--- title: "You've been handed the AI rollout. Where to start with your team" description: "Why the job suits a COO or chief of staff, where to begin, who should go first, and what to show your CEO after a month." url: "https://onetwogrowth.com/writing/handed-the-ai-rollout" canonical: "https://onetwogrowth.com/writing/handed-the-ai-rollout" --- # You've been handed the AI rollout. Where to start with your team Why the job suits a COO or chief of staff, where to begin, who should go first, and what to show your CEO after a month. Nov 7, 2026 Harry Siggins [Subscribe](https://harrysiggins.substack.com/subscribe) Your CEO wants the company using AI, and the job of making that happen has landed with you. There's pressure to move quickly, and usually no plan to follow. So the question people in your seat ask me is a simple one. Where do I start? My answer is to start with your leadership team, and then with a small group of people who want to do this. But before either, it helps to be clear about your own part in it. ## Your part in it I've been in that seat. For the last two of my five years as chief of staff at Quantive, my job was making the company work differently with AI. It started with a Slack message from my CEO saying I was going to AI-ify the company. I'm a generalist by trade, and there was no playbook to follow. And it's a seat I think suits the COO or the chief of staff best, for two reasons. 1. **The mandate.** Their job is to make every function run as well as it can, so working across teams is already theirs. 2. **How they work.** They tend to be cross-functional themselves, and they rely on problem-solving and critical thinking. Better yet, the chief of staff is usually closer to strategic projects day to day as well. If you're in another role, you'll need the same two things, a mandate that reaches every team and a way of working that crosses them. Owning the rollout doesn't mean doing all the building, though. Your part is to set the direction and keep it moving, and to leave the building to someone on each team who does the work every day, because they're the ones closest to it. Setting that direction starts with the people at the top. ## Start with your leadership team How much time to spend with the executive team depends on the company. But the strongest place to start is probably helping your leadership team understand the opportunity AI puts in front of them. Once they see it, they can tell their own teams what those teams could do with it. That conversation is also the time to settle what the rollout is for, because people mean different things by it. - For some, it means everyone in the company using AI. - For others, it means changing how certain parts of the business work, so that specific business results improve. Getting everyone using AI is the traditional learning-and-development route, and it takes longer to show up in those results. So if you're under pressure to show business results, decide which parts of the business you want to change. Then tell people, because most teams haven't been told. In [Gallup's tracking](https://www.gallup.com/699797/indicator-artificial-intelligence.aspx), 25% of US employees said in May 2026 that their organization had communicated a clear plan for bringing AI into the way it works. And once your leaders understand the opportunity, have them join their teams when the hands-on work starts, so they see it come to life. That leaves the question of which teams, and which people, go first. ## Pick a first group that wants it There are two ways to choose. One is to pick the team that would make the biggest difference to the business if it worked at its best. That works when there's a clear piece of work AI could change, but sometimes there isn't one yet. The more important test is the people. Look for people who: - are willing to lean in and can already see the potential - have a piece of work they know could be better, even if they don't yet know how - enjoy this kind of problem - don't wait to be told Their function matters less than those traits, so your first group might be one team, or a few people from several teams. Then give them real time to work with AI on their own work. A rollout spread across everyone at once tends to fall flat, because nobody gets the time to experiment. And a month later, you'll need something to show for that time. ## What to show after a month A month in, your CEO will ask how it's going. By then you should be able to point to three things. - People planning changes to how the business works. - Examples of what the first group has built. - Most of all, time and effort saved on specific processes. Time saved leads the list because of the order in which the gains tend to arrive. 1. First, the work takes less time and effort. 2. Next, because it's now cheaper to do, people do more of it. 3. Last, they change how the work is done from the ground up, though some teams get there sooner. I've written more about that order in [which work to hand to AI first](https://onetwogrowth.com/writing/which-work-to-hand-to-ai-first). Your CEO may also ask about usage. Expect overall use, and what you spend on AI, to go up. At the same time, you may see people rely less on the most powerful and most expensive AI models than they did at the start. That's a good sign, because it means they're using AI more efficiently and are aware of the choices they have at their disposal. But don't expect game-changing results overnight. What you'll see instead is more creative thinking, and teams working with each other in new ways. On one HR team I worked with, one person learned to build with AI on their own work, and now other teams borrow them to help with theirs. Getting there starts with a few conversations this week. ## Where to start this week 1. Set up time with your leadership team to talk through what AI could change for the business, and agree on what the rollout is for. 2. List the people who are already curious and have a piece of work they think could be better. 3. Ask them to be your first group, and protect time for them to work on it. * * * Related: [Which work should your team hand to AI first?](https://onetwogrowth.com/writing/which-work-to-hand-to-ai-first) · [How to get your whole team using AI, not just the few who already do](https://onetwogrowth.com/writing/get-your-whole-team-using-ai) · [Can your team trust what AI gives them? How to check it](https://onetwogrowth.com/writing/can-your-team-trust-ai-output) · [Should your team do an AI workshop or an online course?](https://onetwogrowth.com/writing/ai-workshop-or-online-course) Back to [All writing](https://onetwogrowth.com/writing) Next [Can your team trust what AI gives them? How to check it](https://onetwogrowth.com/writing/can-your-team-trust-ai-output) ## Start with a call. Thirty minutes about your team and its work. If a workshop would help, Harry would be glad to put one together. [Book a call](https://cal.com/harry-onetwogrowth/discovery-conversation) · [Email Harry](mailto:harry@onetwogrowth.com) OneTwo Growth Studio is Harry Siggins’ AI enablement practice in Seattle, WA, running hands-on AI workshops for teams. [harry@onetwogrowth.com](mailto:harry@onetwogrowth.com) · [LinkedIn](https://www.linkedin.com/in/harrysiggins/) · [Harry on AI](https://harrysiggins.substack.com) · [Privacy](https://onetwogrowth.com/privacy)