Why confidence matters more than capability for AI leadership
- Eli Keery
- Jan 22
- 7 min read

This week, we ran the first instalment of our Dine and Debate series for the year, bringing together clients and leading brand voices to discuss the key issues currently shaping the industry. The aim is always to understand different points of view on the evolving landscape and to create space for learning that sharpens understanding of what will drive growth and relevance.
We began with the question of where organisations are lagging in addressing the needs of people and how that lag is quietly stifling relevance. As the conversation unfolded, it became clear that this was less about tools, technology or even innovation cycles and more about confidence, preparedness and what leadership looks like in an increasingly uncertain world.
Unsurprisingly, AI became the focal point.
The familiar questions surfaced. Concerns around the erosion of critical thinking. Ongoing debates about efficiency, whether AI genuinely saves time and money or simply reshapes where effort is spent. And the widely promoted promise that AI creates more space for creativity and exploration, a promise many remain unconvinced of, has materialised in practice.
Before the discussion travelled too far down these well-worn paths, there was an important reframing. These conversations, while understandable, can be reductive. The reality is that AI, much like the digital world more broadly, is no longer a separate phenomenon that exists on a single platform or behind a login. It is embedded into everyday activity and increasingly woven into how we work, consume and interact.
There is no realistic future in which AI is absent from our working or lived realities. The more pressing consideration, therefore, is how we engage with it on those terms. Rather than becoming absorbed in what AI might be taking away, attention needs to shift towards where opportunity sits and how people can be equipped to work alongside it with confidence. This opens up more informed, constructive questioning around how AI is actually being used and to what effect.
All the gear and no idea
As the discussion circled AI and lived experience, another layer became visible. Many of these concerns stem from how unequipped people feel to use these tools well. The Google Essentials AI course was referenced as a useful illustration of this gap. Effective use requires depth in prompting, clarity of intention and the ability to engage thoughtfully with AI over time.
Leaders shared their trial-and-error examples from their own experiences with AI supporting dyslexia in presentation creation. Acting as a creative thought partner and editor, capable of shifting the tone of strategic outputs across different contexts without extensive rework. Then perhaps the simplest but most important application, helping people start projects, is often the greatest barrier of all. These examples reflected the opportunity taken by learning through use, but still flagged how it required hours and patience and in many cases, without guidance.
In sharing these experiences, it became apparent how novel this landscape still is. What might once have been considered mundane quickly revealed itself as a set of compelling case studies in application.
We are at the very beginning.
The questions, impacts and consequences of AI are shifting daily, at a pace that outstrips most organisational learning cycles.
This raises a particular challenge for leaders. There is a long-standing expectation to project certainty, advancement and innovation, always. That expectation is deeply ingrained in society. Yet its realism and its value become less clear when the environment is moving at such speed.
In the room, leaders explored where AI’s potential is already becoming visible. One such being its ability to decentralise and democratise access to specialist knowledge, particularly in sectors such as law. An example shared involved a foreign cleaner being able to take a company to court for unpaid wages without the prohibitive cost of legal consultation. AI could support this process in a language-agnostic way, expanding access to justice that previously would not have been viable.
At the same time, the conversation held space for how AI is also being used in harmful and exploitative ways. Deepfakes. Gendered abuse, including AI used to undress women, as we saw on X recently. Then, beyond consumer contexts, its deployment in military settings. We agreed that these realities of the application of AI mean that attention needs to be placed towards the values underpinning adoption and development.
This tension sits at the centre of the opportunity. The technology itself is powerful, but outcomes are shaped by the knowledge, intent and values that guide its use. That raises a fundamental question. How do people come to understand what is possible and how are they supported to engage with AI in ways that are responsible, confident and grounded?
The scale of the opportunity is significant, but its impact depends on whether it can be shared and repeated, rather than remaining confined to isolated examples. Many organisations are moving quickly, adopting AI one tool at a time. We are saturated with platforms, yet there is little clarity on how to use them well. In some cases, space has been created for experimentation and progress. The question is how widespread that confidence really is and how far down into organisations it reaches.
These conditions surfaced as a leadership priority. If organisations and leaders do not actively articulate values and direction in how AI is used, they leave space for the technology itself / tech companies to shape the terms of engagement.
Pressure, precarity and the emotional context shaping AI use
The conversation situated AI firmly within the wider social climate. Cost-of-living pressures, the long tail of COVID-19 and increasingly digitised lifestyles have reshaped how people relate to work, to each other and to themselves. These conditions form the backdrop against which new technologies are adopted and experienced. They influence not only what people use, but how and why they use it.
From the outset, the intergenerational impact of this moment featured strongly. Across age groups, uncertainty is no longer a temporary phase but a defining condition. Younger workers are facing increased insecurity as AI reshapes entry-level roles and early career pathways. Gen Z is navigating this alongside heightened anxiety and public scrutiny, while Gen Alpha is growing up in a world where AI-mediated interaction is increasingly normalised before work has even begun. At the other end of the spectrum, older generations are finding that experience is gaining renewed relevance, particularly where they can guide AI through informed prompting, contextual understanding and judgement built over time.
Within this shared uncertainty, clear behavioural shifts are already visible. Rising anxiety among Gen Z. The growth of the manosphere. Widespread loneliness is cutting across generations. Under sustained pressure, comfort and ease take on heightened importance. These are not marginal trends but rather signals of how people are adapting to an environment that feels increasingly demanding, exposed and unstable.
Against this backdrop, AI use begins to look different. Remaining critically aware becomes harder when people are stretched thin. Tight deadlines, high output expectations, limited reward and reduced social connection compound one another. We discussed how AI often functions as a coping mechanism. When workloads exceed the time and capacity available, AI becomes a way of staying afloat rather than a considered strategic choice. Ease, in this context, is less about convenience and more about getting by.
This dynamic is particularly pronounced for Gen Z, where higher anxiety levels shape how technology is approached. Digital life has normalised constant commentary and critique. Mistakes are visible, amplified and persistent. The boundary between digital and physical interaction has thinned, allowing behaviours to move easily between the two. This creates an environment of hypervigilance, where fear of public criticism can outweigh the willingness to experiment, take risks or even engage openly with others in person.
AI offers something specific within this landscape. A private space to think, test and make mistakes without immediate judgement. Significantly, many people turn to AI for reflection, support and emotional processing, with some of the most common uses resembling therapy or private rehearsal rather than productivity optimisation. Alongside this, a renewed pull towards in-real-life connection is emerging, as people seek grounding and relief from constant exposure.
These patterns feed directly into how organisations function. We explored the idea of people as brands and how AI intersects with identity, work and self-presentation across generations. Progress in this context depends on recognising the emotional dimension of change. Efficiency and adoption targets alone do not prepare people for transition. When fear and uncertainty go unacknowledged, they surface as disengagement, resistance or withdrawal, dynamics already visible across many workplaces. There is a key opportunity around leaders that creates space for emotional reality surrounding AI adoption, alongside performance expectations that are better positioned to build trust, sustain engagement and move forward together through change people actually feel part of.
Organisational lag, drag and blag… but what did this flag
As the conversation drew to a close, the initial question around organisational lag evolved into a sharper concern around organisational drag. Leaders move quickly, while others struggle to keep pace. Confidence is projected (or blagged), but not always collectively built.
People continue to look to leaders for direction. In an environment shaped by economic instability, technological acceleration and social fatigue, that direction requires cultural awareness alongside strategic clarity. When expectations are set without shared context or dialogue, speed creates distance rather than momentum.
Markets will continue to demand innovation. The more enduring question is whether organisations create shared understanding alongside progress. Clear values, evolving protocols and open conversation around AI opportunity, held alongside fear, mould whether people feel carried forward or left navigating ongoing uncertainty alone.
Organisations need intentional spaces where people can come together to build confidence in uncertainty. Spaces where values are articulated and revisited. Where dialogue replaces silos and leadership is expressed through connection rather than performance
This is the work we do with organisations. We support teams to surface pain points, engage honestly and move forward together, rather than being pulled behind a narrative of progress they do not feel part of. We created Dine and Debate as a mechanism so leaders and businesses from different industries can come together, challenge their own assumptions, understand what’s really happening on the ground and progress with clarity and a shared sense of direction.
If that sounds like a conversation worth being part of, get in touch; pull up a chair and place your order in, we’d love to co-design with you