# The Capability Overhang Playbook — Transcript (2026-06-28) https://aidailybrief.ai/e/2026-06-28 · Listen: https://pod.link/1680633614 --- 260628 in_EDIT: [00:00:00] Today on the AI Daily Brief, the capability overhang playbook The AI Daily Brief is a daily podcast and video about the most important news and discussions in AI All right, friends, quick announcements before we dive in First of all, thank you to today's sponsors, Robots and Pencils, Superintelligent, Mission Cloud, and Outsystems To get an ad-free version of the show, go to patreon.com/aidailybrief, or you can subscribe on Apple Podcasts. And to learn more about sponsoring the show, send us a note at sponsors@aidailybrief.ai. lastly, we've got our next executive agent leadership program coming up. this is the enterprise-grade descendant of Enterprise Claw. You can learn all about that at training.besuper.ai. 260628 ep_EDIT: This is This is a weekend episode, meaning it's a long read, big think, how-to operators type of episode where we get to move beyond the news into the realm of the practical. Although the context for today's episode is at least a little bit going to be what's going on right now The premise of the [00:01:00] episode is, in short, we appear to be in a forced involuntary AI pause, at least when it comes to new models The good The good news about that is that even the previous generation of models like five five And Opus four eight have a lot more capability, particularly within the harnesses we have access to than most of us are getting real value out of So my proposal is that during this forced AI pause where we have a little bit of a breather in terms of the next new thing, this is a good time to try to both in our individual and organizational lives close the capability overhang at least a little bit over-- So what I'm going to do is share what I'm calling the capability overhang playbook, a set of ideas for what you and your organization can be doing in this period. But before we do, I do wanna give a little bit of context, at least as of Wednesday, June 24th in the afternoon when I'm recording this, around why it feels like this might be A bit longer of a pause than we initially thought Obviously, excitement has been building all summer for the next big wave of model releases. We got our hands on Fable 5 ever so briefly, and most believed that [00:02:00] GPT 5.6 would follow closely behind Heading into the week, the rumor mill was indicating that we wouldn't just get GPT 5.6, but also the surprise release of Sonnet 5. And last month at Google IO, DeepMind had indicated that Gemini 3.5 Pro was also expected in June. It now seems model releases are off the menu. Prediction markets collapsed on Tuesday, with odds of a GPT 5.6 release this week plummeting from almost 90% to below 30%. Those in the know suggested it wasn't just OpenAI pushing back release plans, but Google as well. Leo at SynthWave, who is quickly becoming the go-to rumor monger on X, wrote, " 5.6 has been delayed and will no longer release this week. New target is mid-July. DeepMind are not satisfied with the current state of 3.5 Pro, and it will no longer launch this month." Preparations for the launch of Bidi, OpenAI's new voice model, are underway in ChatGPT, and we could see it available as soon as this week. Claude Sonnet 5 is currently availablefor select enterprise customers under an early access [00:03:00] program, and is seen as a stopgap as progress on getting Mythos and Fable 5 back out have stalled. A bit of a disappointing end to the month, but July should prove more fruitful AI Battle noted that we are currently in the longest stretch between updates for the GPT-5 era since the actual gap between GPT-5 at the beginning of August and GPT-5.1 at the beginning of November then, since then it's been 29 days, then 56 days, then 28 days, then 49 days in between each iteration, and we've been now waiting for GPT 5.6 for an absolutely intolerable 61 days Wording of the rumors around Sonnet 5 also isn't all that promising. As Chubby discussed earlier in the week, some editions of Sonnet have been genuinely game-changing, delivering near frontier performance for a fraction of the cost. But if Anthropic is viewing Sonnet as a stopgap, it could suggest performance is not that For Google, they are facing a real challenge. Sentiment has already turned on DeepMind's ability to keep up with the frontier, and mothballing their next flagship model does nothing to help that perception. Then again, releasing a model that was [00:04:00] behind the frontier would do worse. so if they are delaying, I understand the decision Finally, it's looking like we'll have another weekend of not being able to play with Fable Prediction markets are now showing twenty-four percent odds of the government allowing Fable to return by the beginning of next month, and only a fifty-seven percent chance by the end of July, and only seventy-two percent by the end of August. Zvi Mowshowitz commented, "It's not looking like an easy fix, and this suggests non-US persons might actually stay locked out indefinitely." have t- many have tied the GPT 5.6 delay to a broader government crackdown on frontier model releases, but so far we have no solid reporting on that. Policy advisor Dean Ball, who is now at OpenAI, commented, " I'd assume the whole AI industry in America is effectively frozen from new public releases until the US government resolves the fable situation they have stumbled into." As Rand Longevity put it, it feels like we have hit the regulation wall. So let's get back to making some summer lemonades out of all those lemons Okay, so the setup and premise is clear. We're in a forced AI pause, but we're in a forced AI pause where we are all already dealing with the [00:05:00] capability overhang. So what can you do and what can your organization do to close that overhang? What follows is all just my ideas for how to make the most of this time, and we're gonna kick it off with the first part, which is establishing your personal learning agenda In short, I'm about to articulate a very general high-level overview of ideas that I have for everyone closing the capability gap for themselves and their organizations. But I, of course, have no idea where you are with any of this. So my first suggestion is that you actually assess your weaknesses. You actually map out, in other words, what your personal capability gap is or what your organization is working with this means an honest assessment of the capabilities, tools, or workflows you're not good at yet, and naming what you've avoided orfailed to learn or only touched superficially. That list can become your personal learning agenda, which frankly might replace the rest of this playbook be- Now for the sake of us all being in this together, an example of what I might put in here and something that I'm very actively thinking about for this summer is while I have done a ton with what you might call spot agents, individual agents, one of the [00:06:00] very obvious things that I have not done, much to the harm of the potential audience of this show, is wired together an agentic system for turning this content into social media content Now we do have our new website where each of the episodes is chunked into highly shareable little cards. But the next step is to wire that together with an agentic system for distributing that out into the world. So that's the type of thing that I'm gonna be thinking about as I do my own personal assessment But let's provide some general tips for those of you who aren't sure what those weaknesses or challenges are and just want a sense of the types of things that some others might get value out of in this period. The second category of work we're going to call building your personal AI infrastructure And the first one actually has to do with what you do whenever weget the next frontier models that can, one of the things that can be really challenging, especially now as the models are so highly capable, is figuring out how to figure out what the new models are better at than the models that you were previously using. One idea to address this is to build a personal benchmark or eval portfolio. What I mean by this is pinning [00:07:00] down the tasks that matter most in your work and life and turning them into a reusable evaluation set. So that could be what you're using models for, the specific prompts that you would feed in the expected outputs and the success criteria. now imagine you have a set of those. Well, when a new model drops, you're going to be able to actually run it against a consistent set of evaluations and actually more quickly understand where it can fit in your model stack Next up in personal infrastructure, I return to a theme which hasbeen ever present for quite some time now which is building your portable context assets As you heard in our recent episode about the Work AI Institute GLEAN study about bot sitting, one of the things that people spend the most time on, something like 2.4 hours a week in their study, was organizing context for the AI and agents they use This is a huge drain on productivity, it's an exhausting exercise, and while you're not going to be able to get out of it entirely, this is a time period where you can do some work to build more portable context assets. broadly speaking, there are two ways that you [00:08:00] could approach this. First, you could assemble a broad-based personal context portfolio To get an example of what I mean by this, you can check out contextportfolio.ai, which is a project that I released back at the beginning of April The personal context portfolio builder is going to allow you to interact with an agent that through the interview will be building out a set of context documents which then you can share with any new AI tool or agent you're using. you can... Now contextportfolio.ai is live right now But if you prefer, you can also grab the template files, i.e., the identity.md, the role and responsibilities.md, the current projects.md from GitHub directly Another, another resource on this front is called The Librarian, which was built by Jim Sangwine, a software developer who went through our Agent OS program. He describes The Librarian as an agentic OS, a curator that builds a library of context for your AI agents It runs on its own, but you teach it what matters, so the knowledge it keeps reflects how you actually work, and every AI tool you use gets better at the job 260628 ep_EDIT: I'll include a link to that, but it's [00:09:00] codeministry.net/the-librarian. and looks like a super cool project that is actually being maintained and thoughtfully updated as opposed to the context portfolio, which is cool, but a one-off that I did as part of the show this, so one way to do this is to build that broad-based personal context portfolio. Another way to do it is almost to build per project context packs. it may be that when you're using agents, especially for work, what matters is them not knowing everything about you, but them knowing about some specific project that really matters. Dividing your context portfolio and your portable context assets into those per project context packs might be a better approach. those, this is one of those things that you are going to have to do over and over and over again And so why not use this time to do a really good base job once so that you're just maintaining what's already a strong foundation? All right, our next section of closing the capability overhang, is different ways of interacting and learning the current building tools Now caveat, of course, this is the area where there's going to be the widest spectrum of different users among listeners. So feel free to zone out for anything you're well acquainted with. we'll get to [00:10:00] some more advanced things in a little bit But I wouldn't be surprised if even many of you intermediate to advanced users hadn't done everything on this list For example, most people I run into have invested fairly heavily in either Claude Code/CoWork or Codex. That's understandable, and I think it's a reasonable approach to just double down on one, assuming that even if on a feature basis, the harness or the models underneath it are behind temporarily, they're notgoing to be behind long. But for those of you who really want a very broad-based understanding and who wanna be able to use all the tools at any given time, I think it is worthwhile to actually run the experiment where you build the same project within both tools, comparing the interfaces, the way that it interacts with tools and context the feel of the models underneath to decide which of these is better for you or in what context one or the other is better for you Another Another way to put this is since you can't experiment with all the frontier models that haven't come out, you might as well spend some time experimenting with the harnesses that they run in Next up, hearkening back to an episode from a couple of weeks ago [00:11:00] one of the shifting ways that knowledge workers are using AI is to get out of the constraint of file formats like PDFs or spreadsheets or static documents, and moving things into HTML and websites and web apps more broadly Codex launched its sites feature. Anthropic is pushing a similar pattern And if you need some inspiration, go check out my episode from June 7th called "10 Things You Should Build With AI Instead of Sending Files." It's all about this new primitive, the benefits that I see with it, and some specific examples or use cases of where I think an HTML or web app style approach is going to be better than the former way that you used to do things Another one, which I am 100% guilty of as well, is that especially Claude Code, but also increasingly Codex and other tools, have done a ton of work to build function-specific plugins and tooling four different types of work roles and even different industries But if you're anything like me in the day-to-day grind, You get pretty locked in in the ways that you're already using AI, and taking some random time for experimentation can kind of fall to the bottom of the to-do [00:12:00] list, meaning that it falls off the to-do list. I think this is a really good moment, as simple as it seems, to go explore the plugins that are actually available and relevant for whatever your role is, and see how they might change the way that you interact with Claude Code or whatever tool you're using finally in the personal build section, for those of you holdouts who avoided the open claw hype and have skipped my ClawCamp or Agent OS program, it is time Time to go build yourself an actual agent. You're gonna go past a single prompt, you're gonna go past a simple web app vibe code, and build a real full end-to-end agent architecture There are some good learning resources out there for this, but if you need one, Check out AIDB Agent OS.ai It's a free self-directed program that'll help you build your own agentic operating system that helps you work differently in this new agentic way. Bite the bullet. I know it's intimidating, but you have to remember, as long as you give yourself time, whether you're using the Agent OS program or something else, you have the world's most infinitely [00:13:00] patient and knowledgeable tutor in the actual tools themselves. I would recommend, and it sounds simple, but this is how I've learned everything that I've ever learned with AI. Two windows, the window where you're and the window where you're asking the questions. Nathaniel Whittemore-1: Now, 260628 ep_EDIT: yes, you can just do all of these things in one interface within the chat that you're building. But I find it really valuable to be able to screenshot every web developer term that I don't understand, bring it over into the tutor chat and ask it to explain it to me slowly until I get what the build partner is actually doing 260628 ep_EDIT: This one is ultimately just about the commitment to go bigger, but I can't recommend it highly enough. you will feel like a wizard, I promise you I cover the capability gap between AI potential and AI reality every day on this show most companies are still figuring out how to start. Robots and Pencils is already launching and scaling. Agentic generative AI in production at large enterprises in weeks. Speaker 11: AWS Advanced Tier pattern partner more than doubled in a year And they're hiring 50 open [00:14:00] roles. If you're someone who knows this moment is different, who wants to be inside it, not watching it, this is worth a look. robotJune_EDIT: At Robots and Pencils, the best ideas win, and the team is purposefully kept super high quality Speaker 11: This is the kind of place you look back on as the best decision you ever made. Take a look at robotsandpencils.com/careers Nathaniel Whittemore: today's episode is brought to you by the new Executive Agent Leadership Program Produced by super intelligent and by frequent AIDB operators guest, Nufar Gaspar to tell you a little bit more about the Executive Agent Leadership Program, here is Nufar Speaker: The best predictor of agent adoption in an organization is how hands-on their leaders are. Talking about agents is completely different than building them. Our participants, ICs all the way to C-suite, have built working agent fleets, governance frameworks, and the playbooks to scale it. Executive agent leadership is the evolution of enterprise claw. Everything we've learned across three cohorts rebuilt for right now. The token economy, [00:15:00] security, vendor resilience, and architecture to lead agent adoption at scale Nathaniel Whittemore: the next cohort of the Executive Agent Leadership Program is signing up now and will launch, on June 29th You can find out more at training.besuper.ai The average enterprise is spending eleven and a half million dollars on AI this year, and most of them can't prove a single dollar came back. What does AI actually look like when it produces ROI? Ask the healthcare company that just made their payment processing three hundred and twenty times faster, or the law firm whose document research went from three months to ten minutes, or the contact center who reduced wait times by ninety-nine percent. These are real Mission Cloud customers with real results. Mission Cloud is a CDW company and an AWS Premier Tier partner. They're the AI-first, outcomes-obsessed AWS experts who build AI solutions that drive your business forward. Whether you're flooded with AI ambitions but no idea where to start or six months into a deployment that's going sideways, they've seen it and they've fixed it. Stop burning your budgets on AI that doesn't produce results. Start at [00:16:00] missioncloud.com. outsystems_dxRevive_EDIT: This episode of the AI Daily Brief is brought to you by OutSystems, a leading agentic systems platform built for the enterprise. Organizations all over the world are building, orchestrating, and governing agentic systems Speaker 10: on the OutSystems platform and with good reason. OutSystems' open and unified platform allows teams to architect, deliver, and scale governed agentic systems with agility. Teams of any size and technical depth can use OutSystems to build, deploy, and manage AI apps and agents quickly and cost effectively without compromising reliability and security. Without systems, you can rapidly launch ideas from concept to completion. It's the leading agentic systems platform that is unified, agile, and enterprise-proven, allowing you to accelerate growth, reduce operational friction, and deliver real enterprise impact with AI OutSystems. Build your agentic future 260628 ep_EDIT: up, and next up, section four is about exploring model independence. And if you've been listening to this show throughout the Fable 5 situation, and [00:17:00] frankly even before as we started to explore new token efficiency solutions, there are a lot of reasons why people are reevaluating their adherence to a single frontier model right now Now, I think for individuals, the things to explore are using model routers and open models, and there are a number of resources for this. you can go check out and play around with models on Hugging Face. You can go explore something like Open Router. If you're comfortable using APIs, I think it's a good idea to perhaps go build something using Open Router to see how their approach to this works And as you're exploring this, it's worth thinking for yourself: How much does this really matter to you? in what context would model sovereignty actually impact your work? Is cost the bigger consideration, and what would make cost the bigger consideration? Are there dynamics of privacy or portability or control that would influence the way that you think about this? This is one area where I don'tthink you need to come to any conclusions, but the questions that you ask are going to become increasingly important the more powerful these models get and the more governments get involved with those powerful models. And so I think this is a good [00:18:00] time to be starting to ask those questions. Now, Now, there is an obvious organization-level extension of this, which is in general, most enterprises don't really have org-level policies about things like open models or router architectures. And if you do, my guess is that the assumptions that underpin it might not be the same anymore. This is a really good time to reevaluate whether you have those policies, and if you don't, to understand where your organization's instincts are and if they need tobe challenged at all Speaking of organizations, let's move to section five, which is all about the organizational capability overhang playbook. We've talked individuals, but now we'll move to company level First of all, this is a very good moment to review the learning, training, upskilling resources that you are making available to your organization 260628 ep_EDIT: some of you, especially in big companies, are going to be slinking down in your chair realizing thatthere's really very little formal and others might be looking over at some three-minute video course about prompt engineering, realizing that maybe that doesn't hang with today's agentic type of use cases [00:19:00] So are your learning resources actually good enough? Are they contemporary and current with today's tools? and do the people who are supposed to be getting value from them actually know what they should be learning? Are there ways for them to figure that out Do you need new learning resources, i.e. end courses or programs? do you need a better system around your learning resources to better help people figure out what they should be learning? And do you have a way to understand the difference after versus before a person has usedwhatever learning resources you have now this is one of those recommendations that Ithink would be valid and important whether we were in a forced AI model pause or not. But this is certainly a good time to go in on all these details related, Next up, related to that, this is a good time to review the incentive structure for AI use in your organization. In other words, are people rewarded formally or informally for effective AI adoption? Is strong work called out and lauded Are people incentivized to experiment with new use cases or just to execute against known use cases? Are people incentivized to share lessons [00:20:00] and build reusable systems? And is there infrastructure for them to actually do that sharing? do you have any current incentives that accidentally or quietly discourage adoption? Again, given that this is a moment to catch our breath, this is exactly the type of conversation that is worth having. Nathaniel Whittemore-1: In In addition 260628 ep_EDIT: to reviewing your incentives, you should also be reviewing what you measure Now, if you're not measuring anything, any progress here is going to be valuable. But this is also a moment to understand the complexity of what you measure and whether it actually aligns with the goals that you're trying to achieve measuring adoption is different than measuring usage is different than measuring outcomes. and despite what the snarks on X might tell you, each of those things, even silly imprecise measures like token consumption do have their place What you need overall is not one measure versus another. It's an entire measurement philosophy and system that can understand the relationship between what people are doing and how those things are impacting both their individual outcomes as well as larger business outcomes Now, one bias I have as you were thinking about that, one of my big concerns with this moment of token [00:21:00] efficiency that we're moving into, necessarily based on the increasing cost of using AI across agentic workflows, is that I'm really worried that organizations are going to see an overly strong known ROI bias. in other words, very understandably, organizations will say, Hey, we'd really like to increasingly see a relationship between the AI that you're consuming, especially if it's a big chunk of AI on an API basis, and the ROI that we're actually getting out of it as an organization." Nathaniel Whittemore-1: The 260628 ep_EDIT: problem is that if done inelegantly or too heavy-handedly, that could lead directly to people prioritizing what I call efficiency AI use cases. In other words, just doing the existing work but faster or cheaper. And of course, there's nothing wrong with that. That's a great value to try to leverage out of AI, but it should be viewed as a foundational layer, not the ultimate goal. In my belief, the ultimate goal should be opportunity AI. New products, new capabilities, things that weren't possible before We are not operating in a good enough economy where you get to a certain size and performance and you say, "That's good enough. Let's just do it a little bit more efficiently." We operate in an economy that should [00:22:00] always be striving As Robert Browning wrote, " A man's reach should exceed his grasp, or else what's a heaven for?" So set ambitious goals And as we've just discussed, figure out how to incentivize them, figure out how to help people learn how to do them, and then measure to see if it actually works. Now, one small one, if you do happen to have access to Claude Tag Get it up and running You can check out my episode from last week Wednesday about why I think it's more significant than your average feature release and is about a new multiplayer mode of interacting with AI that breaks it out of the individual worker realm and puts it squarely in the workspaces where you're actually operating Lastly Lastly today, let's talk about a few advanced patterns Some of you still, and if this is you and you've made it this far, bless you. But some of you are yawning saying, " Sure, sure, I've got this all under control. Give me something else." Well, for you, let me suggest three advanced patterns that this would be a good time to dig into. The first of all is thinking about prompting AI not as a [00:23:00] process in which you are actively managing and iterating with the AI, but as one where you have set a goal and have architected a loop through which the AI can iterate itself If you go look up agent loops on X, You will find 100 articles chock full of tips from the last couple of weeks. And frankly, even when some of them are derivative, they're almost all valuable This idea of loops and the /goal feature that has become a primitive inside all of these tools is really that in this new agentic paradigm, we have to get out of thinking about this as a tool we manage and instead treat itteam, as an actual teammate or employee where we set the objective and then evaluate on the other side the work that comes out Now I will note that part of what makes loops viable is the sort of clear evaluation criteria that isn't always that clear when it comes to certain types of knowledge work. But that doesn't mean you shouldn't be using loops. It means you should be experimenting to figure out if and how they can be useful for you Next up, for those of you who wanna take that context portfolio idea and take it to the next level [00:24:00] I recommend turning your context portfolios, whether they are your overall context portfolio or your per project context packs, turn them into MCP servers to make them even more transportable to wherever you need to use them This will of course have two benefits. First of all, you'll get a lot more familiar with the MCP server architecture, which currently an important part of the overall agentic ecosystem. And secondly, if you do a good job with it, it will actually make these assets that you've spent time developing for yourself much, much more useful. If the goal is to decrease the time that you spend on context Putting these files into MCP servers that are accessible very quickly, as opposed to having to drop in a bunch of files, obviously is a lot more efficient approach 260628 ep_EDIT: next up, try to interact with and build the ecosystem around them. specifically, take some time to package a recurring capability as a reusable skill This is going to take a bunch of the work that you did with one agent and make it transportable and useful across other projects and agents as well 260628 ep_EDIT: I did a show with Nufar a month or two ago about agent skills, which you can go search up in the archive. But there are [00:25:00] tons of great resources out there about this. And this is an area where if this has seemed a little out of reach so far, this is a really great time to dig in Ultimately, when push comes to shove, there really isn't all that much different about this pause moment than any other time. All of the things I just articulated would be really valuable no matter what models were available but the fact that we are in a comparatively quiet period where we are not just being barraged with a new thing to try every other day does create a moment in time where you can change your objectives just a little bit to actually use this space to close some part of the capability overhang that you yourself or your organization experiences some, hopefully this is some good food for thought And if not, well, sorry for wasting your time. Appreciate you guys listening or watching as always, and until next time, peace ​ [00:26:00] Nathaniel Whittemore's audio recording: