This told essay is based on a conversation with Christy Eddleson, 34, principal assistant at San Francisco-based Utli. The following has been edited for length and clarity.
I work as a chief of staff at a startup, and my company’s goal has always been to build an AI chief of staff. The funny thing is, when I got the role, I had already signed up for the role. But I wasn’t nervous about it. I actually loved the irony of that.
The role of chief of staff involves a lot of context switching, and I think the AI products my company has built are more focused on enhancing my skills rather than letting me take over things completely. Although this product was recently launched, I don’t think it will replace my entire role as an agent.
I think the hardest part of working with AI agents all day long is finding the balance between what’s in your head and what you outsource.
I’m the only non-technical person at the AI company I work for.
I’ve been working in recruitment for the past 10 years, but I wanted to focus on something more practical. This role happened by chance in the spring of 2025.
I’ve known the founders since I was a recruiter at Meta, and they had all kinds of positions they wanted to fill at the startup. I don’t think they even had a name for the chief of staff decided yet. As the conversation progressed, that’s the title we came up with.
I never thought chief of staff would be my permanent role, but it felt like one of the most impactful operational roles I’ve had. Who better to provide feedback on a product than someone who performs such tasks every day?
I’m the only non-technical person on staff, so every day is different. My job is basically something that founders don’t have time for. That includes day-to-day operations, finance, human resources, compliance, conversations with various vendors, contract negotiations, contract reading, and more.
Delegate manual tasks to AI Chief of Staff agents
I have my AI Chief of Staff connected to all my work tools, including email, Slack, Linear, and Granola. So the AI takes in all the context and picks up things that I forgot.
My chief of staff also pulls information from my calendar to let me know what else is coming up. From there, decide which tasks you want to take over.
Before AI agents, you knew you had to look at your task list and do everything based on it. Now I ask myself. What items can I give the AI to find more meaningful problems to solve? That means I have to go looking for those problems too.
One of the things I like to do in the morning is switch to audio mode and do a brain dump, unloading everything I’m thinking about in a chaotic order. I’m not someone that’s really interested in setting up prompts. That’s why I love where my agent is at the moment. You don’t have to be perfect with the prompt, you can ask whatever you have in mind in a very imperfect way and that’s okay.
I always like to challenge myself if something feels a little manual. How can I ask an agent to do it for me? It could be anything from drafting an email or Slack message to having ChatGPT help design office decor.
I like to know what my agents are doing, so I draft items like emails, but I approve most of them before I send them. Although there were no major mistakes made by agents, we put this step in place to prevent mistakes that agents may make.
AI helps negotiate vendor contracts and eliminates asking stupid questions
One of the core parts of my job is negotiating with vendors about the different types of technical infrastructure tools needed to run models, such as compute and inference. I’m not a technical person, so I rely on AI to avoid asking stupid questions in meetings or delaying schedules.
About 30 minutes before the call, I ask the agent, “What’s the latest? What’s your team’s opinion on this tool?” It includes my context for how I use certain tools, as well as the conversations other teams are having about those tools in public channels.
I go back and forth on it and sometimes I ask questions that I’m embarrassed to ask my team. That way, you can be a part of the conversation with your vendors, have power, and get what you need.
Continue reading the Tiny Teams series
I don’t think AI can replace financial tasks or strategy mapping.
I am not currently using the Chief of Staff AI agent for financial operations. Probably because I’m risk-averse and perhaps too cautious. I think where I and many people probably draw the line is finances. Malicious emails are annoying, but it’s easy to apologize. The $500 payment cannot be reversed.
From a personal perspective of keeping myself sharp, I still like to write and handle many tasks myself and have my agent gut-check them, especially the strategic ones.
I like to make mental maps of everything I’m working on, but sometimes the AI works faster than my brain can keep up with. I’m working on ways to keep all that information somewhere in my head, even if my overall attention span has decreased.
There’s a lot of talk about complete automation and the end of certain roles, but I’ve been surprised at how empowered I feel as a worker because I basically have access to the most patient tutor in the world.
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