Bio Matthew Holloway is a design executive with more than 25 years of experience leading cross-functional teams to create products, services, and systems that solve complex problems and deliver meaningful business impact. He views design both as a verb—a disciplined, iterative process grounded in customer and market research, systems thinking, and prototyping—and as a noun—the tangible expression of value, whether through the resulting product, service, or policy that creates clarity, value, and competitive advantage. Summary In this conversation, Matthew and Matthew discuss the challenges and opportunities in technology, particularly focusing on enterprise software, generative AI, and the importance of user experience and empathy in business. They explore the hesitancy in investment, the role of automation, and the need for a balance between technology and human agency. The discussion also touches on the significance of understanding user needs and the impact of AI on human interaction. Takeaways Technology can often be a source of frustration. Investment in enterprise software is currently hesitant. Generative AI has potential in business process automation. Data security remains a top concern for companies. User trust is essential for AI systems to succeed. Empathy plays a crucial role in understanding customer needs. Automation should not eliminate human agency. Design should align with business outcomes. Experimentation is key in technology adoption. Understanding the context of use is vital for effective solutions. Keywords technology, enterprise software, generative AI, business process automation, data security, user experience, empathy, automation, design, AI impact
