What If It Was Always This Simple?
Transforming yourself through simplicity, clarity, saying no, and a razor
You’ve heard it a million times, and said it more: Keep it simple, stupid.
I know I have. Given my pedestrian education, I had no choice. Simplicity wasn’t a clever tactic; it was a necessity. Whether it was dumb luck or divine intervention, I’ve learned that simplicity is one of the most underrated tools in leadership, life, and one of the most potent keys to transformative change.
Draw your attention back to the last time, when dealing with someone, and you’ve said it out loud or with your inside voice:
“Come on, it’s not that hard. It’s actually pretty simple!”
Bubbling with frustration, you hold back from saying it, which in the moment is likely the correct answer. But have you ever paused to consider that there might be another answer? And that's: “Maybe it’s me?”
Perhaps the problem is more complex than you thought. Or maybe you just haven’t conveyed it clearly enough. Possibly you haven’t distilled the idea down to something people can act on and understand. Myriad thoughts can flood in when you turn the question back to yourself. I’ve been guilty of that more times than I can count. And I’ve paid the price for it.
One thing I’ve learned after leading companies both large and small:
The bigger the company, the more you need to make it simple.
The smaller the company, the more room you have to over-explain and guide.
That might sound obvious. But in execution, it rarely is.
Breaking down complex ideas, visions, or problems into clear, digestible pieces is part skill and part art. Sure, you can write the message, build the deck, create the roadmap—but if you can’t keep the execution aligned with the clarity of the original message, you’ll fail. You’ll drift. You’ll lose the room. And worse, you’ll invite in the people I call…
The Masters of Chaos
In every company I’ve led, consulted for, or observed, there’s always a person or a group that refuses to get it. They sit through every town hall, every all-hands, every strategy session… and still ask:
“So… what’s our strategy?”
This, after you’ve told them time and again exactly what it is. INFURIATING!
I recall working at a company where one board member, who paid little attention to anything, would often ask that exact question of the management team during board meetings. Derailing everything we were talking about, frequently confusing everyone in the room. The management team would stop and stare, thinking that this was a joke or we were on some reboot of MTV’s Punked. But no, it was real. Watching this happen time and again, I realized something very clearly:
These people (Masters of Chaos) don’t want clarity. They want confusion.
Because in confusion, they create power. (In this case, indeed, they did by derailing the meetings.)
By muddying the waters, they present themselves as the ones holding the flashlight. The same people who create problems in companies are the ones who can cast themselves as the hero to solve them. They stir chaos, then sell calm. It’s a toxic loop. One that has nothing to do with leadership and everything to do with job security or their insecurity about what they know.
When it happens to you, you do your best to lead them back to the core strategy. These moments are a huge time suck.
Then, before you know it, your day is gone. You’ve spent hours combating, addressing, and cleaning up the mess created by these agents of disorder. I want to here and now, to remind you, to trust your instincts—when you see it, when you feel it in your guts, no matter their title or perceived value, it’s often better to move on without them and stick to your internal compass of what you know to be true and right.
Now, to be clear, I’ve been on the other side of this too.
In my career, I’ve left room for ambiguity in my vision or leadership style. I assumed I was clear enough, when I wasn’t. Making the flawed assumption that my staff had ESP or some magical power to read my mind. I thought that they just “got it.” They didn’t. That’s on me. That’s on you, too, if you do the same. So, in reality, it COULD be you, and it WAS me until I figured it out.
While running XM’s Content and Operations organization, we had so many things happening at once that I had no way of really getting everybody on the same page. So, every Tuesday morning, I’d have full staff meetings, 90 minutes in which everyone would discuss everything we were doing for the next seven days. My staff dreaded these meetings, but we got clarity and dug deep.
Meetings initially started with just 8-10 people, and as the rigor and clarity improved, we brought more and more people to them because they set the tone for the company. Staff members further down the organizational chart wanted to hear about what was happening or upcoming, and even other departments wanted to be included in the meeting. This is noteworthy, as other teams were interested in attending this meeting. Meeting. What was clear was that this meeting turned out to be the best one we would ever have, thanks to the clarity and alignment.
Through the pandemic and now with varying degrees of work-from-home arrangements, it’s needed more than ever. The lack of in-person sessions, or even just walking down the hall, has created massive communication issues and killed organic “hall talk.” We have now taken our weekly ops meetings a step further, to daily stand-ups. With people everywhere at all times, there is no substitute for connection or clarity, and frankly, the best way is to throw everybody on the call for 30 minutes each morning and tell them what you need and what questions they have for you.
I have learned this the hard way: If the company or your team is not clear,
That’s not on them; that’s on you.
When you’re not ruthlessly clear, Masters of Chaos spread like athlete’s foot—subtle at first, then flaring up at all the wrong times.
The WUSN Lesson
The best lesson I ever learned about shutting down chaos and driving clarity came in the summer of 2002.
That spring, Mel Karmazin asked me to fly to the Drake Hotel in Chicago. WUSN, once the crown jewel of country radio, had completely lost its way. I spent a few days holed up in my hotel, listening to the station nonstop. I wrote a report and sent in my thoughts.
Two days later, Mel called and said, “Move to Chicago. Fix it.” (Jesus, that wasn’t on my bingo card, but no chance I could say no to Mel.)
My previous turnarounds had always come with doubts. People questioning my age, my experience, my instincts. I had some modest success at this time with Seattle, San Francisco, and Tampa, but this time, I said yes, but with conditions: full authority, no pushback, and the freedom to get the right people on—and off—the bus. Mel agreed.
Day one: We had a clear plan.
New staff.
New vision.
A list of those who had to go.
We moved fast. We communicated faster. And we didn’t deviate.
We gave birth to “America’s Country Station. 99.5 WUSN” And quickly regained the title of America’s most listened to country station.
Sure, people complained. But clarity, simplicity, and discipline didn’t leave room for noise. Within one month, our new midday host—Lisa Dent (now on WGN)—debuted at #2. Every show saw a lift. And it just kept growing from there.
Within 120 days, I was pulled out of Chicago to lead more stations in New York. But the lesson stuck.
Clarity.
Simplicity.
Discipline.
These are the keys to moving culture and companies forward.
Use a Razor
Leadership isn’t about being the smartest person in the room. It’s about being the clearest.
Masters of Chaos want you to question yourself. When they say, “I’m just not sure what we’re doing here,” that’s not curiosity—it’s subversion. Their chaos is calculated. Because if they can confuse you, they can influence the outcome, or at least cloud accountability. They take hold of your ability to trust your gut, making you think you don’t know what you are doing.
This is where Occam’s Razor becomes your best ally.
Occam’s Razor is a principle from the 14th century, named after English philosopher William of Ockham. Simply put, it says:
The simplest explanation is usually the right one.
It’s elegant in theory.
In business, it’s essential in practice.
When you’re surrounded by politics, slide decks, and shiny-object thinking, the noise creeps in. You start second-guessing yourself, and that internal voice comes screaming back in:
“Maybe I missed something.”
“Maybe it’s more complicated than I thought.”
“Maybe I’m not seeing the whole picture.”
What you’re not doing is trusting yourself to cut through the noise.
So take the Razor. Slow everything down, get quiet, and just ask yourself what is the simplest explanation for this problem. When you get that internal feeling and gut answer, trim the fat and remove the noise.
Then say the simple truth out loud.
Make the Same Point—A Different Way
There’s one question I love asking teams. It reveals more about culture than any survey or slide deck ever will:
“What are the last five things you’ve said no to—and why?”
You’ll get blank stares. Maybe a few head tilts, like a confused golden retriever hearing a strange sound.
Then say this:
“If you’re not saying no to anything, then you’re saying yes to everything. And if you’re saying yes to everything, then you don’t have a strategy.”
That’s when the room changes.
Go back to your clear, simple pillars. Reinforce clarity. Reinforce simplicity.
Start by saying no.
Keep saying no—until all that’s left is what truly matters.
Some of the best leaders I’ve worked for could take a problem, pivot the issue, and map it back to the goal in under five minutes. They didn’t need a process doc. They needed alignment and a gut check.
One time, a board member criticized me for making things “too simple.” They didn’t understand the business, had no desire to, and preferred confusion over clarity. They tried to ridicule and insult me for ‘glossing’ over too many things.
No, I was trying to focus us on what mattered most. That’s when I realized I’d outgrown the job. That’s when I knew I had to go. (More on that in a future piece.)
The Final Cut
Simplicity isn’t basic.
It isn’t shallow.
It’s mastery.
Leadership isn’t about being complicated.
It’s about being understood.
So be clear.
Use the Razor.
Cut the rest.
Your company will thank you later.
Whoa. This is great, and I have only read up until Occam. Masters of chaos exist in all types of environments...I might add. Thanks for sharing these hard-won and earned gems!
I wondered who I learned that from!! Well done Jedi