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[upbeat music] Hello, and welcome back to the Chief of Staff Network podcast. I'm your host, Scott Amenta, founder of the Chief of Staff Network.

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I'm joined today by Tom Guthrie, president of the Chief of Staff Network and my co-founder. Tom, nice to have you here. Great to be here. Thanks, Scott.

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We're here to talk a little bit about San Francisco Chief of Staff Connect, happened last week. I unfortunately was not in the room, but I, uh, would love to hear how it went, Tom.

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So tell us a little bit about the, the day. Yeah, absolutely. Let's see. I, I think it was, it, it was the first stop on our global tour for Chief of Staff Connect.

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We've got seven stops this year, and, and I think it's a pretty ambitious schedule, but our, our real goal is to bring together and activate the global chief of staff community because it is really a global role now.

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I think we chose San Francisco for a reason, which is that chiefs of staff are becoming the central node of AI deployment and AI transformation at a lot of companies, and obviously San Francisco is the epicenter of that change.

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So we wanted to go straight to the source and, and talk to folks who were in the middle of all of that, understand what was going on, bring folks together, and then hopefully ripple that, those learnings out across the entire network and, and across the world.

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So we chose a, a beautiful May Friday to host the event. It was a, a great venue, full of light, full of people. We had about 100 chiefs of staff in attendance, which was... It was cool.

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Our biggest, um, San Francisco event yet. And the vibe was honestly pretty, pretty positive. It's strange out there right now, right, Scott? It's, it's, uh... There's a lot of divergence in, in how companies are doing.

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Some people, especially in San Francisco, people are, you know, uh, we seem to be mi-minting a centimillionaire or billionaire b- every day or two.

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I'm not sure how many of those there were in the room, but you have this, like, crazy exuberance on one side about AI and this existential dread on the other side, and I think those often sit within the same person, within the same company day-to-day.

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And certainly we, we saw a little bit of both of those things at the event.

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But chiefs of staff, I think, are an optimistic problem-solving bunch, and, and that definitely came through during the day and during all the conversations we had. Yeah.

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And I would say that, you know, the, the nature of San Francisco just as a city and the industries that it represents, it typically has more of a, of, of a slant towards pro-technology rather than, uh, you know, being kind of the antagonists of, of the future development.

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We certainly saw- Yeah... that last year at, at Connect. It had, you know, slightly less of an AI focus, but certainly a, a handful of the conversations steered that way, and no exception this year.

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I think we were very lucky also to have, you know, some really interesting people both on stage and in the audience, you know, coming from some of the larger AI companies out there today and certainly kind of industry players that are, are driving all of these conversations forward.

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Talk to us a little bit about kind of like your read on how chiefs of staff are reacting to AI right now.

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We, we just released a report last week that, you know, showed some interesting insights around chiefs of staff who are certainly adopting AI, uh, in their day-to-day workflows.

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As we've kind of both seen, they're very much being given the lead direction of how AI transformation is working inside their organizations, and yet it still feels like we're kind of all behind the curve in terms of real adoption, right?

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Re- really building kind of autonomous agents, real workflows, really instrumenting kind of these tools into the fabric of our organizations. Do you feel like chiefs of staff are really grabbing the reins? Absolutely.

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Uh, but I think that that constantly feeling like you're behind is a little bit of, of the San Francisco attitude that's scaled to the world, right? That's right.

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San Francisco's good at scaling stories and scaling technology products, and I think this story about, "Hey, AI's gonna create this permanent underclass and a group of unfathomably wealthy kind of AI overlords," has become one that's taken the popular imagination.

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Mm-hmm.

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I think, you know, for the folks that sit at AI companies or AI-enabled companies, especially the ones in San Francisco, they see a little bit of behind the curtain of that narrative, and it certainly helped that we had people there from Anthropic, from OpenAI, from Google, from, you know, a lot of the major players in the space.

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But I guess at, at its core, right? Like, I think everybody in the room was an AI user, right? And I think that's, that's borne out in, in the data that we collected.

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It's north of 90%, around 90% of, of chiefs of staff- That's right... were, are, are daily AI users.

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But far fewer of them qualify as AI native, and that also came through, um, in the conversations that we had, um, there. And, and that dovetails with this kind of feeling like you're behind piece.

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I think it's hard for...

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What we heard was that it's hard for, um, chiefs of staff at non-AI native companies, so companies that weren't founded in the last, like, 18 to 24 months, to truly be AI native unless there's broad support from the principal, from the rest of the executive team throughout the entire company, that that's a pivot that people have to make.

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Just because it's difficult to change course on a business that's already in flight, it's not impossible. It just takes time and a lot of deliberate effort.

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I think the least AI-pilled person that I talked to was somebody working at a, at a healthcare company in a sensitive industry who, um, whose founder, executive team were really skeptical and, and cautious about the impact of, of AI on their users, and so have, have not really deployed it that much.

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On the other hand, there are people that have built out full-scale kind of agent swarms and instrumented their companies around, around AI.

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So really ran the gamut, but I think everybody left the day feeling much more, um, kind of on the same page about the opportunity and the risks and having some concrete action steps that, that they could take.

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And we've seen some of those, some of those narratives come out on LinkedIn after the fact and, and people talking about the projects that they're building and the conversations that they're having, which is always nice to see too.

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Yeah. Yeah, and I, and I think the key word there is building, right?

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We've kind of angled all of the Connect events this year towards this idea of moving from force multiplier to builder and really seeing chiefs of staff put on their builder hats.Not just in their own day-to-day use of AI, but in kind of an entire organizational transformation and in how the entire business is adopting AI, both team, um, and in product.

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And, you know, I think we, we had some interesting, you know, folks in the room, Laura Peng from OpenAI, Diane from Clarinet, leading transformation at lots of companies, the Scribe CTO and chief of staff.

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Talk to me a little bit about kind of those workshops, those fireside chats, those panels.

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Did anything jump off the page for you or the others in the room that really inspired people to, like, get out there and r- roll up their sleeves and build a little bit more? I think it's a mindset shift, right?

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Going from being the person supporting the principal and then having that be at the center of what it means to be an effective chief of staff to thinking about the company more holistically.

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Certainly not a- abandoning the, the principle because that's your bread and butter, but thinking about what's possible and, and what you can build with these new tools that are now at your disposal.

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You know, I think that's a, uh, like I said, that's a mindset shift for everybody, uh, and it doesn't happen overnight.

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But what I heard was a lot of excitement around that, whether that's in the, in the Laura Peng workshop, she's from OpenAI, specific workflows that their Codex product unlocks now that were not possible before.

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Diane, who with Clarinet works at a lot, uh, works with a lot of mid-market and, and enterprise clients on how to make their company more AI, um, enabled and, and, and, and native.

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I think the, the excitement and the desire to get going was strong throughout the room. I think the open question is like, "Okay, what, what first? What's next?" Mm-hmm.

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And I think that's one of the things that w- we should explore more and, and build more programming around is, okay, let's sit with people, get their hands on tools, because once you kind of understand what these tools unlock and what you need to build for your company from an infrastructure perspective, then I think you're off to the races.

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And we, we see the folks who've done that just moving so fast, which is exciting. I think that's right.

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We, we've seen kind of similar interpretations of that in our chief of AI fellowship and in other AI webinars that we've run.

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A- and I think there's kind of a, a constant through line that comes up for many of the chiefs of staff that we speak to daily, which is, you know, the, the role can be very heavily operational, very execution-focused, and that sometimes gets in the way of the larger picture where chief of staff really can have, you know, deep impact.

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And, you know, that, that oversight and kind of wherewithal of what's happening across the business, what corners can't be cut, what teams are working on which processes, and knowing that from kind of the ground up is where a chief of staff can be the most effective.

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And I think that's why this kind of transformation work is landing on a lot of their plates. We've had this conversation before.

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I, I think we, we both agree that it is probably one of the most interesting strategic opportunities for a chief of staff to really level up into a true leadership role while staying a chief of staff.

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And whether they keep that title or they call themselves chief of AI or, or what have you, you know, I, I don't think this kind of opportunity has existed in the history of the chief of staff role really growing in the private sector as a whole.

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And so, you know, I think it's, it's on all of us to kind of, um, look at the opportunity, roll up our sleeves, and, and kind of dive head in.

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And I recognize that that's gonna be difficult for lots of people a- and I think that's where these events, you know, really, um, have a positive standing because

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it's, you know, nice to recognize that you're not alone in kind of feeling this, you know, either sense of dread in terms of a larger vision or just, you know, uh, fear of how to get started and, and what to focus on, how to have those conversations with your teams.

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It sounds like a lot of that came out in some of the panels, some of the- Yeah... fireside chats, certainly some of the workshops as well.

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Yeah, and I think that dread is pretty closely related to the feeling that you get if you're, if you've ever made art, right?

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Just the feeling that you get when you're facing down the blank page and starting to write a story or looking at a blank canvas and looking to make your first mark on that canvas.

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There's, there is a fear in, in that act of creation.

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And yet, once you start getting into it, I think that is the most fun thing that you can do, and that's one of the themes that I heard from the conversation I had with the CTO and, and chief of staff at Scribe and, uh, who are both building a lot, and obviously Scribe is kind of a, a, an AI native tool as well.

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And then what I heard, um, our, our collaborator Arti, the conversation she had with Jordan and, uh, Alfredo, who are the chief of staff and CEO at Latch Bio, is like they're just having fun, and you can see it in the relationship that, that, that chiefs of staff have with their principals.

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I, I think there's a reason that anybody who's worked at a startup, the time they wish they could go back to is like the early days when they were just building stuff.

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It's not when OKRs have took- taken over and when it's herding cats.

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It's a lot more fun to be a builder than it is to be somebody who makes sure things get delivered on time or sends an investor update, although those things are obviously necessary.

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So don't be afraid of, like, having a little fun with it too. Yeah.

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I, I think that there was another thing that stood out to me in the agenda of this Connect conference, which was your idea, um, so all, all credit here to you.

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You, you invited some chiefs of staff from cultural institutions that, you know, go well beyond kind of the scope of the, the tech industry that we know San Francisco to, to, to, to dominate. So we had, uh, who was it?

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The chief of staff from- The chief of staff from, from the San Francisco Ballet, and then the COO at, uh, from the symphony, who was the chief of staff.

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And both of them had worked there for seven, eight, nine years each, so they were clearly very... You know, they were, they were in love with the, the institutions that they, that they were a part of.

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But, uh, and I don't, I don't know how, how closely people follow this stuff, but, like, they're both companies or both organizations that have been around for a century or close to it.

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They are some of the top kind of cultural institutions in their fields in the United States and in the world, and they attract top talent along their domains.

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But they're also massively complex organizations in a way that I think tech companies don't appreciate. They both have dozens and dozens of board members.

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I think, you know-In their charters, they're mandated to have somewhere between 50 and 80 board members.

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And so if you're a startup kind of chief of staff who's wrangling a board of like four or five people, uh, imagine that 10 or 12 times over, and I think you'll get a sense of the challenge there.

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Um, they also deal with unions. E-each of them have like six or seven unions that they have to work with, negotiate with, et cetera.

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And balancing, uh, you know, as, as they corrected me, integrating the, um, the cultural kind of, uh, and artistic desire to move the r- their respective art forms forward with the commercial realities and, and, um, pressures, uh, of what it's like to build a kind of a, uh, you know, one of these artistic products in an age where it's a lot easier to open up TikTok and start scrolling than it is to get dressed up and go to the ballet.

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I think it was a fascinating look.

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Uh, I had a lot of fun with that conversation, and I think, uh, we, we wanna do more of that across all of our Connects because believe it or not, the chief of staff role in the world is wider than just tech industry.

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Yeah. And I, I think it's an interesting look at kinda how the chief of staff role has evolved, you know, from public sector to private sector.

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And, you know, while we are talking to and engaging with lots of chiefs of staff across the tech industry, it certainly has a place in higher education, in nonprofits, in these large cultural institutions.

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And while the day-to-day may look different from the outside, actually behind the scenes, as you said, it's just as complex, sometimes even more so.

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And, and, and the role can be, you know, a, a challenge in and of its own. And I, and I think there's a lot to learn from seeing kind of those other perspectives outside of your own core industry. Yeah, I agree.

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You know, getting back to the fun point, what's more fun, talking about the ballet or talking about B2B SaaS company number 346? For me, I'd rather talk about the ballet. [chuckles] That's right.

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So it, it was a good way to break up the day, I'm sure. Totally. Totally. Yeah. Looking back at, at the, the conference last week- Mm-hmm...

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what do you want someone who attended to kinda walk away still thinking about a week later? What do you think those, those attendees are still thinking about?

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Yeah, look, I, I mean, I think the most valuable thing goes back to what you realized when you started the network almost a decade ago, which is chiefs of staff need to be around other chiefs of staff because they're often the only people in that role at their organization.

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And so just being in a room with, you know, 99 other chiefs of staff, I think was one of the big takeaways for each and every member. Like, they're not alone in the role.

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They have peers that they can rely on, and it's been really gratifying to see people following up and setting up kind of ongoing conversations.

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We have follow-up events scheduled in San Francisco already, and where I think we'll plan to do that for all the other Connects as well. So, so just connection is, is the biggest thing.

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But I think if there's one message that I think we wanted folks to take away, and I think they did, is that transition from force multiplier to builder.

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Doesn't matter if you're starting small or trying to build your own company or transform your company, uh, overnight, just taking the-- shifting in that mindset from how do I manage the process that exists today and improve it incrementally to how do I build something new?

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How do I have fun with, with that build process and, and think about ultimate kind of value creation, whether that... whatever domain you're in.

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I think that's the necessary shift for chiefs of staff to make, and one that we saw a lot of folks who attended the event coming away with. Yeah, I agree.

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I think if we look back even to a few years ago, the pace has always felt fast and, and the, the pace of change in this role in particular has also felt like it's kind of constantly moving.

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There, there's more fights on LinkedIn about what the role actually is than I can count. Oh, God.

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And you know, that, that all seems kind of pointless in the grand scheme of where the world is actually going, what impact this role can have in the organizations kind of driving those initiatives forward.

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And I think that's really the heart of what Connect is about, what our community is about, and, and that only comes through in the relationships that are built between chiefs of staff in these live settings.

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So sounds like, uh, we did a good job last week. I appreciate you hosting it, Tom. Yeah. I mean, they'll be the ultimate judge of that, but I, I had a lot of fun. Yes.

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Um, and it was great to meet everybody and, you know, I think we've got, we've got some more coming up quickly that I'm excited for too. Yeah.

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So for those who missed the San Francisco Connect event last week, we have a few others coming up throughout the rest of this year. Austin is coming up next week, so grab your ticket to the Austin Connect.

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We'll include all the links in the description. We're also hosting in Berlin, New York, London, Singapore, and Dubai this year. So have a look at our website and grab your ticket. We'd love to see you there. Definitely.

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Yeah. And I think those, those two core themes of connection, um, and, and becoming a builder are gonna be common throughout.

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Um, but we'll, we'll be adapting the programming, adapting the content, and inviting folks from, from distinct sectors based on, on where those things are.

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So for the Austin event, which we have coming up quite quickly, it's, um, uh, there's a lot of focus on frontier tech and, and kind of building what's next in space and defense and manufacturing and energy and, and those exciting new industries.

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But I think that folks from every industry can take a lot away from the learnings from, from those things, just like somebody who's working in B2B SaaS can take learnings away from the ballet. That's right.

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And, and I think especially as we bring Connect to other geographies, we're also going to see some angles here where there are different perspectives based on region.

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And, you know, that might be everything from adoption to AI to what the role actually means inside their organizations, you know, given kind of cultural definitions and, and, and ways of working.

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And so will be fun to report back on how those events go as well and, and kind of what those connections look like. Yeah. I think it's never been a better time to be a chief of staff.

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No matter where you are in the world, I think you're, you're faced with cooler opportunities, more opportunities to build. You're getting paid more than ever.

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And so it's never been a, a more fun time for us to run the network, I think. And, uh, we've got a lot of great stuff planned. Cool. Tom, thanks so much for joining us.

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And to all those listening, we hope to see you at Connect. Yeah. Thanks, Scott. All right, see y'all soon.

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