How to navigate generational differences in the workplace

In today’s workplace, you’ll find Baby Boomers working alongside Gen Z employees, each bringing vastly different perspectives, values, and expectations to the table. While this diversity can be a tremendous strength, it often creates friction that leaves leaders scratching their heads about how to manage effectively across generations. 

The challenge isn’t new, but it’s more pronounced than ever. As Charlotte Wiseman, founder and CEO of Step Inside, explains in our recent podcast episode, many senior leaders feel “quite disconnected from the fact they’re leading different generations who are driven by different values and have different needs.” 

The solution? Learning to navigate what Charlotte calls “uncomfortable conversations” – discussions that might feel challenging in the moment but are essential for building understanding and unlocking the full potential of your multi-generational workforce. 

The reality of today’s multi-generational workplace 

Before diving into solutions, it’s important to understand what we’re dealing with. Today’s workplace typically includes: 

• Senior leaders with decades of experience who may struggle to connect with younger generations 

• Middle managers who’ve been promoted based on technical expertise but lack people leadership training 

• Aspirational leaders stepping into first management roles with fresh perspectives but needing to learn how to influence upward 

Each group faces unique challenges, but the common thread is learning to work effectively across generational lines. 

Why uncomfortable conversations are necessary 

Charlotte emphasises that underneath apparent generational differences, we all really have some very similar, very aligned values of wanting to do a good job, wanting to feel good about our work, wanting to help the company succeed. The problem isn’t the differences themselves – it’s the assumptions and “othering” that prevents good communication. 

These conversations are uncomfortable because they require us to: 

• Challenge our preconceptions about other generations 

• Admit our own biases and blind spots 

• Sit with discomfort rather than avoiding difficult topics 

• Move beyond surface-level politeness to genuine understanding 

Creating the foundation for difficult conversations 

Start with psychological safety 

Not every organisation is ready for these conversations immediately. Charlotte notes that some companies have high levels of psychological safety where “once they’re given a space, a forum, a structure to have those conversations, it’s relatively easy to facilitate.” Others need foundational work first. 

Before diving into generational discussions, ensure your team has basic psychological safety – people feel included, can express concerns to managers, and won’t face retaliation for honest feedback. 

Develop emotional agility 

Success in these conversations requires what Charlotte calls “emotional agility” – the evolution beyond traditional emotional intelligence. While emotional intelligence was often misinterpreted as “make everybody happy all the time,” emotional agility teaches leaders to: 

• Sit with discomfort without becoming defensive 

• Maintain clear thinking during difficult discussions 

• Stay focused and collaborative rather than reactive 

• Accept that sometimes leadership means making people temporarily unhappy 

Practical strategies for generational bridge-building 

1. Question your assumptions

Start by examining the language and assumptions each generation makes about others. Charlotte warns about “horrible language that gets around about people” based on generational stereotypes. Instead: 

• Ask open-ended questions about motivations and preferences 

• Listen without immediately categorising responses as “typical” for that generation 

• Look for individual differences within generational groups 

• Focus on shared goals and values 

2. Create structured discussion forums

Don’t leave these conversations to chance. Create intentional spaces where generational differences can be explored safely: 

• Focus groups to understand what’s working and what isn’t 

• Cross-generational mentoring programs that work both ways 

• Team workshops specifically designed to explore working style preferences 

• Regular check-ins that include discussions about communication preferences 

3. Address the influence challenge

One particular challenge Charlotte highlights is helping aspirational leaders “influence up” and “get their voices heard.” Create mechanisms for: 

• Younger leaders to communicate with senior management 

• Ideas to flow upward through the organisation 

• Different communication styles to be recognised and valued 

• Fresh perspectives to inform decision-making 

4. Focus on strengths and contributions

Rather than dwelling on what each generation lacks, emphasise what they bring: 

• Experience and institutional knowledge from senior team members 

• Fresh perspectives and technological savvy from younger employees 

• Bridge-building capabilities from middle managers who understand multiple viewpoints 

• Different problem-solving approaches that complement each other 

The conversation framework 

When facilitating these discussions, Charlotte suggests focusing on: 

What are our preconceptions? 

Start by acknowledging that everyone has assumptions. Make them explicit rather than letting them operate in the background. 

What are our respective strengths? 

Help each generation see what others bring to the table. This shifts the conversation from deficit-based to strength-based. 

How can we build understanding and connection? 

Look for practical ways to improve day-to-day collaboration and communication. 

What opportunities can we harness together?

Focus on the future and what becomes possible when generational diversity is leveraged effectively. 

Making conversations productive, not just uncomfortable 

The goal isn’t discomfort for its own sake – it’s growth and understanding. To ensure conversations lead to positive outcomes: 

• Set clear intentions about why you’re having these discussions 

• Establish ground rules for respectful dialogue 

• Focus on behaviours and impact rather than personal characteristics 

• Look for concrete next steps that improve collaboration 

• Follow up to ensure insights translate into action 

The business case for getting this right 

Organisations that successfully navigate generational differences don’t just avoid conflict – they gain competitive advantages: 

• Enhanced creativity from diverse perspectives 

• Improved problem-solving through different approaches 

• Better succession planning as knowledge transfers effectively 

• Stronger employee engagement when people feel understood and valued 

• Reduced turnover as team dynamics improve 

Moving forward: from understanding to action 

Remember Charlotte’s insight that “it’s the micro behaviours that make all the difference.” You don’t need a complete cultural overhaul overnight. Start with small changes: 

• Ask different generations how they prefer to receive feedback 

• Experiment with various communication channels and methods 

• Create opportunities for informal interaction across age groups 

• Regularly check assumptions against reality 

• Celebrate examples of successful cross-generational collaboration 

The courage to lead differently 

Navigating generational differences requires what Charlotte calls “a huge amount of emotional agility.” It means being willing to have conversations that feel uncomfortable in service of building something better. 

As she notes, “you don’t learn so much from comfort. You don’t grow from staying in your comfort zone.” The leaders who embrace these challenging conversations – who create space for different perspectives and help their teams move beyond generational stereotypes – will build stronger, more resilient organisations. 

The alternative is teams that remain siloed by age and assumption, missing out on the tremendous potential that comes from truly harnessing multi-generational strengths. In today’s rapidly changing business environment, that’s a competitive disadvantage no organisation can afford. 

Want to hear more insights on leadership development and building stronger teams? Listen to our full conversation with Charlotte Wiseman on the On the Up podcast, brought to you by Moneypenny.