All CEOs Have Been Rookies

(Originally Published on

Yes, it’s true. From the boardroom to the employees there is a first time for every CEO. Learning how to manage the board of directors and how to lead employees are among the newest challenges for the first time CEO. The startup founder CEO may be a college dropout or the newly promoted rookie may be a former senior executive in a fortune 50 corporation but they are both first timers without the experience to lead as a CEO when they first take on the new role.

My book, The Rookie CEO, You Can’t Make This Stuff Up! (On Amazon here) shares my experiences and stories about 9 rookie CEOs from different backgrounds ands how they executed in their first time CEO role. Regardless of background, how they got to their position, wether millennial, gen z, or baby boomer a first COE role is a first CEO role. Let’s explore some commonalities and differences of these rookies.


  • They followed their own path to get to CEO
  • They bring their own philosophies to the role
  • They bring their own leadership styles to the new role
  • Based on how they lead, they will develop a culture based on the previous 3 bullets

You as a reader may debate the point that millennials and gen z’ers have not yet developed their philosophies or leadership styles yet, This may be true, but it also may not be true. For example, were they team captains or all-stars on sports team at any level? Were they once leaders in boy or girl scout troops? By the time some of these rookies get to their first CEO role, they do have some semblance of skills. I agree these skills may not be fully developed yet, but they have some real life experiences in which to develop philosophies and leadership styles.


Examples may be to win at all costs, meaning they may not be team players. If they were the team captain or team star athlete, they may bring an amount of arrogance to the role and shut out others who help as solid citizens but are not the stars.

Now let’s look at a new startup team that the rookie is building. Typically, their initial startup team may have long time friends, college roommates, or people referred to them by friends but have little to no experience. If the startup is a software company, the friend may be a clever coder, who has never created a commercial product but can write a ton of code, How will this impact the startup? Will this person be easy of difficult to manage. How much equity will they get? How much salary will they insist on receiving?

How a rookie CEO can be better prepared

To be better prepared for these types of situations, the rookie CEO has a few choices to address these potential pitfalls:

  1. Hire a seasoned veteran to the team who has done it before and can help guide
  2. Hire a coach or advisor to help guide their startup and initiatives
  3. Leverage investors’ experiences, but this can be a slippery slope (read The Rookie CEO book for examples of investor types
  4. Leverage CEO peer groups, which are coaches and advisors

Whichever the rookie CEO chooses to implement, the ultimate goal is to minimize costly mistakes. These can be money or time.

When it comes to rookie CEOs who are promoted from within from other senior level positions, or hired from the outside as a rookie CEO, these executives have formed philosophies and leadership styles and have been in a variety of cultures that they may choose to strive for. As you can read in The Rookie CEO book, a rookie CEO can drive the culture and can change it if hired into a company that needs culture refinement.

Each week, we will explore a unique rookie CEO situation for aspiring CEOs and leaders can learn from. If you have experienced other rookie CEO stories, are a rookie CEO, or are a former rookie CEO, please leave a comment to start a dialogue!

Thank you for stopping by to read my inaugural blog on my new site. Happy leading and happy reading!

You can buy my “The Rookie CEO, You Can’t Make This Stuff Up!” book here.




Bill Miller is an executive advisor and consultant, speaker, author, mentor and coach. He has led virtually every major business function in the past 30 years

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Bill Miller

Bill Miller

Bill Miller is an executive advisor and consultant, speaker, author, mentor and coach. He has led virtually every major business function in the past 30 years

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