It usually starts with something small. A founder vents in a WhatsApp group: “This intern asked to leave early because she ‘wasn’t feeling inspired.’” Another replies, “Mine ghosted after two weeks. Didn’t even say goodbye.” The thread unspools: complaints about entitlement, lack of initiative, weird boundaries. Nobody says it outright, but the subtext is clear: “This generation doesn’t want to work.”
And maybe that’s true. But maybe they don’t want to work for you. Not like this.
When you’re running a lean team, managing tight burn, and trying to punch above your weight, a disengaged junior hire feels like deadweight. You start questioning everything—your hiring judgment, their attitude, the whole structure. But it’s not always a hiring mistake. Often, it’s a system mistake. You’re frustrated with behavior, but what you’ve actually built is an unclear environment that miscommunicates what “ownership” really looks like.
Founders often assume Gen Z hires want handholding. What they actually want is scaffolding. Clarity. Direction. Somewhere between the DIY hustle culture of millennials and the quiet quitting language of Gen Z, something got lost in translation. Founders expected loyalty and resilience; young hires expected onboarding and mentorship. What neither side realized is that high-functioning teams don’t run on assumptions. They run on structure, feedback loops, and culture that’s been built—not inherited.
When I first started mentoring early-stage teams, I heard the same refrain over and over. “They just don’t get it.” Founders felt like they were repeating themselves constantly. Gen Z hires felt confused, anxious, and afraid of being wrong. One founder shared that his new junior designer “kept waiting for instructions” instead of taking initiative. When I asked to see the onboarding flow, he laughed. “There’s no onboarding. It’s a four-person team.”
That’s the problem.
Early teams are fast-moving, messy, and resource-light. But that doesn’t excuse a total lack of systems. If your expectation is that a 22-year-old fresh grad can show up and operate with the same context and confidence you’ve built over five years, you’re setting them up to fail. It’s not about coddling. It’s about respecting the complexity of startup work and equipping your hires with enough clarity to contribute.
The breakdown often begins with onboarding—or the lack of it. Many founders onboard by vibe. They assume that if someone’s smart and eager, they’ll pick it up fast. But early-stage work isn’t just task-based. It’s ambiguous, strategic, and often deeply shaped by founder behavior. If your company has no defined decision rights, no calendar cadence, no written expectations, then your new hire is building a mental map off your Slack tone and 3 a.m. Loom rants. That’s not onboarding. That’s chaos.
I’ve seen founders swing to the other extreme too—over-explaining, over-scheduling, trying to manage every output instead of defining clear inputs. The result is micromanagement disguised as mentorship. The team slows down. Young hires stop experimenting. Everyone gets nervous. And still, no one’s happy. You’re doing more check-ins, but seeing less progress. You’re more present, but feel less supported. That’s the paradox: more time together doesn’t mean more clarity. Structure beats presence, every time.
One founder shared a turning point that stuck with me. His youngest hire—a 23-year-old marketing grad—quit after three months. In her exit note, she wrote: “I felt like I was guessing every day. I wanted to ask more questions, but I didn’t want to disappoint you.” The founder was stunned. He thought she was disengaged. In reality, she was terrified of appearing incompetent. That’s what happens when we mistake silence for confidence. When we assume that because someone doesn’t speak up, they’re fine. They’re not. They’re frozen.
Helping Gen Z employees succeed starts with admitting what we never had to fix before. Founders need to build environments that don’t rely on intuition or proximity. Gen Z isn’t going to learn by osmosis if they’re working remotely. They won’t decode your “figure it out” culture unless you show them what figuring it out looks like. You don’t need to build an HR department overnight. But you do need a plan. A 30-60-90 day roadmap. A weekly check-in format. A visible map of ownership—who decides, who reviews, who supports.
The hardest part for most founders isn’t writing the onboarding doc. It’s letting go of the resentment. That quiet judgment that sounds like, “When I was that age, I didn’t need all this.” Sure. But when you were that age, the world was different. Expectations were different. Burnout was a badge of honor. Today’s Gen Z hires are more mentally aware, more system-sensitive, and less willing to normalize dysfunction. That’s not a weakness. That’s an opportunity.
When Gen Z tells you they’re overwhelmed, they’re not saying they want less work. They’re saying they want clearer work. When they set boundaries, they’re not rejecting your mission. They’re asking for sustainability. If you keep interpreting these signals as laziness or entitlement, you’ll miss the leadership development opportunity right in front of you.
I’m not saying every Gen Z hire is perfect. Some will be flaky. Some will check out. Some won’t be ready for startup pace. But your job isn’t to wish for the perfect team. It’s to design the system that makes imperfect people better. You can’t control attitude. But you can control architecture.
Start with expectations. Be explicit about what a good week looks like. Define outcomes—not just tasks. Teach your team what done looks like, what “ready to share” means, and how to self-check before looping you in. Give feedback fast, and normalize asking for it. When your youngest hires feel seen, supported, and accountable, you’ll stop hearing “I didn’t know” and start hearing “Here’s what I tried.”
Next, teach visibility. One founder I work with uses a Monday Loom ritual: every team member records a 2-minute update on what they’re working on, what’s blocked, and what support they need. It builds context without taking more meeting time. It trains team members to articulate their thinking and exposes weak spots early. Gen Z hires thrive on transparency—not surveillance. Show them the map, and they’ll start navigating.
Finally, let go of the belief that mentorship has to be a time-suck. It doesn’t. Good mentorship is a system. Not a feeling. You don’t have to be your team’s emotional support animal. You have to be their clarity machine. That means building templates, documenting workflows, and modeling what strategic thought sounds like. When you narrate your decision-making out loud—even just once a week—you’re giving your team a playbook they can learn from and build on.
Helping Gen Z employees succeed isn’t about changing your standards. It’s about changing your systems. Stop waiting for them to act like seasoned operators. Start designing the conditions in which they become one. If your first reaction to a mistake is, “They should have known better,” pause. Ask yourself: “Where should they have learned that? Did I make it teachable?” Most performance problems are clarity problems in disguise.
You can keep venting in your founder group chats. Or you can build a team that actually works. Not just fast, but together. Not just loyal, but aligned. It doesn’t take a perfect playbook. It takes consistent clarity, structured support, and a little less judgment. Because Gen Z isn’t the problem. Your system might be.
And if that sounds harsh, here’s the gentler truth: once you shift your mindset from complaint to design, the work gets lighter. Your hires grow faster. Your team stops guessing. And you, the founder, finally get what you’ve always wanted—not just help, but momentum. The kind that doesn’t rely on you being in the room, fixing everything.
That’s what real leadership is. Not just demanding better. Designing for it.
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