# Leading in 2026: What to Expect & How to Thrive | Singularity University Source: https://www.youtube.com/watch?v=3G5ZQjyTqo4 Recap page: https://rapidrecap.app/video/3G5ZQjyTqo4 Generated: 2025-12-15T23:03:14.223+00:00 --- ## Quick Overview The major finding from leaders in the last year is a surprising return to basics in communication and meeting structure due to increased discontinuity, alongside the massive conflict between the need to transform systems and the simultaneous requirement to maintain high operational performance. **Key Points:** - The biggest pattern observed in the last 12 months was a "return to basics," involving fundamentals like having agendas, shared context, and decent conversation skills, because what leaders previously relied on has 'truly truly come to an end.' - Leaders are struggling with two conflicting mental models simultaneously: the need to 'transform' by building new systems and the need to 'perform' by driving immediate operational results. - The breakthrough solution to the transform/perform conflict is to 'transform how you are performing,' meaning setting metrics based on the desired future end-state performance rather than clinging to current metrics. - Regarding AI, the biggest issue is leaders are 'still putting old mental models and old ways of working onto this,' using powerful technology to solve yesterday's problems, leading to reliance on error-filled outputs from consulting firms. - The speaker notes a global 'crisis of fear' among leaders who are defaulting to seeking certainty and control by looking backward, rather than operating with courage and creativity toward the unknown future. - Startups and large organizations exhibit a gap in mindset regarding speed and risk-taking; startups celebrate trying 50 ways and failing, whereas legacy executives are systemically incentivized against failure. - To transform a company, one must close five gaps: Vision/Purpose Gap (setting a massive north star), Expectations Gap (defining roles in transformation), Metrics Gap (creating new future-state metrics), Resourcing Gap (providing support), and the Courage Gap (maintaining boldness when fear arises). **Context:** This discussion, part of Singularity University's monthly series featuring experts and alumni, featured Kyle Herman, who represents Be Courageous (a transformation agency) and Oxford Leadership. Kyle shared insights gathered from working with global leaders across more than 40 industries in a 'remarkably disruptive year,' focusing on patterns emerging from rapid change and the integration of new technologies like AI. ## Detailed Analysis Kyle Herman identified two massive themes dominating leadership work in the past year: a 'back to basics' return due to unprecedented discontinuity, and the severe conflict arising from needing to simultaneously transform organizational systems while maintaining high operational performance. The solution he advocates for is 'transform your performance,' which involves measuring against the desired future state rather than trying to manage transformation and performance in isolation. Concerning Artificial Intelligence, Herman cautioned against the hype, noting that many AI initiatives fail because organizations apply old mental models to new technology, essentially using futuristic tools to solve outdated problems, which risks outsourcing thinking and decision-making, leading to costly errors and 'hallucinations.' Furthermore, he observed a global 'crisis of fear' among senior leaders who lack clarity on the future and default to seeking certainty, contrasting this with the courageous, risk-tolerant mindset prevalent in startups. He stressed that the most vital question leaders forget is the 'customer or consumer question'—serving external needs rather than solely focusing internally on business efficiency. For actual transformation, Herman detailed five critical gaps to close: setting a compelling vision/purpose, clearly defining role expectations, establishing new future-state metrics, ensuring adequate resourcing and coaching, and actively managing the 'courage gap' when fear and resistance inevitably surface. ### Key Patterns in Disruption - Return to basics in communication and meetings - Massive conflict between transform and perform mandates - Solution is to 'transform your performance' by measuring the end-state. ### AI Implementation Challenges - Leaders apply old mental models to new tech, solving yesterday's problems - High failure rate (citing a McKinsey study reference) due to hype and over-reliance - Risk of outsourcing decision-making and creative thinking. ### Leadership Mindset and Fear - Observed 'crisis of fear' causing leaders to seek certainty and look backward - Contrast between legacy executives seeking control and startup founders embracing risk and failure. ### The Customer Focus Gap - Organizations are too introverted, forgetting the 'customer or consumer question' - Future success depends on connecting with unmet customer needs rather than just pushing new technology. ### Framework for Transformation - Starting a transformation requires closing five gaps: Vision/Purpose, Expectations, Metrics (creating new future metrics), Resourcing, and Courage. ### Organizational Siloing - Large organizations built for scale often struggle with necessary rapid pivoting due to functional siloing - Need for 'transversal cross-functional metrics and goals' to unite departments around a shared customer outcome.