The Four Leaps

Most of us care about growing and progressing in our careers. Regardless of our underlying motivation (money, mission, fun), we have a natural desire to “move up”—to elevate our roles and our impact.

Unfortunately, most of us will hit a wall at some point, reaching a level where we struggle to progress further. Very few of us, mathematically speaking, will end up as CEOs of scaled-up organizations.

I’ve had the privilege of hearing the full career histories of hundreds of CEOs over the past 15 years, and hundreds more CXOs/functional leaders. As I have stared across those (thousands!) of hours of dialogue, I have found that there are 4 key inflection points or “leaps” where the rules of the game change, and where leaders must redefine themselves in fundamental ways.

Leap 1: From Individual Contributor to Manager

What changes: Everything! My work output is no longer fully under my control. Success is now a function of my ability to hire the right people, delegate and hold them accountable.

Common Pitfall: Hiring mistakes, ineffective performance management.

Mindset shift: “I am only as good as my team.”

Leap 2: From Manager to Managing Managers

What changes: I must shepherd other people through their own management journeys, helping them chart the course I just took myself—but without doing their job for them.

Common Pitfall: Limited/ineffective talent development, micromanagement.

Mindset shift: “I am a coach, not a taskmaster.”

Leap 3: From Managing Managers to Leading Functions (“CXO”)

What changes: I now have a boss who has (probably) never done my job. I am the highest authority in my domain. I must learn to speak in terms of business impact rather than functional action, and also learn the languages of my cross-functional peers.

Common Pitfall: Siloed thinking, turf protection.

Mindset shift: “I am here to make my peers successful.”

Leap 4: From CXO to CEO

What changes: It’s all on me. I have no peers. I have very little domain depth in most of the areas under my purview. My leadership approach must change, fundamentally. I have neither the time nor the functional skills to compensate for my team’s shortcomings.

Common Pitfall: Countless! Key among them: fragmentation of effort (trying to do too much, often due to compensating for others' gaps).

Mindset shift: “I am here to set strategy, assemble great leaders, and unblock them. Everything else is a distraction.”

In my experience, the most substantial and challenging leaps are #1 and #4. Interestingly, these are also the points where improving our ability to evaluate talent matters most—specifically, learning to hire (Leap 1) and learning to hire senior leaders whose jobs we’ve never done (Leap 4).

Put another way…if you really want to be a CEO, get good at hiring!