Leading Across Generational Differences 

May 3, 2024 | About L2L, Age Diversity, All Blogs, Generational Differences, Leadership

Here’s just a sample of what I’m hearing and seeing between leaders and employees of different generations:

Younger employees aren’t taking responsibility for their work.

My supervisor doesn’t give me enough direction or feedback.


I value flexible hours and stopping work when I finish my tasks.

I need employees to be more responsive to my calls and emails.


Employees are reluctant to have face-to-face conversations.

I’m not feeling connected to colleagues or feedback on Slack.


I hold firm boundaries between work and life.

We are more than generous with the time off we provide.


I want my organization to make a statement about political issues that align with my values.

We are not a social justice organization and I want to focus on our business.


It’s hard to step outside the generational norms and values we hold, in order to lead and manage across these differences.

There are no easy answers, but let’s dig into some ways forward.

What We Can Learn from Dawn Staley

We can take a lesson from recent remarks by Dawn Staley, the coach of the University of South Carolina women’s basketball team, which won this year’s NCAA Championship.

Staley gave a press conference before her team’s Final Four game this year, in which she described how she brought her young, undisciplined players up to the team’s standards. In doing so, she revealed her approach to generational differences.

Staley has called this young group of players “daycare” for all the attention, energy, and oversight they require. They talked too much, acted silly instead of serious, and were generally undisciplined and falling short of team expectations.

“They were just so young,” Staley says. “You have to insert yourself as a coach to say that’s not how we do things. But you can’t expect that from the jump because they haven’t been that way. So we had to create the habits.”

All leaders can learn from her wisdom as we manage, train, empower, and support our employees of diverse ages and different generations. Helping employees meet our high standards starts the same way for any leader–as Staley says, “meeting people where they are at.”


Knowing Your People

We don’t need to accept less than our standard, but we have to start shaping performance by meeting employees where they are, which means getting to know them.

What we accept is that they may not know how to meet our expectations. We accept them as humans. We listen deeply and with compassion, investing the time and energy to get to know and understand them–their identities, their stories, their strengths, their worldview. We build a relationship with them.

And then we find out what they need to meet our standards. This is the very definition of equity–understanding what different people need to do their best work, and giving them what they need.

Where are younger workers coming from?

It’s hard to avoid generationalizations, but there are some cultural characteristics particular to each generation that impact members’ relationship to work, their communication style, feedback preferences, and comfort with technology.

Generationally, Millennials and Gen Z have been raised with:

Structure. More organized activity and team sports, less free time and boredom. College tracks as early as middle school, career tracks in high school. Generally more direction, explicit expectations, and supervision.

Feedback. From reactions on social media to affirmation and encouragement of self-expression, the expectation for giving and receiving feedback is immediate and direct.

Access to and comfort with technology, but not necessarily training on how to use it.

Getting Curious About Our Discomfort

Let’s be honest–leaders are used to people adapting to us. We’re accustomed to others being curious about what we’re thinking, what we want, and how to work with us.

When we feel otherwise, it’s uncomfortable. It can feel like disrespect or just make us annoyed. And because we’re human, our natural bias is toward restoring our comfort through sameness.

But discomfort is not always a signal of an interpersonal problem. Often, discomfort can signal that the relationship is lacking and we need more deep regard for each other and our differences.

I’ll share a personal example with you.

When working with a new and younger employee, my discomfort was activated by their freely offering me feedback less than two weeks into the job. And my storytelling was activated about what they presumed they knew better than me, without knowing me or the organization yet.

It took some inner agility for me to pause so I could reflect on myself–how I hate being told what to do and will often respond by doing the opposite. I know this is my issue and that it can make me challenging to work with.

I also know what I need: feedback that shows an understanding of a situation’s full context and background, rooted in awareness of the giver’s perspective, biases, and assumptions.

In the space of the pause, I could also change the story in my head about what it means to be “a good leader” and “a good employee.” I didn’t need to have all the answers or find someone who was a “better fit.” Neither of us needed to change who we were.

What I needed was to deepen our understanding of each other. My job as a supervisor is to help them be the best version of themselves, for us to keep our differences and find ways to navigate them well.


I Have Been the “Problem” Generation

Understanding our generational differences is a relief. It’s a new identity and difference for us to hold. And it reframes our conflicts from intractable interpersonal difficulties to a difference in expectations and practices.

Looking back, I can see how generational awareness could have eased conflicts in my own career.

Many years ago, I was a young, independent, know-it-all employee at a large firm. I was a non-conformist who was not interested in asking for permission or doing things any way other than my own. I didn’t adhere to hierarchy or rules that didn’t make sense to me, and I was perfectly comfortable taking on the agency to figure things out on my own.

These characteristics of my generation served me well in our firm’s Silicon Valley office, in the culture of the dot com boom, mavericks, and risk-takers.

But put me in our New York office with Baby Boomer and Traditionalist supervisors, and I became a huge problem. I saw myself as young, filled with excitement, energy, and ideas, ready to bring about change.

My supervisors and colleagues saw me as disrespectful of rules and traditions, unmanageable, and honestly, annoying. I laugh now remembering the time I was written up and gave my boss the perfect Gen X response of, “I don’t accept your write-up.”

What saved me was that I was producing great results, but it got to the point where people avoided me, refused to invite me to social gatherings, rolled their eyes when I talked, and once, told me to “shut up.”

So I speak with empathy and experience about the friction of generational differences. I know they can feel like interpersonal conflicts that require consequences.

But I believe that age diversity is just another difference–like race, gender, class, and other identity markers–that we can leverage to make our organizations incredibly innovative.

Building Responsibility and Agency

We have to stop expecting people to take responsibility and agency without any training–this is a generational perspective. 

I’m not suggesting that as leaders we alter our standards. Rather, that we can instill agency and responsibility in employees who were raised with more structure, direction, and feedback than we were. In fact, it’s structure, direction, and feedback that will help them gain flexibility and independence while maintaining their identity.

And the truth is, if employees don’t receive what they need from us, they will go work somewhere else. We can bemoan their “lack of loyalty” all we want, and we can allow our biases to speak about them as “entitled” or “needy.”

Or we can work with the people who are in front of us, who bring the perspectives, insights, concerns, and creativity that we need. We can build them the supportive systems and structures that help us all thrive, and we can give them clarity about their expectations and accountability.

What other choice do we have but to be human with them?

Letting Ourselves Be Ourselves

As leaders, we can’t build trust or strengthen relationships without first being our authentic selves. If we aren’t ourselves, we can’t expect others to be authentic with us, let alone vulnerable and in relationship.

If we want a vibrant, innovative culture where we age is a welcome kind of diversity, we have to intentionally develop and practice the skill of understanding our identities, which is the topic of Session 1. In this way, we’ll come to understand other people’s identities and what makes our perspectives different. Understanding identity is the key to leading across our differences.

To return to Dawn Staley for a moment, this video of her team doing silly impressions of her is hilarious and also very revealing of the culture she has built. Staley feels safe enough to let her authentic self be seen. Her players feel safe to see her, and they see her well enough to mimic her accurately. And she has the compassion to laugh at herself and the confidence to know that humor doesn’t undermine her power or responsibility.

This is my wish for all of us–to see and be seen in our full humanity. I do this work because I believe it’s possible. Thanks for being with us as we journey forward into this future.

Do these topics resonate with you?

Join us for Session 2 of The Future of Equitable Work Leadership Intensive: Navigating Multi-Generational Workplaces and Leveraging Age Diversity.

How do we lead across generational differences, and their varying communication styles, world views, conflict management skills, feedback expectations, and values?

We can leverage age diversity by understanding how our perspectives and expectations can be shaped by the events, political climate, and technology of our generation. We can build awareness and inner agility to disrupt age bias. And we can build structures that enable and support people’s agency to hold responsibility and create their own safety.

Tuesday, May 28, 2024, 10:00 a.m. PDT / 11:00 a.m. CDT / 1:00 p.m. EDT

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