Executives Build AI Chiefs of Staff to Drive Organizational AI Adoption
TL;DR
- Building a personal AI chief of staff enables executives to gain "brutal truth" feedback on time allocation and meeting effectiveness, fostering self-awareness and strategic prioritization.
- Executives using custom AI agents can automate meeting preparation and email triage, freeing up cognitive load and enabling more focused strategic work.
- Personal AI development, even for simple tasks like memory capture, serves as a critical gateway for executives to understand AI capabilities and drive organizational adoption.
- Organizing company-wide "builder days" with clear goals, tools, and recognition significantly boosts AI tool adoption across diverse functions by reducing friction and fostering hands-on learning.
- Leading AI adoption requires executives to be hands-on builders themselves, demonstrating authenticity and credibility to encourage widespread organizational change and experimentation.
- Leveraging markdown files as a source of truth for personal AI agents simplifies content management and enables flexible, agentic access to context for improved decision-making.
- Customizable AI interfaces, like a note-card design, enhance user experience and personal satisfaction, making AI tools more engaging and integrated into daily workflows.
Deep Dive
Rachel Wolan, Webflow's Chief Product Officer, demonstrates how executives can leverage AI by building personalized tools, showcasing a proactive approach to AI adoption that bridges individual workflows with organizational change. Her custom AI chief-of-staff application integrates with her calendar and email to manage workload, provide meeting preparation, and offer critical self-feedback, illustrating the tangible benefits of hands-on AI development for leadership. This personal application of AI serves as a foundation for driving broader AI adoption within her organization through structured "builder days."
Wolan's AI chief-of-staff application allows for hyper-customized executive assistance by directly integrating with her Google Calendar and Gmail via API tokens. This enables the AI to analyze her schedule, identify opportunities for delegation or making meetings asynchronous, and even flag calendar clutter. A key function is its ability to provide "brutal truth" feedback, such as calling out when her activities resemble a senior PM role more than a CPO, forcing introspection on time allocation and priorities. The system also drafts responses for emails, archiving irrelevant messages and highlighting important ones, though managing the sheer volume of communication remains a challenge, suggesting that current models may struggle with extremely disparate and context-light information. Beyond daily tasks, the AI assists with event preparation by analyzing guest lists and generating discussion topics, utilizing markdown files as a content source for personal context and product information, which simplifies data management and can bypass some security concerns by running locally.
The second-order implication of Wolan's personal AI development is its role in fostering organizational AI adoption. She champions this through "builder days," dedicated events where her entire team stops regular work to build prototypes using AI tools like Cursor, Figma, and Make. This initiative aims to boost confidence, drive adoption, and move teams beyond early adopters to the early majority of the adoption curve. The structured approach, including warm-up assignments, dedicated support channels, and a judging panel with prizes, encourages experimentation and demystifies AI capabilities. Feedback indicates these events are perceived as fun, empowering, and eye-opening, leading to sustained use of AI tools and a deeper understanding of what is possible, effectively transforming organizational workflows and individual skillsets.
The ultimate consequence of this dual approach--personal AI development and organizational builder days--is the creation of an "AI-native executive" and workforce. By demonstrating the practical applications and benefits of AI hands-on, Wolan builds credibility and encourages her team to embrace these tools. This not only enhances individual productivity and decision-making but also cultivates a culture of continuous learning and innovation, positioning the organization to navigate the evolving landscape of AI-driven work more effectively.
Action Items
- Build personal AI chief of staff: Integrate calendar and email APIs to automate meeting prep and triage (ref: Google Calendar API, Gmail API).
- Implement builder days: Organize cross-functional events with defined tracks and support channels to drive AI tool adoption (3-5 days per quarter).
- Create AI agent guardrails: Define specific API permissions (e.g., read-only calendar, draft-only email) to prevent unintended actions.
- Develop markdown-based content strategy: Store personal context and product release notes in markdown files for agent consumption.
- Measure AI adoption impact: Track prototype creation and tool usage (e.g., Cursor, Make) post-builder days using a dashboard.
Key Quotes
"I started coding when I was 16, and you know, it's obviously been kind of a lifelong journey of building and tinkering and, you know, making mistakes. And so I feel like I, I kind of built that resiliency pretty early in life. And now, uh, in my, my current role, you know, I probably hadn't coded in about, you know, six or seven years. And then when all of the new app gen tools came out, I think Vibe Coding is like one year old now. Um, I was like, hey, I'm gonna try this out. And, you know, it was, it felt magical, right?"
Rachel Wolan explains that her early experience with coding and building, even with mistakes, fostered resilience. She describes how the advent of new generative AI tools reignited her passion for coding, leading her to build personal applications, which felt "magical" and distinct from previous experiences.
"I completely agree. And one of the things I want to call out about how you're talking about building this software is one, you're building it for an N of one, you're building it for yourself, so it can be really hyper-customized. Two, you're building sort of a multimodal interface to this, in which it can be a web app, or it can be something just like a little bit more close to the metal in terms of in the terminal or in Cursor. And then I love this idea of being able to build ephemeral widgets that are useful that you can just toss away."
Claire Vo highlights that building software for oneself (N of one) allows for hyper-customization and a multimodal interface. Vo appreciates the concept of creating temporary, useful tools ("ephemeral widgets") that can be discarded once their purpose is served, emphasizing the flexibility of personal AI development.
"So let's talk about your morning triage and how you start your day every day using this AI Chief of Staff."
"That sounds good. So in this case, what I actually gave it was a question. I said, hey, how can I make my week, my last week better? What, what could I have done? Because I, I think that I don't have a Chief of Staff anymore. I used to have a Chief of Staff at another company. And so I knew that this was something that they would be like, kind of combing through my calendar and like, hey, you're not blocking your energy, right? Um, and you're not like, kind of taking care of yourself. And so, you know, the other, the main thing that they kind of called, called me out on, which I thought was really funny, um, so we just had our customer conference about a month and a half ago, and, you know, I haven't taken quite as many customer calls. And it's basically calling me out and saying, you know what, you're not spending enough time with customers, and that's where you get energy from."
Rachel Wolan describes using her AI Chief of Staff to analyze her past week and identify areas for improvement, specifically regarding self-care and customer engagement. Wolan notes that the AI pointed out a lack of customer calls, a critical observation that her human Chief of Staff previously made, highlighting the AI's ability to provide insightful feedback on time management and strategic focus.
"And so are you coming to this every morning and this is sort of a meta analysis of your calendar? Which again, I've had a Chief of Staff, we did every Friday where we were like, what, what are you doing, girl? Like, let's, let's fix this. But tell me how you would use this on a daily basis."
"So tell me about my day tomorrow. What can I delegate? And so this will run for a couple of minutes. And when it comes back, it'll tell me, this is what's coming up tomorrow. Uh, this is what I think you can actually, you can do something else. This is, you know, I think the, the thing, the way that I would like to make this smarter is this is who you should delegate to. And then, you know, I'm still kind of working on my, my Slack agent, so I can't show you. But what I want to do is basically like send notes to my admin and be like, hey, could we go do this?"
Claire Vo asks Rachel Wolan about the daily use of her AI Chief of Staff for calendar analysis and delegation. Wolan explains that the AI can identify tasks for the following day that can be delegated or handled differently, and she intends to further develop a Slack agent to automate sending delegation notes to her admin.
"And so are you coming to this every morning and this is sort of a meta analysis of your calendar? Which again, I've had a Chief of Staff, we did every Friday where we were like, what, what are you doing, girl? Like, let's, let's fix this. But tell me how you would use this on a daily basis."
"So tell me about my day tomorrow. What can I delegate? And so this will run for a couple of minutes. And when it comes back, it'll tell me, this is what's coming up tomorrow. Uh, this is what I think you can actually, you can do something else. This is, you know, I think the, the thing, the way that I would like to make this smarter is this is who you should delegate to. And then, you know, I'm still kind of working on my, my Slack agent, so I can't show you. But what I want to do is basically like send notes to my admin and be like, hey, could we go do this?"
Claire Vo inquires about the daily application of Rachel Wolan's AI Chief of Staff for calendar management. Wolan explains that the AI can identify tasks for the next day that are suitable for delegation or alternative handling. Wolan also expresses her goal to enhance a Slack agent to streamline sending delegation requests to her administrative assistant.
"I tell it to be mean to me. That's why I wanted to like keep me in line. You know, I'm, I'm one of those people who likes to try to take on too much. I think sometimes."
"Um, okay, so it's basically telling me to make certain meetings async. That's a great idea. It's telling me to delegate a couple of these. This is also probably a great idea. I don't think I can delegate this one, but good call. Um, it's telling me there's too much clutter on my calendar. This is one of those things where somebody's just like, put something on my calendar. I don't know this person. Um, so that's definitely optional and I haven't accepted. And then it's like,
Resources
External Resources
Books
- "The Innovator's Dilemma" by Clayton Christensen - Mentioned in relation to the normal distribution curve of adoption for new technologies.
Articles & Papers
- "How to Generate a Markdown Powered Personal App" (How I AI mini-episode) - Referenced as a resource for storing and displaying personal app content using markdown files.
People
- Clayton Christensen - Author of "The Innovator's Dilemma."
- Hillary (from Whoop) - Mentioned for sharing a tip about using numbers in prompts.
- Mark and Dason - Source of the idea for a daily priority note card.
Organizations & Institutions
- Anthropic - Mentioned as a potential builder of a generalized chief of staff product.
- Atlassian - Offers "Atlassian for Startups" program providing free seats on premium editions of their products.
- Cloudflare - Mentioned as a startup that relied on Atlassian for growth.
- Cova - Mentioned as a startup that relied on Atlassian for growth.
- Google Cloud - Provided the API token used to access calendar and email.
- Hex - Dashboard used to track team usage of Cursor.
- Miro - Mentioned as a startup that relied on Atlassian for growth.
- National Football League (NFL) - Not explicitly mentioned, but implied context for sports analytics.
- New England Patriots - Not explicitly mentioned, but implied context for sports analytics.
- Pro Football Focus (PFF) - Not explicitly mentioned, but implied context for sports analytics.
- Webflow - Company where Rachel Wolan is CPO; also has a new appgen product.
Websites & Online Resources
- Atlassian.com/startups/howai - URL for more details and eligibility for Atlassian for Startups.
- Graphite.dev/howai - URL to check out Graphite, an AI-powered code review platform.
- Howiaipod.com - Website for the "How I AI" podcast.
- LinkedIn - Platform where Rachel Wolan can be found.
- Twitter - Platform where Rachel Wolan can be found.
Other Resources
- AI Chief of Staff - A personal agent built to manage calendar, prep for meetings, and assist with daily tasks.
- AI Native Executive - A concept discussed regarding executives leveraging AI tools.
- App Gen Product - A new product released by Webflow for marketing teams.
- Builder Day - An event where an organization stops regular work to build prototypes, aiming to boost confidence and spark adoption.
- Cursor - An AI-powered code editor used by the team.
- Figma - A tool used during Builder Day.
- Gemini 3 - A model Rachel Wolan plans to use in her AI Chief of Staff app.
- Graphite - An AI-powered code review platform.
- Jira - An Atlassian product.
- Loom - An Atlassian product.
- Make - A tool used during Builder Day.
- Markdown - A file format used for personal resources and documentation, favored for its ease of understanding by AI models.
- MCP (Multi-modal Contextual Processor) - Not explicitly defined, but implied as a system for accessing company data.
- Personal Software - Software built by individuals for their specific needs.
- Vibe Coding - A term used to describe building applications with AI tools.