From Dues to Dialogue: Leading Growth Conversations Differently

A Subtle Brew, A Stronger Pour

The first pour of tea often holds boldness. The second reveals subtler notes. Leadership is no different.

Picture this: You’re across the table from a direct report. You’ve just outlined expanded responsibilities — a stretch assignment that could put them in the running for promotion. Instead of excitement, you get the pushback:

“That sounds like a lot more work. If I’m taking this on, where’s the pay increase?”

For many seasoned leaders, especially those who cut their teeth in the era of “paying your dues” and “do the job before you get the job,” that moment lands like a challenge. Maybe even like disrespect. You remember the late nights, the unpaid stretch projects, the years you carried weight without recognition because that’s what it took.

Respectfully, your story of growth isn’t theirs.

The Fault Line Beneath Leadership

The narrative of “paying dues” was once the unspoken contract of corporate advancement. Today’s workforce — particularly Gen Z and younger Millennials — sees a different landscape. Corporate life looks less stable, promotions feel uncertain, and loyalty doesn’t guarantee security.

Where one generation sees grit, another sees risk. Where one sees dues, another sees debt without promise.

This isn’t a generational problem. It’s a communication and expectation-setting opportunity.

Gen Z vs. Gen X Leadership Narratives

Gen X and older leaders often view added responsibility as the natural precursor to advancement. Do more, prove more, earn more. But for many Gen Z professionals, the rules of the game feel opaque, if not stacked against them. Recent workforce data reinforces this perspective: Deloitte’s 2025 Gen Z & Millennial Survey highlights that younger workers increasingly see career growth as non-linear, shaped more by skill-building and purpose than by traditional ladders.

Research underscores the tension: younger employees increasingly expect clarity, reciprocity, and visible development opportunities (Lev, 2024). Meanwhile, senior leaders frequently assume that the “old rules” of advancement are still universally understood (Schmidt & Muehlfeld, 2017). The gap isn’t entitlement; it’s erosion of trust and knowledge transfer.

When left unaddressed, that gap hardens into resentment on both sides: leaders perceive pushback as a lack of work ethic; employees perceive expectations as exploitation. Trust crumbles in the silence between.

Why It’s Not Entitlement

It’s tempting to write off the new perspective as entitlement — a refusal to do the hard work. But that’s a myth.

That same Deloitte study (2025) found that nearly half of Gen Zs (48%) and millennials (46%) do not feel financially secure, and 63–65% worry about long-term job stability in the face of automation. For many, “paying dues” without clarity looks less like grit and more like gambling. The instinct to demand reciprocity is a survival strategy, not a shortcut.

Rupčić (2024) reminds us: intergenerational learning is not automatic. It requires deliberate mentoring, explicit knowledge transfer, and leaders willing to unlearn outdated scripts. When those steps don’t happen, younger employees default to external advice, which is often oversimplified and wrong.

Only six percent of respondents (Deloitte, 2025) defined reaching a leadership position as their primary career goal. Growth, for these generations, looks less like a ladder and more like a web of skills, purpose, and security.

From Transaction to Partnership

As leaders seeking to push beyond the “paying dues” narrative, stop treating pushback as a sign of weakness. See it as an opening.

Great leaders aren’t too big to learn. They’re big enough to listen.

When you trade defensiveness for curiosity, you reframe the conversation from “prove yourself before I invest” to “let’s shape a path that makes sense for both of us.” One-sided wins breed silent losses.

Transparency is not indulgence. It’s education. And it’s one of the fastest ways to rebuild trust across generations. Lev’s (2024) research on Gen Z leadership highlights that clarity and reciprocity aren’t seen as luxuries; they’re baseline expectations that drive commitment and retention.

The same Deloitte study revealed that 86% of Gen Zs and 84% of millennials want mentorship and guidance, yet most managers spend less than 15% of their time developing people. The gap isn’t ability — it’s priority. Leaders who make space for education and partnership will earn trust across generations.

Questions That Open Dialogue

When the words “I deserve more pay” land on your desk, resist the reflex to shut it down. Instead, ask:

Reflective Questions Leaders Can Use

• “Can you walk me through how you see your current contributions stacking up to the next role?”
• “What skills or experiences do you believe you’re ready to stretch into right now?”
• “How do you envision your career path here in the next 12–18 months?”

These aren’t tricks. They’re bridges. Simple ways to turn a defensive standoff into an exploratory dialogue — turning conflict into curiosity.

Trust as Currency

Unchecked, the old “dues-paying” narrative does more than stall one career conversation. It corrodes the very trust leaders rely on to drive culture.

Failures in intergenerational knowledge transfer often result in fractured teams and diminished organizational memory (Schmidt & Muehlfeld, 2017), while trust in leadership is a critical driver of employee engagement, as highlighted in Edelman’s Trust Barometer data (2025).

The emotional aftermath is real: leaders feel dismissed, employees feel exploited, and both retreat into silence. The cost isn’t just turnover; it’s cultural erosion. Rupčić (2024) underscores that intergenerational learning isn’t only about trust-building; it’s a proven driver of organizational sustainability. When leaders fail to mentor across generational lines, they don’t just lose talent — they weaken the enterprise itself.

Nearly half of Gen Zs and millennials say they don’t feel financially secure in 2025, and this anxiety directly bleeds into engagement and retention. Leaders who dismiss concerns about compensation as entitlement miss the deeper truth: money, meaning, and well-being are inseparable in today’s workforce.

Evidence in Practice

Consider the leader who doubles down on “paying dues.” They assign stretch work, offer little clarity, and dismiss pushback as whining. The employee disengages. Resentment builds. The leader labels them “not ready,” and the cycle repeats with the next hire.

Now contrast the leader who leans into curiosity. They ask clarifying questions. They explain how promotions actually work in their organization. They acknowledge the tension without defensiveness. Even if the promotion doesn’t happen immediately, the trust account grows, and so does commitment.

The difference isn’t semantic. It’s survival. Leaders who cling to outdated scripts invite three predictable costs: attrition that drains talent pipelines, disengagement that erodes performance, and stalled innovation that leaves organizations lagging (Deloitte, 2025; Schmidt & Muehlfeld, 2017). Curiosity doesn’t just preserve trust — it safeguards competitiveness.

🍵 Small Sips: Reflection Practices for Leaders

This month, try these self-awareness practices:

1. Interrogate Your Own Story

Where do your beliefs about “paying dues” come from? Do they serve you, or are they artifacts of a system that no longer exists?

2. Audit Your Transparency

When was the last time you explained — clearly and directly — how promotions work in your organization? Would your team give you the same answer if asked independently?

3. Notice Your Reflex

The next time someone pushes back, observe your immediate emotional response. Is it frustration? Defensiveness? What does that reveal about your leadership integrity?

A Final Pour

The truth is simple: the old contract of “pay your dues” has expired. The new contract is dialogue. Leaders who understand this don’t lower the bar; they elevate the conversation.

♨️ I’m The Executive Tea Lady™, and I believe in steeping leadership differently. If that’s your flavor too, join the conversation in The Monthly BREW™, a newsletter for those who believe leadership is more than a title. Grab a cup here.

References

1. Deloitte. (2025). 2025 Gen Z and Millennial Survey. Deloitte Insights. Retrieved from https://www.deloitte.com/us/en/insights/topics/talent/2025-gen-z-millennial-survey.html
2. Edelman. (2025). 2025 Edelman Trust Barometer: U.S. Report. Retrieved from https://www.edelman.com/sites/g/files/aatuss191/files/2025-01/2025%20Edelman%20Trust%20Barometer_U.S.%20Report.pdf
3. Lev, T. (2024). Generation Z in Search of Leadership – Model of Intergenerational Leadership for Creating Commitment (MILCC). Cross-Cultural Management Journal, XXVI(2), 193–206. https://doi.org/10.70147/c26193201
4. Schmidt, X., & Muehlfeld, K. (2017). What’s So Special About Intergenerational Knowledge Transfer? Identifying Challenges of Intergenerational Knowledge Transfer. Management Revue, 28(4), 375–411. http://www.jstor.org/stable/26407256
5. Rupčić, N. (2024). Intergenerational Learning and Knowledge Transfer. In Managing Learning Enterprises. Knowledge Management and Organizational Learning, vol 14. Springer, Cham. https://doi.org/10.1007/978-3-031-57704-8_13