Leadership, Untangled

Episódios

• When AI Makes a Five-Year Business Plan Impossible | Keith Mackay 15.06.2026 48min

  Keith MacKay has spent 35 years inside the software economy as a CTO, founder, board advisor, and teacher, and now advises private equity and corporate clients as Managing Director of the Software Strategy Group at EY-Parthenon. In this conversation with Blaire, he breaks down what's actually happening when investors try to put a value on a software business in a world where AI capabilities are improving by roughly 40x a year, and a five-year hold period now spans a timeframe that's almost impossible to model with any confidence.The conversation moves well beyond investment strategy into something every leader needs to think about. Keith makes the case that the people having the most success working with AI aren't necessarily the most technically gifted, they're the ones who can communicate clearly, break problems into pieces, and hold context across a conversation. He also gets into why AI adoption is tracking almost exactly the same curve as cloud computing, why treating AI as a cost-cutting tool rather than an augmentation tool tends to backfire, and what the coming squeeze on token economics might actually mean for how organisations make better decisions about where AI is really adding value.AI capabilities are improving at roughly 40x year on year, making five and seven-year investment horizons almost impossible to plan around with confidenceOlder developers are outperforming younger ones with AI tools, because the skill that matters most is being able to clearly describe and break down a problem, which is a management skill, not a coding skillThe waterbed problem: accelerating code writing with AI just pushes the bottleneck into testing, deployment, and change management"It's never technology, always psychology" — accountability can't live inside an AI, and organisations that forget that create expensive problems downstreamContext is everything: AI has no memory between sessions, and in long sessions the quality of responses degrades as earlier information falls out of the context windowAI adoption is following the same curve as cloud, including the early phase of spectacular, unanticipated costs before cost controls catch upThe organisations getting it right are using AI to augment human judgment, not replace it — particularly in roles that require handling a wide range of problems or situations that demand accountabilityConnect with Keith MacKay:LinkedIn: https://linkedin.com/in/keithmackaySubstack: https://tlcmentor.substack.comMedium: https://medium.com/@keithwritesIf this conversation sparked something for you, subscribe so you don't miss the next episode. And if you know a senior leader navigating AI, change, or what it means to lead differently right now, share this with them.I hope you enjoy this episode! Give it a like, share, and subscribe to not miss the content coming your way weekly.- Blaire and the Leadership, Untangled podcast teamConnect with Blaire Palmer on LinkedIn: https://www.linkedin.com/in/blairepalmer Visit the That People Thing website here: https://www.thatpeoplething.comListen to Leadership, Untangled on these podcast platforms: Spotify: https://open.spotify.com/show/033yHMeN64GTZsBAVJ0NsUApple: https://podcasts.apple.com/podcast/leadership-untangled/id1896928199Amazon Podcasts: https://music.amazon.com/podcasts/a5f7fe3a-2c0d-4d29-971b-22665b976c1a#LeadershipUntangled #blairepalmer #thatpeoplething #leadership #futureofleadership #leadershipdevelopment #organisationalchange #AIandleadership #executivecoaching #changemanagement #CEOmindset #workplacetransformation #punksinsuits #seniorleaders #peoplestrategyLeadership, Untangled is a podcast for senior leaders navigating real, complex change inside large organisations. Hosted by Blaire Palmer, CEO of That People Thing and author of Punks in Suits, each episode is a genuine conversation with leaders and practitioners who are living through the challenges that define this era of work: AI disruption, shifting workforce expectations, culture transformation, and what it actually takes to lead differently when the old playbook no longer holds.Blaire brings 25+ years working alongside boards, C-suites, and global organisations including Airbus, Roche, GSK, AXA, Heineken, and Santander, combined with the questioning instincts of a former BBC Radio 4 producer. If you lead inside a complex organisation and you're tired of leadership content that recycles the same ideas, this is the show for you.Leadership Untangled, Blaire Palmer, That People Thing, leadership podcast, future of leadership, organisational change, senior leaders, CEO mindset, leadership development, AI and leadership, change management, executive coaching, workplace transformation, culture change, Punks in Suits, human leadership, leading change, private equity, technology leadership, AI due diligence, software strategy, leadership habits, people strategy, complex organisations, executive leadership, B2B leadership