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Deborah Wain

LDL Leadership Development

Senior Consultant

Is generational stereotyping limiting your leadership potential?

Are your leaders falling into the generational stereotyping trap? Deborah Wain of LDL Leadership Development reveals how the real challenge isn't managing different generations – it's letting go of age-based assumptions that may be limiting leadership potential. Discover four practical strategies that prioritise individual connection over generational labels.
brown game pieces on white surface, depicting generational stereotyping

Having ascended the rungs of corporate achievement, business leaders are typically faced with recurring questions about their youngest staff members. How do I manage this new generation? Why don’t they work the way we used to? Why do they expect so much so quickly? 

These concerns are nothing new. Each new generation is frequently met with suspicion or misunderstanding by older generations. And while the labels change – from Baby Boomers to Gen Z and now Gen Alpha – people across generations tend to want very similar things from work: purpose, respect, fair treatment, opportunities to grow, and a sense of belonging. 

Two decades ago, my training consultancy – LDL, Leadership Development – was asked to contribute to a Guardian article discussing the ‘new generation’ then entering the workplace. The concerns it raised about changing expectations, values and motivations are almost identical to what we hear today. 

Generational labels vs individual connection 

In truth, the real challenge for leaders today isn’t managing generational differences, but letting go of generational stereotypes

Too often, we fall into the trap of over-relying on generational labels and underinvesting in individual connection. While diagnostic tools, psychometric profiles and broad trends can offer insight, they should never replace the simple but powerful act of listening

Rather than focusing on age-based assumptions, effective ‘multigenerational’ leadership means recognising individual strengths, building inclusive teams, and creating environments where everyone can thrive – regardless of when they were born.

Be curious about people

Giving people a good ‘listening to’ is not about sitting in silence as they vent their frustrations or give voice to their ambitions, mirroring their body language in a performatively empathetic way. Active listening is a skill that demands full attention to the other person. This includes asking relevant, purposeful questions and resisting the temptation to reach for simplistic labels. 

Former Liverpool FC manager Jürgen Klopp once said that he is relentlessly curious about people. I love that sentiment. It encapsulates a winning leadership philosophy of ongoing care, curiosity and individual growth. Klopp genuinely engages with individuals as unique and complex human beings.

Being curious about people means tuning in to each individual person on your team rather than making generic assumptions: How do they learn? What motivates them? How do they want to grow? 

It means being able to adapt your leadership style to each person. This is not about abandoning structure or lowering expectations, it’s about applying empathy and curiosity in equal measure.

Here are four practical leadership actions to help you navigate the multigenerational dynamic:

1. Be curious, not prescriptive

Use one-to-ones to ask thoughtful, open questions. Avoid assumptions about what a person wants based on their age. Here are a couple of examples:

  • “What gives you a sense of purpose in your work?”
  • “How do you prefer to receive feedback or recognition?”

2. Build trust with consistency

Regardless of generation, your team will look for clarity, fairness and follow-through. Ensure your expectations are transparent, and your support is reliable. If you say you’re listening, show it in your actions.

3. Flex your style, not your standards

Tailor your communication style, not your expectations. For example, younger team members may want more frequent check-ins – great! Offer that without compromising on performance or accountability.

4. Focus on career growth conversations

Generational theories often over-emphasise the new generation’s sense of ‘entitlement’. In reality, most people want growth and are willing to work at it. Make career and development conversations a regular feature of team life, not an annual tick-box exercise.

Unlocking the true value of diversity

The multigenerational workplace isn’t a leadership challenge. It’s a leadership opportunity. When leaders engage people as individuals and avoid generational stereotyping, they unlock the true value of the diversity on their team – in terms of age, experience and perspective.