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Navigating the Crossover: Embracing the Future of Leadership in a Millennial Dominated World

I‘m intrigued and engaged by the future and change. When I start to see patterns and emerging trends, I tend to go into research mode. That's because when I was in capital markets, a piece of feedback that I got from my boss that stayed with me was that I should always hold a point of view, do research, connect with key points and be prepared to talk about, and evolve, my point of view. There’s lots of change happening in the business climate through interconnection and leadership. There’s a trend I’m seeing and I want to share my point of view. It’s a trend that some leaders don’t agree with.  


The macrotrend in leadership that I’ve been focused on for the last year is the demographic shift in the workforce. We’ve researched and validated what I’m sharing. We are calling this trend Crossover Leadership. February 2024 is when our research crested into more reality. After 65 years, boomers are no longer the dominant demographic in the workforce. 

The leadership I was practiced in is not going to hold for the future, and the difference for me is that I sit in the middle zone because of my coach bias. My leadership development style and coaching skills contain attributes that align with the future of leadership. Pivotal Growth has been focused on human-centric connections, collaboration, and empowerment since it started in 2017. We’re now adopting these attributes and styles for a future workforce that’s ready to lead with different styles. We’ve been working to prepare companies and leaders to succeed in these new workforce conditions. 

The Data Behind the Trends

Pivotal Growth engaged Dalhousie’s Coburg Research in 2022 to do an in-depth report on today’s types of leadership versus what has been the timeless leadership methodologies that experienced leaders know. I wanted to validate that what leaders prioritize and how they engage, including what value and purpose they have in their role, is entering into an accelerated change dynamic. 

Our research brought us to confront an even bigger consideration when the consultants doing the project noticed one glaring omission—millennial consultants didn’t see themselves reflected in the leadership types and styles that were in the report. A couple omissions for them were: “A commitment to sustainability, a prioritization of a collaborative working style, and a managing style that was more question focused rather than teaching/telling.”   


It made me question how quickly leadership style may need to evolve into what the new suite of leaders are going to be like. How do companies and leaders prepare for training and eventual placement of top-level millennial leaders? 


Coburg Research went back to dig deeper into the research of millennial leadership. They brought back a very comprehensive document on the types of leadership they identify with. We’ve continued to advance our research and how to assess it. 

What We Learned

Boomers and Gen X have been following the institutional definitions of leadership styles for 65 years. But today’s leaders aren’t falling into those definitions as easily. They hold their own point of view on what leadership should look and feel like. These new and emerging leaders are starting to engage with different agendas, styles, global priorities and purpose. Our future of leadership is being shaped by these emerging and engaged millennials. As the leadership table demographic changes, there’s an opportunity to create a generational shift that aligns and co-exists until full Crossover Leadership transpires. 


Having synthesized perspectives, data and results led me to realize that leaders have an opportunity to lead this shifting leadership style, and proactively engage a millennial workforce. Leadership as we know it only works for a finite period going forward. 

Here Are The Five Themes PGI Thinks You Need to Know and Follow:

  1. The future is a millennial dominated workforce. Millennials now lead Canada’s population, overtaking boomers’ 65-year dominance. (Source: Stats Canada, February 2024

  2. New leadership strategies are essential for staying competitive and innovative in a rapidly changing business environment. 

  3. Evolving leadership mandates mean that new leadership styles are needed to attract and retain talent. The best managers will embody a growth mindset, purpose, collaboration, and an empathic emotional intelligence (more on this in another blog), as well as coaching skills. 

  4. Expanded diversity of purpose and ways of work means that generational shifts bring more focus to purpose, tech agility, sustainability and positive leadership styles

  5. The crossover in leadership is ahead. Leadership tables will evolve to new leadership cultures, operations and strategic planning. 

What Does This Mean For Leaders?

Executives now have an opportunity to proactively evolve, align and embrace a millennial dominated workforce and leadership table. They can be the change leaders to prepare their organization and leadership table for the future workforce. Embracing this shift in leadership will facilitate a smooth transition and cultivate a culture of inclusivity and sustainability. 


We have taken a point of view, validated it with research and now have three working hypotheses that we will work with companies on. 


  • Leadership strategy and the way leadership is enacted holds the potential to change so it’s ready for millennial leaders 

  • The way we deploy leadership development programming will evolve for the millennial students of leadership 

  • Further formalization and adoption of mentoring in organizations 


This last point on mentorship is represented well in an article I read in Forbes. In 2013, 52-year-old Chip Conley joined Airbnb as head of global hospitality and strategy. He quickly became one of the most trusted advisors to CEO, Brain Chesky (then aged 31), and eventually mentored more than 100 people at the company, being affectionately called its “modern elder.” Conley pointed out that a crucial part of successful cross-generational mentorship is for it to be mutual, with wisdom being shared in both directions. 


The best teams and results will be achieved through managing, leading, coaching, sponsoring and mentoring.  

Future Readiness

Pivotal Growth has been working on building solutions for leaders in preparation for this shift. We are creating a change in how leaders are taught, and in strategies and culture.  


Pivotal Growth’s response to this real time Crossover Leadership is a three-part business model update. 

  1. A Future of Leadership Program for experienced and executive leaders  

  2. An enhanced diagnostic tool focusing on the specific requirements for millennial leaders 

  3. A Relationship Assessment Tool to help multi-generational teams align, thrive and co-exist 

Our history at Pivotal Growth has been around understanding leaders and leadership. And this deep intimate work demands that everything we do is our commitment to understand your business challenges, while also being one step ahead. 

Next Steps

Whether you’re a leader who agrees with my point of view or you see it as an over extension to the trend, you share the same action plan. Revisit your engagement, retention processes and reporting. Begin to follow your data and insights with a demographic filter. We’ve been using a generational demographic filter for the eight months in our leadership diagnostics. There are lots of insights to leverage for the future. 


If you feel you need to get a gauge on the attributes, skills and styles of your leaders, we can take you through out Future of Leadership Program. It incorporates leadership themes prioritization, leadership DNA pulse and a Future of Leadership design session. Contact me or Yemisi Iyilade to talk more about the future leader persona of your organization. 


About Lisa Haydon

Lisa W. Haydon is a seasoned operational leader and entrepreneur with over three decades of experience in banking, capital markets, technology, and professional services.  


With a keen vision for aligning people, processes, and outcomes, Lisa has become a driving force in the field of leadership development. She brings innovation to the forefront by leveraging data-driven strategic cohort programs, generating value-added insights, and adopting AI-enabled technology. Her pioneering work with high-growth companies and high-performance leaders led to the design and commercialization of a proprietary leadership diagnostic solution. 


She is known for her unique ability to navigate complex business challenges, understand diverse leadership styles, and deliver transformational results. 


Lisa and her team are a group of forward-thinking, technology- and people-focused professionals who become a trusted partner in the pursuit of leadership-driven success. 



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