Millennials now outnumber Baby Boomers, facilitating the speed of corporate and company cultural changes. We will explore why this is the case, what challenges these new CEOs and leaders are faced with, and some suggestions to help navigate the new Millennial and Gen Z-led company.  

Growing up, I remember my father talking about “the kids today” which was me, rock and roll music and the Beatles, hippies, and many crazy things we did that he was not used to experiencing. Well, it was the same with me and my kids except I did influence their music choices to an extent. Today, my daughter is on Gen X – Millennial border and is a leader who has shared information with me, and her generation are becoming CEOs in droves, many from traditional businesses and jobs. Many are also entrepreneurs and CEOs at startups.  Gen Y is also now coming into CEO roles as they start their own online type of companies and bring their background, philosophies, and leadership styles that are different than in the past causing a myriad of cultural changes in the workplace.  

Combining generational leadership changes with the pandemic and work-from-home changes, company and market dynamics have experienced a wave of dynamics for all generations in almost every company. 

For this article, we will use a generational chart for discussion purposes. I learned that different sources have some of the generational definitions with different ages, a couple of which I call out. I primarily used Wikipedia for the chart but added a comment about Deloitte’s perspective from two of their reports.  

Generation Age Year Born Nicknames Alternate Views 
Greatest Generation 94+ 1901-1927 GI Generation  
Traditionalists 76-93 1928-1945 Silent Generation  
Baby Boomers 57-75 1946-1964 Baby Boomers  
Generation X 41-56 1965-1980 Gen X  
Generation Y 25-40 1981-1996 Millennials Deloitte: 1983-1994 
Generation Z 9-24 1997-2012 Gen Z Deloitte: 1995-2003 
Generation Alpha Up to 8 2013 and up Gen Alpha  
Generations Defined 

As I have experienced and researched, here are some basic attributes of our Millennial friends, as they have moved from pre-pandemic to their current state. As with any analysis, these are not blanket statements that apply to all Millennials, but they are observed and written about in many cases directly from the generation themselves. 

Attributes of Millennial CEOs and Leaders 

  • Sensitive to the needs of Gen Z, the younger generation hitting the workforce 
  • Similar to Gen Z upbringings: tech natives, social media, mostly strong economy except for some 2008 bumps in the road as well as 2020 related to Corona Virus. 
  • Many were born into households with Computers and/or laptops 
  • They got their Cell Phones at a young age, and today pretty much have their lives inside of their mobile device  
  • Gaming consoles, as many are hardcore gamers 
  • Streaming Services have become mainstream over the past year or so, with many “cutting the cord” 
  • Optimistic but cautious 
  • Innovative and creative 
  • Personally, they are trying to balance the movement to an all-digital world 
  • A unique place of helping non-tech savvy Baby Boomers and onboarding Gen Z into business 
  • How to gracefully utilize and exit baby boomers 
  • How to integrate Gen Z 
  • Company cultures are changing 
  • Passionate about businesses having a broader and deeper positive impact on society in general, Millennials want to provide input to their employer and want to be heard! 
  • It seems they are actively involved in sharing their opinions on working from home vs. Working remotely 
  • Millennials and Gen Z prefer flexible hours and schedules, and unlimited PTO and vacations, etc. 
  • Most have an opinion on politics, diversity and inclusion, purpose and cause  
  • Live balanced lives: work vs. external interests  
  • Desire support for employee’s well-being, mental health, and the environment  

Millennial CEO Challenges 

As the Millennial generation has begun to move from lower- and mid-level management roles into senior management and CEO roles, they have new challenges.  

  • Leading a team with older members 
  • Managing a board of directors with older members 
  • Balancing personal and business lives with their families – pandemic work from home brought new experiences and requires innovative ways to lead 
  • Most successful Millennial leaders listen to their elders, and highly weigh their input but implement what is right for the new day, and the cultural transformation they are going after 
  • Many care about their community, social causes, diversity and inclusion, and global crisis issues – and want to make the world and the company a better place to live and work 
  • Bumps in the road include leading through politically charged times, the pandemic, and retiring tribal knowledge in Baby Boomers 
  • The Millennial CEO is driving changing corporate cultures based on their individual backgrounds, philosophies, and leadership styles 
  • Many are transparent as leaders from their social media upbringing, which can often cause issues with employees but is also appreciated by some 
  • Navigating through traditional leadership trail left behind 
  • There is no precedence for how to handle new situations from the pandemic, climate change, and social justice and some of the above-mentioned challenges 
  • A new challenge is dealing with stress and anxiety in the workplace – too many Zoom type meetings, isolation, family issues around home education/remote schooling, and the pandemic 
  • Since less than half of Millennials and Gen Z’ers see businesses as a force for good in society (Deloitte), the new CEO can have a huge impact on improving these numbers and life in general. 

Some things may never change completely, but can be enhanced and refined 

  • Millennial leaders need to surround themselves with the best team members possible 
  • Build trust, listen, learn and focus; ask questions; empower your team 
  • Be authentic 
  • Leverage a diverse team by generation; learn from the Boomers, Communicate across team members and functions, leverage Gen Z mindsets and emerging skills 

Company Structure under Millennial Leadership 

  • Eliminating layers of management and using the “flat” leadership style 
  • Facilitate cross-functional collaboration and success via excellent communications skills  
  • The work environment is important, be it home or office – ensure employees have tools, space, and policies to protect and make them successful 

Some types of today’s Millennial CEO 

  • Value policy less than predecessors 
  • Value collaboration and flexible work/life balance more than predecessors 
  • Devalue hierarchical corporate structure 
  • Value remote worker flexibility with flex hours 
  • Millennial women CEOs are changing the game completely, opening up more opportunities for women and minorities – however, they are at a crossroads, which I think is temporary, because of the pandemic/WFH/School 


  • As digital natives, the Millennials and Gen Z  grew up with computers, phones, and the cloud 
  • Barriers to entering a new business are low, as they can start a software or cloud company easily at home 
  • Online opportunities from social media to eCommerce to the web, Millennials create unique applications that make a difference in the world. 

In Summary 

Just like when my generation took over from my parent’s generation and things changed over decades, today is repeating history but with their beliefs and backgrounds, philosophies, and leadership styles to create new transformational company cultures. 

Generational changes bring needed change. There can be some painful times, but mostly you get new fresh ideas, new ways to do things more efficiently and differently, and with new energy. I remember when my age group were the new leaders! I can’t tell you how many times I heard, “We have always done it this way” – which is the signal that it needed changing!

As new CEOs, regardless of generation, remember that behavior matters, words matter, and continuously listen and learn by asking questions. Your team, employees, and investors are watching and listening to everything that you say and do.

I expect to see many changes in business with the number of Millennials and Gen Zs taking over leadership and influential roles over the next few years continuing. New CEOs and leaders will bring their philosophies and leadership styles to the forefront and as I write about in my book, The Rookie CEO, You Can’t Make This Stuff Up!, the new CEO brings their background, their philosophies, and their leadership styles to the company or startup and they create the culture. It’s what my PPLC (Path to CEO, Philosophies, Leadership Styles and Culture) framework is for the making of a CEO.  You can find a blog article here to describe the PPLC framework or buy my book here!   

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