In a recent LinkedIn post, Kieran Flanagan explores a new paradigm for work he terms ‘AI mode,’ drawing parallels to Airbnb CEO Brian Chesky’s ‘founder mode.’ Flanagan positions AI mode not as a way to delegate tasks, but as a method for deepening engagement with one’s craft through the strategic application of artificial intelligence.
Flanagan begins by referencing Brian Chesky’s approach to running Airbnb, which diverged from conventional wisdom. Instead of merely hiring good people and stepping back, Chesky immersed himself in the details, operating with high agency and treating the company as a craft. This, Flanagan suggests, is the essence of ‘founder mode.’ He then introduces ‘AI mode’ as the equivalent for craftspeople and operators, characterized by the intersection of deep domain expertise and high AI agency.
Deepening Engagement Through AI
Flanagan illustrates his concept with personal and observed examples. He recounts his own experience using Claude Code for a deep analysis of ASPs (Average Selling Prices) across business segments. Rather than delegating the task, Flanagan actively participated, working with the AI as if it were a team of analysts. He describes the process:
“AI didn’t abstract me from the work, it pulled me deeper into it.”
This experience, according to Flanagan, highlights how AI can enhance, rather than diminish, an individual’s involvement in complex tasks. As he notes, the AI’s ability to access internal systems and assist in data pulling and chart creation allowed for rapid iteration and a more profound understanding of the business metrics.
AI Mode in Sales and Operations
The concept extends to practical applications in sales and operations. Flanagan shares observations of a top sales manager who has built an entire operating system around AI tools. This manager is leveraging platforms like Agent.ai, HubSpot, and Claude Code to automate pipeline management, build agent teams for campaign marketing, and develop sales playbooks.
Flanagan emphasizes that this sales professional is not handing over his craft to AI but is using it to gain a more granular understanding of his sales process and book of business. As Flanagan points out:
“He didn’t hand his craft to AI. He used AI to go deeper into every detail of how he sells. He knows his book of business better than anyone because he built the systems to understand it and work it.”
This approach allows the sales manager to maintain a high level of control and insight, using AI as a powerful assistant to amplify his expertise.
AI Mode in Creative Work
The application of ‘AI mode’ is not limited to analytical or sales-focused roles. Flanagan also describes using AI for a more complex creative endeavor: writing a book. He details building a custom app with an AI agent trained on the book’s audience, goals, and bestseller criteria.
This AI system assists by storing chapters, annotating weak narratives, suggesting areas for improvement, and providing reader-like feedback. Flanagan states his objective was not to delegate the writing process itself:
“I didn’t hand the writing to AI. I built a system so I could stay obsessively close to every detail of the book, move fast, iterate fast.”
In Flanagan’s view, this allows for accelerated iteration and a maintained deep connection to the nuances of the book’s content and structure.
The Compounding Advantage of AI Mode
Looking ahead, Kieran Flanagan predicts that individuals operating in ‘AI mode’ will experience significant compounding advantages. He argues that proficiency in directing AI, understanding its value versus its limitations, and integrating it with domain expertise will create a rapidly widening gap between those who adopt this approach and those who do not.
According to Flanagan, those who master ‘AI mode’ will continuously improve their skills each week, becoming more adept at leveraging AI to enhance their core competencies. This proactive and deeply integrated use of AI, as described by Flanagan, represents a fundamental shift in how high-level work can be approached and executed.
📝 About This Content
This article is based on insights shared by Kieran Flanagan on LinkedIn.
📅 Originally posted on March 3, 2026 | View original post on LinkedIn →