Changemaker Interviews

Jeff Skipper Helps Leaders Master the Art of Change

Published

11 months ago

April 14, 2025

Jeff Skipper Helps Leaders Master the Art of Change

Jeff Skipper has spent over 25 years helping organizations design disruption and lead change from the inside out. His clients have included household names like IBM, Suncor, Goldman Sachs, and The Salvation Army, but his work is far from corporate buzzwords and boardroom jargon. At his core, Jeff is someone who believes in the power of transformation—both for organizations and the individuals within them—by helping them master the art of change.

With a Master’s degree in Organizational Psychology and certification as a Change Management Professional, Jeff has built his career by asking one question over and over: how do you get people to embrace change?

Reinvention, Three Times Over

Jeff didn’t begin his career with all the answers. In fact, he remembers his very first consulting gig back in 1994 so vividly—because he was so nervous, he couldn’t remember the conversation afterward. That feeling of impostor syndrome followed him until he landed a role at IBM in 1996, where he learned how to consult with confidence.

Years later, the work caught up to him. “In 2008, I left IBM as a burned-out husk,” Jeff says. Starting his own business wasn’t just a career move—it was survival. With no business background, he studied how successful companies managed their cash flow and slowly began applying those lessons. He shifted from worker bee to leader, from unsure to unstoppable.

By 2014, Jeff found himself facing another barrier. The demand for his services was growing, but he couldn’t clone himself. That’s when he made another bold move: switching to value-based fees. Clients weren’t just looking for deliverables—they wanted results. That shift changed everything, and his business surged once again.

Sharing What Works

Today, Jeff runs his own consulting firm and continues to support organizations through strategic transformation. But he’s also focused on something deeper: helping the next generation of consultants and entrepreneurs learn the ropes.

He’s launching a new course for coaches and consultants, distilling decades of trial and success into practical advice. His two books, Dancing with Disruption (2023) and High Impact Workshops for Leading Change (2024), are packed with the same insight he shares with clients and peers.

“I love seeing people excel,” Jeff says. “When their eyes light up with understanding or triumph, it’s the greatest sensation to know you enabled that to happen.”

The Value of Outside Perspective

One of Jeff’s strengths is bringing an outsider’s eye to complex problems. He’s a voracious news consumer and constantly watches global and industry trends to understand where the future is headed. That insight helps him identify patterns and blind spots that internal teams may miss.

“It’s too easy when you’re on the inside to get locked into perspectives shared by everyone else,” he explains. Jeff helps organizations challenge assumptions, spot real opportunities, and avoid costly mistakes.

Paying It Forward

Early in his career, Jeff benefited from the generosity of experienced professionals who offered their time and advice. “They would often say, ‘When I was in your position, I needed someone to help me,’” he recalls. That spirit stuck with him.

Now, he gives back in multiple ways. His website offers free downloadable resources, including The Executive Interview Guide—a practical tool for preparing leaders to ask better questions and lead more focused conversations.

He also volunteers with the Association of Change Management Professionals and leads webinars to share consulting techniques and lessons learned.

It’s all part of a larger belief: we rise by lifting others.

Growth through Adversity

Like many professionals, Jeff has had moments that left a mark. One, in particular, happened early on at IBM when he gave feedback to a manager. The manager took it as a personal criticism and publicly berated him. That moment shook Jeff’s confidence for years.

“I don’t mind admitting that I needed professional help to overcome it,” he says. But once he did, it unlocked new levels of confidence and impact in his work. It’s a reminder that even difficult moments can lead to powerful growth—if we choose to work through them.

Advice for Those Just Starting

Jeff has reinvented himself three times over. Each pivot led to growth, and each step required an investment in new skills. His advice to those starting out is simple: don’t hesitate to invest in yourself.

“People become so focused on the tasks at hand that they fail to look ahead and recognize the skills that will propel them,” he says. “It takes money to make money. Spend the money to improve your skills or to get the help you need. Two heads are better than one.”

Leading with Purpose

At the center of Jeff’s career is a set of personal values. As a Christian, he believes in putting others first. He recalls helping set up a mic for a speaker at a conference, even though it wasn’t “his job.” In that moment, he realized that titles and roles mattered less than making sure the event succeeded for everyone.

That perspective—serving others and helping them grow—is woven into every project he takes on.