Podcast Summary - “ Turning High Potentials Into Rockstar Leaders with Rachel Bolton of Stanley Black and Decker, Inc."
From Sales Floors to Leadership Strategy
Rachel Bolton didn’t start out in Learning and Development, she started in sales. That origin story might seem like a detour to some, but for Rachel, it was a critical foundation. It gave her a deep appreciation for people, for solving real-world problems, and importantly for coaching others to succeed. “I had a leader notice that I always turned around and shared what worked,” she said. “He encouraged me to consider a training role.”
At the time, Rachel’s cheeky response was, “No, trainers are people who can’t do.” Luckily, she gave it a chance and immediately got hooked. She remembers the thrill of seeing someone succeed after applying something she taught. That moment was addictive. Fast forward a couple of decades, and she’s now the Director of Enterprise Leadership Development at Stanley Black and Decker, helping scale leadership development programs and workshops that stick.
Building Better Leaders, Every Day
Rachel describes herself as a “leadership development strategist” and a “workshop whisperer”. A playful title that underscores her talent for creating memorable, impactful learning experiences. Whether she’s designing programs, facilitating workshops, speaking on panels, or coaching individuals, her focus is singular: turning high-potential associates into rockstar leaders.
Across roles at Home Depot, Wesco, and now Stanley Black and Decker, Rachel has stayed committed to this mission. She believes leadership development is about more than content, it’s about creating the kind of learning experiences people remember, and that inspire lasting change.
Currently, she’s rolling out enterprise-wide leadership workshops at SBD, and her passion is contagious. “I wish I could present every single piece of content,” she joked, “but I’m one person. We really rely on great facilitators.”
Trends and the Road Ahead
When asked about the biggest changes in the L&D field, Rachel was quick to call out the rise of artificial intelligence (AI). Like many, she sees it as a powerful tool—not a threat. “It’s disruptive, but it’s also a major productivity booster,” she said.
She’s also noticed a shift toward microlearning. Instead of two-day events, organizations are leaning into short, focused learning bursts such as 30-minute modules or 15-minute coaching sessions. It’s a reflection of modern learners and modern pace. “People want to gain skills quickly. Microlearning meets them where they are.”
Looking ahead, she predicts a growing emphasis on what she calls “power skills”, formerly known as soft skills. “Things like resilience, adaptability, and human connection are going to matter more than ever,” she said. As AI automates more technical tasks, the uniquely human traits like empathy, courage, and creativity will become even more essential. “We do business with people, not platforms,” Rachel added.
The Most Critical Skill in L&D? Facilitation.
Rachel was quick to identify facilitation as the most vital skill for today’s L&D professionals. “Strong facilitators can scale impact across the enterprise,” she explained. “We need people who can read a room, adjust on the fly, and bring content to life.”
Even for those in non-facilitator roles, she advises developing presentation skills. “Host a lunch-and-learn. Lead a team meeting. Practice presenting,” she urged. “It makes you invaluable to your team.”
If Budget Was No Object…
Stanley Black and Decker already offers strong executive support for learning, which Rachel deeply appreciates. But if she had both full leadership backing and an unlimited budget? Her first move: invest in coaching. “Everyone deserves a coach, not just the C-suite,” she said.
She’d also invest in more in-person events. “Virtual is efficient, but in-person sessions offer something deeper. People connect, collaborate, and remember what they learned.”
Mentorship That Changed Everything
Rachel’s move into corporate learning wouldn’t have happened without one bold request and one generous mentor. She reached out to Deedee Crawford at The Home Depot on LinkedIn for an informational interview and got more than advice. Deedee believed in her before Rachel fully believed in herself. “She said, ‘You could absolutely do this.’ And that changed everything.”
Rachel credits Deedee with giving her the push she needed to apply for—and land—her first corporate trainer role. “She was the first person to celebrate with me when I got the job,” Rachel recalled. “Mentors like that see something in you that you may not even see yourself.”
Where She Turns for Insights
When it comes to staying sharp, Rachel relies heavily on LinkedIn for industry news and thought leadership. She also loves the Coaching for Leaders podcast hosted by Dave Stachowiak, and she’s a fan of the Corporate Learning Network for webinars, newsletters, and peer connection.
For reading, her top pick is Radical Candor by Kim Scott. “Before you can design leadership programs, you have to understand how to give feedback and have tough conversations,” she said. “That book lays the foundation beautifully.”
Rachel Bolton blends strategic insight with a facilitator’s heart. Whether she’s designing experiences or cheering on a mentee, her work centers on creating leaders who don’t just manage—but inspire.
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