining your worth with Amy Murrell, Chief People Officer at Rest Super, and hosted by Tomas Haffenden. Amy Murrell spent much of her early career thinking that she could have it all, but what came was a realisation that if you’re succeeding in one area of your life, you’re almost certainly failing in another. In this candid conversation, we cover:Navigating your career as a new parentThe impact of other’s opinions on your self-worth and the importance of backing yourselfLessons from bad leadership and what to look for in who you work forThe questions you need to ask to ascertain whether a role is the right one for you This podcast is brought to you by Ashton Media – the organisers of ANZ’s leading events for senior leaders across the marketing, customer experience, HR and L&D industries. For more information on our events and how you can be involved, visit https://ashtonmedia.com.au/symposiums/ And to continue to conversation with your HR community, follow our PeopleX by Ashton Media page on LinkedIn here https://www.linkedin.com/showcase/am-peoplex-collective/

Burnout, Business and Bravery with Nyssa Packard, Senior Director of CX at Skyscanner, and hosted by Tomas Haffenden.Nyssa Packard has always believed in the goodness of people. From McDonald's to Danone to Booking.com, she climbed the corporate ladder with an open heart. But after a decade, she left it all behind to chase her entrepreneurial dream.What followed was a journey through the highest highs and lowest lows – one that pushed her to illness, forced impossible choices, and taught her the hardest lessons about trust, boundaries, and survival.We cover:The importance of happiness in your workplace environmentThe potential life-threatening implications of burnoutRole modelling vulnerability as a leaderNavigating work and life as a self-proclaimed perfectionistThis podcast is brought to you by Ashton Media – the organisers of ANZ’s leading events for senior leaders across the marketing, customer experience, HR and L&D industries. For more information on our events and how you can be involved, visit https://ashtonmedia.com.au/symposiums/And to continue to conversation with your CX community, follow our Customer Collective by Ashton Media page on LinkedIn here https://www.linkedin.com/showcase/am-customer-collective/