{"id":620935,"date":"2026-09-19T11:18:24","date_gmt":"2026-09-19T11:18:24","guid":{"rendered":"https:\/\/www.newsbeep.com\/il\/620935\/"},"modified":"2026-09-19T11:18:24","modified_gmt":"2026-09-19T11:18:24","slug":"how-to-get-from-ai-assisted-to-ai-native-oreilly","status":"publish","type":"post","link":"https:\/\/www.newsbeep.com\/il\/620935\/","title":{"rendered":"How to Get from AI-Assisted to AI Native \u2013 O\u2019Reilly"},"content":{"rendered":"

When considering the history of AI, Richard Sutton observed that brute force and compute scale has always trumped human expertise, and when you look for it, you can see this \u201cbitter lesson\u201d play out throughout tech history. In his keynote at Ai4 2026, Tim O\u2019Reilly explains why grappling with the bitter lesson is the forge of effective AI corporate strategy, as companies figure out what to embrace and what to let go of. Drawing on his recent conversations<\/a> with Trail of Bits CEO Dan Guido, Tim argues that AI\u2019s business impact actually hinges on organizational adoption\u2014the hard, unglamorous work of restructuring workflows, data, and incentives around what AI can do. Trail of Bits has modeled that process and documented it in a playbook<\/a> other companies can use. Here, Tim shares some of the practices, like capability ladders, shared config repos, and company-wide hackathons, that helped Trail of Bits make AI a structural component of its business. This doesn\u2019t mean that AI-native companies \u201csit back and let the progress of AI carry us forward.\u201d Human expertise still matters, and it\u2019s often the differentiator that helps organizations rise above their competitors. As Tim concludes, \u201cThe world is full of great problems. And so if AI takes away and makes easy something small, celebrate it and go work on something big with the new powers that we\u2019ve been given.\u201d<\/p>\n

Takeaways<\/p>\n

02.33<\/a> The bitter lesson is real, and it can catch any of us.
The bitter lesson is Richard Sutton\u2019s contention that human expertise doesn\u2019t really matter, that it will eventually be outmatched by computing scale. O\u2019Reilly\u2019s Whole Internet User\u2019s Guide & Catalog was the first catalog of websites and the first site on the web to have advertising. It grew into Global Network Navigator, which was the first web portal. But O\u2019Reilly\u2019s products were manually curated. Yahoo came along and expanded on these ideas, but O\u2019Reilly and Yahoo were both beaten by Google, which simply threw a bunch of compute at the problem. Now ChatGPT has changed the game again.<\/p>\n

06.27<\/a> AI-native workflows require a different mindset.
When O\u2019Reilly set out to develop a product that assessed learners\u2019 capabilities and gave them a skill path to level up, the team used AI as an assistant, to write quiz questions, for instance. But LLM chatbots can already identify skills when given context about a developer. Evolving toward an AI-native skill path builder meant reconceptualizing the product as a more interactive experience that reflects where capabilities are today. However, even the most well-thought-out workflow can be hindered by gaps in access or knowledge. As Trail of Bits CEO Dan Guido says, \u201cYou have to build a system in which expertise compounds.\u201d<\/p>\n

10.28<\/a> AI adoption is a human problem.
Moving up the framework for AI adoption from AI-assisted to AI-augmented to AI-native isn\u2019t just a technical challenge. It\u2019s psychological. Only 5% of Dan\u2019s staff was actually on board when he started the transformation; 70% were just quietly going through the motions, and 20% were actively resistant. He traces this to a handful of biases: self-enhancing bias, opacity, intolerance for imperfection, and above all, identity threat, the fear that AI won\u2019t just replace the work someone does but who they are. Getting teams on board requires the organization to reframe AI as a tool that enhances identity, not something that will take it away.<\/p>\n

16.44<\/a> A status ladder helps team members understand where they\u2019re at and where to focus next. Hackathons compound that knowledge across the company.
Trail of Bits has a three-level status ladder: not engaged with AI or actively resisting it, experimenting with AI, and building AI that strengthens the organization\u2019s overall capability. Level zero isn\u2019t treated as a skill gap. It\u2019s treated as working against the company\u2019s goals, and the other two levels get a more detailed capability matrix broken out by department, since what a security auditor does with AI looks nothing like what someone in accounting does. O\u2019Reilly is building its own version of this, drawing on the technical and business skill data it already has across its platform. Trail of Bits runs a hackathon every two months, each with a stated objective and learning goals announced a week ahead. Success is measured not by what got shipped but by where people land on the capability ladder afterward. Then the work gets fed into a shared skill repo, giving the entire company a set of reusable artifacts, and what one hackathon turns up becomes something the next one can build on.<\/p>\n

24.37<\/a> Turn scar tissue into infrastructure.
Drew Breunig talks about the problem of prompt debt<\/a>: prompts that grow more complex and more tuned to one specific model until they\u2019re no longer portable. Trail of Bits flattens this complexity by turning every failure into a global, copy-pasted fix hosted in a company-wide repository. They\u2019ve also standardized the safety net, with sandboxes for different needs and a seven-day cooldown on every new package from outside that gets installed\u2014rules the whole company follows. To make this all work, employees need the chance to try things out and iterate on their failures. Dan says the only real mistake he made was not giving people enough unstructured time to experiment.<\/p>\n

32.44<\/a> Human expertise still matters.
AI can make companies more productive, but it\u2019s not a magic weapon. It\u2019s a medium<\/a> that people can use to share or extend their unique expertise and perspective. O\u2019Reilly\u2019s mission is to share the knowledge of innovators: You can think of the company as a matching marketplace for people who have expertise and people who need it. Agents offer a valuable new means of getting that expertise to customers in the tools they\u2019re using to make business decisions. O\u2019Reilly CTO Andrew Odewahn has noted that faster local decision-making has splintered central planning, so it\u2019s harder than ever to get the big-picture view a good corporate decision needs. O\u2019Reilly\u2019s Expert MCP server lets customers access our content and use it to increase organizational intelligence. For instance, you can ask an AI tool to analyze a team\u2019s workload and write a hiring case based on how O\u2019Reilly\u2019s own experts would review the request, and you\u2019ll get a grounded argument with solutions authenticated by citations from actual practitioners. O\u2019Reilly is building this capability into an organization-wide grounding layer it calls O\u2019Reilly Expert Intelligence. It\u2019s in beta now, and you can check it out<\/a>.<\/p>\n

Is cybersecurity part of your job in any way? If so, we\u2019d like to know what you think for a report we\u2019re writing. Just answer these quick 11 questions. Thanks in advance!\u00a0Take the survey ><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"When considering the history of AI, Richard Sutton observed that brute force and compute scale has always trumped…\n","protected":false},"author":2,"featured_media":620936,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[20],"tags":[345,343,344,85,46,125],"class_list":["post-620935","post","type-post","status-publish","format-standard","has-post-thumbnail","category-artificial-intelligence","tag-ai","tag-artificial-intelligence","tag-artificialintelligence","tag-il","tag-israel","tag-technology"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts\/620935","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/comments?post=620935"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/posts\/620935\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/media\/620936"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/media?parent=620935"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/categories?post=620935"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/il\/wp-json\/wp\/v2\/tags?post=620935"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}