Leadership Development in the Age of AI

Rachel Bolton, Director of Enterprise Leadership Development, Stanley Black & Decker

At Stanley Black & Decker, I serve as Director of Enterprise Leadership Development, where I’m responsible for architecting scalable, future-ready programs that grow leadership capability across our global enterprise. My focus spans high-potential development, coaching-based leadership, executive presence and organizational effectiveness.

I build leaders. From the shop floor to the C-suite, we’re activating mindsets that fuel innovation, inclusion and strategic thinking. Right now, we’re embedding “Leader as Coach” across the organization, equipping people leaders with coach-like capabilities that reflect what the workforce demands today: empathy, adaptability and real-time development. We’re also evolving our Leader Profile—a research-backed capability model—into tangible learning experiences that stick. Every program I design has one purpose: to move from learning to behavior change, with measurable impact.

Blending Technology with the Human Touch

One major misconception has been about AI somehow replacing the human touch. In reality, the magic happens when AI augments human development. AI doesn’t remove the coach; it scales the impact. It fills the gaps between live coaching moments and accelerates insight by surfacing blind spots, patterns and nudges when leaders need them most.

Another pitfall is thinking of AI as just another shiny tool. AI platforms should be rooted in behavioral science and designed for practical application, not theoretical dashboards that no one acts on.

“AI in leadership development isn’t about perfection— it’s about momentum”

Three things: personalization, contextual relevance and behavioral reinforcement. A truly effective platform doesn’t just spit out scores and call it a day. It knows who the leader is, what they’re working through and how to actually help them grow. It reads the room. It doesn’t say, “You scored low on collaboration, “and walk away. It delivers real-time nudges, micro-coaching, and feedback loops that help the leader practice collaboration in the heat of the moment.

And let’s be honest about integration. If the platform isn’t showing up where leaders live, like their calendar, inbox or daily checkins, it’s just another app collecting digital dust. The best platforms feel like an executive assistant with a PhD in leadership—smart, supportive and always a step ahead. Not sure they have made that yet.

Turning Strategy into Action

My approach begins with a question: What behavior are we trying to shift? From there, we work backward. AI should support your existing development architecture, not override it. That means anchoring it to leadership frameworks, performance reviews, coaching initiatives and capability models already in place. And don’t forget change leadership. Leaders need to understand why they’re integrating AI. I see it not as a replacement for human coaching, but as a force multiplier, providing every leader a development companion between workshops, mentoring conversations or live coaching sessions.

I would advise all leadership professionals not to let fear of the unknown stop them from creating what’s next. AI in leadership development isn’t about perfection; it’s about momentum. Start small. Pilot with a team. Co-design with internal champions. Collect stories, not just data. You’ll be amazed at how quickly buy-in grows when leaders see their own growth reflected back to them—on their schedule, in their language, with tools that meet them where they are. Let’s face it: The future of development is blended. Its tech + touch. Data + dialogue. AI + humanity.

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