Rethinking the Leadership Pipeline in the Age of AI-Redefined Roles

Image: Vimal S via Unsplash

If the future of leadership feels less like a steady climb and more like running up a down escalator, you’re not alone.

Across the agency and consultancy leaders I’ve partnered with this year, a consistent, shared concern has emerged… louder and more urgent than ever. And while AI dominates many of our strategic conversations, it’s not the usual fear around which model to choose or which platform to adopt that’s keeping leaders up at night.

The real anxiety? The leadership pipeline.

More specifically: how do we prepare future leaders to step into roles that are changing faster than we can define them?

The Pipeline Is Built for the Known.
The Future Is Anything But.

Leadership development has historically been a strategic, even formulaic endeavor. Identify high potentials. Give them stretch opportunities. Mentor them through increasing levels of responsibility. Equip them with frameworks, playbooks, and organizational knowledge to make effective decisions when they eventually inherit a role.

But that assumes something foundational: that the role they’ll inherit is relatively known.

Today, that’s no longer a safe assumption. AI is reshaping how we work, make decisions, structure teams, and even define what “leadership” looks like in practice. As technology evolves faster than most organizations can adapt, leaders in waiting are being asked to step into roles that don’t resemble the ones they were being groomed for.

In many cases, there is no playbook—just a landscape of change, ambiguity, and increasing complexity.

This reality is creating a gap—one that traditional leadership development models weren’t designed to fill.

The Emerging Leadership Challenge: Decision-Making in Ambiguity

The core question is no longer, “Are we preparing the right people?”

It’s: Are we preparing our people to lead when the context they’re leading in doesn’t yet exist?

This is why AI isn’t the central challenge—but the context that amplifies it.

We are entering an era where leadership will be less about answers and more about navigation. Less about certainty and more about learning in real time. Decision-making, then, becomes the differentiator—not just what decisions are made, but how they’re made under pressure, with imperfect data, in dynamic systems.

And for many organizations, the leadership pipeline isn’t optimized for that kind of readiness.

A Practical Shift: Developing “Navigation Capacity”

The most effective approach I’ve seen with clients isn’t about accelerating existing development tracks—it’s about reframing leadership readiness entirely.

Here’s a shift you can consider:

Start building navigation capacity rather than preparing for specific roles.

Navigation capacity is the ability to:

• Stay grounded in purpose while operating in ambiguity

• Make decisions aligned with evolving priorities

• Ask better questions when there are no clear answers

• Adapt with integrity when the map no longer matches the terrain

To do this well, you don’t need a whole new development system—you need intentional shifts in how you coach, challenge, and support your emerging leaders. Here are three practical approaches to start:

1. Design Role Experiments, Not Role Ladders

Instead of mapping out a linear path to the next job title, design short, intense role experiments that give emerging leaders exposure to complexity—especially in cross-functional, tech-adjacent, or AI-impacted areas.

The point isn’t mastery. It’s comfort with ambiguity and systems thinking.

Ask: What’s a 60-day challenge we can give this person that pushes them outside of their normal decision-making patterns?

2. Coach Decision-Making, Not Just Deliverables

When reviewing work or progress, don’t just ask, “What did you do?” Instead ask, “How did you decide that was the right approach?”

This helps surface patterns in how someone thinks—especially under pressure—and gives you the chance to coach the thinking, not just the outcome.

It’s a subtle but powerful reframe: leadership is about how you think, not just what you execute.

3. Pair Them With “What If?” Mentors

Instead of only assigning mentors with similar functional backgrounds, match emerging leaders with people who specialize in asking big-picture, disruptive, “what if” questions.

These mentors challenge assumptions. They stretch comfort zones. They train adaptability.

And most importantly, they normalize ambiguity—so your leaders learn that uncertainty isn’t a threat; it’s the water they’ll be swimming in.

Building the Leadership Pipeline We Actually Need

It’s not that traditional leadership development is broken—it’s that the world it was designed for is gone.

If you’re in the business of building leaders, whether in an agency, consultancy, or beyond, the game has changed. The question is no longer how to scale skills for known roles—it’s how to cultivate adaptive decision-makers ready to lead through what’s next.

So as you look at your current pipeline, ask yourself:

Are we developing leaders for the roles we know—or for the futures we can’t yet see?