Newly released today: a chat I had with Randy Wootton of the SaaS Builder podcast.
If you’re a CEO — especially one growing out of startup mode or leading a large organization — I hope you’ll give it a listen. Later on in this post is a breakdown of some of the topics Randy and I hit on. But the overarching message is: CEOs need a good system.
Every discipline has its own basic principles and best practices, whether it’s sales or programming or auto repair. We humans have gotten good at codifying these principles so that new entrants can learn rapidly.
Salespeople get playbooks and scripts.
Programmers get training in data types, control structures, key functions.
Mechanics learn the major vehicle systems and common breakdowns.
CEOs get… basically nothing.
In fact, many new CEOs don’t even realize they need anything. They got this far through their own smarts and tenacity, didn’t they? The CEO job is just the next step up. CEOs also tend to be dominant, confident types, and that often leads to a sense that they can just power through and learn on the job.
In our conversation, Randy mentions that he wishes he’d had a system for the CEO job earlier. I wish I had one too! I am grateful that I had the opportunity to, over a couple of decades, piece together scattered best practices into a coherent whole. My hope has always been to offer that holistic system to others, so they don’t have to follow a breadcrumb trail of high-stakes, on-the-job learning over many years before they master the job.
There’s a lot to be said for experiential learning. But the harsh truth is that when you become CEO, you may not have time to slowly train yourself in how to run an organization from the top. If you go down enough blind alleys and make enough errors—even ones you learn from—the board may decide you’re out of a job. Record-breaking CEO turnover numbers indicate that boards are likely not feeling patient. About 11% of newly hired CEOs don’t make it past their first year.
Everything boards want to see in a CEO is reflected in a good system, one that ensures the organization is in balance and delivering on key metrics. This isn’t a system most of us have the luxury of easing into. Mastering a good model of the CEO role is your first step in delivering results.
Here are some of the topics Randy and I talk about:
The move from specialist to generalist. All executives need T-shaped careers, but when you become CEO, the top of the T has to get a LOT wider.
Inflection points on the CEO journey. Leading a company of 20 people is very different from leading a company of 100 people. To say nothing of leading one of 5,000 people. The military has built in structures for handling these differences—a platoon (typically about 20 people) is led differently from a company (100 or more people). In the private sector, we’re a lot looser with these structures, but CEOs must contend with the fact that complexity ramps up exponentially as headcount grows.
Prediction and predictability. Leadership teams often get bogged down with historical trends but fail to turn around and look to the future. When CEOs start asking their executives for forecasts, it can be a real aha moment.
Strategic balance. Should a company be customer-centric? Employee-centric? Or should it focus on shareholder value? You can find gurus who will swear by one approach or the other. What’s the actual answer?
Give it a listen, send me any thoughts you have, and have a great week!



