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Law Practice Magazine

The Leadership Issue

Mind the Gap: Leadership Across Generations

Jessie Spressart


  • When leaders move past stereotypes and assumptions—and help their organizations do the same—they can help everyone, regardless of age, be at their best in their environment.
Mind the Gap: Leadership Across Generations
Timofey Zadvornov via Getty Images

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With the convergence of new ways of working and the arrival of a new generation to the workforce, the legal industry is at an inflection point. As the world continues to emerge from the COVID-19 pandemic, law firm leaders are faced with a changing landscape that is not returning to the “before times.” Leaders have the opportunity to seize the moment and transform their leadership style to one that is more agile, nimble and able to navigate the challenges ahead. Doing so requires a shift in how they think about the seemingly insurmountable differences between the five generations working in their organizations today.

Law firm leaders can better prepare themselves to meet the continuing challenges of the uncertain world by leveraging their generationally diverse workforce. It is essential they reject generational shaming and bias to move the legal industry forward. Below are three ways leaders can rethink their assumptions and improve their leadership across all generations.

Understanding the Generational Landscape

We are fortunate to have five generations now at work in our firms. The breadth of experience across the age range is expansive, and the benefit generational diversity brings to firms is immense: The variety of perspectives and experiences can strengthen the service we provide to our clients. And yet we are obsessed with categorizing each generation, as if it were possible to get a detailed data set to accurately describe billions of people with different ethnic, academic, geographical and eco- nomic backgrounds in just a few words or attributes. A person’s generational identity is only one aspect of who they are.

For ease of reference for this discussion, however, here is a brief overview of each generation. Much ink has been spilled describing each generation using mono- lithic traits, attributes and values to group them together. I prefer to connect each generation with the events that shaped their worldview and the technologies most prevalent for them as they came of age.

Generation Z (1996–2015-Ish)

Generation Z grew up in a post-9/11 world. They’ve known the Great Recession and the economic growth that followed and came of age in the Trump era. They are entering the workforce in the middle of a pandemic or its aftermath, and their adult lives are indelibly linked to it. Known as “digital natives,” Generation Z does not know a world without the internet. They may dimly recall flip phones, but smartphones and continuous connection are the norm for them. They have grown up with their lives documented on social media—their parents’ accounts and now their own.

Millennials (1981–1995)

Millennials’ experience was shaped by the first Gulf War, the Columbine High School mass shooting and 9/11. They remember a world before instantaneous internet connections, but modern technology has always been a part of their lives, at home and at work. Their parents had dial-up before high-speed internet existed. CDs, DVDs and videotapes are part of their growing-up experience before the advent of streaming services.

Generation X (1965–1980)

Generation X came of age during the AIDS epidemic, watched the fall of the Berlin Wall and experienced the dot-com boom (and bust). This generation grew up as home computers started to proliferate in the very early days of dial-up internet.

Phone calls and emails are often their preferred way of communication. They may not have had a cellphone until well after college. They remember having one phone line for the entire family and answering machines with cassette tapes to record incoming and outgoing messages!

Baby Boomers (born 1946–1964)

Boomers were shaped by the Vietnam War and the Civil Rights Movement, the Watergate era and the economic upheaval of the 1970s. From handwritten and typewritten papers in school and college to computers at work (but no internet), Boomers came of age on the cusp of a technological revolution. They value phone calls and face-to-face communication.

Traditionalists (born 1925–1945)

Shaped by the Great Depression, World War II and post-war prosperity, this generation relied on good old paper and pen and typewriters as they came of age in the work- place. They have seen the advent of many kinds of technology, from fax machines to computers and the internet to the lightning-fast digital and mobile communication we use today.

Leaders whose thinking about the “younger generations” starts and ends with thinking about needing to understand Millennials have a mindset shift to make: The oldest Millennials are entering their 40s. They have started joining the partner ranks and are already assuming leadership positions. Members of Generation Z are starting to arrive at firms as associates and young business professionals in administrative and business support roles. The perception of Millennials as the youngest ones to be “dealt with” is one that we must push back on, as we will see.

Rejecting Generational Shaming to Eliminate Hidden Bias

The first imperative for leaders who plan to seize this moment of intergenerational opportunity is to challenge the harmful stereotypes each generation has applied to it. Descriptive words like slackerworkaholicentitledcluelesschange-aversedisloyal or out-of-touch may have come to mind while reading the generational descriptions above. However, words like these restrict our understanding of others rather than expand it. We are used to being told to interrupt our biases regarding race, ethnicity and gender, and rightly so. We also need to overcome age bias.

Generational shaming assumes that one or more generations needs to lose so that another can win—the prize being power, relevance, influence or resources. We must move past harmful assumptions such as “Older people are less adaptable to change” or “Younger people don’t want to work hard and just want everything handed to them.”

George Orwell wrote, “Each generation imagines itself to be more intelligent than the one that went before it, and wiser than the one that comes after it.” Indeed, in our clickbait-prone world, it’s easy to find headlines that disparage one generation to boost another. “OK, Boomer” has become

an acceptable response (along with an eye roll) to anything that Generation Z thinks archaic and out of touch to such an extent that Chief Justice John Roberts questioned whether its utterance in hiring discussions could qualify as age discrimination (the answer is potentially yes).

Equally dismissive and destructive is the “Kids these days” mantra, which sug- gests that the younger generations bring nothing but wide-eyed stares and empty minds, only partially ready to be filled with the experiences that others older than they worked hard to earn. A 2017 study published by the National Institutes of Health found that “employees threatened by age- based stereotypes concerning work performance are less able to commit to their current job and are less oriented toward long-term professional goals.” Moving past stereotypes and shaming will have a positive impact on the experiences of everyone in our organizations.

There are many ways to push back against generational bias and stereotyping. The two I offer below are immediately actionable, and when leaders form these habits, they can improve the quality of interactions with people in their organization across generations.

Rethinking Our Assumptions and Reframing Our Expectations

What do you mean when you say ______?

We all know that defining terms is important if we want to make headway on legal matters where there may be confusion. Yet when it comes to a concept like work-life balance, few people pause to ensure that everyone agrees on that term’s definition. Author Adam Kingl writes about this generational “semantic discord.” He suggests that the failure to define the term and understand what different generations mean when they invoke it has led to miscommunication and mistrust between age groups. Kingl reports that when Millennials and Generation Z clamor for work-life balance, it is a where request. They don’t want to have to be in the office just because face time was once the norm and preferred by older generations. Instead, they’d like to be trusted to get their work done from wherever they are—at the office, home, a coffee shop or the beach. On the other hand, Kingl says, Generation X and Boomers hear the request for balance as a when request and think younger folks want to clock out at 6 p.m., expect to work fewer hours and advance in their careers without putting in the time necessary to do the work well and learn the ropes. This implicit bias leads to an assumption—and a trope—that younger generations feel more entitled, want to work less, are less diligent and are less committed to their career.

What’s more, we now know the answer to the where question: When the world pivoted to work from home in 2020, it became clear that people didn’t need to be in the office every day to get the job done well. This is not to say that face time is unimportant or that being in the office should always be optional. However, the desire and ability of many lawyers (of all generations!) to work from anywhere, anytime, significantly impacts their work-life balance.

If we take a step back and reconsider what is being asked for, we can see that failing to define terms can lead to distrust and blame. Other terms are worth similar investigation, like recognition and development. When younger generations ask for recognition, are they asking for more compensation? Maybe. But they also may be looking for more feedback on their work or wish they would be praised for their contributions in a practice group or firm- wide email. When it comes to development, are they asking for stand-up opportunities? Training? Coaching? Assuming what people mean may lead to progress if you get it right; it can be disastrous if you don’t. Getting clear on terms will reduce miscommunication and can light the path to mutual understanding.

Clarify expectations and communication preferences.

Consider the following snippets from conversations I have had in recent months:

  • A first-year Generation Z associate I was coaching confided that they wanted clarification on a partner request but were hesitant to reach out. “Am I allowed to call the partner?” the associate asked.
  • The head of a practice group lamented, “No one picks up the phone anymore! Why can’t people just call when they have questions? I have way too much email to deal with as it is.”
  • While at a conference earlier this year, I dined with a partner who shared that she thought she had an easygoing style with her team. “When something isn’t urgent, I tell them to get back to me at their convenience,” she said.
  • “I really wish the partner in charge would give me an actual deadline,” a midlevel associate told me. “I never know when the work actually needs to be done, and it’s difficult to prioritize my work.”

In one scenario, a young associate lacks the confidence to get the information they need; while elsewhere, a partner is frustrated by the way in which others communicate with him. We also see someone with seniority using a term that lacks clarity, which can cause miscommunication, con- fusion, frustration or anger. I asked the partner what “at their convenience” meant to her. Was it a day? A week? “Oh, well, I’d expect to hear back within a couple of days,” she replied. I suggested she be more explicit with her expectations since “at your convenience” is well-meaning but vague. “They’ll be concerned about what ‘convenient’ means for you,” I said, “and may think they have to get it done immediately, when in fact, they have more time.” Alternatively, they might have other priorities, and “convenient” could mean several days, creating frustration when the work isn’t back quickly enough.

Managing expectations (our own and others’) is essential for productive and clear communication. We all have preferences for how we like to communicate with others both in modality (phone, email, text, face-to-face) and style (direct, warm, collaborative, inspiring). It is challenging, if not impossible, for people reporting to you to meet your expectations if you don’t make them explicit. Don’t make it a mystery! If you prefer phone conversations and voice- mails to texts, let your team know (especially if they’re Generation Z, who are less likely to think to use the phone for a voice call by default). If you want daily check- ins on projects, make that clear, so you’re not left wondering why it has been a week with no updates. When there are teams with multiple generations, it is essential that these expectations be made clear early on to avoid miscommunication and frustration or anger.

Just as there is no one correct way to communicate, there is no right or wrong work style. There are also many preferences regarding work style and the circumstances in which people work. Generation X, Millennial and even Generation Z attor- neys and professionals may have small children and need to flex their work time around child care. Others may be caring for elderly parents or have other demands that require a different kind of flexibility. It’s essential to focus on outcomes. Let those reporting to you get to work in the way that suits them best and stay out of their way. Unless there is a specific reason (other than your personal preference) why a task must be done a certain way, allow others to find the best way for them. Doing so fosters autonomy and helps develop competence, which we will see are essential values that all generations share.

Foster High-Quality Connections to Cultivate Intergenerational Strength

There are three psychological needs that, when met, fuel optimal functioning in individuals: autonomy, belonging and competence. In addition, the desire for respect, as well as meaning and purpose, are near-universal values. These values and needs occur across generational, gender and cultural boundaries, yet the ways people under- stand and express them in their lives are not uniform across the range of experiences.

  • Autonomy is the sense that one has some say over what they do and when they do it.
  • Belonging is the feeling that you are connected to others and that others have a connection with you.
  • Competence is the belief that you can do the job at hand or acquire the skills you need to do what you need to do.
  • Meaning and purpose refer to the notion that every person has a calling and that working in a field that aligns with this can generate the feeling that what they do matters and is worthwhile.
  • Respect is the desire to feel valued and have one’s work appreciated by the people with whom one works.

If we all have these needs and values, how do we adjust when our expression of them doesn’t necessarily match across generations? It is important to pay attention to how they show up differently and honor those differences while seeking common ground. One way to do this is to cultivate high-quality connections across the organization.

High-quality connections are essential for individuals and organizations to perform at their best. They may be short-term experiences—saying hello at the start of a meeting or when seeing someone in the hallway, or genuinely connecting during a shared task or interaction. They also may be generated over a longer term, like when a team is fully engaged and excited to be working together toward a goal.

People who experience high-quality connections report three consistent characteristics:

  1. Vitality, or being energized by the connection;
  2. Positive regard or feeling seen and respected; and
  3. Mutuality, or the sense of vulnerability and responsiveness on both sides of the interaction.

Similarly, researchers have found that  high-quality connections have three consistent elements:

  1. Connectivity and openness to new ideas and possibilities;
  2. Flexibility, or the ability to withstand strain and be resilient; and
  3. Emotional capacity, or the ability to express both positive and negative emotions.

High-quality connections are associated with increased trust across organizations and higher levels of psychological safety, which is an essential element of thriving organizations. They can create moments of learning and mutual inquiry and have been shown to improve organizational processes and collaboration between individuals and teams. When individuals experience high-quality connections, they are more likely to be engaged with others and to form attachments in their work environment.

How can leaders foster high-quality connections? According to Jane Dutton, a psychologist and researcher who studies these types of connections in the workplace, there are four types of questions that are designed to create connections with others. Leaders—or anyone for that matter—can ask these questions to cultivate curiosity, openness and connection with others:

  • Questions that convey genuine interest in another person (What is most meaningful for you at work these days?)
  • Questions that inject positivity (What makes you feel valued here at the firm?)
  • Questions that offer help and assistance (What is your biggest frustration right now, and how can I help?)
  • Questions that uncover common ground (What is an activity or hobby you enjoy doing outside of work?)

Finding moments where these high-quality connections can occur spontaneously can be more challenging in our hybrid world. Virtual meetings have lost the aspect of small talk that often accompanies in-person meetings. When fewer people are in the office, there are fewer opportunities to strike up a conversation at the coffee station. Yet it is vital to reignite the possibility of these moments. Perhaps it is by asking a question from one of the categories above at the start of a meeting or by creating a micro-meeting initiative where people across the organization are paired up for brief interactions to connect in a nonbusiness–related way.

In the wake of the pandemic, many people feel lost and uncertain about professional relationships. Thinking creatively about how to cultivate connections can help individuals in an organization get to know each other—for the first time or after a period of disconnection due to remote work. What’s more, this is an ideal opportunity to be intentional about breaking down generational silos.

Bridging the generational gap can be challenging, but working to ensure every- one is heard and valued has many benefits. Every generation has something to teach and something to learn. We all have experiences and knowledge to share. When leaders move past stereotypes and assumptions—and help their organizations do the same—they can help everyone, regardless of age, be at their best in their environment. Minding the generational gaps has positive implications for client service, collaboration and teamwork, innovation and well-being. It should be at the forefront of leaders’ agendas for moving forward in our post-pandemic world.