The Road to UNBOUND - Office Hours - The Last One Before Boston: Know Thyself, Then Find the Human Who Slowed Down
Hosts: Chris Carolan, Casey Hawkins, George B. Thomas · Guest: Sarah Lane-Hawn
September 10, 2026
Office Hours is the informal half of The Road to UNBOUND. No script, no segments, and no expectation that anyone stays the whole hour.
This is the last one before Boston, and the host opens by saying so: bittersweet, maybe not sad, because he has plans for after UNBOUND that nobody on the call has heard yet. Four in the room: Chris Carolan, Casey Hawkins, George B. Thomas, and the guest, Sarah Lane-Hawn, who runs a B2B revenue operations practice and arrived out of the overwhelm and into the excitement, having cleared the goals she wanted done before the event.
The first half is about the event itself. Sarah skimmed the speaker list and realized she only knew three or four names, and decided that was the good news. A year of HubSpot ads from the airport in, and a drive through Boston looking for billboards that were not up yet. George on whether this year will feel completely different, the way the year everything went white and a DJ booth appeared did, and on the sound of the new name: not you and AI, you and I. Sarah on missing every meetup by a day and planning to hover outside them anyway, because the rooms that put the human first and the tech second were the best part of her first year. George on knowing the fastest escape route to his room from anywhere in the building, and the Irish goodbye that follows. The buddy system, the nursing room, and Sarah's standing offer: if you need a person to be quiet with so you are not standing alone, find her. And a decision she called humbling and George called empowering: after a year of health issues since her son was born, she is bringing a mobility scooter so she can be there for all of it. Know thyself.
The second half is Sarah's AI activation story, told in the order it happened. Trust earned incrementally, the way she gives it to anyone. Treating the AI like an entry-level hire at first. Then thirteen years of operations patterns she kept seeing across clients, a conversation with Ryan Ginsberg about building an app to package them, and Ryan's answer: that is not the solution, learn to use AI well. Six weeks of mentorship in the spring, and a new brand of prepackaged solutions going to market at UNBOUND, managed first, self-service in six months. The advice that follows: start with the problem, not with how to use AI; expect to get it wrong and sometimes waste a day; take notes; and if you are hitting a wall, you are probably using the wrong tool, so ask the AI which one you should be using instead.
From there: Casey on why it did not click until she saw AI in her own work. George on the domino effect, on vibe-coding HubSpot CMS by teaching his assistant a module, and on asking what CLI or MCP to hand the assistant so it can just do the thing. Chris on building the UNBOUND Unboxed webinar campaign on a morning walk, registration page and UTM links included, from a system he built the blocks for over months. My AI is not your AI. Trust and safety built the way it is built between humans: over time, by repetition. The sparkle emoji, a fairy lullaby, and fairy doors hidden somewhere in the conference for anyone who spots one.
The close: everyone's activation story is a human who slowed down enough to be followed, and UNBOUND is a good place to find yours. Boston is September 16 to 18.
Moments from this stop
9 short cuts from this conversation.
Casey HawkinsIt didn't click until I saw AI in my own work
Chris CarolanA webinar campaign built on a morning walk
George B. ThomasLess humbling, more empowering: know thyselfGeorge B. ThomasMy AI is not your AIGeorge B. ThomasTell your AI assistant to be the explorer for youSLSarah Lane-HawnFairy doors hidden in the conferenceKey takeaways
Know thyself. Sarah Lane-Hawn told the room she is bringing a mobility scooter to Boston
rather than lose two days of the event to a hotel room, and called the decision humbling. George B. Thomas would not let that word stand: "Here's the thing. Know thyself. Know thyself. And ladies and gentlemen, there's so many people that don't know themselves, that push themselves to limits that they were never supposed to actually try to achieve. I'm proud of you for making that decision."
Ryan's answer was not an app.
Sarah Lane-Hawn had thirteen years of operations patterns she kept seeing across clients and went to Ryan Ginsberg to build an app around them: "And he finally went, Sarah, I don't think that's the solution. I think you need to use AI and I think you need to know how to do it efficiently. To be able to do this better. So we actually turned it into a mentorship training. And so he took six weeks and helped me develop kind of systems of how I wanted to use AI for my own business." That was March or April. The prepackaged solutions go to market at UNBOUND.
You're the app. Chris Carolan on why that mentorship worked after Ryan had been at it
only six months himself: "So maybe the smartest among us. Find a way to activate yourself with the AI tools. And now, like, you're the app, maybe? Like, you're the scalability. You're the human that has now found AI capability that scales in a way that we've never experienced."
Start with the problem, not with how to use AI.
Sarah Lane-Hawn's advice for anyone at UNBOUND who has not started: "Like the problem isn't how to use AI, right? Like that's, that's not, that isn't it. And so just taking the time to say like, what am I actually trying to solve for? What am I interested in? What am I trying to do? And then just start playing with it. Be curious, know that it's not going to be perfect and you're going to have to learn."
You are probably using the wrong tool.
Sarah Lane-Hawn, who says she is not an explorer of tools: "If you're running against a wall where you're like, okay, why is this not working? Like, I know AI is supposed to be able to do this. Yes. But you're probably using the wrong tool with the wrong type of AI system to do the thing that you're asking it. And so start by that question." George B. Thomas took it one step further: "If knowing thyself means you know that you're weak in being an explorer, then tell your AI assistant that it's supposed to be an explorer for you."
A webinar campaign built on a morning walk.
Chris Carolan on the UNBOUND Unboxed campaign he asked for that morning: "There is no template in my system. What I do have is an agent called Broadcast. That is responsible for marketing and content hub in HubSpot and how it works. And there are expertise packs. And by the end of my walk, which was about an hour, where I'm just on my phone, like driving clock code, and At the end, I get to send an email to George and Casey and the rest of the group that's." Registration page, HubSpot campaign, UTM links included, from someone who had never built a UTM link.
My AI is not your AI.
George B. Thomas on why trust in an assistant is built the way it is built between people: "Let's take this completely away from digital and talk about trust and safety with humans. How is that built over time? Over time. And the repetition of good. I almost swore. And the repetition of good things happening over time. So if you're sitting here and you're dabbling with AI, guess what? There's going to be no trust and or safety." Casey Hawkins on the moment it clicked for her: "it was not until I really saw AI in my own work that I was. Was getting the benefit."
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