Things Leaders Do

The Gen X Leader's Guide to Managing Millennials and Gen Z

• Colby Morris

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Ever get frustrated trying to lead someone who sends emails in lowercase with no punctuation... but somehow they're your top performer? If you're a Gen X leader, you're sandwiched between generations with completely different values and expectations. In this episode, Colby breaks down why leading younger generations feels so challenging—and gives you practical strategies to bridge the gap without losing your edge.


What You'll Learn

  • Why your frustration with younger employees isn't really about them (it's about conflicting operating systems)
  • How to use Simon Sinek's "Why First" framework to create genuine buy-in
  • The 5 biggest mistakes Gen X leaders make with Millennials and Gen Z (and what to do instead)
  • What younger generations are really looking for from leadership (hint: it's not ping pong tables)
  • A practical 3-step action plan you can implement this week


Key Takeaways

The Real Issue: The tension between generations isn't about entitlement or work ethic—it's about fundamentally different experiences that shaped different expectations.

Start With Why: Before explaining what needs to be done, explain why it matters. Connect every task to a bigger purpose.

The Four C's: Younger generations want Clarity, Consistency, Coaching, and Care from their leaders.

Your Weekly Action Items:

  1. Audit your leadership mindset—where are you still leading like it's 1999?
  2. Practice the "Why First" framework on one delegation this week
  3. Ask one team member: "What's one thing we could change to make your work more meaningful?"


Episode Quotes

"That frustration you feel when they ask 'why' isn't about their entitlement. It's about your discomfort with a different way of working."

"The question isn't whether you should adapt. The question is: what's it costing you not to?"

"EQ isn't soft—it's the hardest skill to master and the most important one for results."


Resources Mentioned

  • Simon Sinek's Golden Circle (Why-How-What framework)
  • Things Leaders Do One-on-One Series (previous episodes)
  • Visit nxtstepadvisors.com for more leadership tools


Connect with Colby


Reflection Question

What belief about leadership are you holding onto that might be holding your team back?

Things Leaders Do is hosted by Colby Morris, helping leaders create clarity, build cultures people want to be part of, and lead with purpose.


Speaker 1:

You ever get frustrated trying to lead someone who sends emails in lowercase, with no punctuation, but somehow they're your top performer? Or maybe you've got that Gen Z employee who's incredibly sharp but turns off Slack at 4.59 pm with zero guilt? Leading across generations isn't new, but if you're a Gen X like me, it's more complex than ever. See, we're sandwiched between boomers who value loyalty and grit, and younger generations who expect flexibility, purpose and emotional intelligence. Hey, leaders, I'm Colbyby Morris, and this is Things Leaders Do, where we tackle real leadership challenges with real solutions. Today, we're diving into one of the biggest challenges that I think Gen X leaders face how to lead younger generations without losing your mind or your edge. Let's just call it like it is Leading millennials and Gen Z can be frustrating.

Speaker 1:

You show up early, stay late and still feel like you need to prove yourself. Meanwhile, zayden, your 27-year-old team member, wants to talk about work-life balance and vulnerability and questions whether we really need that 8 am meeting. Here's what I've learned after working with hundreds of Gen X leaders through this exact challenge. The frustration isn't really about them, it's about us. Think about it. We were shaped by completely different forces. Gen X grew up independent, skeptical, self-sufficient. We were latchkey kids who figured things out on our own. We didn't get participation trophies and we definitely didn't expect to love our jobs. Work was work. You showed up, did your thing and you went home. That experience made us incredibly gritty and resilient, but it also made us guarded. We learned to keep our heads down, prove ourselves through output, not to ask too many questions.

Speaker 1:

Millennials and Gen Z they grew up differently. They were coached, mentored, encouraged to speak up. They expect collaboration, feedback and flexibility. They want to know not just what to do but why it matters. So that tension you feel, it's the collision of two completely different operating systems. Here's the hard truth, that frustration you feel when they ask why. It isn't about their entitlement, it's actually about your discomfort with a different way of working. And if you want to lead them effectively, you've got to get comfortable with that discomfort. Here's what I've seen happen.

Speaker 1:

When Gen X leaders make this shift, they don't just become better at leading younger generations, they become better leaders. Period. The skills that engage millennials in Gen Z clarity, purpose, emotional intelligence those same skills make everyone on your team more effective. The question isn't whether you should adapt. The question is what's it costing you not to. So let's talk about Simon Sinek's golden circle. You probably know this already Start with why, then move to how, then what. But most leaders, especially us Gen Xers we flip this thing backwards. We lead with what needs to be done, maybe touch on how, and rarely explain why. Here's the shift.

Speaker 1:

Millennials and Gen Z don't just want to know their tasks, they want to understand the mission behind the work. They need to see how their effort connects to something bigger. So instead of starting with the task, start with the purpose. Give them the why first, then show them what they'll do to achieve it. So here's an example the wrong way. I need you to update the client database and clean up the contact information. Can you have this done by Friday? Yeah, they won't respond to that. Here's a better way. We're losing potential deals because our sales team can't find accurate client information quickly. It's costing us credibility and revenue. So what I'd like you to do is update our client database and clean the contact information so our team can respond faster and more professionally. Can you have this ready by Friday so we can test it before next week's big prospect calls? It's the same task, completely different buy-in level.

Speaker 1:

Here's a real example from my own team. I had a marketing coordinator who kept missing deadlines on his social media posts. My first instinct was to micromanage or get frustrated. Instead, I sat down and explained the why I said. Here's what I realized I never told you. When we post consistently, we stay top of mind with potential clients who are looking for help. Every post is a touch point that can lead to a conversation that changes someone's business. What you're creating isn't just content, it's connection. Now here's how we're going to make sure you have what you need to hit those deadlines consistently. The result he started treating those posts like they mattered, because now he understood they did Start with. Why, then, show them the what? It's not about being trendy, it's about being effective.

Speaker 1:

All right, let me walk you through the five biggest mistakes I see Gen X leaders make with younger generations and, more importantly, what to do instead. Mistake number one expecting people to pay their dues the way you did. Look, we earned our stripes through years of grunt work, late nights, proving ourselves over and over and over. So when a 26-year-old asked about growth opportunities six months into the job, our knee-jerk reaction is you haven't earned that yet. But here's the thing they don't need to earn opportunity the same way we did. The economy is different, job mobility is different, expectations are different. A better approach Shift to a development mindset. Instead of asking have they earned it, ask how am I helping them grow into it? Ask how am I helping them grow into it. Give them stretch assignments. Let them shadow you in meetings. Create pathways for growth, even if they're not the traditional ones you went through.

Speaker 1:

Mistake number two avoiding feedback because it feels awkward. We grew up in a no news is good news culture. If you weren't getting yelled at, you were probably doing fine. But for younger generations, silence isn't neutral, it's anxiety inducing. A better approach Give regular, clear, constructive feedback. I'm talking weekly, not annually. Millennials crave it. Gen Z expects it. And here's the secret when you give good feedback regularly, the difficult conversations become easier because you've built that foundation of trust. And then mistake number three assuming loyalty should be automatic. Assuming loyalty should be automatic. We stayed at companies for years, even when we were miserable, because that's just what you did. But younger generations watched their parents get laid off. After decades of loyalty. They've learned that companies aren't loyal to them. So why should they be loyal to companies? A better approach Earn loyalty by investing in people, provide purpose, development and genuine support. They'll stay for leaders who care about their growth, not for company logos or paychecks alone.

Speaker 1:

Mistake number four leading from authority instead of influence. Our leadership models were usually hierarchical. The boss said jump. You asked how high. But younger generations? They were raised to question authority, to think critically and expect to have a voice. A better approach, invite collaboration and model humility. Ask for their input. Admit when you don't know something. You'll earn respect by being real, not by demanding it because of your title.

Speaker 1:

And mistake number five thinking emotional intelligence is soft. Emotional intelligence is soft. This might be the biggest one. We were taught to check our emotions at the door right. Keep social work and personal separate. Never let them see you sweat. But here's what I've learned after years of leadership coaching EQ isn't soft. It's the hardest skill to master and the most important one for results. People perform best when they feel psychologically safe, seen and supported. A better approach Get comfortable with emotions yours and theirs. And hear me, and hear me. Check in on how people are doing, not just what they're doing. Create space for vulnerability. The leaders who mastered this don't just get better performance, they get innovation, they get creativity and loyalty. All right, now let me tell you what they're really looking for, and it's not free coffee.

Speaker 1:

Here's a conversation that completely changed how I think about this whole generational thing. I was working with a tech company where the Gen X leadership team was frustrated because their younger employees kept asking for more feedback and better communication. Their younger employees kept asking for more feedback and better communication. These executives were rolling their eyes, thinking we already have quarterly reviews. What more do they want? So I sat down with one of their millennial team leads and asked her straight up what do you actually need from your manager? Her answer surprised me. She said look, I don't want a ping pong table or unlimited PTO. I want a manager who checks in with me regularly and actually listens when I talk. I want to know if I'm on the right track before my quarterly review and I want to understand how my work connects to something bigger than just hitting this month's numbers. That's when it clicked for me. This isn't about entitlement or neediness. It's about a fundamental shift in how people want to be led.

Speaker 1:

Think about it, gen X leaders we often grew up in environments where you separated work from personal life. You clocked in. You did your job you clocked out. But for millennials and Gen Z that separation doesn't really exist and, honestly, in today's world it can't. They bring their whole selves to work because modern life requires it. They're dealing with student loans, caring for aging parents, navigating a housing market. That's completely different from what we experienced. Work isn't just a paycheck. It's part of their identity and their path to building the life they want.

Speaker 1:

So what they're looking for from leaders is actually pretty straightforward. One clarity what's expected of me? Not just the task but the standard, not just the deadline but the priority? Two consistency Will you follow through on what you say? If you promise feedback, will you give it? If you commit to supporting their growth, will you actually do it? Three coaching Will you help me get better? This doesn't mean hand-holding. It means investing in their development, giving them stretch opportunities and helping them connect the dots between where they are and where they want to go. And then four, care Do I matter to you as a person or am I just a resource?

Speaker 2:

This is a big one.

Speaker 1:

They want to know that you see them as a human being, not just a function. This is where your one-on-ones become absolutely critical. By the way, if you haven't listened to my one-on-one series yet, pause this episode and go do that, because your regular check-ins are where these four needs get met. That's where trust gets built. That's where the bridge between generations happens. Don't assume disengagement. Don't assume entitlement. Start a conversation, ask questions, get curious about what makes them tick. Here's what I discovered when you meet these four needs clarity, consistency, coaching and care you don't just get better performance from younger generations, you create the kind of leadership environment that brings out the best in everyone. Now your action plan for this week. Let's make this practical. Here are three things you can do this week to start bridging the generational gap on your team. First, audit your leadership mindset. I want you to get honest about where you're still leading like it's 1999. Ask yourself am I expecting people to prove themselves the same way I had to? Am I giving feedback regularly? Am I still operating on the no news is good news model? When someone asks, why, do I get defensive or do I see it as an opportunity to create buy-in? Write down your answers. Be brutally honest, because awareness is the first step in this change. Second, practice the why, first framework.

Speaker 1:

This week, pick one significant task you need to delegate Before you explain what needs to be done. Start with why it matters. Here's a simple template, here's why this is important. And then insert the bigger purpose. Here's what I need you to do to achieve that. Insert the specific tasks and here's when I need it. Insert the deadline. Try it once, see how differently the conversation goes. See how much more engaged they are when they understand the mission behind the work. More engaged they are when they understand the mission behind the work.

Speaker 1:

And third, have one genuine conversation. Pick one person on your team, preferably someone from a younger generation, and ask them this question what's one thing we could change to make your work more meaningful or effective? And then listen, really listen. Don't defend, don't explain why things are the way they are. Just listen and take notes. Let me tell you what happened when I did this with my own team.

Speaker 1:

One person said I'd love to know if I'm doing a good job. I don't really hear much unless something's wrong. Another said I wish I understood how my work connects to some bigger goal. Sometimes I feel like I'm just checking boxes. Those two comments completely changed how we structure our team meetings. In one-on-ones Now we start every meeting with what's going well before we dive into problems. We spend time in our quarterly planning sessions connecting individual roles to company objectives, and that result Morale improved, retention improved and, honestly, I became a better leader because I stopped assuming people or that I knew what people needed and started asking you don't need to fix everything this week, you just need to start the conversation.

Speaker 1:

So here's my question for you what belief about leadership are you holding on to? That might be holding your team back. If this resonated, share it with another Gen X leader who's wrestling with how to lead these younger generations. Well, and if you want more tools for people-first leadership, if you need coaching or a keynote speaker, visit my website nextstepadvisorscom. There's no E in that. Next, it's just NXT. I want to thank you for listening to Things Leaders Do Keep building bridges between generations, leading with clarity and rethinking leadership norms. And you know why? Because those are the things that leaders do.

Speaker 2:

Thank you for listening to Things Leaders Do. If you're looking for more tips on how to be a better leader, be sure to subscribe to the podcast and listen to next week's episode. Until next time, keep working on being a better leader by doing the things that leaders do.