On What Happens When You Ask Why, Finding the Fences & Inviting People In
My First Two Weeks as VP of AI Engineering
Chesterton’s Fence for Leaders: My First Two Weeks at Rocket Money
People have a very specific idea of what someone is supposed to do in their first two weeks in a new role (especially leadership roles).
Learn the deployment process. Find the documentation. Set up my dev environment. Attend onboarding sessions. Make a good impression. Show value quickly.
But I spent weeks 45 and 46 doing something completely different.
The Movie I Keep Watching
Here’s what I’ve seen play out too many times:
Smart executive joins organization. Sees obvious inefficiency in first week. Removes it in second week. Three months later, first major security breach in five years.
That “redundant” approval step was catching edge cases nobody remembered existed. The person who built it left two years ago. The documentation never explained the why, just the what.
Or this one: New VP inherits codebase with redundant-looking error checking. Same validation happens three times in three places. They remove two instances because “clearly” unnecessary.
Within a month, edge cases that happened 0.1% of the time start crashing the entire system. That error checking wasn’t redundant. It was a scar from a production incident. Every line of “weird” code is somebody’s hard-won lesson. The VP never asked why it was there.
This is Chesterton’s fence.
G.K. Chesterton said: if you encounter a fence across a path and don’t know why it’s there, don’t remove it. Not until you find out why someone built it in the first place.
What I Did Instead
Week 45 I set up a lot of meetings. Not onboarding meetings. Reconnaissance meetings.
30 minute 1:1s. Recurring time with peer VPs, directs, skip-levels, cross-functional stakeholders. I wasn’t learning how deployment works or where the docs are (though discovery skills matter). I was building a 3D model of how the organization actually functions.
What does this org actually reward? What gets projects killed? Where are competing visions for my team? Which technical decisions are locked vs just seem locked?
Week 46 I flew to Washington D.C. for two days to spend time with Rocket Money’s senior leadership team. We had some great strategy discussions about how we shape AI for helping people have better financial health.
It was a different elevation, same principle. Observe the contours before proposing to reshape them.
My goal for my role is exploring three elevations in this role:
Application level: how we provide best AI experience to users
Organization: how I reduce friction for introducing AI tools/frameworks
Individuals: how I help people find AI productivity workflows
Each elevation has its own Chesterton’s fences. Each requires understanding why things work the way they do before proposing changes.
What Happens When You Understand the Fence First
When you understand why the fence is there, you can invite people into change instead of casting them about by executive decree.
You can say: “I see we have this approval step. I learned it was built after the 2022 incident. That made total sense then. Here’s what’s changed since then. What if we evolved it to handle the new context?”
Now the team is with you. They’re not defending the fence because you attacked it. They’re collaborating on whether the fence still serves its purpose or needs to evolve.
People get energized when they’re participants in change, not subjects of it.
Move too fast and you pay the cost in change management overhead. I’d rather understand the existing contours before reshaping them.
What I’ve been thinking about
Grit and Gumption Aren’t Enough Anymore
Grit and gumption used to be pure advantage. Having them meant you’d go further than people without. With AI, they’re no longer enough on their own.
But here’s the opportunity: people with grit and gumption who learn to use AI can leapfrog everyone else. The ability to persist when things get hard still matters.
Stack this new combo with willingness to learn, stay curious and plastic, you can go even further.
The skills stack that makes someone successful just expanded.
Inviting In vs Pushing Down
Moving from startup entrepreneur to corporate intrapreneur, I’m learning the most important stakeholders aren’t usually people above you. They’re the teams you lead.
It’s critical to invite people into what you want to achieve rather than push it down.
Inviting means you understand the goal and communicate it so people know why it matters to them.
On Keeping Commitments
Commitments are a big part of the way I try to live and work. I’ve been thinking about this idea:
“If you keep commitments to yourself first, you’ll likely keep commitments to others. If you keep commitments to others first and you’ll likely fail to keep commitments to yourself.”
It feels like a variant of the big rocks paradigm from Seven Habits of Highly Effective People, one of the essential books that impacted my life.
What I’m Reading and Watching
I’ve started re-reading Zen and The Art of Motorcycle Maintenance and reminded of this quote: “You look at where you’re going and where you are and it never makes sense, but then you look back at where you’ve been and a pattern seems to emerge.” Perfect timing for first weeks at new company. I feel like it’s the best quote to describe the path my life has taken.
The Prof G Podcast‘s episode had a really great insight on resilience. The truth is the system makes it easier for people with privilege to be resilient, but that doesn’t change the fact that doing the things that make someone resilient increases likelihood of being more durable.
I also found this piece on The 20-Minute Writing Exercise That Neuroscientists Say Can Solve Your Hardest Problems. Intriguing approach to problem-solving through structured writing.
The Big Pattern
Week 46 I was in D.C. sitting in strategy sessions about how we build AI for financial health.
Every instinct said “share what you learned at Plumb, propose solutions, show value fast.”
But I kept coming back to Chesterton’s fence.
Every organization has its own scars, its own hard-won lessons baked into how things work. The VP who deletes “redundant” validation without asking why creates cascading failures three months later.
This week I was also helping my daughter understand equal signs with equations on either side. She wasn’t getting it. So I tried explaining it one way. Didn’t work. I tried drawing the equal sign as a mirror and two diff. eyeballs on either side. Finally she understood the idea was to find what’s missing to make the two sides of the mirror (or equal sign) click. That clicked.
A different person often needs a different mental model.
This principle is the same as leadership: find the right approach for who’s in front of you, not the approach that worked last time.
This week crystallized something about how I want to lead in this next chapter.
Engineers investigate before deleting. Leaders need the same discipline with team topology, processes, culture, technologies. When you understand why the fence is there, you can invite people into change instead of casting them about by decree.
You can say “I see we have this process. I learned why it was built. Here’s what’s changed since then. What if we evolved it?” Now the team is with you, collaborating on whether the fence still serves its purpose.
People get energized when they’re participants in change, not subjects of it.
The future isn’t AI OR human craft. It’s not speed OR strategic patience. It’s finding your unique synthesis of both.
Stay curious,
Chase
