chevron-down Created with Sketch Beta.

Law Practice Magazine

The Big Ideas Issue

The Power of Intentional Intergenerational Mentoring

Rachael Bosch


  • Intergenerational mentoring enhances personal development and promotes continuous learning across generations.
  • Successful mentoring programs should be voluntary, mutually beneficial and championed by senior leadership
The Power of Intentional Intergenerational Mentoring Penn

Jump to:

In the heartwarming hit series "Ted Lasso," the unexpected camaraderie between Rebecca Welton and Keeley Jones blossoms, offering viewers more warm fuzzies than a basket of puppies. Beyond the laughs and heartfelt moments, their bond mirrors the often overlooked but utterly fantastic perks of intergenerational mentorship. Compared with the state of mentoring in most law firm environments, Rebecca and Keeley seem a bit of an odd couple––the wisdom-packed veteran lawyer teaming up with the tech-savvy new kid on the legal block is not a story we hear very often. Moreover, it's not a story we create systems to support and duplicate.

Away from the screen and inside the halls and Zoom rooms of legal practice, the analogous alliances between seasoned attorneys and their younger counterparts provide untapped opportunities for growth, understanding and the exchange of invaluable wisdom. With Zoomers (Gen Z) set to overtake Boomers as a percentage of the U.S. workforce in 2024, the times they are a changin'. These unique cross-generational relationships have the ability not only to enhance personal development but also to fortify the profession with a deeper sense of community and continuity. Intergenerational mentoring is less about stiff handshakes across oversized desks and more about casual chats that have the potential to do more than define case strategy. It’s where veteran lawyer stories meet Instagram stories, creating an environment ripe for wisdom-sharing and, perhaps, just perhaps, a chuckle or two.

In the dynamic and competitive world of law, success often hinges on an attorney's capacity to navigate complex legal landscapes. Likewise, a law firm's longevity can be closely linked to its ability to adapt and evolve. What if the secret to thriving in this environment doesn't lie solely in understanding new legal precedents or being the earliest adopter of technology? What if it's about bringing generations together to mentor and learn from one another? That's the crux of understanding and leveraging intergenerational diversity in modern law practice.

Understanding Generational Diversity in Law Firms

Generational gaps within the workforce have been a topic of conversation for decades, but the legal field, with its blend of tradition and innovation, offers a particularly unique backdrop for blending different generational mindsets. From Baby Boomer senior partners, who've seen the field transform over the years, to Gen Z new associates and law students, who are digital natives entering a rapidly changing market, each generation brings a unique perspective.


Birth Years

 Dominant Behavioral Characteristics



 Traditionalists, value hard work, strong   interpersonal skills

 Baby Boomers


 Competitive, goal-centric, resourceful

 Generation X


 Independent, tech-savvy, value work-life balance

 Millennials (Gen Y)


 Collaborative, tech-integrated, value innovation

 Generation Z


 Digital natives, socially conscious,   entrepreneurial

 Generation Alpha*


 True digital natives, progressive, learning-centric

*generations not represented in most legal environments

The first step to harnessing the power of generational differences is actively engaging in empathy and understanding. By taking the time to understand the unique perspectives of the different generational cohorts, legal professionals are actively working toward a more inclusive work environment and deepening connections with colleagues. So often, the "workplace generations" conversation defaults to clickbait, cheap shots and low blows disparaging this group or that. We've all heard it, so let's get it out of the way: Baby Boomers are obsessed with holding on to power, Gen X feels like the forgotten group, often overlooked for promotion, -Millennials demand too much and bring too much "woo" to the workplace and Gen Z doesn't want to work!

OK, now that's done, let's reframe and look at how to make the most of these behavioral and social perspective differences.

The Benefits of Intentional Intergenerational Mentoring

In the apprenticeship model of the legal industry, mentoring has always been a valuable professional development tool. While many mentors recognize the immense benefit they get from mentoring junior professionals, the bulk of the benefits are typically seen by those receiving the mentoring. When mentorship, which is often intergenerational by design, takes on an intentional intergenerational focus, its benefits multiply because now, not only can seasoned lawyers offer their wisdom and experience, but younger colleagues, often more tech savvy and with a fresh perspective on work, can help their leaders stay ahead of the ever-changing curve. The intentional intergenerational mentoring described in this article is sometimes referred to as reverse mentoring.

Understanding leads to empathy and building mentorship bonds without the traditional seniority trappings has the capacity to increase understanding of different lived experiences. This is the cornerstone of building inclusive and progressive work environments. Recently, while speaking at a law firm retreat, I was asked what partners could do to get junior associates more engaged in work. My answer was quick but not easy––listen to them and try to understand their perspective. For the most part, Gen Z associates don’t hate work, and they aren’t avoiding you; they have a different relationship to work based on their lived experience. They tend not to trust institutions because institutions have let them down.

In addition to the exchange of experiences, intergenerational mentoring fosters a more cohesive workplace. It breaks down silos, enhances communication and instills a sense of shared purpose through connection. Beyond the more obvious benefits of intergenerational mentoring, initiatives like this provide support to a growing law firm trend; development does not stop at partnership anymore! Sure, partner development tracks have existed before, but typically, they have a heavy focus on business development and very little engagement in difficult conversations or managing and leading diverse groups. Intergenerational mentoring continues to send a message that regardless of your experience, seniority or title, we all have room to learn and grow.

From Legal Tech Savvy to Wisdom and Experience

Intergenerational mentoring serves as a conduit for the exchange of invaluable knowledge and insights. The collaboration between different generations brings together varying strengths and perspectives, creating opportunities unseen and unknown.

For instance, Millennials and Gen Z are often recognized for their adeptness at legal technology and social media––areas that some older lawyers may underestimate or even demonize. The younger generations' proficiency in these domains can be harnessed to navigate the ever-evolving landscape of the legal profession. On the other hand, Baby Boomers and Gen X, with their wealth of experience and wisdom gained over years of practice, can provide nuanced insights and strategic guidance that only come with time.

This diversity in expertise, when shared through a mentoring relationship, leads to the emergence of innovative solutions and the expansion of service offerings. One junior associate I spoke to recently shared an anecdote of teaching a more experienced partner how to include them in a hybrid learning opportunity. In pre-pandemic days, junior lawyers would frequently learn by sitting in a partner’s office while that partner spoke to clients or opposing counsel. In the world of hybrid, many law firm leaders have expressed distress over the loss of such learning moments. However, this junior associate who was told they couldn’t attend the client video meeting because of the client's cost-consciousness provided a technological solution. The partner could join the video meeting but then call the associate and keep them on speakerphone. This understanding of how to use technology to recreate a classic law firm learning moment is a fabulous example of the benefits of a digital native generational cohort.

Intergenerational mentoring not only strengthens the relationships of the mentorship pair but also drives progress and success for the firm. The partner above will likely use this technique with other hybrid associates, and they’ll likely share the tip with their peers. By fostering an environment of collaboration and continuous learning, organizations can leverage the collective wisdom of different generations, propelling them toward a future filled with growth and innovation.

Practical Tips for Successful Intergenerational Mentoring

Implementing an intentional intergenerational or reverse mentoring program in a law firm is not without its challenges, but with the right approach, it’s entirely achievable. The largest roadblock we encounter with law firms whenever we are supporting the implementation of progressive organizational change is the typically small but loud and influential opposition party. When it comes to changes like reverse mentoring or upward feedback, these voices tend to appear within the more senior ranks of the organization. As with any change management process, there will be naysayers. I encourage you not to let a small group of people who are disinterested in learning from other generations bring down your initiatives. Instead, make the program voluntary.

Conversely, the skepticism of reverse mentoring from younger attorneys often stems from a lack of trust and transparency. Will conversations be held confidential, what does participating (or not) mean for their advancement within the firm? Providing clear objectives and onboarding, as well as ensuring that intergenerational mentors are also advocates for their mentees' career progression, goes a long way in allaying these fears.

Once you’ve gotten past your naysayers, it’s time to focus on those who want support. Structure and communication will be the foundation for your successful initiative and must be thoroughly mapped out in advance of any launch. When it comes to both, the program needs to be seen as expressly mutually beneficial; the mentor should gain just as much as the mentee. One structural way for this to happen in your existing mentoring programs is to emphasize round-robin mentoring, where both individuals take turns sharing and learning, regardless of their position or seniority.

When it comes to communicating the benefits of your program, lean on senior leadership and true believers in development to champion the initiative. Find internal case studies from partners whose ascent to leadership was influenced by a more senior partner's guidance or who was able to implement a win for a client based on a unique insight from a junior associate. Even without a formal reverse mentoring program, I assure you these examples exist in your organization. Use these personal stories to underline the importance of embedding intergenerational learning into the firm's culture.

Equally critical is the need to set clear goals and expectations, clearly define the roles of the mentor and mentee and periodically review the program's impact through feedback. Don’t skimp on this step. We recommend formal materials with defined roles and rules as well as a program kickoff where questions and concerns can be addressed. Finally, regular check-ins throughout the process ensure that the partnership remains constructive and that any issues can be addressed promptly.

Poised for Change

Mentoring across generations isn't just a feel-good practice; it's a strategic imperative for law firms looking to future-proof their businesses. In an age where the only constant is change, intergenerational mentoring programs can be the linchpin for developing adaptive, well-rounded attorneys at all levels of seniority.

Inspired by the charming relationship between Rebecca and Keeley, we see how intergenerational mentorship can truly enrich a workplace. Their unlikely friendship reminds us that when we blend the wisdom of seasoned pros with the fresh ideas of newcomers, magic happens. It's all about listening, learning and laughing together, proving that mentorships can make law firms not just more innovative but also more inclusive and fun. Let's embrace these diverse pairings, fostering a community where everyone grows together, one friendly mentorship at a time.