I've been thinking about our session yesterday on and off since we wrapped, and wanted to share some additional thoughts before we kick off with the full company.

This is not just about ‘AI’ this is about the age old fallacy that stops businesses from winning which is that what got us here won't get us there.

What got us here was a specific mindset. We scaled by hiring exceptional people. When something broke, we added a person. When a team was stretched, we added more people. When we needed a new capability, we hired for it. And honestly it worked insanely well, and we currently sit in a room full of A players. I'm the biggest champion of this team and this culture, and nothing about what I'm saying changes that. This is also not me being critical of how we got here - the instinct to "hire our way through it" was mine too. It's the muscle we built over years of scaling businesses, and it did exactly what it was supposed to do!!

But that same mindset is now the thing holding us back. Every time we solve a capacity problem by adding a person instead of building a system, we get short-term relief and take on long-term leverage debt. And leverage debt compounds the same way technical debt does - almost completely out of sight or mind until one day you wake up running a company that is expensive to operate, slow to change, and almost impossible to restructure because every system has a human duct-taped to it instead of actual infrastructure.

That is the path we are on if we don't deliberately break the loop. And the loop won't break itself.

Someone has to break it and that someone is us right now.

So to reiterate when I say "AI-first," here's what I actually mean:

When a problem shows up in the business, the first solution we reach for is an AI solution.

Not the only solution. Not "AI or nothing." The first solution we consider. Before we hire, before we add a meeting, before we bolt on some new process with a lame tool that's going to get eaten for lunch by AI in a year anyway lol.

We ask: can AI solve this, or get us 80% of the way there???

It's first-principles thinking which we have built this company on. Instead of "we've always hired for this, so let's hire again," we strip it back to: what's the actual problem, and what's the most leveraged way to solve it right now, given the tools that exist today?

Here's the part I really want to reinforce: this is uncomfortable on purpose. If it didn't feel uncomfortable, we wouldn't be changing anything. The reason "what got us here won't get us there" sucks in the short term is because everything that got us here is familiar and comfort is the enemy of the next version of this company.

We are trying to build a multi-billion dollar institution. The Disney of Business. You don't build that by doing more of what already works. You build it by being willing to be bad at something new, publicly, in front of your team, until you're great at it :)

I’m willing to fall on my ass in front of all of you, are you willing to in front of your team?

If you keep a perfectionist mindset, all change will be hard for you. Until I let go of this myself, leadership felt insanely hard and taxing. Until I realized perfection doesn’t inspire anyone, it only intimidates people.

I want you all to think about this entire AI-first initiative as the single best opportunity you've had in a long time to show your team what great leadership actually looks like.

Not TELL them, SHOW them.

This is literally part of my book, there are two jobs a leader has when you want to change behavior on your team:

1. Define what good looks like.

2. Role model it first.

This initiative is the most well-defined opportunity for you all to do both at the same time than we have had in a long time. Consider it a test of your leadership. I know its testing mine!

Step one (define what good looks like) is already done for you and will be along the way during this initiative. We did that in yesterday's session and I'm doing it again right now by writing this. "Good" is: when a problem hits your desk, your first move is to ask whether AI can solve it or get you 80% of the way there, before you reach for a hire, a meeting, or a new process. "Good" is: you can articulate the AI-first audit on any headcount request before it leaves your function. "Good" is: you know the six foundational skills (after we have taught them), you're actively building them, and you can speak to where your team is on each one.

Consider that the easy part lol.

Step two (role model it) is entirely on you. And this is where most leaders fail, not because they don't agree with the change, but because they underestimate how much their team is watching. I can write every memo, Neil can run every training, we can put every resource behind this and if you as a leader aren't visibly using AI, visibly changing how you hire, visibly being a beginner again in front of your team, nothing will change. Culture doesn't trickle down through policy. It trickles down through BEHAVIOR. The soft shit. Your team is watching what you do 10x more than they're listening to what you say.

So I want you to reframe this whole thing in your head. This isn't "another initiative to roll out." This is the moment your team gets to see the caliber of leader you actually are. When we look back on this year, the leaders who will have earned the most trust, pulled the most talent toward them, and built the most durable teams are the ones who used this exact 12-week window to define "good" clearly and role model it shamelessly and IMPERFECTLY.

One last thing for you to consider.

We haven't done this before. NONE of us have. That's actually the fucking point!!! If we keep defaulting to what we've always done, we'll keep getting what we've always gotten: A bigger company, not necessarily a better one.

But we get to do this for the first time, together. Define what good looks like. Role model it, and lean on EACH OTHER for support and ideas 🙂 You are not alone, we are all learning together in real time.

Ok I will stop rambling now, but I really wanted to impress upon you all the opportunity this presents 🚀

– Leila

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