Barbara Cominelli - Moving Beyond AI "Pilot Purgatory" & The "Dare and Care" of Leadership

"Without an AI strategy today, you have simply no strategy."Barbara Cominelli’s resume reads like a masterclass in global tech leadership. Having driven transformation at giants like Microsoft, Vodafone, and JLL, she is now the Executive Chairman of Spindox, steering corporate clients through the complex, and often messy, reality of AI integration.In this episode of Good Company, Michael Wilson sits down with Barbara to explore why so many enterprises are stuck doing endless AI experiments without ever achieving real business value. She shares unfiltered insights on the terrifying rise of "Shadow AI," why true transformation requires both technical and business fluency, and her powerful "Dare and Care" framework for leading people through unprecedented change.The Highlights:Curing "Pilotitis": Why companies are suffering from a disease of having endless AI pilots but zero enterprise scalability, and the fatal disconnect between CIOs and business lines.Beyond the Efficiency Trap: Why using AI simply to cut costs and automate tasks is missing the bigger picture. Barbara explains how to use AI as a true "growth engine" to unbuild and rebuild your business.The "Shadow AI" Epidemic: With up to 50% of employees secretly using unapproved AI tools, Barbara breaks down how leaders must build trust by defining strict "never fail zones" alongside safe innovation playgrounds.AI as the New Interface: A fascinating case study of a major corporation abandoning traditional website navigation for a fully intent-driven, conversational AI assistant that builds curated pages on the fly.The "Dare and Care" Mandate: Why the ultimate responsibility of a leader right now isn't just tech adoption, but managing the human transition; protecting employability, up-skilling teams, and considering the environmental impact of large language models.The "Made in Italy" Edge: Celebrating the Italian tech ecosystem's creativity and rapid problem-solving capabilities, and the critical need to scale AI literacy across the country.The Soundtrack: The story behind her choice of The Police's classic, "Every Breath You Take," and its significance throughout her life."When I wake up in the morning, I say 'Dare and Care'; I want to see them hand in hand. Dare to reinvent the business, and care for the people to make that reinvention possible."Listen now for a masterclass in human-centric AI strategy and transformative leadership.Good Company. Real conversations with interesting people.*