Boomers Had Fax Machines. Gen Z Has Boundaries. We’re All Adjusting.
We built careers by learning the game and playing it well. But what happens when the next generation rewrites the rules?
Welcome to this week’s edition of Reframed by Ashley R. I write for high achieving professionals who rarely get the space to think through what they want next or how to lead in a way that actually works for them.
I'm Ashley Rudolph—a former tech executive turned coach for leaders and next-gen execs in the creative, tech, and lifestyle industries.
I’ve been sitting on this topic for a while…
Everyone seems to have an opinion on Gen Z in the workplace, but here’s what no one is saying: this shift is also challenging for leaders. And that discomfort is worth examining.
THE SCENE: STORY TIME
Last year, I attended a leadership conference where panel after panel of Millennial and Gen X leaders discussed Gen Z in the workplace: what they needed, what they lacked, what they should be doing differently.
But then a young woman stood up, visibly frustrated, and asked why Gen Z wasn’t actually represented on stage. I still remember the shift in the room when she stood up. You could feel the tension.
That moment stuck with me.
It made me hesitate to write about this topic. I didn’t want to sound like just another out-of-touch person analyzing Gen Z from the outside. Every few weeks, another headline pops up: Gen Z is getting fired! Gen Z is struggling at work! Gen Z doesn’t want to work! And while I have my own moments of shock and awe in group chats and 1:1s (some of these stories…whew lol), I’ve held back from writing about it because, quite frankly, I didn’t think I could or should tackle this topic here.
But then I had a thought: the whole reason I started writing The Operator’s Edge is because the "playbook" for being successful at work is pretty nebulous. And this specific topic keeps coming up—in coaching sessions, DMs, and all over my feed. Leaders aren’t just noticing the shift; they’re feeling it. And if high-achieving professionals with years of experience are struggling to navigate this dynamic, that tells me one thing: it’s worth talking about.
REALITY CHECK: THE IMPACT
What’s Happening and Why: A Contextual Reset
Maybe you've had an employee show up to a client meeting in athleisure (on purpose) while everyone else is in a suit seemingly under the assumption that 'business attire' was open to interpretation.
Or an employee with an EOD deadline who left the office at 5PM without mentioning they hadn’t finished their deliverable, thinking they’d just wrap it up the next morning. And you're thinking, did the word deadline imply optional?
Maybe you expected managing a team to be challenging, but you probably didn’t expect it to feel this...disorienting.
It’s not just that expectations aren’t being met. It’s that they don’t even seem shared.
And that’s because we’re leading through one of the biggest shifts in workplace culture in decades.
For Gen X and Millennials, workplace norms weren’t just taught, you learned, often the hard way, that they had to be absorbed. You watched how your boss handled a tough client, overheard how colleagues framed emails, learned when to push and when to stay quiet. Success wasn’t just about performance; it was about fluency in a language no one explicitly taught. And as a generation where the dominant culture preached hyper achievement and wanting to prove ourselves, we embraced it.
You didn’t question the system, you figured out how to work it.
Maybe you’re still finding your footing as a leader.
And now, just as you’ve finally accumulated enough experience to enter the next phase of your career…everything started changing. In very real ways.
Teams are smaller. Organizations are constantly restructuring. And your workload is only growing because your company is setting bigger goals each year.
The “room” you once learned from? It barely exists anymore. The unspoken rules that got you here are being rewritten in real time.
So now, you find yourself managing people who have never worked five days in an office. Who didn’t spend their twenties watching power dynamics unfold over impromptu coffee chats. Who expect clarity on things you were simply expected to pick up. Who expect things that we were taught were earned with time, experience, and seniority.
At the same time, many are incredibly sharp and driven. There’s no shortage of Gen Z professionals who are ambitious, eager to learn, and navigating this new landscape with intention. But even the most high-achieving among them are doing so without the same workplace playbook that guided previous generations.
Gen Z didn’t develop their workplace instincts from years of in-person, trial-and-error experiences. Many of them entered a workforce that was already remote or hybrid, where norms that used to be obvious (communication expectations, office behaviors, workplace social cues) can arguably now feel ambiguous at best. (Forbes).
It’s not just that Gen Z is struggling to adapt to traditional workplaces. Workplaces—still adjusting to hybrid work, evolving norms, and competing values—are struggling to adapt to them, too.
And who’s caught in the middle? You.
WORK WITH ME
→ Ready for a smarter strategy behind your next move?
That’s the work we do inside Elevate — a one-on-one coaching experience for high performers navigating career pivots, leadership growth, or defining what’s next.
THE FRAMEWORK: HERE’S WHAT WORKS
Beyond the Problem: Strategies That Actually Work
At its core, this isn’t just a Gen Z challenge, it’s a workplace challenge. Because sometimes the real question isn’t about a specific generation at all. It’s:
• How do I navigate a conversation with someone whose motivations are different than mine?
• What do I do when their expectations don’t match what I need (or what I can realistically provide)?
• How do I work with someone who brings a completely different context to the table?
These dynamics show up everywhere: across generations, across functions, across seniority levels. The skill isn’t just understanding others—it’s learning how to bridge these gaps while still getting what you need to move work forward.
Great leaders are good at managing down, up, and across. The best leaders? They excel at managing through. Through uncertainty, through misalignment, through shifting expectations.
That’s what these next strategies are designed to help you do. Here’s what’s working for managers that have cracked the code with Gen Z.
1. A Mindset Reset: Assume Nothing, Be Explicit
So much of work operates on unspoken rules, the little things you’re expected to just know. If norms aren’t being met, avoid defaulting to they should know this and instead, ask yourself: Are my expectations actually clear? Have I provided enough context?
State the basics. Work hours, in-office expectations, Slack/email response times—spell them out. It may feel unnecessary, but without these, misunderstandings fester and frustration builds on both sides. If your workplace has clear policies, then manage against them. Setting expectations clearly isn’t about restricting autonomy; it’s about making sure everyone understands the framework they’re operating within. Clarity isn’t control. People resist uncertainty. And when expectations feel murky, frustration builds on both sides.
Provide context. Work is a strange place. From the outside, it looks structured: rules, hierarchy, carefully scheduled meetings where big decisions are made. But inside, it moves differently. There are power shifts you don’t see coming. Priorities change overnight. Deadlines mean different things to different people. None of this is written down. No one teaches it to you. You just have to notice. Providing context or “the why” behind the chaos (at the appropriate altitude) goes a really long way. Invest a few extra minutes to explain the why behind that last minute assignment. And when they hand it in, tell them what was great about it, what they need to improve, and what the impact is of the work that they’re doing.
2. Leveraging Strengths Instead of Just Managing Weaknesses
It’s easy to fixate on what’s not working and just as easy to overlook what is.
Think about the following → What skills, competencies, and interests does your team bring to the table (as individuals)?
Example: A client of mine led a strategy offsite for her team. What made it unique wasn’t the agenda, it was how she facilitated it. She gave the team space to articulate what kind of work energized them, what clients they were most excited about (that they weren't yet working with), and most importantly, what impact working with those clients would allow them to make. She helped them connect their day-to-day efforts to something bigger, making their work feel more meaningful and self-directed. And as their leader, she appropriately pointed out what skills they needed to build in order to work with those types of clients.
What happened next? The team started manifesting their client list, literally. They found themselves naturally pitching and attracting the kinds of clients/partners they had set out to work with. A few months later, my client looked back at the deck from the offsite and realized that without even forcing it, the team had made significant progress toward the business goals they had outlined.
The takeaway? When people see their skills and passions reflected in their work, engagement follows. Not because it’s forced, but because it’s intrinsically motivating.
A strategy offsite or this level of input may not be practical in every workplace, but I share this example as food for thought. Do you create opportunities for providing input or giving feedback, formally and informally? You’d be surprised at the answers a simple “what do you think about this?” surfaces.
3. Mentorship: Bridging the Gap Between “How It Used to Be” and “How It Is”
Workplace evolution is normal. If work didn’t evolve, we’d all still be in factories, clocking in and out under the same rigid structures. But today, the way we work is shifting fast: hybrid models, digital communication, and new generational expectations are rewriting the rules right before our eyes.
In the middle of all this change, something critical is getting lost: mentorship.
I also understand why.
Leaders today are stretched thinner than ever, balancing smaller teams, tighter budgets, and the complexities of a hybrid workplace.
Let alone navigating RTO mandates.
And mentorship—the thing that used to naturally pass down workplace knowledge has become an unintended casualty. It’s hard to feel like you can make the time.
The result? A growing gap between how things used to work and how they work now, with fewer experienced professionals taking time to pass down industry nuances, workplace etiquette, and career navigation strategies.
If you only have five minutes, use them. Mentorship isn’t a luxury; it’s how workplace culture, knowledge, and leadership get passed down. Without it, we all lose. Strong leadership isn’t just about managing today, it’s about shaping the next generation.
Good luck! See you next week.
Ashley
What do you think?
Have you noticed this shift in your own workplace? Leave a comment below.
LEVEL UP
Work with me
Leadership isn’t just about mindset. It’s about strategy. Execution. Positioning.
I help high performers stop over-proving themselves and start leading without hesitation, without burnout, and without waiting to be chosen.
If you’re ready to move with confidence and clarity, let’s talk. Clients describe working with me as having their own personal strategist.
Ready to have me in your corner?
Click here to learn more about my program →
THE WRAP UP: ADDITIONAL RESOURCES
Curated Articles, Just for You
If you’re interested in diving deeper into Gen Z’s workplace expectations, challenges, and food for thought, in terms of shifting your management approach, here are some valuable reads:
Gen Z in the Workforce: Challenging or Change-Makers? (Forbes)
Young People Are Taking Over the Workplace—And That's a Problem for Bosses (WSJ)
SUBSCRIBE
→ Already subscribed? You’re in good company.
My readers work at places like A24, DoorDash, IDEO, Disney, and Harvard — and they’re all here for the same reason: to lead with more clarity, confidence, and intention. If you’re not subscribed, click the subscribe button below.
Well said!