Leveraging Leadership

How Chief of Staff Network Sees the Future: From Chief of Staff to Chief of AI

• Emily Sander • Season 1 • Episode 217

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Scott Amenta, founder of Chief of Staff Network, shares key findings from their recent AI report, including that 84% of surveyed companies are already piloting AI tools and that change management and ethical concerns are major barriers. He talks about the new role of the Chief of Staff in AI adoption, working closely with CEOs and CTOs, and highlights the launch of several new programs like the Chief of AI Fellowship and Launchpad for aspiring Chiefs of Staff. The episode also covers real-world examples of AI change management and how Chiefs of Staff are navigating this fast-changing landscape.


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Who Am I?

If we haven’t yet before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want. 

 

Time Stamps:

01:36 Overview of Chief of Staff Network
03:27 The Role of Chief of Staff in Modern Organizations
05:23 AI's Impact on the Chief of Staff Role
09:09 AI Adoption and Challenges
27:37 AI Training Initiatives
29:46 Chiefs of Staff and AI Decision Making
32:45 AI Use Cases for Chiefs of Staff
37:12 Challenges in Measuring AI Impact
42:16 Chief of AI Fellowship Program
45:14 Launchpad Program for New Chiefs of Staff
47:37 Power Skills Program
48:58 Chief of Staff Connect Conference

emily-sander_1_07-23-2025_080256:

My guest today is Scott Amenta and he is the founder of Chief of Staff Network. Scott, it's great to see you again.

scott-amenta_1_07-23-2025_170256:

Yeah, likewise could have be in here.

emily-sander_1_07-23-2025_080256:

How are things in, uh, Berlin

scott-amenta_1_07-23-2025_170256:

Berlin is, uh, raining, pouring in dark, so typical Berlin, but, but, but not in the summertime. Usually it's bright and sunny. So this is unusual.

emily-sander_1_07-23-2025_080256:

Yeah, I'm sorry. Yeah, I'm up in Seattle and it's actually pretty sunny here. So we've, we've

scott-amenta_1_07-23-2025_170256:

We, we've swapped. Yeah.

emily-sander_1_07-23-2025_080256:

we swapped, but thank you so much for stopping by. We had, uh, Rahul on last year and he was kind enough to take us through Chief of Staff Networks salary report at that time and kind of talk about some fun things that you all were doing. So you're here to talk to folks about the Chief of Staff Network's AI report, and I'm really, I'm personally. Genuinely interested and excited for what, uh, you're gonna share there. And then you have several new offerings and programs and initiatives that you're working on that I wanted to, uh, make sure we get a chance to talk about and get that information out to folks as well. So that'll kind of be the back half of the episode, but feel free to kick us off anywhere you'd like to start with the AI information.

scott-amenta_1_07-23-2025_170256:

Yeah, sure. I mean, maybe let me start with a quick introduction of Chief of Staff Network and then we'll, we'll get into kind of the, the reasoning behind.

emily-sander_1_07-23-2025_080256:

assuming everyone knows Chief

scott-amenta_1_07-23-2025_170256:

I, I, as I hope so as well. Um, but, but maybe not for, for some new listeners or, or people just exploring the role for the first time potentially. Um, so Chief of Staff Network is, uh, one of the leading kind of professional communities and organizations for chiefs of staff. Um, we, we help kind of active chiefs of staff level up in their role, accelerate their career, uh, find their path forward, whether it's into more advanced kind of senior levels of the position. Uh, or onto the next thing, whether it's BizOps or COO type roles, strategy roles. Um, we've worked with thousands of chiefs of staff over the last seven plus years. I started the community, uh, back in 2017 when, when I was a chief of staff and in my first chief of staff kind of tenure. Um, when I was feeling as lonely as you can imagine, in the role with kind of no, uh, support network or guidance or clarity on kind of what I should be doing, how I should be measuring myself. Or what a chief of staff even really was at that point. And um, you know, I was lucky enough to find a few other people kind of in my shoes and recognize that there was a much bigger opportunity to kind of make sure that, you know, I wasn't the the last one to feel that way. And every new chief of staff could find, you know, a home kind of in the community to, um. Ask people questions, get answers in real time, um, and, and also explore kind of how this role has evolved outside of the political spectrum and, and into kind of private and, and, and publicly traded companies. And, um, you know, I think especially in startups, the role has kind of really taken off like a rocket ship. And, um, you know, there, there's numerous reasons for that, that we can kind of get into. Um, but, but the big thing is organizations are more complex. CEOs need help. Uh, I've made a case for kind of this two-headed CEO, um, multiple times. And, and, and I think it stands like chiefs of staff are there as strategic executors and operators on behalf of their principal. They're there to kind of multiply the impact and the output. And, you know, that's very different than kind of a more traditional administrative role. Equally critical in different ways. Um, and, and those two can work, you know, side by side. But yeah, our mission is to see more chiefs of staff get into the role, uh, and, and to see the role proliferate kind of across industries.

emily-sander_1_07-23-2025_080256:

Yes. And I, I love what you're doing and you know, my, my small part in all this is I am tired of hearing, oh, you're a chief of staff. That means you're an ea. No, no, I, I try not to roll my eyes when I, when I hear that, but elevating the role to, similar to what you described, where it's a high level strategic, in my mind it's a C-suite role. There's different levels of that, but it, it's to that and like you said, a force multiplier, and you're a game changer. You're a leverage point. So I love everything that you guys are doing. And then, you know, you kind of mentioned, but your hallmark. Your Hallmark offering is the 900 plus Slack channel where you can connect with the chief of staff literally all over the world, like mul, like multiple continents. We're talking about here,

scott-amenta_1_07-23-2025_170256:

That's right. So that, that's our pro membership, um, that gets members access to a private Slack group that's, that's been around for, for years. Um, so the, the, the history in that Slack group and just kind of the, the ongoing conversations are unparalleled. Um, but it also gets us access to all of our programs and courses and, and live events, both virtual and in person. Um, we run multiple conferences, big conferences throughout the year. We can talk a little bit bit more about that, uh, towards the end of the episode. Um, but, but first I wanted, we wanted to start by talking about, uh, AI and, uh, what, how, how, how AI is impacting the chief of staff role. And, you know, we were looking and starting to experiment with a lot of the AI tools. Around two years ago, you know? Right, right. When GPT, I mean, even before GPT was coming out, we were already playing with some of the tools and, you know, started to recognize very quickly that, that the fundamental shift here that all organizations are going through at this point, um, was going to impact how chiefs of staff spend their time, um, and operate within their companies. And I, I won't sit here and say that the chief of staff role is going to go away forever, and AI will be kind of. It's immediate replacement. Uh, in some cases that might be true and, and certainly for some parts of the role, it definitely is true. Um, but I think what, what actually is happening is chiefs of staff have kind of found themselves at the crossroads of probably one of the most interesting times on the internet. And, and this applies not just to tech companies, but to all companies, um, and, and nonprofits and government alike, um, and, and chiefs of staff have a very unique opportunity. To be the orchestrators, be the kind of change management, um, you know, implementers in their organization, both in deciding kind of which tools and how are these tools going to be implemented across teams. But, but also as importantly, and this is where the chief of staff kind of really comes into play, is, is how do we manage the humans? In adopting and adapting to that change as well. And when we started to think about this, we, we realized actually the chief of staff may no longer be the chief of staff. Uh, we've been calling it chief of AI now for, for the last year and a half because in, in a lot of ways the staff is no longer just human. The staff is also agentic workforces and, uh, and, and workflows and, and, and AI making decisions or, or doing some of the grunt work that otherwise. A human might have been spending weeks and or months doing, um, and, and you know, the opportunity to go from zero to good. Has now been shrunk down to seconds. Right. Good to great. Still takes a little bit of time and, and, and, and often a human's involvement to actually make a decision about, you know, what does great actually look like in this context. Um, and, and, and so we're not writing off chiefs of staff entirely or, or humans entirely for that matter. Um, but we are definitely saying that the role has changed, um, and, and whether active chiefs of staff realize it or not, that change is coming for them at some point. And that point is not five years ahead. That's in the next 18 months probably. And so our new mission really is how do we prepare chiefs of staff, both active and new and in and incoming, um, to adapt to kind of this new reality. And so in order to do that, we, we set out to find some data and, and understand a little bit more about kind of what was going on in various companies, you know, behind the scenes and, and, and how the role is kind of being impacted by, by those changes.

emily-sander_1_07-23-2025_080256:

Very cool. And so, I mean, did you reach out to kind of your 900 strong group and cohort and, and ask some questions and, and kind of maybe walk us through some of the highlights of that report?

scott-amenta_1_07-23-2025_170256:

Yeah, sure. So we, we always start with that group. They're, you know, they're kind of the bread and butter, um, but the audience is much bigger than that. So we're, we're lucky enough to be able to reach out to thousands of chiefs of staff, both active and, and past, um, to, to collect data. I'll, I'll start from the top. I kind of like, I've got a few key takeaways in, in my head. Um, the first one is really like, pretty obvious AI adoption is growing. It's already high, right? 84% of the companies that we surveyed are already piloting AI in some ways Now, that that doesn't mean that they're necessarily have implemented across the board, um, you know, have, you know, implemented it even in individual teams. It doesn't mean that adoption has been consistent across the whole organization, but the executive team for sure is already thinking about it. Um, and has either, you know, started to mandate or started to require, um, you know, or, or started to, uh, enforce, right? Like different AI tools to be used by, by various teams. Now obviously, security governance come into play, you know, pretty quickly from, from that point forward. Um. That's kind of like one of the next big things that, that, that we saw is that tends to be one of the biggest key barriers as well in terms of adoption, right? A ai, uh, security ethics, governance and, and then of course change management. So, um, security and ethics, 41% of the companies that we surveyed presented that as kind of the main barrier to entry in terms of how do we get over this hump. Not, not just the learning curve, but. The actual, like distillation of AI tooling, kind of across the org. Um, the other piece is change management and, and change management has a few layers. Um, one of course is training, right? How do we train our employees to use the tools? Um, how do we make them motivated and inspired to experiment with, with various tools?

emily-sander_1_07-23-2025_080256:

That's a

scott-amenta_1_07-23-2025_170256:

Um, how do we remove the fear of having used those tools? It, you know, it may be my eventual replacement. Um, and so that dialogue, that communication, uh, as we'll get to, that's where chiefs of staff thrive, right? Working from top down and ground up simultaneously, um, where they have kind of the eyes and ears and, you know, thoughts of the executive team,

emily-sander_1_07-23-2025_080256:

Mm-hmm.

scott-amenta_1_07-23-2025_170256:

are also hearing kind of the real life stories of I don't have enough time to even experiment with ai. Like, my plate is full. So how do I, how do I move from. You know, the already 60 hours, I'm working a week to squeezing in an extra four or five hours to learn the tool and, and shift the behavior. Um, you know, that, that can be really tough. And so, um, yeah, chiefs of staff, like their ability to work top down and, and ground up that, that's, that, that's a key point of, of one of the findings.

emily-sander_1_07-23-2025_080256:

Yeah. It's, funny you kind of, as you were saying those things, I'm remembering conversations I've been having where Yeah. I have a chief of staff who's at a startup and they're doing clinical trials and she can't use AI because of different regulations and things like this, so she's like, Emily, I know it would save me. Personally, individually, so much time in my personal workflow, and I know we could deploy this in certain parts of the company, but there's the regulation piece, so that's, that's a, um, a barrier for sure. I think the change management piece, I'll, I'll let you finish your report and takeaways here, but I'd love to dig into that change management piece because that's, um, I agree a hundred percent. I think that's where chiefs of staff are bread and butter tried and true. That's, that's in their wheelhouse for sure.

scott-amenta_1_07-23-2025_170256:

That's right. And I think we can dig into it now actually.'cause like the, the next main point is, is obviously not the chief of staff alone, right? The, the chief of staff needs a set of partners that can help guide that change management, that implementation, those decisions of. Which tools are we going to buy? You know, what, what's right for our organization? What problems are we trying to solve? And, and what do the outcomes of those problems or solutions actually look like? Um, that's not going to be, you know, this is not a lone wolf situation where one person is gonna magically change the whole company and, and build everything they need, um, to, to support the organization going forward and like bring them into the new century. Um. What, what we've seen is, is actually what, what we've dubbed the AI triad, and that is typically the CEO, right? That's the visionary of the group. That's the person saying, okay, this is, you know, this is kind of where this organization needs to go, um, with ai. Um, that's either going to be, here's how we're using AI to change our operations, or here's how we're using AI to actually build it directly into our product, right? Um, Zapier is a really good example of this. They've built AI, kind of AI tools across their entire product, right? Their suite has changed dramatically over the last 24 months. Um, it's not just build a workflow, it's now build an agent. Um, but they've also gone through the same internal shift, cultural shift, uh, in terms of getting their own employees to use ai. And that's not just Zapier, it's other AI tools as well, and, and, and building kind of that, that. Day-to-day behavior of, um, attempting to solve problems or do the work with AI as a copilot. Um, and so the, the CEO EO is kind of the starting point for that, right? Like that, that's the most top down version. The, the next one in line is the chief of staff, right? That that's the operational leader. That's the person that the CEO o is eventually gonna go to say, okay, how do we actually get this done? Right? Who do we need to talk to? Which relationships are going to be, um, you know, constrained or, or have strain? Um, you know, who, who's going to be our champions? Who's gonna give more pushback? Which teams should we be concerned by? Right? That's very much like ear to the ground. Um, go figure out kind of what we don't know already when we start to announce and talk about this more publicly within the company. A third person in line and, and they're all equals, it's a triad. Um, is, uh, is the CTO, of course, right? Or, or maybe head chief product officer. Um, but, but someone technical or more kinda sitting on the product engineering side. Um, look, a lot of AI tools today, like if you're just using, uh, GPT interface or Claude or Gemini, um, there's lots you can get away with on just chatting with an LLM. Um, and, and that's kind of like the first step for most people. Um, the reality though is like when you want to get into more complex workflows, when you want to actually have the agents, uh, executing things on your behalf, you know, maybe with a human in the loop, you're probably gonna get or need some more technical ability to help kind of implement those more complex workflows. Right. You're, you're now touching your, your data sets, right? You're giving that LLM access potentially to customer information, hopefully not financial information, but who knows? Um, and, and, and those were decisions need to be made, right? Like that, that's governance, right? How, how do we think about, um, what's acceptable use of these platforms? And so you really need that CEO, that chief of staff and that CTO. Uh, pairing together to say, okay, like, here's how we're gonna think about this change. Um, and, and here's how, uh, here's the pushback that we've heard. Here's the technical considerations that we need to, um, think about. And here's the vision that we're gonna pitch to the team in terms of how we communicate, not what we're doing. What, what is always fine. Why is always the more important question to answer. Uh, and, and especially why now, right? Because in, in a lot of cases what we've heard is. A, a strategy has been set, right? Especially last year. It's like, all right, the, the 2025 strategy was set and then like January rolled around and all of a sudden all the LLMs got significantly better, right? And that's all we read about day in and day out. And so, you know, every CEO is sitting there with shiny objects syndrome saying, we need to be doing that and we need to be doing this. And you know, this, our competitors are doing this. And so there, there's a lot of, um. Uh, Italian word ajara, like there, there, there's a lot of, uh, you know, pent up kind of emotions of like, we're not moving fast enough. Um, you know, we're going to be left behind. How, how do we make sure that doesn't happen? And what's very often missing is the strategy of here's what we actually is important to us right now. Right. Is it saving costs in this particular, uh. Part of the organization, is it building out this part of our product? Because we think there's a market opportunity there. What happens too often is scattershot, and so you, you need that triad to really be kind of the brains behind the strategy first.

emily-sander_1_07-23-2025_080256:

I love it. Yeah, there's, there's so much good stuff in what you said. I have, uh, a chief of staff now who you mentioned moving into the chief AI role, and she has basically done that where they've said, you know, so and so your job now is to. Um, be our, be our AI person. So go out to conferences, network with people, make sure we're on the cutting edge of things, report back what you're seeing and help us integrate this into the teams

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

makes sense for us. And then also, conversely, we want. You to be the face of our company for ai. We wanna be a thought partner in our industry. And so we're gonna put you out there. Um, and she's got a background in, in doing these types of things. So her role has morphed pretty significantly in the last 18, 24 months.

scott-amenta_1_07-23-2025_170256:

Yeah, that, that's really interesting. And I, and I think we're gonna see a lot more of that, where the, the chief of staff in some capacity has kind of assumed a lot of responsibility around this AI adoption. And, um, and again, it's not just tooling, right? A lot of it is like the, the people side of the business.

emily-sander_1_07-23-2025_080256:

Yeah, and I mean the we, I have a, another chief of staff who is in charge of global AI change management, and holy cow, that's a job and a half, right? So literally global teams, different cultures, different level of familiarity and openness to change in general, technology in general. And then, like you said, there is that layered effect of. Am I training on this so I can be replaced at one point or some of my colleagues can be replaced. That is, um, a piece of it, but this is a rolling cadence of communication and here's the latest updates and here's what we're gonna use it for. I think someone asked me, I was going back and forth on LinkedIn with someone last week, and he was like, Emily. Is AI going to replace the chief of staff? And I kind of gave the same answer you did in a less eloquent way. And I was like, there's decisions that live on top, quote of ai. There's decisions of, you know, the first decision has been made for us. You, you alluded to that AI is here, it's a thing. But the second layer of decisioning is where are we gonna deploy this in the company? How, and those two are just huge oceans of possibility. So, you know, do we use Ag agentic AI for our customer service teams? If yes, great. There's a whole flood of information of how you can do that still. Are we using that for accounting? Okay. Is that all accounting? Is that payroll? Is that invoicing? Like all these different decisions, um, that go into it. So just wanted to throw that out there and kind of, you've spoken with thousands of chiefs of staff. Whatcha kind of hearing on any of those?

scott-amenta_1_07-23-2025_170256:

Yeah. I mean, I think the, the, the other thing to recognize is a, not all the change is going to happen at once, right? And, and so chiefs of staff. Have kind of the unique perspective sitting higher up in the organization, but again, like listening kind of across the organization to try to identify those first bottlenecks, those first gaps of, okay, like this is where we could potentially be using the solutions that exist today, um, to fix x, y, and Z problems. I, I think that's number one. Like.

emily-sander_1_07-23-2025_080256:

Hmm.

scott-amenta_1_07-23-2025_170256:

Most employees won't be able to see or connect those dots well enough to say like, okay, this is where a, they, they might in their individual roles, but, but not, not holistically. So that, that's the first advantage of the chief of staff is, is having kind of that very wide purview of the organization, not, not on, unlike the CEO. Um, that the second thing to say is like, strategy's not going to be replaced overnight by ai, right? AI will help you distill data. Um, provide recommendations, see around corners or, or, or, or give you input that you might not have thought of yourself, but it's not going to, and I say not yet,'cause maybe we will get there. But today, like the, the, the systems that exist today, at least from what I've seen, will give you plenty of ideas, but won't really help you actually like, make that decision. You know what I mean? And, and I don't think you want it making that decision yet. Um, and so the, the good news though is, you know, you can use AI to help distill that data and, and come up with the ideas of, okay, here's my company strategy. Here's the last board decks, uh, here's, um, our OKRs for the year. You know, help me distill the, here's the market, right? Go do some deep research on our competitors and, and what exists in the market. Now you can prompt it to say, okay, given all that information, what are we missing here? What, what, what poke holes into our strategy that exists today. What, what are gaps that we need to fill? What are potential, you know, market opportunities that we could be approaching given the skill sets that, you know, our team has, et cetera, et cetera. And that's a perfect use for ai, right? That, that will give you a distilled kind of different strategy docs. And you can even have the agents like put on different hats, like, okay. You're gonna be the naysayer who hates our existing strategy, you know, wants to do something totally different, pivot the company, uh, you know, you wear that hat. Next one is, you know, something more in between, right? And, um, you know, each one of those agents can come back and give you a totally different strategy that then you, the human can decide on. And, you know, you can do that at like the most macro level of your organization down to the most kind of finite, um, you know, problems that that one team or one employee might have.

emily-sander_1_07-23-2025_080256:

Yeah, but it starts and ends with a decision. A human,

scott-amenta_1_07-23-2025_170256:

That's right.

emily-sander_1_07-23-2025_080256:

is the, which is the key part to, to highlight there. Yeah. I mean, I mean, I'm just curious, have you, the example I was thinking of with the global change management chief of staff, decided with the leadership team, had a whole round of conversations around, let's use this for customer service. Our folks right now, they took a poll survey. The chief of staff was in charge of that. Is fear this, like people are scared of this, they don't know what it is. Are you gonna replace my job? All these things. So there was a whole cycle of front running this thing, and there was a whole layer of the change management that was, we need to take our employees fear. enthusiasm and being excited for this and be, and feeling empowered for this. So there was that layer and then there was, okay, which specific teams around the globe are good

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

for early adopters? Where can we deploy this? And then have a, a story to tell, look, here's how we rolled this out for this team. It worked really well and now here's what they're able to do and look how much easier their lives are and look how much better the lives of the customers are. And that's just a simple, straightforward example, but um, this

scott-amenta_1_07-23-2025_170256:

No, and it, and it, it tracks exactly with what the report showed as well. So what, what we saw is 54% of the organizations that were queried are prioritizing AI implementations that very strictly are targeting like operational efficiency and productivity. And, and, and I think there's a, I think there's a relatively obvious reason for that, because if you can show an employee. That you just made them more productive by using the tool. You, you're not fearmongering in the sense of, oh, now that you're more productive, we don't need you anymore. It's no like you are using this tool, right? This is a, AI is not, we talk about AI as like this big thing, but AI is just a bunch of tools, right? We, we've been using tools for as long as the Internet's existed, so you know, it's not like you give a project management team Asana and all of a sudden they're like, well, Asana's gonna replace our job. You know, Asana is one of the tools that they use.

emily-sander_1_07-23-2025_080256:

and takes over the world.

scott-amenta_1_07-23-2025_170256:

Yeah. Look, I might bite my tongue in like a couple months. We'll see. Um, but uh, yeah, I mean, I think, and I, and I think that's kind of the, the, the best way to implement change at, at this current state is, you know, how do you help and support the employees that are going to be using these tools so that they're more efficient, they're more productive, you know, and, and they've got kind of clear measurable outcomes. Having used those tools that they can display, you know, in their performance reviews, et cetera. Um, you know, I, I've heard of, and, and I've seen some use cases where, um, some companies have taken like very drastic or even dramatic routes of change management. You know, up to the point of like, well, if you're gonna make a new hire, you've gotta justify, uh, why AI can't do that role for you. I forget what company that was. That one was in the news. Um, I, I've seen other examples where, you know, AI has become kind of like a fundamental part of their, um, you know, end of year performance reviews and, you know that that is one of the ways that that employees are, are going to be measured. I, I think that there's such a big learning curve happening right now as we speak, that that might be a little bit. It pushing the edge of kind of what most teams are ready for. I, but I think that is probably going to be the norm go, you know, over the next year or two years.

emily-sander_1_07-23-2025_080256:

It's interesting you say that because I was talking with the chief of staff and he, he was, um, not debating, but they were discussing internally where the AI function should live. Is that CEO? Is that chief of staff? Is that r and d? Is that hr? Where does that live? And they had it in their learning and development and as part of their. performance reviews, they would have, did you complete these types of trainings? And they, it was

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

types of trainings and they added AI as part of that. But one of the things the chief of staff worked on was getting the most updated information on ai, which is, you know, what, changing hourly. And so this was, you know, let's stay ahead of it, but let's. Build these training modules in for people to go through and, and learn and be comfortable. And that's just kind of what they expected of an employee, of a staff member to, to keep themselves, um, educated and informed. But they teed up these trainings for them. So that was kind of an interesting round of discussions they

scott-amenta_1_07-23-2025_170256:

Yeah, it's an an interesting way to kind of start the AI adoption cycle by, by putting it kinda squarely with the learning and development kind of department. Um, because at least it then it in, in some ways, it promotes this idea that no, we actually want to empower our teams to, to be learning these tools. Um, it's not just happening quietly in the background where, you know, some stealth engineering team is secretly going to replace you all that, that's not what you want to, to message. And so I, I think it's important that companies are, you know, actively trying to get their employees, um, to use and experiment and, and. You know, I think the best examples are where you see companies like on their Slack, they have Prompt Fridays and they're, you know, they're actively promoting this idea of if you do your work with ai, let us know about it. And, you know, share your prompt and, you know, let let other people give feedback on how that prompt could have been better or, you know, where, where you went wrong. If it's a multi shop prompt, right. Um. And, you know, I think that's, that's kind of the opportunity for the chief of staff as well, is to start building those cultural norms, um, that help the organization change over time, right? This is not an overnight shift as much as we want it to be.

emily-sander_1_07-23-2025_080256:

Yeah.

scott-amenta_1_07-23-2025_170256:

and, and people take, people take time to recognize the differences of what's available versus what is happening today and, and what that means for them. Um, and so again, going back to like the, the people component of this, this is where chiefs of staff are most valuable.

emily-sander_1_07-23-2025_080256:

Yeah, for sure. else is important to highlight off of the report?

scott-amenta_1_07-23-2025_170256:

Um, let's see. I mean, I think we, we did a second report that was more focused on, uh, kind of organizational change. So Chief of AI report, part one was more like what's happening with the chief of staff AI triad inside the companies. Part two was more about, um, how do companies, you know, think about buying tools and, and what's going into the decision making of, you know, there's a whole array, there's a new AI product every day at this point. Um, and they're all funded somehow. Um, uh, and so how do you make that decision, right? Like what, what, what is best and what are other companies doing? Um, you know, I, I think the most obvious thing kind of coming out of that is. A, the majority of people are still using chat GPT. Um, you know, you see larger enterprises have adopted kind of more specific solutions. I, I think Gemini and, and Google's whole suite of AI products personally is probably the sleeping giant here. Um, in the sense that they don't get a lot of like the publicity that, you know, open AI and, and even anthropic and, and certainly grok get. Um, but the Gemini suite is. Amazing. And there's plenty that you can do with it. It's actually like very well integrated into Google Docs and Google App script and that there's lots of kind of workflows and stuff that you can build on top of it, um, because it's so well integrated into that suite. And so I think between Microsoft and Google, those will probably be the eventual breakouts, um, in terms of enterprise AI adoption. Um, now there's tons of rag tools as well, and so. Yeah. This is an opportunity, I think, right now for chiefs of staff to just understand the landscape and the language. They will be part of that eventual decision making. We, we've certainly seen that in our community, like lots of chiefs of staff are the ones testing and making recommendations to even their engineering teams about kind of what tools are going to make the most sense across the company. Again, that's that very wide purview, like gives them the capability to say like, actually this is the right tool probably for us in relation to our customer service team or our finance team, or who, who, who have you. Um, and so that, that's a trend that's definitely picking up chiefs of staff being the decision makers for AI tools. They're, they're not often decision makers on a lot of technologies, but, but this one I think is one that's a, a breakout.

emily-sander_1_07-23-2025_080256:

And then just outta curiosity, we've mentioned the operational efficiency pieces, which is in some ways the obvious one. What other use cases have you seen may be more strategic or just maybe more creative? You kind of talked about the market research and some competitor intel. Is it just about sucking in so people have more information quicker to make a decision, or are you seeing other use cases for it? Just curious.

scott-amenta_1_07-23-2025_170256:

In in terms of a AI use cases.

emily-sander_1_07-23-2025_080256:

Yeah,

scott-amenta_1_07-23-2025_170256:

Yeah, I mean, so everything from, uh, competitive intelligence, right? Like, and so if we just take the chief of staff role by itself, what, what are some of the things that a chief of staff is doing day to day that AI can be very supportive on, uh, if not replaced entirely? Um, so, you know, in internal comms is an interesting one. Uh, if you're managing a senior leadership team meeting, right, with multiple stakeholders and comms that need to then ladder out across an organization regardless of the size, um, you know, some of the most obvious tools are, okay, how do we record that conversation? How do we distill those notes? How do we turn it into, um, you know, with, with kind of a, a framework, if you will? How do we turn it into a format that is. Um, consumable by different parts of the organization. And then how do we get it out to those relevant stakeholders in a timely manner. Uh, that's a process that a chief of staff would probably be doing on a regular basis by themselves. You know, maybe taking notes by hand or having recorded it, but, you know, obviously the transcription tools are great now. Um, but you can take that multiple steps further by actually like putting it into those relevant formats. Putting it in an email to each stakeholder that needs to see it, making sure that the communication is consistent, but the points are relevant to them, um, which could be dozens of emails and, and sending it out, you know, every Monday after that meeting, 30 minutes after that meeting happened. Um, and so that there are things like that where, um, those are, those pieces of communications are strategically important, um, but very time consuming in a lot of cases. Putting together board decks, putting together, uh, all hands presentations, right? Um, gathering all of the most recent kind of insights and feedback that's happening across a thousand Slack channels in your organization, which completely unwieldy, um, you know, can now be distilled by AI in seconds. And so, you know. Putting your ear to the ground as a chief of staff is, is no longer just about having all those one-on-ones. It's about having AI also be kind of your copilot in distilling, Hey, what's happening in this particular channel at this, you know, in this week that I need to be aware of? Right. What, what, what is the product and engineering team and fighting over for the last two weeks? Um, and make sure that gets back to me without me actually having to have that real life conversation. Still have that real life conversation though, but, but, you know, use AI as your, as your partner.

emily-sander_1_07-23-2025_080256:

Yeah. And I think, you know, when I think of chief of staff, it's chief of staff and it's taking care of people, and so. One-on-ones are great and in person, you know, there's, there's no replacement for a lot of the intangibles, but it's like, how are people doing? we're thinking about this strategic decision, does the company have an appetite for that right now? Is that gonna throttle the teams? Are people raring to go and super excited and can't wait for it? Or is it like, please don't load One more thing on us. We're, we're at capacity now, type of thing. So kind of the, the pulse checks and, and that part of the chief of staff role. Um. you mentioned earlier, you kind of alluded to this, but do we have talent on the team that can be used in this way we don't know about? So

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

thinking about this resource, whether it be a person, a team, or a process. And really there's the, there's the capacity and capability within that entity to be used in a different way, but we're just not thinking about it. But if we say, Hey, we we're trying to solve for X over here. Tell us the talent and tell us some options within the team. You know, things like that where you just have so much more information at your fingertips, but you know, making

scott-amenta_1_07-23-2025_170256:

I think.

emily-sander_1_07-23-2025_080256:

keep coming back to that, and then using the data to your advantage.

scott-amenta_1_07-23-2025_170256:

Yeah, I think that's a really, that's a really interesting use case, especially in larger organizations where, you know, every cog in the machine, if you will, kind of can, can get lost. And that organization may have opportunities that they should have presented to that employee, but that employee was, you know, not made known when the opportunity arose. And so, um, what was looked over and, and I think there's, there's tons of opportunities for AI to kind of like. Dissect the profiles of the internal team, and as you just said, like help make the decision about who, who might be relevant for a particular project or problem to go solve. The other thing I'll mention is like most companies still today fail to measure the AI impact that they have implemented adequately. Um, and that that was another kind of key learning from the report is that there's. Still a lot of room to grow in terms of moving from, um, testing and piloting AI building use cases to also having kind of measurable results. And so it's still a lot of throwing paint at a wall right now, I would say is generally what we've seen now, now look like this report is four months old, so a lot has changed in four months. We should probably run the survey again at the end of the year and see kind of what, what has changed. Um, but, but I would stand to reckon that like, yeah, most, most organizations probably still are struggling to actually measure the impact.

emily-sander_1_07-23-2025_080256:

Yeah. Do you have any suggestions or recommendation or just, you know, we have a few data points here that seem to be things are at least trying. I know that I've spoken with people who, um, have they, they always have. AI tools available. And so usage is one, and then one company has, I forget what they call that exactly, but it's basically. You know, you went through a training and then we told you to do this next time

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

your normal task. So like, okay, they did the thing. So they measured if they did that. But then above and beyond, I think they call it like voluntary something. If, if people proactively by themselves were like, Hey, I have this, I'm gonna use it not for the mandated thing, or not for the thing I just got trained on, but for this other thing. And they counted like those voluntary usages. and then. I'm kind of trying to think. We used to have this thing where if anyone across the company had an idea how

scott-amenta_1_07-23-2025_170256:

Hmm.

emily-sander_1_07-23-2025_080256:

an internal workflow or a marketing campaign or a, you know, a talk track for customers, whatever, across the board, and we use that, they would get one like called out at all company meeting and two rewarded financially for it. And so I'm

scott-amenta_1_07-23-2025_170256:

Cool.

emily-sander_1_07-23-2025_080256:

an opportunity somewhere for some people or some company to say, Hey. gonna give you the training and the latest information on ai, and if you have an idea for your group or for yourself or for your client or whatever, and you bring it to us and we end up deploying that across the company, we'll call you out and we'll reward you for that. So I'm just kind of wondering what you've been

scott-amenta_1_07-23-2025_170256:

Yeah, that, that's interesting. Some, some mo motivational factors to, uh, get, get employees sharing ideas and, and, and leveraging the, the technologies. Um. I, I haven't actually seen that firsthand. I, I think what we have seen is, um, is, you know, chiefs of staff, like actively promoting use of the tools, but also looking for ways to measure that usage. And that's really difficult to do today on. If you're just using like the, you know, open AI chat JT interface or Claude, um, it, it is actually, these are, these are very like, personalized instances. Even if you're on a team plan, um, it's hard to track and even share prompts, right? Like I could build a multi shop prompt and want to share that with my team member to get in, uh, input. I can copy and paste it, of course, but like, if, if that was a long dialogue, it's actually hard to share kind of that entire, that entire thread with someone else on my team. Um, so, you know, and I think this is where we've seen like some other tools. We, we, we've, uh, been working with a tool called elx. They've, um, been supporting us in the chief of AI fellowship and they're great because you can actually see in real time, uh, who's prompting what the prompts are, right? Like you, you can actually like, get that kind of internal analytics of what's working and not working across different teams. Uh, it also gives them, you know, employees access to multiple, uh, uh, LLMs kind of in one interface, which is also helpful because not every, not a, every LLM is not great at the same or equal. They, they have kind of specific use cases that some are better or worse for. Um, so I think more tools like that will probably see. Heavy adoption over the coming months because it, it's really helpful for companies that are just starting to get their feet wet and, and don't want to commit to a specific solution and need some visibility into what their team is doing within those solutions. Um, yeah, Lex and other tools like that are, are, are good opportunities.

emily-sander_1_07-23-2025_080256:

Gotcha. Good call out. Yeah, and I mean there, there's, this is a big topic and it's evolving as we go, and like you said, you could easily take another, uh, survey at the end of the year and maybe get similar data, but maybe drastically different data. Just in a short time span. So would, would love to have, keep this ongoing conversation going.'cause I think there is so much happening and so much good that can come from it. I know, I know it is scary for people, but if, if you embrace it, there are, there are pockets of huge advantages and lift you can give your team. Um, but you mentioned kind of the AI fellowship and I know you have other things going on at the Chief of staff network. So what, what is coming up for you and what are you, what are you personally excited about?

scott-amenta_1_07-23-2025_170256:

Yeah, so we've launched, uh, a handful of new programs just in the last, like 12 to 18 months. Um, and a lot of it is centered around this kind of core idea that chiefs of staff are. Um, both going to be focused on AI change management, working with agents, uh, and also very focused on the kinda human side of the role still. And so if you look kind of at the, the spectrum of things that we're offering to our members and, and non-members alike, um, it really kind of runs all along kind of that, that line of thinking. Um, so the first one is chief of AI Fellowship. Um, this one says it in the name. It's very targeted at chiefs of staff who are actively kind of going through that change, um, kind of considerations within their company and are both trying to upskill on how to use tools and think about prompting and, and think about, um, you know, use cases kind of across different LLMs, et cetera, but, but also are actively thinking about the strategy and governance and kind of. Of change orchestration that they need to make across their teams and just how to have those difficult conversations and what mental frameworks they can use, um, to kind of approach what are pretty hairy problems, but, but need to be solved immediately. Um, so Chief of AI Fellowship, we're now in our third cohort. Um, honestly, the demand has been through the roof, so we'll continue to run that throughout the year. Um.

emily-sander_1_07-23-2025_080256:

a group of, uh, other chiefs of staff going through the same thing? Is that trainings and modules

scott-amenta_1_07-23-2025_170256:

They are, they are cohort based programs. Um, they, it runs over six weeks. Um, there's a live session once per week. Uh, we host office hours as well. Uh, and then there's homework in between each session as well, uh, with guidance. Um, and then there's a kind of presentation at the end. Um, and yeah, it's, uh, it's both a community building kind of program because you're there. In support with other chiefs of staff, right. Kind of going through the same thing. And so a, a lot of the sessions are both, um, kind of demo workshopy, presentation led, but also lots of breakouts and dialogue between participants who are, are just trying to learn like, oh, you're at a thousand plus person organization. Like, what does this look like for you? Because I'm trying to do the same thing.

emily-sander_1_07-23-2025_080256:

Hmm. Yeah.

scott-amenta_1_07-23-2025_170256:

you know, these are conversations and, and I think the beauty of community is like, you don't see those chats on LinkedIn. Um, they're, they're not, they're gonna happen behind closed doors. They're gonna happen in a trusted environment, and you know, that we are the stewards of that environment, that that is the most important thing to us. So, um, yeah, chief of AI fellowship, that, that's been probably one of the most interesting dialogues, uh, certainly this year. Um, we have, uh, another program that we just launched called launchpad, which is for chiefs of staff, like very early in, in their career. Um, so these are either aspiring chiefs of staff. I, I've written recently about kind of the EA shift into chief of staff. Uh, I wrote today in our, in our newsletter about, um, you know, all the consulting firms kind of fundamentally changing and we're gonna have a C of X consultants. Well, they're all gonna be looking for chief of staff jobs soon if they're not already. Um, at least I'm convinced. And so launchpad is really designed for. Um, getting your feet wet in the role, getting prepared for the role, thinking about how to build that principle, you know, relationship. Um, thinking about, you know, what, uh, what kind of strategies or, um, kinda frameworks you should use to, uh, orchestrate decisions across an executive team. How do you level up in the chief of staff role? This is a conversation that, um. You know, I think has been very opaque for, for too long. We have a leveling framework. It's been widely used, but not every chief of staff is, you know, the same. Right. Some are junior, some are more senior. There are certainly levels within this role that, that, that need to be, uh, assessed. And so fundament, yeah.

emily-sander_1_07-23-2025_080256:

And, and, sorry. And that one, uh, is also, you have a co cohort, you have office hours. I believe RT is one of the folks involved with that.

scott-amenta_1_07-23-2025_170256:

Yeah, so RT is one, one of the leaders of that, uh, along with Juhi Cbra and Rachel Peck. Um, all former chiefs of staff, all now executive coaches like yourself. And, um, yeah, just I've learned a ton from the three of'em. Rachel and her newsletter has been a, have been a godsend to me. Um. And so yeah, we're, we're excited to have them partner. I'll be teaching one or two of the sessions as well. And then there are office hours kind of in, in between,

emily-sander_1_07-23-2025_080256:

Yeah.

scott-amenta_1_07-23-2025_170256:

also runs for six weeks. There's, I think 12 sessions. Pretty intense. Um, but Yeah. we're really excited for the launchpad

emily-sander_1_07-23-2025_080256:

Artie was um, an early friend of the show, one of our very first chief of

scott-amenta_1_07-23-2025_170256:

really.

emily-sander_1_07-23-2025_080256:

I always, I always wanted to give her a shout out'cause uh, she helped, she helped start it all in in a lot of ways. But, uh, excellent. So that's launchpad for aspiring and new Chiefs of staff. And then there's at

scott-amenta_1_07-23-2025_170256:

Okay. The, the, the last, the last two. I'll do'em quick. Um, so one, one is called power skills. This is, we talked about ai. So this is the polar opposite of that. It's the, it's the human side of the role. It's, you know, how do I, uh, get really good at negotiation? How do I get really good at communication with executives? How do I get. Better at, you know, influencing without authority when I am not actually managing these people directly. Um, these are, you know, they're soft skills, but the soft skills are the hard skills. And so, and, and these are the types of things that you don't always have an opportunity to practice directly or in a safe environment where you can kind of role play and, and workshop things out and, and bring situations and scenarios to a group. That can give their input and opinions on how you should approach a problem. That that's the goal of power skills. Um, that's multiple courses, multiple sessions. Uh, we'll be running throughout this year. We are launching, uh, actually one on offsites tomorrow, um, which is interesting. And, uh, yeah, that, that encompasses kind of like everything else about the chief of staff role and that that will continue to evolve. So there's, I think, six programs, but we'll continue to grow that as we learn more and. The role is evolving and that, that's the most interesting thing about it.

emily-sander_1_07-23-2025_080256:

Beautiful. And we'll have links to all that in the show notes for sure. And then you also have conferences. I want just briefly to touch on

scott-amenta_1_07-23-2025_170256:

Yeah. So that, that's the last one. And that, that kind of like culminates everything right. Is like, you know, it's, it's targeted to senior chiefs of staff, but, but all chiefs of staff are welcome. Um, the conference is called Chief of Staff Connect. We ran, uh, the first one in New York last year. It brought in around 160 chiefs of staff. Um, we did a smaller version in San Francisco this year, in May, and we've got two more coming up. One in October in New York and one in London in November. Um, so our first kind of big event, we, we host lots of small events in London and kind of across the eu, uh, but it's a little closer to home for me as well. So, short, short flight.

emily-sander_1_07-23-2025_080256:

Very cool. Yeah. Selfishly, you'd have a, have a Hallmark kind of event in London. Yeah. That's, that's gonna be amazing. So, and timing wise, what are these things generally, do you know? Or just

scott-amenta_1_07-23-2025_170256:

Uh, yeah. So the New York event is October 23rd and 24th, and London event is October 19th and 20th.

emily-sander_1_07-23-2025_080256:

Oh, wow. Okay. Pretty close together. All right, and, and then you also mentioned your newsletter, which I don't wanna kind of, uh, miss. I subscribe to that. I read your article on the consultants piece this morning

scott-amenta_1_07-23-2025_170256:

good.

emily-sander_1_07-23-2025_080256:

that the chief of staff advantages that they're from inception to execution and all those things. So I think that adds a lot of value and is free to subscribe to,

scott-amenta_1_07-23-2025_170256:

Chief of Staff Digest is free to subscribe to. Um, I, I would call out like we also have an amazing job board. It's updated multiple times a week. Um, we highlight kind of all the key chief of staff roles. We've also expanded that to. All operations roles. So if you're interested in finops or BizOps or Rev ops, um, you can go to four operators.com. Um, that's kind of our parent community. We also run BizOps Network and Legal Operators. So there are some sister communities, two Chief of Staff Network and uh, yeah, operators kind of has, uh, a bunch of other resources, but, but the job board especially and um, there's an ops jobs newsletter that goes out once a week that kind of highlights all of those roles as well.

emily-sander_1_07-23-2025_080256:

Beautiful. Yes. And I've sent people to those things as well. So lots and lots of information. So please listen to what Scott has said. Rewind, listen to it. Again, all the information with links will be in the show notes for you, so definitely check those out. But Scott, it was, it was great to have you on. Thank you for. the latest information, uh, with our audience. And I again, hope to have a continuing conversation with you and your fantastic team at the Chief of Staff Network as, as things develop and evolve with the role in AI and many other things. So thank you once again.

scott-amenta_1_07-23-2025_170256:

Yeah, Emily, thanks for having me on and thanks for being such a great supporter of the community. Um, and your podcast is amazing. So this is a real, uh, special treat.