Mentoring Millennials: Old and New Challenges

By Alison Pivonka

According to a study released in May 2019 by the San Diego Regional Chamber Foundation, “Millennials at Work: The Purpose-Driven Generation,” what millennials desire most in their new careers — second only to a purpose-driven organizational culture — is “support with coaching and professional development.” This can mean different things to different people, but in the legal profession it centers on very traditional ideas of mentorship.


With the retirement of more and more baby boomers, millennials have become the largest segment of the American workforce and nearly 40% locally. Many lawyers in this age cohort, newly admitted to the bar, are beginning their practice while others are arriving on the cusp of true independence and partnership.


Since the early days of practice, where joining a firm roughly equated to signing on for an apprenticeship, the marketplace has changed dramatically and the very foundation of mentoring in many fields has been put to the test. Even before Sheryl Sandberg jumped into the discussion in her 2013 book Lean In, where she went so far as to title a chapter “Don’t Ask Anyone to Be Your Mentor,” the principles of what this relationship means to a new generation, and a new economy, have been the subject of debate.


There is no serious controversy that the apprenticeship style of mentoring is now the exception rather than the rule in our profession. Increasingly emphasis is on the “a la carte” approach of identifying and serving specific training needs, rather than the formation of a one-on-one relationship in which an accomplished senior practitioner molds and counsels a junior colleague over a period of years. The pressures of efficiency, productivity, value delivery and time-based billing all contribute to remaking what was once a straightforward, if one-size-fits-all, transition into the practice.


This presents a challenge to firms and their senior lawyers, who can find it harder to justify the value proposal of one-on-one training in a dynamic economy. Some wonder openly whether investing in training is practical in an environment where younger attorneys frequently emphasize mobility and personal fulfillment above loyalty. Indeed, the Chamber study reports that over half the millennial employees surveyed are thinking of leaving their jobs in the next six months, acknowledging that the perception of millennials’ “willing[ness] to job hop” is not without factual basis. A lack of committed training, however, may itself pressure a young practitioner to move on and make this reluctance a self-fulfilling prophecy.


Don G. Rushing, retired co-chair of Morrison & Foerster’s litigation department, now consults and teaches trial advocacy skills. He acknowledges these pressures and believes many are not new, but emphasizes that associate training is mission critical. Firms, he says, impliedly agree with new associates and clients alike to train and educate their young lawyers in the practice: “Part of the value proposition is that we hire the best and the brightest, and we give them the best possible training.” Cutting training short because it diverts from client service — or, for young lawyers, cuts into their billable hours — he says, is “extraordinarily shortsighted.” While training frequently takes the form of seminars and in-house group training, Rushing nonetheless emphasizes that the role of real one-on-one mentorship is as important as ever.


Despite both the new and the perennial challenges of providing it, the idea of what good mentoring is has not changed. “Everyone understands what coaching is,” notes trial lawyer Deborah Wolfe, who devotes an increasing share of her own practice to mentorship. “It’s a necessity. And, it’s a service to the community.” It is not a matter of instruction alone. Skill development, she says — for example, teaching young practitioners how to build professional relationships with others — “cannot be done online.” This requires time and personal interaction, and an understanding of the individual needs and strengths of the young practitioner; in a word, a productive relationship with a mentor.


Millennials desire this type of relationship as well. According to the Chamber study, they cite “ongoing feedback, clear goals, transparency and collaborative goal setting” as necessary to their new careers.
In Rushing’s view, this goes to the very heart of associate training: “A critical part of it is spending time together across the desk and taking the time to discuss how the assigned work fits into the overall strategic plan, as well as the specifics of work product and delivery.” Collaborative goal setting, Wolfe points out, is a key aspect of good mentoring: “Coaching to the concerns” of younger practitioners — in effect, giving them say in setting the agenda and strategizing with them — provides immeasurable benefit.


Delivery of training and mentorship, particularly outside the more structured setting of a large firm, requires shared responsibility between senior and junior attorneys. “We need,” Wolfe emphasizes, “to take a flexible approach to making sure these resources are available to the next generation of practitioners.” This flexibility can include retaining an outside professional mentor and coach — either by or on behalf of the junior lawyers — seminars and targeted training, simply spending time in a courtroom watching oral argument, or volunteering time serving the indigent, where experience comes quickly. Observing what makes a good professional, aggregating those observations, and swapping notes with peers is a tried and true way to grow as a practitioner.


“My advice to junior lawyers has always been to think of yourself as a business,” says Michael Whitton, former managing and hiring partner in the San Diego office of Troutman Sanders. “Write a business plan. Where do you need help? The role of the mentor is to see that you get that help.” Investing in oneself first, he points out, makes younger lawyers better consumers of their own training and development. “I am still learning on a regular basis, devoting my own time to becoming a better practitioner,” he notes. “Young lawyers need to develop the habit of investing in themselves.”

Alison Pivonka (pivonkaesq@gmail.com) began her practice as a trial lawyer in 1991 and provides mentorship and counseling to developing associates and mature practitioners looking to breathe new
life into their work.