(It’s) OK, Boomer: How Reverse Mentorship Enhances Leadership

Steven Robertson is an internationally acclaimed author, a recognized keynote speaker and a respected executive with 30+ years’ experience consulting for A-list clients.

And his mentor is 24.

Robertson is one of a growing number of business leaders currently challenging the traditional notion of mentorship. Invigorated dyads of seasoned professionals and more recent (often younger) hires are engaging in “reverse mentoring,” redefining mentorship as a fancy word for “relationship” — one built on trust, expertise and sharing.

“Whenever you hold someone accountable, that’s mentoring,” says Robertson, whose mentor, Jack, is holding him accountable to conceptualize and execute a new app for his corporate consulting company, Bold Training. “Jack says, ‘Steve, where you are today is great, but I know where you could be tomorrow, and I’m not going to stop until you get there.’ It’s gold.”

This type of relationship harnesses today’s multigenerational, diverse workforce to spark innovation, shape workplace culture and drive business growth, says Dr. Andrea “Andi” Simon, Founder and CEO of Simon Associates.

“Reverse mentoring is a methodology that opens minds to each other and builds bonds,” she says. “It creates a culture of true intimacy and inclusiveness.”

Former GE CEO Jack Welch is often credited with creating the concept of reverse mentorship in 1999, when he paired junior employees with the top brass to improve executives’ comfort level with the newfangled “World Wide Web.”

Like the internet itself, reverse mentorship has evolved into something limitless and indispensable. It brings underrepresented voices to the C-suite, builds companies’ core strengths and deepens leadership skills. Dr. Simon and Robertson offer insights about the benefits of reverse mentorship — and share actionable steps for leveraging this valuable trend.

What Is Reverse Mentorship?

Before we go any further: No, asking the intern how “you make your TikTok go viral” does not count as reverse mentorship.

More than just flipping the script on traditional top-down training, reverse mentorship is an intentional, goal-oriented component of a broader culture of listening and learning. It enables senior leaders to adapt to technology and culture from younger team members, while also fostering mutual respect and understanding of evolving values and expectations.

“When you find a mechanism to show people that they’re validated and they mean something, even though they’re early on in their journey, retention is good,” Robertson says. “When retention is good, recruitment is good, engagement is good. And when retention and engagement are good, your customer experience is good.”

Why Should Executives Engage in Reverse Mentorship?

Less experienced team members shed light on current cultural values, customer preferences and evolving workplace expectations. Plus, digital natives add technological fluency and new cultural insight to your team — locking these valuable members away in the proverbial mailroom might not be to your company’s advantage.

A Vistage small business leader recently shared with Dr. Simon the story of an intern who was the first in the company to learn a new software and use it to create a product so good that the company presented it to a client.

“The client loved it,” says Dr. Simon, a frequent Vistage speaker. “The company hired the intern because he gave them the added value of what his capabilities could bring.”

By tapping those capabilities through reverse mentorship, business leaders can stay ahead of industry shifts, drive organizational growth, foster cultural awareness, strengthen team connections and bridge generational gaps.

Staying Ahead of Industry Shifts

Robertson describes the effort to build cross-generational trust as essential in a workforce shifting from a majority of “ownership” generations to a majority of “subscription” ones. While older members of the workforce owned CDs and DVDs (and 8-tracks, if they’re being honest), younger generations grew up subscribing to nearly everything from music to movies to the clothes in their closets.

“If you’re trying to lead out of an ownership mentality, it’s ‘Do what I say, because I’m the boss.’ The subscription mindset is, ‘If you have authentic value, and I understand your motive, I’ll subscribe,’” he says.

BNY Mellon’s Pershing was an early adopter of this mindset shift: When the company struggled to recruit and retain Millennials in 2013, it launched a reverse mentorship program that led to a 96% retention rate in the first three years.

As Robertson puts it: “I tell business leaders, ‘You’re not hiring employees, you’re onboarding subscribers.’”

Driving Organizational Growth

Administrators at a hospital that had been experiencing growing pains sought Dr. Simon’s expertise in integrating younger doctors into a culture dominated by more seasoned staff. They piloted a reverse mentorship program — and built a culture that embraces innovation and expertise in equal parts.

The hospital’s experience mirrors industry analyses that find reverse mentorship fosters innovation, engagement and resilience. One recent study attributed 67% of employee performance improvement to reverse mentorship, a figure that doesn’t surprise its adherents.

“You can learn a lot from the folks right around you, if you open your mind to it,” Dr. Simon says.

Fostering Cultural Awareness

By deeply listening and demonstrably learning, leaders who engage in reverse mentoring make the kind of changes that build a stronger culture, such as Microsoft’s expanded benefits packages for diverse families or a London law firm’s gender-neutral restrooms.

“I’ve had CEOs of companies say to me, ‘Nobody hangs around after work,” says Dr. Simon, who applies her doctorate in anthropology to corporate consulting. “And I say to them, ‘Well, why don’t we find out what they would like to hang around for?’”

Millennials comprise 35% of the workforce, while Gen Z is expected to make up 30% by 2030 — that’s 65% of the workforce filled by two generations famous for their teetotaling.

“Older folks who have been used to socializing over wine or beer after work as a way to get to know each other are finding that that doesn’t work anymore,” she says. “This is a time of change. Reverse mentoring helps companies to find that change.”

Bridging Generational Gaps

With five generations tightly squeezed into one workforce, reverse mentoring leverages the power of diverse experiences to enhance decision-making. The result is a future-proofed workplace with effective leadership today and a strong leadership pipeline for tomorrow.

In his book, “Aliens Among Us: The Disconnected Generation,” Robertson says the world is being reshaped by Gen Z, whose workplace expectations, Robertson contends, are unlike any generation that has come before (hence, their designation as “aliens”).

“Gen Z is never going to become like us. We are going to have to become like them,” he says. “And when we do, what we’ve discovered — from Fortune 500 to Fortune 50 companies on — is that what we were doing with and for Gen Z actually applies to every generation of the workforce. When we use accountability to build relationships and trust, that changes the engagement. It’s beautiful.”

How Does Reverse Mentorship Deepen Leaders’ Understanding of Evolving Workplace Expectations?

Reverse mentoring highlights what the younger generations value, such as relational equity and accountability. As well as what they don’t care about (or worse, are made genuinely uncomfortable by), such as performative after-hours socializing.

Robertson says one way in which understanding younger generations’ expectations of fairness helps companies to grow is by identifying who is punching above their weight class — and who is just weighing the team down.

“Nothing will kill a great employee faster than watching you tolerate a poor employee,” he says. “Your best performers leave, they unsubscribe, and they go where they have value, and the motive is good.”

Reframing Work-Life Balance

Reverse mentorship also helps uncover generational differences in priorities. For example, as an anthropologist, Dr. Simon said that early in her career, her work was her identity. But for younger generations, titles alone do not shape their sense of self. They need something more out of the job — whether it’s professional development opportunities or the chance to break free from traditional hierarchies.

Zappos embraced the importance of honoring individuality when it eliminated job titles and instituted a “holacracy,” a self-governing system of operating that leans hard into this you-could-work-anywhere-so-please-choose-us way of thinking about employment. The company also famously invests in its people — and attracts top-tier talent as a result.

“In today’s environment, more people work to live than live to work,” Dr. Simon says. “They can move from place to place more easily without feeling the loss from leaving.”

Sparking Honest Dialogue

By being open to real-time feedback about their performance, company culture and blind spots, leaders are using reverse mentorship to create a safe, non-hierarchical space for younger employees to share hard truths, such as misaligned goals or what’s missing from DEI efforts.

This goes to the heart of the “subscriber” model of employee, Robertson says.

“You build subscribers by building trust, and you do that by bringing application to their information, helping them accomplish and become who they want to become,” he says. “When people ‘subscribe’ to you, it’s because they trust you. They know your motivation is to grow them, and this builds a relationship of trust.”

Enhancing Leadership Effectiveness

One of the most profound effects of reverse mentorship is that it inspires leadership humility. From Accenture to PepsiCo, business leaders are benefiting from learning and growing — and transferring that growth to the entire organization.

“When you have leaders that have this mindset of mentoring, coming alongside, investing in, then all of a sudden you have a transformational culture. When you have that, the narrative becomes: ‘You won’t believe this great thing that happened at work today,’” Robertson says. “Reverse mentoring validates your culture through the stories that get told. That’s how culture becomes real.”

What Steps Can Leaders Take to Implement a Reverse Mentorship Program?

Launching a reverse mentorship program requires intentionality, a clear set of goals, and the ability to be comfortable with discomfort, Dr. Simon and Robertson say. Creating a plan at the outset helps veteran leaders enter into the relationship feeling intellectually curious, rather than threatened. In turn, younger, emerging leaders are empowered to realize their own career goals.

1. Set Clear Goals

Define what you hope to achieve from reverse mentorship and align those objectives with your organization’s goals.

“You have to be intentional about it and not be uncomfortable with the hard data,” Dr. Simon says. “Ask yourself, ‘What do I want to see as the outcome? You have to be very clear at the beginning about what you think this should achieve, because in the absence of that clarity, anything could happen.”

2. Identify the Right Pairings

Common sense dictates that the best approach is to match mentors and mentees based on complementary skills and knowledge gaps, taking into account personality and communication style compatibility.

Or not.

Robertson once teamed up a “grumpy” CFO with a creative, somewhat scattered young marketing team member on a delicate project. An organic trust blossomed, and weeks later, when the CFO needed a creative way to tell an important story to the company’s leadership team, guess who he turned to?

“The CFOs showed up at the meeting in a costume, and did this whole theatrical presentation,” Robertson says. “When you build trust, beautiful things can happen.”

3. Foster Open Communication

The deep listening that comes with reverse mentorship creates a safe space for honest dialogue and feedback, encouraging active listening and mutual respect.

“[Harvard professor and author] Amy Edmondson writes about personal safety in the workplace, and why it’s so important to be able to safely say to somebody, ‘You really take control in meetings, and perhaps those of us who are newer and not as experienced as you, could share the ideas that we’ve had,’” Dr. Simon says. “But it requires a young person having the confidence that when they say this, they’re not going to lose their job. It comes from a culture of true intimacy and inclusiveness, and reverse mentorship is a great methodology for achieving that.”

4. Measure Impact

You’ve set the goals, you’ve made your pairings, and you’ve created a culture of trust. Now what?

“The question is, ‘If I’m going to put the whole company through this, what do I want to see as a result?’” Dr. Simon says. “What will I measure so that I can know whether this has value?”

Measuring the results should tie into the goals you set out at the outset — whether it’s better output, or more intangible metrics such as morale. Review these metrics regularly and gather feedback from both mentors and mentees to continuously fine-tune the project.

What Are You Waiting For?

Where can small business leaders find effective examples of reverse mentorship in action? In their own Vistage peer advisory groups.

“When I speak to Vistage groups, I’m intrigued by the elder and the younger leaders in the same room, learning from each other,” Dr. Simon says. “There’s a two-way conversation going on with each adding value quite effectively.”

While the organic exchange of ideas likely comes more easily in a peer group than in a company, Robertson says he finds that Vistage members are often open to challenging their perspectives and questioning their legacy experiences — prerequisites for implementing reverse mentorship in the workplace.

“When the CEO shows up differently, everything is different. The accountability, the way people treat each other. You’ll be amazed at how powerful it is,” he says. “Does it take deliberate focus? Yes. Anything worth time and energy does. But if you want to create a way for the younger people to hold the older ones accountable, you’ve got to create a different environment.”

Reverse mentorship helps to build that environment. One that blends humility with experience — and inspires seasoned leaders and early careerists alike to hit “subscribe.”

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