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Dates and Venue

29 - 30 April 2026 | Excel London

29 - 30 April 2026 | Excel London

Four Questions That Heads of Learning Should Ask But Don’t

Four Questions That Heads of Learning Should Ask But Don’t

Four Questions That Heads of Learning Should Ask But Don’t
  • Event: Learning Technologies UK 25
  • Date: 23 April 2025
  • Speaker: Nigel Paine, Managing Director, Nigelpaine.com
  • Estimated read time: 9 minutes

 


 

Quick read summary

This session explored why many learning functions struggle to stay relevant during periods of rapid organisational change, despite increased investment in technology and skills initiatives.

It matters now because generative AI, economic pressure and shifting workforce expectations are exposing the limits of course led learning models and siloed expertise.

Readers will gain a practical way to rethink the role of learning, using four fundamental questions to reshape decision making, operating models and leadership behaviour.

 


 

Learning needs better questions, not better courses

Nigel Paine’s core argument was simple. When learning teams fail, it is rarely because they lack effort or technical capability. It is because they are solving the wrong problems.

Much of L&D remains focused on delivering outputs, courses, frameworks, platforms, rather than addressing the deeper organisational issues shaping performance and behaviour. When learning stays inside its own box, it becomes self referential, optimising its own processes while missing the bigger picture.

The challenge for learning leaders is not to keep up with every new tool, including AI, but to ask more ambitious questions about purpose, value and impact.

 

Question One: What problem are you really trying to solve?

Requests for training often mask deeper issues. A sales course, for example, is rarely the real problem. The underlying challenge may be anxiety, misaligned incentives, unclear priorities or a lack of trust.

Paine argued that heads of learning need to step back and ask what their role is in the organisation and what they want to be remembered for. In a world shaped by AI, the purpose of a learning function cannot be reduced to content production.

Learning leaders who do not ask this question risk becoming operationally busy but strategically invisible.

 

Learning across three horizons

Paine drew on the three horizons model to explain how learning teams become trapped in the present.

The first horizon is day to day delivery. Without it, credibility disappears. The second horizon is improving existing workflows, doing current work better with the same resources.

The third horizon is the most neglected. It asks what happens if the current model no longer works. What would the organisation look like if core assumptions were challenged or disrupted.

Most learning teams rarely make time for this horizon, yet it is where long term relevance is shaped.

 

Question Two: How easy is it to ask for help?

A powerful indicator of organisational health is whether people can admit uncertainty.

In some organisations, asking for help is normal and encouraged. In others, it is seen as weakness and quietly punished. Paine described this as a critical divider between organisations that adapt and those that fracture under pressure.

Generative AI can amplify this divide. Where work is individualised and competitive, AI deepens silos. Where collaboration is normal, AI strengthens shared capability.

Relying on a few high performers may feel efficient, but it leaves nothing behind when they leave. Learning that spreads expertise builds resilience.

 

Decency, kindness and learning at scale

One of Paine’s most strongly held views was that decency and human kindness are not soft values, but performance enablers.

People do their best work when they feel safe, respected and part of something. Organisations that prioritise systems over human judgement often end up protecting processes that no longer serve the work.

Learning, in this context, is about enabling people to think together, share problems and adapt systems as the organisation evolves.

 

Question three, what is your AI vision for the workplace?

Allowing staff to use AI tools is not a strategy. An AI powered organisation requires a shared vision of how humans and machines work together.

Paine challenged learning leaders to create space for collective thinking about what AI could genuinely enable, not just automate. This includes how decisions are made, how knowledge flows and how teams learn together rather than individually.

Without this vision, AI adoption risks becoming fragmented and shallow.

 

Question four, what will L&D look like in five years?

The final challenge was future facing. Paine argued that learning leaders must imagine where their function is heading, even if they get it wrong.

Those conversations, held openly with teams and stakeholders, help learning earn influence. A seat at the table is not requested, it is earned by shaping direction and helping the organisation navigate uncertainty.

 

Practical application, translating the questions into action

Questions leaders should be asking

  • What organisational problems keep resurfacing despite repeated training
  • Where does expertise sit, and how easily does it spread
  • How do people really experience asking for help
  • What would meaningful human and AI collaboration look like here

Signals to watch

  • Learning requests framed only as courses
  • High reliance on a few experts
  • Silence or defensiveness when problems are raised
  • AI adoption without shared principles

Common pitfalls

  • Treating AI as a content accelerator
  • Protecting systems that no longer work
  • Confusing activity with impact

What good looks like

  • Learning teams facilitating organisational conversations
  • Shared ownership of problems and solutions
  • Continuous learning embedded in work, not bolted on

 

Key takeaways

  • Learning impact depends on asking better questions, not delivering more content
  • Psychological safety and collaboration shape organisational learning capacity
  • AI amplifies existing behaviours, it does not fix broken ones
  • Long term relevance requires time spent on future horizons

 

Quote of the session

“If you don’t ask good questions, you’ll get rubbish answers.”

Nigel Paine, Managing Director, Nigelpaine.com

 

Final thoughts

Learning leaders face a choice. Stay inside the box and optimise delivery, or step into a broader role shaping how organisations think, learn and adapt.

The questions Paine posed are uncomfortable, but they offer a route to renewed relevance. In an era of rapid change, learning earns its place by helping organisations make sense of what comes next.

 


 

Speaker

Nigel Paine, Managing Director, Nigelpaine.com. An organisational learning specialist and author, known for his work on learning culture, leadership and knowledge sharing.

 


 

Watch full session


 

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