Leadership in Chaos – Leaders Digest: 38th edition.


Leadership in Chaos: 38th edition.

ai + hi, light and shade, disagreement.

Hi 👋, welcome back to our 38th edition 🙌.

“Ninety percent of success can be boiled down to consistently doing the obvious thing for an uncommonly long period of time without convincing yourself that you’re smarter than you are.”

Shane Parrish


Change: ai + hi.

Are you a thinking machine, that feels? Or a feeling machine, that thinks? Neuroscientist Antonio Damasio made it clear. Humans are the latter. We are feeling machines. And, in this dehumanising era of AI, it’s never been more important to remember that. We are messy, irrational and unpredictable. And this is what we need to focus on as Rishad Tobaccowala wrote in staying human in the age of AI. The future, he believes, will be a combination of AI, and what he calls HI. This consists of four uniquely human strengths: intuition, insight, imagination, and interaction. Which made us think of the advice Jacob Collier received from Quincy Jones: “follow your goosebumps, they’ll never lead you wrong”. Goosebumps, as Collier says, are non-cerebral; they come from the bottom of your feet. And like all feelings, they move faster than thought. It’s important not to forget about these kinds of primal conductors, and the unique humanity that drives them.

A thought for leaders: There’s a difference between computational and emotional intelligence. Both are important, but as Damasio points out, we are emotional feeling machines. In this rationally bent AI world, it’s easy to forget that as we race to coat the world in technology. Easy to forget that the customers we serve, and the people we lead, are human. And deep down, will always be guided by goosebumps and driven by feelings. All the tech stacks, systems, and agents won’t replace that. As you personally and professionally invest in AI, you have to ask yourself, am I, are we, equally investing in the right level of HI?


Resilience: light and shade.

AI giant Anthropic just completed what it describes as the largest qualitative research study ever conducted. Ran by AI bot Claude, with a sample of 81,000 global users (bias noted), their central finding is that the benefits and harms of AI aren’t oppositional, but entangled. They called it “light and shade”, which consists of five key tensions.

  1. Using AI to learn, but growing so reliant you cease to think.

  2. Being impressed by AI’s judgment, but getting burned by its mistakes.

  3. Finding solace in AI, but fearing it replaces human connection.

  4. Saving time on tasks, but watching the treadmill speed up on others.

  5. Dreaming of economic freedom, but dreading potential job displacement.

Benefits and danger, hope and fear, entangled. They also found that the dangers are felt even more by those benefitting the most, i.e. someone who values emotional support from AI, is 3x more likely to fear becoming dependent upon it.

A thought for leaders: Things used to be more black and white. Good vs evil. Clear vs unclear. Today it’s different. More Chiaroscuro (as Anthony Mayfield wrote about here). The borrowed word describing the artistic technique of contrasting light and shade. The idea of light-clear and dark-obscure. Not black and white, and certainty and absoluteness, but gradations. More paradoxical. A recent BCG study, in fact, identified the productivity exhaustion paradox, where using more AI demands more checking, creating more cognitive drain, and more exhaustion. AI transformation programs aren’t simple. There will be light, and there will be shade (dark). As leaders, we must remember this and tread carefully.


Culture: disagreement.

 

We recently discussed psychologist Solomon Asch’s consensus experiments in the 50’s, and the tyranny of an organisation quietly bound to prevailing views. Tim Harford also wrote about it, and the refreshing power of disagreement. He refers to Asch’s experiment but adds an additional nugget. In the experiment, Asch asked participants to judge which lines shown were the same length. The experiment demonstrated that people will go against the evidence of their own eyes to align with consensus. Tim unpacks an additional valuable insight. Group consensus is much weaker if even a single person dares to disagree (especially so if that dissenter is extreme in their views). Even if the dissenter offers a wrong answer, the dissent punctures group pressure regardless. Because it demonstrates that disagreement is possible. It gives permission. Tim also references Charlan Nemeth, author of No! The Power of Disagreement in a World that Wants to Get Along, who cautions against “contrived” dissent. If a red team, blue team, or devil’s advocate is merely performative, it’s useless. It needs to be taken seriously for it to be effective.

A thought for leaders: One of the things that struck us, reading again about Asch’s experiment, is the benefit of disagreement in achieving effective outcomes. In the study, scores improved when disagreement was seen as something permitted. When we’re unwilling to disagree, we’re at a higher risk of getting things wrong. Conformity can choke critical thinking. Arrogance diminishes wisdom, as the Arabian Proverb goes. As a leader, do you see the value in disagreement, do you create the conditions for it, and importantly, are people incentivised or disincentivised for disagreeing?


Podcast: EP 32 – Prioritising & Planning in Chaos

Related to our ai + hi discussion, this podcast episode explores the tension leaders face when uncertainty is at its highest: the instinct to pause planning, versus the need for more clarity than ever.

 

As we navigate the rise of AI, this feels particularly relevant. Because while AI can optimise, analyse and accelerate, it can’t replace the deeply human judgement required to set direction. That’s HI in action.

Ian unpacks why priorities bring order to chaos, why leaders struggle when there are no “right answers”, and introduces a practical framework for planning through the three C’s: Context, Coherence and Credibility.

A timely reminder that leadership is not about certainty, but about making deliberate choices, even when the path is unclear.

You can listen to it here.

Enjoy revisiting or newly discovering it 😊


You can follow Flow Group on LinkedIn here.

Hope you enjoyed, and please share your thoughts in the comments section below.


P.S. This month’s featured artist is Nairobi-born, London-based Phoebe Boswell. Her interdisciplinary practice spans drawing, video, animation, sound and writing, forming installations that respond intuitively to the environments they inhabit. Movement, memory and the infrastructures that quietly shape daily life underpin Phoebe Boswell’s latest commission for London’s Underground, where escalators become both conduit and canvas. Water threads through the work as a conceptual and historical force, linking subterranean rivers with human passage above them.

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