Who Floats My Boat? Lessons From 100 Operators on the Biggest Sailboat in America

On Wednesday, September 16, I set out to Philadelphia to listen to operators, business owners, and those interested in systems and the impact it could make in our businesses and lives. I never expected what it would turn out to be; finally seeing a reflection of those who came with their values, their intrinsic truths of what it means to be human, and a fearless meeting of automated systems in operators managing businesses big and small. Basically, I finally found out who floats my boat…. who knew??

In an era where fear-based marketing, rage-bait marketing, and guilt/shame marketing is hotter than ever, and conveniently obfuscates fabrications from honest truths, I found a strong throughline within every breakout session I went to: a focus on the authentic relationships that we foster within our business, with ourselves as owners and operators, and with our business's audience.

Ops Ahoy was a 2-day conference where I got to meet and talk to operators and operator-business owners of small businesses who truly cared about systems and how to bring them to the forefront while managing and growing their business. While people in the world outside our boat asked questions like, "How much of the business can we make disappear into software?", "How few people can we run with?", "How many agents can replace roles?", "How quickly can we turn human work into an autonomous workflow?" — Derrick, Karl, Hannah, Le-An, Monica, and Barbara constantly centered humans first, asking questions like, "How do we build systems that make people better at their work instead of just faster at it?" "Does this system help people make better decisions when something unexpected happens?" and "What kind of business are we creating for the humans who have to live inside it every day?"

See the difference? I think a lot of what we're seeing right now with firings, AI drift, and burnt-out team members being forced to use AI even when it's not warranted comes from an undervaluing of the real work that humans do that's invisible and taken for granted. I understand the eagerness and fantasy to completely replace the work of humans (kinda, not really). But before we use AI to automate anything and everything we can think of, there does need to be real questions asked to understand your business, your business's relationship with its audience, and the work of your team members. Get closer to it before you automate it away! Is this really work that AI can replace?

Throughout the breakout sessions from the Ops Ahoy captains, I realized that even in the AI storm of it all, the same strategies, questions, and problems remained the same. If there isn't a well thought-out strategy and goal, AI can only help with so much. Just like James Clear wrote, "You do not rise to the level of your goals. You fall to the level of your systems," you do not rise to the level of AI's capabilities. You fall to the level of the strategy underneath them. The problems and questions being asked are the same ones we've always been concerned about before AI even got here, and they are the ones we'll continue to be concerned about after.

Here are the top lessons I learned on the biggest sailboat in America:

The system is never just the system

Derrick's session on process mapping was one of the first places this clicked for me. On paper, process mapping sounds like the typical extremely-operations, systems, map-this-out sort of play: you know, find the steps, identify the bottleneck, make the workflow cleaner. But he actually opened his talk with a real story about history — about one man who wanted to build something complete in the time he was given, and the completely unconventional methods he used to get there. NO ONE was thinking of doing this at the time! But through human ingenuity, he was able to keep his goals top of mind and break all the rules to get there.

Delegation still requires us to understand the work first

Le-An's conversation around a "second brain" and virtual assistance brought up another version of the same idea for me. We have so many more options now for where work can go. It can stay with us, move to another person, become an automation, get handed to AI, or become some combination of all four. That sounds wonderful until you realize somebody still has to understand the work well enough to decide where it belongs.

Hannah's session on dashboards hit another nerve I have been thinking about a lot lately, because I LOVE a good metric. Give me a dashboard and I will happily disappear into it. But a dashboard is still only a representation of what happened. It can tell you conversion went down, delivery slowed, capacity changed, or a number moved in a direction you do not like. But it cannot automatically tell you why. Hannah literally pulled out a table to explain the difference, and it was really powerful!

The why might be sitting inside a client conversation, or something your audience has started saying that has not made its way into a spreadsheet yet. The number matters. But only because of the story around the number matters too.

AI is becoming part of how we think, not just how we work

The conversation I had with Derrick's right-hand Camille described AI as a kind of third level of consciousness, and that idea really stayed with me because it gets at something much bigger than automating tasks.

We are starting to use these systems to remember things for us, organize our ideas, challenge our thinking, interpret information, communicate, research, decide, and increasingly act on our behalf.

At that point, AI is no longer sitting neatly outside the human thinking process as another piece of software. We are going to become more and more intertwined with it as time goes on. How does that change us?

What happens to our judgment when the machine is always available to suggest the next answer? What happens to our expectations of other humans after spending all day with something infinitely fast and agreeable? What parts of thinking do we want assistance with, and which parts do we still need to struggle through ourselves?

Then there were the conversations that happened outside the sessions

Some of my favorite insights did not happen on a stage at all.

I talked to Marco, who builds fresh pasta in his business in Switzerland, and Dot, who works in manufacturing for the military. Both had an outsized concern for their team — how their team worked, how they felt, and how that reflected on them as managers and owners.

Systems eventually have to survive contact with reality. Real people use them. Real people misunderstand them.

That feels particularly important right now because AI demos (oh, don't we love those) tend to show us the happy path. But operations lives in everything that happens when we leave the happy path.

When we have people in Silicon Valley wanting to go there — pushing automation as far as it can possibly go and turning formerly manual processes into software — operators eventually have to ask a different question: what kind of business do we end up with when it gets there?

And there's already some evidence that AI can make each of us better while making all of us a little more alike. In one Science Advances experiment, people given AI ideas wrote stories that were rated as more creative (notedly, they were less creative to begin with), but the AI-assisted stories also became more similar to one another. Depending on how much AI help participants had, the increase in similarity represented roughly 9 to 11% of the range seen in the human-only group. The researchers described what's happening pretty perfectly: individuals can gain creativity while the group collectively produces a narrower range of ideas.

A separate study looking at 2,200 college admissions essays found something similar: as more essays were added, each new human-written essay contributed more new ideas than each new GPT-4 essay, and that gap actually became more pronounced as the collection grew. Even changing the prompts and model parameters did not remove the homogenizing effect.

I do not think that means businesses should back away from AI. Quite the opposite. But it does make me much more protective of the places where sameness is expensive.

Look, a business, when you strip away the dashboards and workflows and CRMs and automations, is still a collection of relationships. There are the relationships between the people inside it, and there is the relationship between the business and the people outside it who choose to pay attention, trust it, buy from it, recommend it, come back to it, or decide that something about it feels distinctly theirs.

If we automate away all the strange little decisions, stories, conversations, instincts, disagreements, and bits of judgment that created that distinctiveness in the first place, we may end up with an incredibly efficient business that nobody feels very much about either way.

And THAT is where I think the operator's role gets more interesting in the age of AI. We are not just asking where the system can remove work anymore. We are asking where the system should create enough room for the humans to make the business worth caring about.

Interested in this conversation and want to find out how you can keep it going? My AI masterclass is happening tomorrow, September 25th at 12pm EST! Click here to register. My platform only allows me 10 spots on its tier, so it's limited — I'll be shutting it down once we reach the max number of people.