Leading in 2026: What to Expect & How to Thrive | Singularity University

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.