The Learning Leader

Why the Leaders Who Keep Learning Will Lead the AI Future

It's an old saying often heard in higher education, but I didn't fully appreciate its wisdom until I began coaching CEOs, founders, and senior executives:

"The more I learn, the less I know."

As I reflect on the shifts in leadership necessary with the growth of Artificial Intelligence (AI), I realize that the most effective leaders I work with have something in common: they don't pretend to know everything. In fact, the more successful they become, the more curious they become!

They ask more questions.They seek different perspectives.They challenge their own assumptions.They actively look for opportunities to learn.

Ironically, the least effective leaders often do the opposite. As their experience grows, so does their certainty and certainty, more than ignorance, is often what limits growth.

Today, AI is transforming virtually every industry. Knowledge is available in seconds. Entire business models are evolving. Customer expectations are changing faster than strategic plans.

Perhaps the greatest competitive advantage is no longer knowing more, it's learning faster!

That's why I believe every CEO, founder, and senior leader must become The AWS Learning Leader™.

The New Competitive Advantage

There was a time when competitive advantage came from expertise so the leader who knew the most often made the best decisions.

Today, AI can summarize a 200-page report, analyze market data, draft proposals, brainstorm ideas, and recommend solutions almost instantly. Knowledge has become abundant. Learning has become the differentiator.

The question is no longer: "How much do you know?"

It's becoming: "How quickly can you learn, adapt, and help others learn?"

Organizations that consistently outperform won't necessarily possess more information, rather they'll build a greater capacity to learn.

Why Learning Leaders Build Better Organizations

Peter Senge's The Fifth Discipline introduced the idea of the learning organization—one in which people continually expand their capabilities, challenge assumptions, and learn together. Nearly thirty-five years later, that idea may be more relevant than ever. Organizations themselves don't learn, people do. People learn best when leaders create the conditions for learning.

The Center for Creative Leadership (CCL) emphasizes that learning cultures are cultivated through continuous reflection, experimentation, collaboration, and leadership support—not simply by sending employees to occasional training courses. Learning isn't an event. It's a leadership practice.

Learning Requires Psychological Safety

One lesson I've learned from coaching leadership teams is this:

People don't stop learning because they lack intelligence, they stop learning because they don't feel safe.

Amy Edmondson's pioneering research on psychological safety demonstrates that teams perform better when people feel comfortable asking questions, admitting mistakes, challenging assumptions, and offering different perspectives without fear of embarrassment or punishment.

Think about your own organization. Can people comfortably say:

• "I don't know."

• "I made a mistake."

• "I see this differently."

• "Can someone help me understand?"

If not... learning has already slowed. The Learning Leader understands that curiosity grows where psychological safety exists.

Learning Agility: Preparing for What's Next

One of the most practical leadership frameworks is Korn Ferry's Learning Agility model. Rather than measuring what leaders already know, Learning Agility measures their ability to learn from experience and succeed in unfamiliar situations.

It includes:

🧠 Mental Agility — thinking critically and solving complex problems.

👥 People Agility — learning through relationships and diverse perspectives.

🔄 Change Agility — embracing experimentation and uncertainty.

🎯 Results Agility — delivering outcomes in new and unfamiliar situations.

🪞 Self-Awareness — understanding your strengths, blind spots, and impact on others.

These aren't simply leadership competencies, they're becoming business necessities.

AI can process information. It cannot replace judgment, humility, adaptability, emotional intelligence, or the willingness to learn.

The Leadership Shift

Many leaders still believe their primary responsibility is to provide answers. The AWS Learning Leader™ believes something different. Their responsibility is to create environments where people continuously learn which means shifting from:

Traditional Leader	The AWS Learning Leader™
Has the answers	Asks better questions
Rewards certainty	Rewards curiosity
Protects expertise	Shares learning
Avoids mistakes	Learns from mistakes
Directs people	Develops people
Focuses only on performance	Focuses on performance and learning

Notice something important. None of these shifts reduce accountability and they increase capability.

Why Leaders Stop Learning

One of the greatest myths in leadership is that experience automatically leads to wisdom yet experience only becomes wisdom when we intentionally learn from it. In my executive coaching practice, I rarely see leaders stop learning because they lack curiosity. Instead, leadership itself creates barriers and recognizing them is the first step toward overcoming them.

Barrier #1: "I Don't Have Time"

The most common response I hear is: "I'd love to spend more time learning... I just don't have time."

Ironically, leaders who don't invest time learning often spend far more time solving avoidable problems later!

Leadership Action: schedule one hour every week as Learning Time. Protect it like your most important executive meeting.

Exercise: Ask yourself, “what recurring challenge would improve if I invested one hour learning instead of ten hours reacting?” (Hint: one of the easiest ways to learn is to simply ask the perspective of two to three others who have no vested interest in the outcome of the challenge)

Barrier #2: Success Creates Certainty

Success can quietly convince leaders they've already found the right answers but the strategies that built your business five years ago may not build it over the next five, especially with AI changing markets at unprecedented speed.

Leadership Action: every quarter ask your leadership team, "What assumptions are we making that may no longer be true?"

Team Activity: Hold a ‘Challenge Our Thinking Workshop’. Make it fun. When people are relaxed, they think deeper. Start each question by giving each person two minutes to think individually before sharing and watch the ideas flow!

Each executive identifies:

• One assumption to question.

• One process to stop.

• One experiment to try.

  
  

Barrier #3: Fear of Looking Incompetent

Many leaders secretly worry: "If I admit I don't know, people will lose confidence in me."

Research on psychological safety suggests the opposite. Leaders who demonstrate humility often build greater trust because they create permission for others to learn as well.

Leadership Action: once each month tell your team, "Here's something I'm learning right now..."

Reflection: complete this sentence, “The leadership capability I most need to develop is...”, then identify one or two steps to focus on moving forward. Learning shifts from something extra leaders need to do, to now being incorporated into your daily role.

Barrier #4: Rewarding Performance More Than Learning

Many organizations celebrate results, yet fewer celebrate learning. Employees notice.

When mistakes are punished instead of explored, feedback, insights and learning diminish while innovation slows.

Leadership Action: after every major project ask:

• What worked?

• What surprised us?

• What didn't?

• What should we do differently?

Team Exercise: introduce a monthly Learning Spotlight where every leader shares:

✅ One success

✅ One failure

✅ One lesson

✅ One experiment for next month

Normalize learning—not perfection. This is very powerful to incorporate into regular monthly or quarterly meetings where even one or two insights that are surfaced can be a game changer.

Barrier #5: Leaders Talk More Than They Learn

As leaders gain experience, they often ask fewer questions and provide more answers which results in curiosity quietly disappearing.

Leadership Action: adopt the 70/30 Rule. Listen 70%. Speak 30%.

Weekly Challenge: during your next meeting, resist answering the first question you're asked. Instead ask:

• What do you think?

• What options do you see?

• What might we be missing?

For many leaders, this is very difficult to do but watch how the conversation changes.

Barrier #6: Learning Happens Individually Instead of Collectively

Too many organizations treat learning as something individuals do through courses or books. Learning organizations learn together so knowledge becomes organizational capability.

The Learning Pyramid Percentages

• 90% retention: Teaching someone else or using the knowledge immediately.

• 75% retention: Practicing by doing or hands-on application.

• 50% retention: Participating in group discussions or exchanging ideas.

• 30% retention: Seeing a demonstration or watching someone perform a task.

• 20% retention: Audio-visual learning like watching videos or listening to recordings.

• 10% retention: Reading text from books or articles.

• 5% retention: Listening to a passive lecture

Leadership Action: end every leadership meeting with one question, "What did we learn today?"

Team Activity: create a visible Learning Board where leaders regularly share:

📚 Something learned

💡 One new idea

❓One unanswered question

🔬 One experiment underway

When learning becomes visible, it becomes cultural.

The AWS Learning Leader™ Framework

The AWS Learning Leader™ is an evidence-based leadership development framework that helps leaders strengthen self-awareness, learning agility, coaching, feedback, and change leadership to create high-performing learning cultures.

The AWS Learning Leader™ prepares leaders for this new reality by developing the human capabilities AI cannot replace—self-awareness, learning agility, emotional intelligence, critical thinking, coaching, communication, adaptability, ethical decision-making, and the ability to build psychologically safe, high-performing teams. Rather than simply teaching new skills, the program develops leaders who continually learn, unlearn, and relearn, creating a culture where innovation, curiosity, and continuous improvement become everyday practices.

Reflective Leadership Questions 🤔

Ask yourself:

• When was the last time I deliberately changed my mind?

• What am I learning today that prepares me for tomorrow?

• Do people feel safe admitting they don't know?

• Am I rewarding curiosity—or certainty?

• What learning habit would have the greatest impact on my leadership?

The AWS Learning Leader™ Challenge

For the next 30 days, intentionally build one learning habit.

Choose one:

✅ Read ten pages every morning.

✅ Listen to one leadership podcast each week.

✅ Hold one After-Action Review every Friday.

✅ Ask five coaching questions before giving advice.

✅ Learn one new AI tool alongside your team.

✅ Share one lesson learned every Friday.

Small habits lead to big leadership transformation!

Action Steps

✅ Begin every leadership meeting with: "What have we learned since we last met?"

✅ End every major project with an After-Action Review.

✅ Create one monthly "Learning Conversation" with your leadership team.

✅ Celebrate thoughtful experiments—even when results aren't perfect.

✅ Invest in coaching, mentoring, peer learning, and cross-functional collaboration—not just training courses.

Build Your Future

The old leadership advantage was expertise. The new leadership advantage is learning.

As AI continues transforming our workplaces, the leaders who succeed won't necessarily be those with the highest IQs or the longest résumés.

They'll be the ones who remain curious enough to keep growing, humble enough to keep learning, and courageous enough to help others do the same. Because in the end... the organizations that thrive won't be those that know the most. They'll be the ones that learn the fastest.

That's what it means to become The AWS Learning Leader™. In a world changing faster than ever before, that may be the most important leadership capability of all.

Jerome Dickey