
“So, tell me about your leadership style. What is it actually like working for you?”
💚 Welcome to the weekly newsletter for ambitious leaders staying sharp and staying human in the age of AI.
Every edition is:
Curated: One standout piece I read, watched, or listened to this week + my riff on what it means for you
Counterintuitive: A surprising angle that shifts how you see your day-to-day.
Cross-pollinated: Draws unexpected connections between the worlds I live in—sales, sports, and Stanford.
📬 If you like this, share it with a fellow leader. It’s a low-lift way to stay connected to the people you care about when your calendar has zero room for 30-minute Zoom catch ups.
The Problem
What would you say to a highly sought-after candidate who asked you:
“So, tell me about your leadership style. What is it actually like working for you?”
Maybe you’d say something about servant leadership. Or that you’re empathetic, but still hold people accountable. Or maybe that you want to get the absolute best out of your team.
As you hear the words come out, you know they sound like everyone else. They don’t give the candidate any insight into who you actually are.
Right now your leadership is probably a collection of accidental habits. You react to fires, you manage people based on instinct, and it works. But you haven't defined your craft.
The Discovery
I recently watched an interview with Taylor Swift1 discussing her songwriting.
Whether you are a fan or not, what struck me was how well-formed her points of view are. She has specific rules. She has deeply held beliefs about how she communicates. She treats what she does as a true craft.
This is what so many leaders miss. We might be great at the mechanics of our jobs, but we haven’t spent time reflecting on the human elements that actually make our leadership work.
There is a psychological reason why defining your craft is so powerful. It is known as Narrative Identity Theory2, pioneered by Dr. Dan McAdams.
The research shows that when humans actively construct a coherent story about their past experiences, beliefs, and values, they achieve a cognitive state called self-concept clarity.
When you have high self-concept clarity, you dramatically reduce decision fatigue. You stop being reactive. You become consistent under pressure because your brain isn't guessing how to behave in a crisis—it already knows the narrative.
When you distill your beliefs into a defined perspective, your leadership stops happening randomly. It becomes a choice.
The Experiment
You might think you need to perfectly figure out your leadership style before talking about it. In reality, the uncomfortable, messy friction of trying to explain your gut instincts out loud is exactly what forces your brain to clarify them3.
This week, I want you to step into Taylor’s seat.
I reverse-engineered three questions she was essentially answering about her songwriting, but adapted them for your leadership. Grab a notebook, or pull up a voice-memo app on your commute, and force yourself to answer these out loud:
1. The Origin: What kind of leadership did you first fall in love with? Who modeled it for you, and what specific element did you steal for yourself?
2. The Conviction: What is a very strong, deeply held opinion you have about how a team should operate—a "hill you will die on" that other leaders might disagree with?
3. The Constraint: What is a hidden boundary or constraint you find yourself constantly working within (e.g., a fully remote team, a tight runway, extreme regulatory compliance), and how does that constraint force you to adapt your communication style?
The Takeaway
When you can tell a coherent story about your craft, you become a magnet.
Candidates aren't just evaluating the compensation package; they are evaluating you. If you can clearly articulate your philosophy, your rules, and how your past informed your present, you instantly stand out.
As a bonus, the people who disagree with your philosophy will self-select out. The people who align with it will run through walls to work with you.
Join the community of leaders staying sharp
and saying human in the age of AI.


