Use the AI Tools Yourself, Then Show Your Colleagues
Episode Summary
The plainest instruction Kenn So gives, then director of corporate development and strategy at Smartsheet, is for an executive’s own desk: use the tools in your own work and show other employees how you do it, because he thinks a colleague watching you work is more persuasive than anything you could announce. He will not name a single tool, saying everyone uses several at once and no one of them supersedes the rest, and getting a feel for the different flavors is what shows you what they can do. He closes on a cadence rather than a principle: try a new one every quarter. Around that habit he wants a structure, an AI committee of champions with executives on it for buy-in. He is also watching a change in how AI companies get bought, where the acquirer hires the key people and licenses the models, and says hiring them away is effectively the acquisition.
Key takeaways
The instruction he gives for an executive’s own desk is the plainest thing on the episode: start using the tools in your own work and show other employees how you leverage them. He puts it underneath the committee and calls that layer micro educational campaigns
His reason for the micro educational campaigns is a claim about how people learn. He thinks nothing is more powerful than seeing your teammate or your colleague in the same team using it, because you see the value directly
His advice on learning is to stop asking which tool and start using several. Everyone has preferences, he says, and everyone uses multiple AI tools at the same time; no single tool kind of supersedes them all; and getting a feel of the different tools and flavors of it is a powerful thing to see for yourself, and a way to be a model for others
Asked what an executive early in the journey should do, his first answer is a structure rather than a tool. Create an AI committee, which he describes as a group of people, leaders and champions who see the value of AI and are committed to pushing forward the adoption of AI tools across the company
The composition of the committee carries a two-sided reason. He wants a diverse group representing different functions, so the organization can see the different use cases but also all the different risks of using these tools
He puts executives on the committee for a stated reason. Have a group of champions and ideally executives there as well to have buy-in, so the push for adoption across the company has backing
On where AI is actually in production at his own company, he calls his own answer no surprise. In February 2025 a lot of the value and a lot of the excitement was coming from the software engineers, on Copilot-like tools, which he called the biggest use case of generative AI at the time across all companies
On what the freed capacity is for, he answers from his own desk rather than with a policy. A lot of knowledge work is finding and synthesizing information; horizontal AI tools are good at exactly that; and instead of reading ten documents for one data point he can have it in thirty seconds
His newsletter subject at the time is a change in the shape of AI acquisitions. Instead of mergers and acquisitions, the structures are being called licensing and acquisitions, or L and A
The acquisition mechanism he describes has two halves that happen together. The acquirer hires the key people out of the startup and separately pays licensing fees for the models those people built, which he illustrates with Google hiring the Character AI founders
His conclusion about the structure is blunter than the deal terms make it sound. When you hire the people away you are effectively really acquiring the company, in essence
For an executive who wants the business-strategy view rather than the adoption view, he names Stratechery by Ben Thompson, because it focuses on the business impact, and then adds what he calls a shameless plug for his own newsletter
On board-level risk he says he does not know whether a single resource exists, and offers two things. Run a workshop with the AI committee, and look at the new trend of AI-focused law firms, which he says can be complemented with the usual outside counsel and then synthesized for the board
His closing ask is a cadence rather than a principle, and he sizes it deliberately small. Keep trying the tools yourself, not every one of them, but probably a new one every quarter, because a significant new product or user experience arrives about that often
About Kenn So
Kenn So was director of corporate development and strategy at Smartsheet, the work management software company, at the time of this conversation, and is now with OpenAI in corporate development. He also writes Generational, a newsletter on the business strategy and technology of AI that he started to clarify his own thinking and find the signal in the noise, and kept going because people kept reading. He has followed the field since before deep learning was popular. He comes at enterprise AI from the corporate development side, which is where his interest in how AI companies actually get bought comes from, and his argument on this episode is that AI spreads through a company by being used and shown rather than announced.
In this episode
| 00:41 | Welcome, and who Kenn So is |
| 02:12 | What Generational has been covering lately |
| 02:17 | A new acquisition structure for AI startups |
| 02:53 | Licensing and acquisitions: hire the people, license the models |
| 03:22 | Hire them away and you have effectively acquired the company |
| 03:34 | The people, not the technology |
| 04:31 | Which departments are using AI in production |
| 04:36 | Engineering first, and why that is no surprise |
| 05:23 | Where the freed-up capacity goes |
| 05:56 | Ten documents, or one data point in thirty seconds |
| 06:18 | Guidance for executives early in the journey |
| 06:26 | Create an AI committee |
| 06:55 | A diverse group, so you see the use cases and the risks |
| 07:18 | Champions on the committee, and executives for buy-in |
| 07:43 | Micro educational campaigns, and watching a colleague work |
| 08:06 | A suggestion from the host: rotating the executive sponsorship |
| 08:46 | What resources he recommends for executives |
| 09:52 | Learn by using the tools yourself |
| 10:20 | Why he will not name a single tool |
| 10:45 | Stratechery, and a plug for his own newsletter |
| 11:32 | Risk management, and what to bring to the board |
| 11:50 | A workshop with the AI committee |
| 12:05 | AI-focused law firms as a new kind of resource |
| 12:32 | What listeners should take away |
| 12:40 | Try a new tool every quarter |
In Kenn’s words
“I think it’s to create a- an AI committee”
Kenn So (06:26)
“using the tools yourself is probably the biggest thing you could do at the micro level”
Kenn So (09:52)
“getting a feel of the different tools and flavors of it is a powerful thing for yourself to see”
Kenn So (10:20)
“nothing is more powerful than seeing your teammate or your colleague in the same team using it”
Kenn So (07:43)
“So when you hire them away, you’re effectively really acquiring the company, in essence”
Kenn So (03:22)
“probably you just need to try a new one every quarter”
Kenn So (12:40)
Resources
Kenn So on LinkedIn: His LinkedIn profile
Smartsheet: The work management software company where he was director of corporate development and strategy at the time of this conversation
Generational: His newsletter on the business strategy and technology of AI, which he calls a shameless plug at 11:19
Unpacking Big Tech’s quasi-acquisitions of GenAI companies: His own piece on the licensing and acquisitions structure he describes at 02:17, setting out the pattern across several deals
Recommended on air
Stratechery: Ben Thompson’s publication, which he names at 10:45 as the resource for an executive who wants the business-impact view rather than the adoption view
AI Realized Summit: The event he recommends at 09:13, for curated content and a network of enterprise executives outside the tech hubs
Named on air
Character AI: The startup in his worked example at 02:53. Google hired the Character AI founders and key people and licensed the models they had built
Copilot-like tools: His description at 04:47 of what the software engineers at his company are using
AI-focused law firms: The new trend he points at for board-level risk at 12:05, which he suggests complementing with the usual outside counsel
Ideas and terms discussed
The AI committee: A cross-functional group of leaders and champions, with executives on it, responsible for pushing adoption and for seeing the use cases and the risks together
Micro educational campaigns: His name for the layer below the committee. Use the tools in your own work and show colleagues how, on the grounds that watching a teammate is more persuasive than being told
Licensing and acquisitions: The structure he says is replacing mergers and acquisitions for AI startups: hire the key people, license the models they built, and the company is effectively acquired
Rotating the executive sponsor: Raised by Christina Ellwood at 08:06 as something she has heard companies do: each executive takes a turn on the committee and learns by doing it. His build on it at 08:27 is that each one would share how they used the tool and how it changed their team’s workflow
A new tool every quarter: The cadence he closes on, sized so that an executive can keep it. Not every tool, but enough to know what a new generation of them can do
Frequently Asked Questions
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An executive early in the AI journey should start by creating an AI committee rather than by choosing a tool. Kenn So of Smartsheet describes it as a group of leaders and champions who see the value of AI and are committed to pushing its adoption across the company, drawn from different functions so the organization sees the range of use cases and the range of risks at the same time. He does not claim the idea as his own, saying it is probably something he has heard and discussed at the AI Realized conference.
Transcript 06:18 to 07:18
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AI champions need executives behind them so the push for adoption has buy-in rather than only enthusiasm. Kenn So of Smartsheet wants champions drawn from several different functions, because a single function sees only its own use cases and only its own risks, and he wants executives alongside them specifically for that backing. At his own company he describes having lots of champions who are super eager, and leadership supporting the work.
Transcript 06:55 to 07:43
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Employees take up AI tools most readily after seeing a colleague put one to work. That is why Kenn So of Smartsheet pairs the committee with what he calls micro educational campaigns. The campaign is deliberately small: start using the tools in your own work, then show other people how you are doing it. His reason is that the value becomes visible rather than described: a colleague seeing the work done differently takes it up in a way that being told about it does not.
Transcript 07:18 to 08:06
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Engineering is where a software company sees the value first, though other functions are using the tools too. Asked which departments at his own company were using AI in production, Kenn So of Smartsheet said in February 2025 that a lot of the value and a lot of the excitement was coming from the software engineers, on Copilot-like tools, and put the rest in what he calls different pockets, and he called the engineering case the biggest use case of generative AI at the time across all companies. He treats the answer as an obvious one rather than a finding.
Transcript 04:31 to 05:23
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Licensing and acquisitions, or L and A, is a structure where a large company hires the key people out of an AI startup and separately pays that startup licensing fees for the models they built, rather than buying the company outright. Kenn So of Smartsheet describes it as the recent trend in the market and gives one example, Google hiring away Character AI founders and key people while licensing the models. His conclusion is that hiring the people away is effectively the acquisition, because the most important resource for an AI company is the people, the researchers, the brilliant minds.
Transcript 02:12 to 03:22
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Executives can learn about board-level AI risk from a workshop with their own AI committee and from law firms that specialize in it. Kenn So of Smartsheet says he does not know whether a single resource exists, and offers those two. He offers the workshop without elaborating on it, beyond the committee already being the group that sees the different functions and their different risks. The law firms are a category he describes as a new trend, which he suggests complementing with the usual outside counsel and then synthesizing for the board.
Transcript 11:32 to 12:32
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[00:41] Christina Ellwood: Welcome to AI Realized Podcast, for enterprise executives leading AI deployments. From addressing security, data, and operations challenges to managing the organizational and management changes, AI deployment presents the opportunity to redesign our organizations from the inside out. I’m Christina Ellwood, your host for today’s episode. We’re talking today with Kenn, the Director of Corporate Development and Strategy at Smartsheet. Kenn, welcome to AI Realized.
[01:10] Kenn So: Yeah. Excited to be here. Thanks for having me, Christina.
[01:14] Christina Ellwood: In addition to your work at Smartsheet, you’re the publisher of a newsletter about the business strategy and technology of AI. What inspired you to start this publication?
[01:25] Kenn So: I think it’s more of a personal curiosity. Like, I have been in the AI space for a while, even before deep learning was popular, and I’ve always just been following it. And given the two years ago, there was so much noise around AI, generative AI, ChatGPT, and so on, it started just as an outlet for me to clarify my thoughts and really look for the signal among the noise, and then writing was a great way to, to do that. And then when I started writing, people just-- some people resonated with it, and I just kept at it. There continues to be a lot to learn in this space, so I just kept, keep on writing and people just keep on reading.
[02:12] Christina Ellwood: Great. What are some of the recent topics in your Generational newsletter?
[02:17] Kenn So: Yeah. I think one is how a lot of the big tech companies are trying to use a unique acquisition structure to acquire other startups. I wouldn’t say they’re small startups because they were acquired for billions or hundreds of millions, which is really big, but how they’re doing that in a unique structure. And maybe as for those listeners who don’t know some of the recent transactions is like the, they’re now calling it instead of M&A, which stands for mergers and acquisitions, they’re calling the new structures licensing and acquisitions, so L&A. So they hire the key people from these startups. So for example, Google hired away Character AI k- uh, founders as well as key people, while also licensing, paying license fees to Character.ai for the models they built. So in a way, if you think about it, right now, the most important Oh, when-- resource is not such a great word, but the most important resource for AI companies are the people, are the researchers, are the brilliant minds. So when you hire them away, you’re effectively really acquiring the company, in essence. And that’s the recent trend we’ve been seeing in the market, but also a recent piece I’ve written about in Generational.
[03:34] Christina Ellwood: Even if you’re not looking to, uh, get access to the technology per se, the people themselves that have knowledge and experience in AI are, are mighty precious in today’s market. Um, how are you at Smartsheet in your role as a corporate, uh, uh, development and strategy person looking at, uh, talent acquisition? Are you looking at, um, both recruitment and acquisition, or what’s your strategy there?
[03:58] Kenn So: Yeah. I think we are taking a broad approach in Smartsheet wherein I think in my role, we’re always looking for the right set of opportunities, regardless of whether that’s hiring the best talent or acquiring the best technology that’ll accelerate our roadmap or figure out what will, maybe on the bigger scale, accelerate our growth as a company from a financial perspective. So we’re really looking at everything, and I think in the AI space especially, where it’s moving so fast, we have to be looking at everything so that we know what’s happening and we’re not missing out on anything.
[04:31] Christina Ellwood: So Kenn, at Smartsheet, what departments are currently using AI in production?
[04:36] Kenn So: So we ha- are using a bunch of tools, but I think where we’re seeing a lot of value and a lot of excitement, no surprise, is from our software engineers. They’re really using Copilot-like tools to help them be more productive. But I think that’s no surprise. I think that’s the biggest use case of generative AI today across all companies, and hence why you see still a lot of startups are getting funded at high valuations and at large rounds is because of the potential of this being able to accelerate a software company’s software engineers to build new products is really high value. So we have a lot of our engineers use these tools, but we also see different pockets, different functional areas use these tools. But I think number one is the engineering department.
[05:23] Christina Ellwood: So you implied there’s more efficiency, and it sounds like you’re using that to be-- to build more features for your customers to, to invest in product. Are there other areas where you’re investing that freed up, um, set of capital resources, like perhaps training your employees or some other areas of the business?
[05:42] Kenn So: Yeah. I think the general productivity as well of, hey, for when it comes to maybe I can use my personal example of like how I use tools to look for information and summarize it. A lot of the jobs inside software companies or knowledge workers in general is finding and synthesizing information, and these AI tools, horizontal AI tools are really great at that. So I’ve been using a lot of it to do that. So instead of having to read through 10 documents to find the one data point that I need, if I can get it in 30 seconds
[06:18] Christina Ellwood: What is your guidance for enterprise executives who are early in their professional journey at leveraging these tools?
[06:26] Kenn So: Yeah. I think it’s to create a- an AI committee. That’s probably something we’ve heard and discussed actually at the conference, AI Realized conference, is the importance of having an AI committee. And what an AI committee is, really a group of people, leaders, and champions who see the value of AI and are committed to making sure or at least pushing forward for the adoption of AI tools across the company. And ideally, what you wanna have there is a diverse group of people representing different functions, so you’re able to see the different use cases, but also all the different risks as well of using these tools. Luckily, for example, at my company Smartsheet, we have lots of champions who are super eager about adopting these tools, and very fortunate that we have leadership supporting that as well. But I think that’s the biggest thing, really have a group of champions and ideally have executives there as well to have buy-in to push AI adoption across. And I think there’s also-- that’s the kind of like maybe the high level, the big picture advice, but maybe also starting at the individual micro level is starting to use these tools in your work and being, showing it to other employees of how you leverage this. So like micro educational campaigns, because I think nothing is more powerful than seeing your teammate or your colleague in the same team using it, and so you just see the, the value directly as well. So I think that’s another advice.
[07:58] Christina Ellwood: It’s, it’s also a modeling, isn’t it?
[08:01] Kenn So: Exactly. Exactly.
[08:03] Christina Ellwood: Yeah. So I think that’s always a powerful, um, tool. Um, I, I’ve also heard of some companies rotating the executive sponsorship on that committee because it’s such a great way for the executives to learn, to have the, the insights brought to them instead of them having to go out to get them, that there’s a little competition about who gets to be on that committee.
[08:27] Kenn So: That’s so interesting. Yeah, that’s such a great idea, right? Imagine like each executive has to share how they’ve used the tool, how it’s changed their workflow for their team. It’s... That’s such a great idea.
[08:40] Christina Ellwood: Yeah. This is how we all get, get good at this new set of technologies, is we share our ideas, right? Our primary listeners are executives like yourself. What resources do you recommend for executives who are listening, who want to learn more about leading in their organization, learning how to use the tools, and providing benefit back to the organization, and guidance for how to take advantage of the new advantage that, uh, AI is bringing them, whether that’s the, the freeing up of resources or that is, um, perhaps a strategic advantage they’re gaining in the marketplace?
[09:13] Kenn So: Yeah. There’s a couple of things, resources, and the first one I can think of, and I’m not saying it because I’m on this podcast, is really listening to this podcast as well as attending the AI Realized Summit because- It’s really noisy in the AI space, and you really need curated content and network of-- with fellow enterprise executives to learn from them, especially a network of people who are not in the tech hubs like San Francisco, so that you get to see other people who are in the same stage as you are in terms of adoption and learn from them what are the challenges. I think AI Realized Summit and podcasts are really great. I think number two, I think the best resource is to learn for yourself as well. So using the tools yourself is probably the biggest thing you could do at the micro level, because once you start using it and adopting it, really, maybe you even have to force yourself to adopt it and try new things, but that’s where you get to see the power and the risk as well of those tools. And the reason why I don’t suggest a specific tool is because everyone has their preferences, uh, or everyone uses multiple AI tools at the same time, like I do. And there’s really no- not just one tool that kind of supersedes them all, but really getting a feel of the different tools and flavors of it is a powerful thing for yourself to see and maybe to our point earlier, Christina, to be a model for others. And maybe the third thing is depends on what your goal is. So if your goal as an executive is to increase adoption of AI tools internally for employees to be productive, there’s a different set of resources. But if your goal is to learn about the latest in, in technology and thinking about what that means for business strategy, especially if you’re in the software and tech world, is really condensed and concise resources like Stratechery by Ben Thompson is really great one, wherein it really focuses on the im- business impact. And gonna do a shameless plug, considering reading my personal, uh, newsletter blog as well, where I synthesize really the most impact-- what I think is the most impactful trend in AI every now and then.
[11:32] Christina Ellwood: Yeah, I really enjoy your Generational Newsletter very much myself. Another role that the executives play, of course, is in risk management for their organizations. Do you have suggestions on where they can learn about the different deployment models or the different risks that they need to account for, and how they might advise the board?
[11:50] Kenn So: Yeah. I don’t know if there’s, is a single resource. Um, what I found to be helpful is two things. Um, one is learning from having a workshop with the AI committee, which we’ve talked about. Number two is looking for what’s this... There’s this new trend in the legal field of AI fo- focused law firms, where they really focus on the risk of a- that AI imposes, and I think they are a great resource in terms of thinking ahead of what are the pitfalls and the likes. And the, you could complement them with the usual outside counsel, and that’s a great resource as well, that you could then synthesize and present to the board.
[12:32] Christina Ellwood: Great suggestion. So as we wrap up, what would you like listeners to take away from our conversation today?
[12:40] Kenn So: I think number one thing is to keep on trying the tools yourself. There’s always a new tool. I’m not saying you have to try each and every one of them, and probably you just need to try a new one every quarter. 'Cause every quarter a new kind of s- significant new product or user experience comes out in the space. And if you haven’t tried those yet, I think you’d be remiss to not know what’s the latest, because each generation of these tools are so powerful, impactful, whether it’s for yourself as an individual or improving the productivity of your employee and organization.
[13:16] Christina Ellwood: Oh, that’s, that’s a great suggestion. Kenn, Director of Corporate Development and Strategy at Smartsheet and author of the Generational Newsletter, thank you for talking with me today on AI Realized.
[13:27] Kenn So: Thanks for having me, Christina. Enjoyed the chat.