Paul Olean taught me a lot early in my career.
Some lessons were about marketing. Some about sales.
But the best ones were about leadership.
Here’s one I’ve carried with me ever since:
If you’re the employee — don’t just bring your boss a problem.
Think it through. Bring ideas for how to fix it.
I said to my wife, “Heads up, I’m probably getting fired today.”
She offered some encouragement. I hung up, sweating, and walked to the CEO’s office.
Back up.
I was a marketer at a startup. I had pitched a massive direct mail campaign—$200k+ on one bet. The CEO approved it. I ran with it.
Months o...
Scaling sales teams often make the same mistake:
They try to manage behavior instead of building a system.
Endless one-on-ones, activity policing, skills oversight—it all piles up. Leaders get overwhelmed. Reps feel micromanaged. And performance stalls.
The fix isn’t tighter management. It’s a sys...
When your boss is overly focused on the small details of your work, it can feel overwhelming. But understanding whether they are micromanaging or simply lacking confidence in you is key to resolving the issue. Here’s what to consider:
If your boss is paying too much attention to the details of your...
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