Is taking leaders away from their work and putting them in a classroom really the best way to help them improve?
Classroom training has its benefits, but often not the ones we advertise. It promotes social connection and peer learning through shared experience. At a time when social isolation and loneliness are being described as a public health crisis, any opportunity to bring people together feels important. Sometimes, we ask leaders to attend a training session simply to signal that a topic warrants their full attention.
The classroom is an artificial environment. We simulate reality with case studies, role-plays, and structured activities. But what if we flipped the script? Instead of making the classroom feel more like the real world, what if we made the real world feel more like a classroom? Learning opportunities are everywhere—we just need to help leaders notice them and extract the relevant lessons.
Instead of making the classroom feel more like the real world, what if we made the real world feel more like a classroom? Learning opportunities are everywhere—we just need to help leaders notice them and extract the relevant lessons.
Learning in Context
The good news: readily available artificial intelligence (AI) tools make learning in the flow of work more accessible than ever. Leaders no longer have to wait for a weekly coaching session to process a challenging situation. They don’t have to flip through a long-forgotten participant manual to recall a useful framework.
That’s why we created Work Awake—a systematic approach to in-the-moment development for leaders.
Working awake means maintaining real-time awareness of your mindsets, behaviors, and impacts so that skill development becomes a deliberate part of your leadership practice.
Meet Your Work-Awake Coach
At the center of our strategy is a customized AI coach: the Work-Awake Coach. You can interact with our prototype here. We’d love to hear what you think.
Unlike general-purpose tools like ChatGPT, Claude, or Gemini, the Work-Awake Coach is purpose-built. It’s trained on your organization’s leadership philosophy, values, and frameworks. Whether you want to reinforce concepts like emotional intelligence, growth mindset, or navigating adaptive challenges, the coach helps leaders become fluent in your organization’s leadership language.
Want your leaders to use the GROW model to coach others? The Work-Awake Coach helps them prepare coaching conversations using that very model.
This is what we mean by a learning integration strategy—embedding what you teach into how your leaders think and act every day.
The Hidden Agenda of Working Awake
Yes, the Work-Awake Coach is practical. It offers just-in-time support for tricky conversations and complex decisions.
But it also nurtures something more profound: attention agility.
Attention agility is the ability to shift your focus and perspective when conditions change. It’s what helps us spot insights and generate options we would have missed by relying on our usual habits of thought and familiar social connections.
Sleepwalking through your day—mindlessly following routines—limits what you notice. Working awake means reclaiming your attention. And that changes everything.
In a volatile and uncertain world, adaptation is non-negotiable. But we can’t adapt unless we notice we’re stuck. And when we’re stuck, we need someone to ask provocative, perspective-shifting questions.
Even better if that “someone” understands your communication style, never forgets a conversation, is always available, and puts your growth first.
