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Understanding Perspectives in Multi-Generational Teams

Leadership effectiveness across generations comes from being curious enough to ask the right questions.

Recently, my coaching client Emma provided clear feedback to her team member Raj about changing his approach on a key project.  

Emma was frustrated when, two weeks later, nothing had changed! 

“Why won’t he just do what I asked?” she questioned. 

This scenario is incredibly common, especially when leading a team comprising different generations.  

With up to five generations now in the workplace (Traditionalists, Baby Boomers, Gen X, Millennials, and Gen Z), perspectives and communication styles can vary dramatically. 

The Assumption Trap 

Here’s what I’ve noticed in my 20+ years as a leadership coach: when someone isn’t acting the way we think they should, we assume that we KNOW the reason why. 

In reality, you usually have no idea what’s really going on. 

You are likely viewing the situation solely through your own generational lens and life experiences.  

You might be making an assumption based on your perspective and not theirs. 

For example, you might assume a Gen Z team member isn’t committed when they question processes.  

Or you might think that someone’s desire for work-life balance means that they lack dedication. 

The Wisdom of Seeking Understanding 

This is where Stephen Covey’s wisdom comes in handy. In his book The Seven Habits of Highly Effective People, he says, “Seek first to understand before being understood.” 

Each generation brings different values, communication styles, and work expectations.  

Understanding these differences is crucial for you as a leader. 

Most leaders only half-listen.  

They listen to respond rather than to understand the other person’s perspective. 

Asking the Right Questions 

I encouraged Emma to create a list of open-ended questions to better understand Raj’s perspective.  

But these couldn’t be just any questions. They needed to be curious, not judgmental. 

“Why haven’t you done this yet?” would only create defensiveness. 

Instead, we crafted questions like: 

  • “What challenges are you running into with this task?” 
  • “How do you see this project differently?” 
  • “What support would help you move forward?” 

These non-judgmental questions allowed Emma to genuinely understand Raj’s perspective before attempting to solve the problem. 

The Breakthrough 

When Emma finally had this conversation, she discovered something surprising.  

Raj (a Gen Z team member) wasn’t resistant to her feedback (from her Gen X perspective).  

He simply had a different approach to achieving the same goal, one that actually incorporated some innovative digital solutions Emma hadn’t considered. 

By truly understanding his perspective, Emma not only resolved the immediate issue but strengthened their working relationship. 

Where are you making assumptions about your multi-generational team members? 

What can you do today to slow down and truly understand another person’s viewpoint, especially when they come from a different generation? 

Leadership effectiveness across generations doesn’t come from assuming we have all the answers. It comes from being curious enough to ask the right questions. 

Vanessa Judelman

Vanessa Judelman is an author, coach, and sought-after leadership expert. Over the past 20 years, she has created a proven formula to develop results-oriented leaders who feel empowered and confident in their job. Vanessa is the author of Mastering Leadership: What It Takes to Lead in Today’s Fast-Paced World. Order your copy here.

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