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What I Learned After 20 Years in HR: Leadership Development is Broken

Updated
5 min read
What I Learned After 20 Years in HR: Leadership Development is Broken

The AI Revolution Makes Now the Critical Moment to Fix It

After two decades in HR, I've watched large investments wasted on leadership programs that never truly delivered. I've seen executives nod enthusiastically during workshops, only to revert to old habits days later. I've witnessed CFOs slash leadership budgets the moment revenue dips, despite knowing that's precisely when strong leadership matters most.

The hard truth? Most leadership development fails because it's built for a world that no longer exists.

The introduction of AI in the workplace changes everything. We're no longer just developing leaders to manage people—we're preparing them to lead alongside AI, navigate continuous disruption, and develop human-centred skills that technology can't replace.[2]

If leadership development was important before, it's now mission-critical. Organisations that fail to invest in upskilling and reskilling will be left behind. But after years of watching programs succeed—and just as many fail—I know that how you implement leadership development is just as important as what you teach.

Here's what I've learned about what works, what doesn't, and why now is the time to rethink leadership development with the Orion Model.

Why Traditional Leadership Development No Longer Works

In my experience, most leadership development fails because it's built on the wrong assumptions:

  • It treats leadership as an event, not a process – A two-day seminar doesn't build leadership habits any more than a weekend at the gym gets you fit

  • It focuses on knowledge over application – Many programs teach what leaders should do, but not how to actually do it in real scenarios

  • It assumes everyone learns the same way – Standardised programs ignore that leadership is contextual, personal, and requires customised development paths

  • It lacks accountability – If leaders aren't supported and challenged to apply what they've learned, they default to old habits

  • It measures the wrong things – Attendance and satisfaction scores don't equate to real leadership impact

We can't afford to waste time on training that doesn't stick. With AI automating routine tasks, the value of leadership has shifted toward complex problem-solving, emotional intelligence, adaptability, and strategic thinking—all skills that require consistent practice, not just theory.[3]

This is where the Orion Model provides a scalable, real-world alternative.

What Works: Building a Leadership System, Not Just a Training Program

1. Shift From One-Time Training to Continuous Learning

The most successful leadership programs I've seen embed learning into daily work rather than isolating it in classrooms. The Leadership Gym is built around this principle—leaders learn by doing, refining, and iterating over time.

Why This Works: Continuous learning prevents the "training high" followed by the "application drop-off." Leaders need ongoing reinforcement to make new behaviours stick.

What Doesn't Work: Expecting leaders to change after a single training event. Without practice, they revert to old habits.

2. Train for Adaptability, Not Just Competency

One of the biggest risks AI presents is the rapid obsolescence of skills. Organisations need leaders who can pivot, think in systems, and make decisions in uncertain environments.[4]

Why This Works: The Orion Leadership OS Framework trains leaders in Systems Thinking, Collective Leadership, and Leading Change, which are future-proof skills that AI can't automate.

What Doesn't Work: Teaching fixed leadership models that assume a stable business environment. AI-driven change means leaders must be comfortable navigating ambiguity.

3. Make Learning Personalised and Context-Specific

No two leaders face the same challenges, yet many organisations force all leaders through the same curriculum. The Orion Model allows leaders to customise their development through different learning formats:

  • Micro-Courses (45 min) for quick insights

  • Workshops (150 min) for deep dives

  • Practice Labs (85 min) for real-world application

  • Play Labs (85 min) for experiential learning

  • Meetups (60 min) for community learning

  • Learning Labs (85 min) for structured skill practice

Why This Works: Leaders engage more when they choose their learning path based on relevance to their current challenges.

What Doesn't Work: Generic training modules that don't feel immediately applicable—leaders disengage when training doesn't solve their immediate problems.

4. Build Leadership Muscle With the Right Level of Challenge

The best leadership programs push leaders beyond their comfort zones without overwhelming them. The Leadership Gym provides a structured way to progressively develop new skills over time.

Why This Works: Leaders grow when they apply new skills in real-world challenges with structured support.

What Doesn't Work: Programs that either don't challenge leaders enough or throw them into high-stakes situations without guidance.

Why Now? The Impact of AI on Leadership

The urgency to implement a better leadership model isn't just about improving current training—it's about preparing for a workplace that is being fundamentally reshaped by AI.[5]

AI is replacing tasks, not leadership—but leadership is changing.

  • AI is automating routine decision-making → Leaders must develop higher-order strategic thinking and problem-solving skills

  • AI is increasing workforce agility → Leaders must learn to navigate continuous change and uncertainty

  • AI is reshaping human collaboration → Leaders must develop emotional intelligence, collective leadership, and adaptability

  • AI is raising ethical and strategic dilemmas → Leaders must make decisions that balance technology's potential with human responsibility

Organisations that delay investing in AI-ready leadership will struggle with misaligned teams, ethical risks, and strategic blind spots.

The Orion Model: The Best Path Forward

After 20 years in HR, I've learned that the most sustainable leadership development programs don't just train leaders—they change how leadership is developed across the entire organisation.

The Orion approach does this by:

  • ✓ Embedding leadership development into the work itself through The Leadership Gym

  • ✓ Providing leaders with personalised learning paths instead of one-size-fits-all training

  • ✓ Developing the four AI-ready leadership competencies that will define the next era of work

  • ✓ Building a scalable system for leadership development, not just a temporary programs

For HR leaders looking to future-proof their organisations, the time to act is now.

Final Thoughts: Don't Wait for the Change to Force Your Hand

Every organisation will eventually need to rethink leadership development. The only question is whether they do it proactively, on their own terms, or reactively, in response to disruption.

AI isn't waiting. The workplace is shifting faster than ever. Leaders who aren't actively developing new skills today will be unprepared tomorrow.

Next Steps

This isn't just about making leadership training better—it's about ensuring leadership remains a competitive advantage in a world where AI is rewriting the rules.

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Orion Group

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