The Lives of Lawyers: How Lawyers Can Manage Generational Conflict

In 2018, I had the great fortune of seeing jazz musician, Kamasi Washington, play in a live outdoor concert attended by thousands of people. He had just released “Harmony of Difference” the year before and in one of the interludes, took the opportunity to speak about the album and the importance of difference, saying something along the lines of “difference is meant to be celebrated, not only tolerated.” What he said has stuck with me ever since – it was so succinct and so wonderfully accurate. It resonated with me on a personal level.

I’m the fourth of five children and the first American-born member of our nuclear family of seven, born in Queens, New York City, the most ethnically diverse place on the planet. My younger sibling and I are Gen Y/Millennials, our older siblings who were born in Israel are Gen X, and our parents are Baby Boomers who were born in Eastern Europe just after World WWII. Attending a diverse public school and growing up as a third-culture kid in a family spanning continents and generations was not without its challenges, but provided me early on with the first-hand experience of close contact with people who have different perspectives on virtually everything. This proved to be a huge asset when I began working as a lawyer in my mid-20s.

Why Generational Stereotyping Can Be Destructive for Lawyers

Because I was born in 1985, I’m one of the older Millennials. As a corporate lawyer for most of the 2010s, I recall that conversations at the workplace and in the media about Millennials increased with time, as more and more younger Millennials began to enter the workplace. The defining characteristics of our generation became more pronounced and noticeable with each passing year.

The conversations at work reflected the discussions in the media, which seemed to be overly critical of our generation. I often heard Gen Xers complain about the younger millennials whom they perceived as lazy, self-centered, too laid-back, and not respectful enough of the office hierarchy or formalities like the dress code. I resented this. I felt like it was not a fair characterization, and what’s more, that it was an uncomfortable and ultimately inefficient source of friction, directly tied to decreasing employee satisfaction and retention. I felt that there was another narrative worth exploring and invited my colleagues to consider things differently.

In my previous posts in this Lives of Lawyers series, I’ve advocated for more empathy—vis-a-vis our clients and each other—viewing it as one of our most valuable assets as lawyers and an effective means of reducing friction, improving relationships, wellbeing and productivity. Miscommunication, resentment, and lack of mutual respect come together to make for a missed opportunity to gain strength from diverse perspectives. It’s also undoubtedly a significant contributor to poor work relationships marked by mistrust, diminished employee wellbeing, and fosters inefficient work practices. Trust is critical in the practice of law—a partner has to trust an associate before letting them handle negotiations, to cross-examine a witness on the stand, or even to communicate directly with a client.

Millennials comprise about 35% of the workplace. And as Boomers continue to push back retirement, today’s professional world has the most extensive range of generations to date. Several generations work together under the same roof, especially at law firms, where experience and age are viewed as a boon, not a burden. Understanding each other is more important than ever. We can no longer afford to bury our heads in the sand and avoid dealing with the elephant in the room—especially today, in the midst of a pandemic and economic crisis.

Building healthier intergenerational working relationships comes down to understanding that it’s a matter of different work habits, communication styles, and expectations—not better or worse or non-existent, but different. To me, empathy in the workplace means understanding first and foremost that everyone—our peers, colleagues, bosses, juniors, opposing counsel, and clients—are human beings, with concerns and needs, anxieties, insecurities, motivations, and drives, both inside and outside the office. Empathy in practice means really listening and paying attention to one another, trying to bridge gaps instead of widening them. In the wider real world context, it means not deriding Millennials for being “Millennials” who are “lazy and don’t want to work,” but rather taking the opportunity to consider that perhaps there’s another narrative at work here—that Millennials are questioning what value is, how it is created, and whether hours in/hours at is a relevant metric of productivity.

In the hopes of fostering better, healthier intergenerational relationships at the office, and stronger, more effective work practices, what follows is a brief overview of Boomers, Gen X, and Gen Y, their likes and dislikes, and tips for relating to them and each other. I’ve emphasized similarities to drive home the fact that we’re not so different after all! For purposes of this post, note that I excluded Gen Z (those born after 2000) because it’ll be a few years before they start graduating from law school and entering firms as associates and interns.

Millennials / Gen Y (born 1981-1999)

Often described as being self-centered…as not following through, being unprepared, spoiled, unable to handle criticism, entitled, and the unfortunate by-products of helicopter parenting. But studies have also shown them to be “eager, ambitious, and genuinely talented,” team players, driven by fairness and real productivity. Millennials are the first digital natives – having grown up with the Internet, computing and smartphones, and social media. Mark Zuckerberg is a Millennial!

Even for those older Millennials among us who largely enjoyed the 1990s and early 2000s, all Millennials have been impacted by entering the workforce at a time of recessions—the economic recession of 2008 and the current coronavirus-induced recession. This generation is marked by high rates of unemployment, job insecurity and staggering student debt, unlike Gen Xers, for whom secondary education proved to be financially worthwhile.

Tips for working with millennials:

  • Millennials tend to believe in flat organizational structures more than Gen Xers and Boomers.
  • Raised on instant communication and social media, 24/7 communication is the norm for Gen Yers, but communication should be brief and meaningful. Millennials strongly prefer text over phone calls and tend to want to know what’s going on before diving into a project. They desperately want to get it right and are scared of failure because of the pervasive job insecurity they have faced.
  • Learn from and respect their digital literacy, as well as their preference to use technological tools like ZERØ to automate administrative tasks. Nothing seems more inefficient and counterintuitive to Millennials than the idea of doing manual and time-consuming tasks when there’s existing tech to automate it.
  • Choose text over phone calls.
  • Allow for remote work and flexible schedules. Understand that they are not accustomed to working 9-5 and that the line between their work and home lives is often quite thin if it exists at all.
  • Communicate performance expectations and discuss career paths. Like Boomers, Millennials need guidance, reassurance, praise, and tend to be more sensitive to criticism than their Gen X peers. Provide feedback, but gently.
  • Fairness, sharing, and networking matter to them.
  • Embrace diversity and pro bono. Commit to a greater social good, and be genuine about it.
  • Gen Yers are focused on results more than fixed hours or dress codes. Output is more important to them than tradition.
  • Millennials care—in fact, a tremendous amount. They want to feel like their lives and actions mean something. Encourage their passion. Engage them. Actively involve them in decisions and listen to them.

Tips for Millennials:

  • Asking “Why?” is not the same as undermining or necessarily a criticism and could lead to more discoveries!
  • Prepare for meetings!
  • It’s okay not to know the answer, even when pressed for one. If you don’t know, be open and honest, but follow up with “I’ll find out,” and follow through.
  • Ask for feedback, and work together with your peers to understand what kind of feedback would be constructive for all involved.
  • Resist the tendency to view older colleagues as being dated and having less to offer. Technology is continually changing, and today’s competency is obsolete tomorrow. Tech-savviness, or a lack thereof, does not reflect someone’s intelligence or potential to contribute real value to the team. Don’t discount the value of experience.

Gen X (born 1965 – 1980)

Although today’s mid-life Gen Xers are viewed as well-adjusted humans with entrepreneurial tendencies, in the 1990s they were labeled as disaffected, cynical slackers. Once referred to as the “Latchkey” generation, Gen Xers were shaped by hands-off parenting (think Stranger Things), high rates of divorce, and single parenting, as well as shifting social values. Unlike Millennials, who are mired in student debt, Gen Xers are considered to be the last generation for whom “post-secondary education was broadly financially remunerative.

Tips for working with Gen X:

  • Gen Xers tend to crave independence and be turned off by micro-managing. Give them space!
  • That said, they do value open communication and tend to value feedback and especially negative feedback more than Millennials or Boomers, though not as frequently as Millennials who crave guidance, feedback, and praise quite often.
  • Much like Millennials, today’s Gen Xers care about company culture and want to work in an exciting, engaging culture where they have opportunities for personal growth, as well as flexibility that allows them to spend more time with their families then their parents could. Unlike Boomers, they tend to have little faith in big corporations and big government.
  • But unlike Millennials, they tend to prefer traditional office hierarchy and are driven by money and position in careers. Career paths and expectations should be communicated clearly and adhered to.
  • Like millennials, they are extremely driven by social justice and a positive work/life balance.
  • Although they’re into networking, much like Millennials, they crave less frequent communication, no doubt connected to the fact that social media, texting, and instant communication came into being when they were already well out of high school and college.

Tips for Gen Xers:

  • Avoid the temptation to sit in a closed office all day. Get out there and interact!
  • Consider whether goals are met instead of insisting on structure and form. Working around the clock is not necessarily productive. Consider placing a premium on quality time over face-time.
  • Please don’t confuse the answer “I don’t know” with “I don’t care.” Millennials often use their devices as an extension of their memories and may not store as much information in their heads.

Baby Boomers (born 1946-1964)

Boomers were born in the aftermath of WWII. They were the first to grow up with TVs. They came of age when conservative values began to unravel, amid a deepening socio-cultural divide (e.g., Vietnam War, Woodstock, the feminist/sexual revolution, Watergate), which some experts say exists still today. In the U.S., most came of age in a time of increasing prosperity and government subsidies for post-war housing and education, which instilled in them a profound optimism, leading them to believe and expect the world to improve over time.

Tips for working with Boomers:

  • Boomers develop rapport and maintain trust through one-on-one interaction, conference calls, face-to-face meetings, and phone calls.
  • Prefer to get as much information as possible – be communicative, stay accessible, and visible.
  • Unlike Millennials, which are the first generation of digital natives, they tend to be less technologically savvy by instinct, but that stereotype doesn’t always hold true.
  • Invest in your relationships. Get to know them over lunch or coffee.
  • Boomers tend to prefer formal presentations and being involved in consensus-based processes.
  • Much like Millennials, Boomers appreciate recognition and rewards – show your appreciation.
  • Boomers want to feel like useful and productive members in the workplace and to feel wanted and rewarded.

Tips for Boomers:

  • Lean on and actively learn tech-competency from younger generations. Stay current and on top of tech trends. Proving to your younger colleagues that you are up-to-date will help gain their respect. For younger generations, tech-competency is just as, if not more important, than meeting preparation.
  • Be respectful, don’t let age be a barrier to mutual respect. Treat your colleagues as peers despite the age difference, listen to what they have to say,
  • Provide feedback in a helpful and constructive way.
  • Stay open. Don’t be dismissive or intolerant of how others work just because it’s different from your style. Listen, understand the motivations underlying their approach.
  • Show the value of your experience. Don’t rest on your laurels. Roll up your sleeves and lead by example, not demands.
  • Stave off resentment by treating your younger colleagues as peers, not as children who don’t know better.
  • Actively mentor your younger colleagues by advising, teaching, and guiding them and learning from them in turn. Rather than push your views on them, make suggestions, offer feedback, explain the why of how you do things, and let them know that you can offer help if needed.


  • Amy Sapan

    Originally from New York and based out of Tel Aviv since late 2010, Amy Sapan has over eight years of corporate legal experience, principally in the fields of high-tech and private investment fund formation. She has previously held positions at Amit, Pollak, Matalon & Co. and Yigal Arnon, two of Israel’s leading law firms, as well as Dickstein Shapiro LLP in New York City, now defunct. She received her J.D. magna cum laude from the Benjamin N. Cardozo School of Law, and her B.A. in International & Area Studies summa cum laude from Washington University in St. Louis. She is a member of the NY State Bar and the Israeli Bar Association. She is passionate about gardening, art, craft, dance, swimming, ecology and movement.