Almost Timely News: ๐️ How I Use AI As a Keynote Speaker & Facilitator (2026-09-27)
Almost Timely News: ๐️ How I Use AI As a Keynote Speaker & Facilitator (2026-09-27)31 people do not follow me everywhere I go
Almost Timely News: ๐️ How I Use AI As a Keynote Speaker & Facilitator (2026-09-27) :: View in Browser
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Click here for the video ๐บ version of this newsletter on YouTube » Click here for an MP3 audio ๐ง only version » What’s On My Mind: How I Use AI As A Keynote Speaker & Workshop FacilitatorThis week, let’s extend on a newsletter issue I did a couple weeks ago about how I created a speaker second brain, looking at how I use AI as a keynote speaker and workshop facilitator. This issue is explicitly for people who are event planners and organizers, but also for anyone else who wants to think about how to use AI as part of the public speaking process. When someone hires me as a speaker for their event, workshop, or conference, they’re generally looking for one of two things:
This newsletter tackles item 1. We’ll defer item 2 for another time, but the short version there is that’s a paid add-on. How do I use AI as a speaker? How does it benefit you? Let’s dig in. Part 1: PhilosophyI break a lot of rules when creating content for events. One of the biggest rules I break is about cognitive overload; the rule of thumb is that you generally want One Big Idea as the cornerstone of your talk or workshop, and then 2-3 supporting ideas. That makes you a memorable speaker, often motivational and powerful, easy to refer by word of mouth. But the challenge with that approach is that also leaves audiences hungry. A properly focused One Big Idea is something you can transmit in a minute. You don’t need an hour for it. You certainly don’t need a full day for it. For example, my friend and colleague Marcus Sheridan wrote a book years ago titled They Ask, You Answer, a content strategy for businesses where you focus your time and effort on answering the real questions customers have. Marcus’ book is so good, the idea is so good and so self contained that you don’t need to even read the book. The title alone conveys the entire strategy, tactics, and execution. I haven’t read the book (sorry, Marcus) because I don’t need to. That’s why my YouTube series that I’ve been doing for years has been titled You Ask, I Answer — because it’s literally that book brought to life. When it comes to teaching, I follow the practices of my martial arts teachers, like Stephen K. Hayes, Mark Davis, and many others. When you attend a workshop or a clinic with these folks, you’re usually not focusing on one idea. You’re focusing on a whole bunch of ideas at a time, and the entire time, you’re taking notes, practicing, trying to soak up as much as you can. During one seminar with master instructor Fumio Manaka, he taught the entire set of Togakure family sword techniques from all of the secret scrolls he was licensed to teach. That two and a half day workshop was pure overload - imagine trying to learn 5 or 6 big ideas, and then imagine a weekend learning several dozen including 17 techniques that normally take 2-3 years EACH to master. When I asked Sensei Manaka why he was teaching in this manner, he said very directly, “I’m teaching you everything now because I don’t know when I’ll see you next - maybe never. This way you have enough to practice for years.” True to his word, that workshop was in 1998. I haven’t taken a workshop with Sensei Manaka since, yet all of the material from that workshop I’m still practicing today. That’s how I approach teaching, especially in workshops. I try to pack as much material in as practical because I don’t know when I’ll see you next, and I want you to take away as much as you can, armloads of material to go practice over time. It might be years before I see you at another workshop, so the more benefit you can get in a single event, the more you have to work with. Is it overwhelming? Yes. Is it too much? In the days before AI, yes. But today, it’s a resounding no, and here’s why. Part 2: How I Use AI Before the EventI just got back from teaching a full day workshop with the Laboratory Products Association in Philadelphia, my fourth event with the LPA. I love teaching at associations and companies because it lets me do a super deep dive into a particular industry or company and think through use cases that aren’t generic. Real value from AI comes from practical application, not theory - the more relevant and specific a use case, the more someone is likely to get value from it. Before an event, I’ll use that second brain database to explore what techniques are relevant to the audience from the over 7,000 slides I’ve built over the years. That plus the event agenda helps me decide how I’m going to approach things. One of the most important words that I use with my second brain is scaffolding, and it comes in two varieties. The first is cognitive scaffolding, where every concept you introduce is built upon something the student already knows, or has already been taught. For example, in the martial arts, you teach the basics first - how to punch, kick, block, move your feet. Then you start scaffolding, putting together combinations of punches and kicks, blocks and parries, building on what the student has already learned. Finally, you teach the kata, the predefined routines of proven techniques so that the student understands how it all fits together. This is an inductive style of teaching - you start small and you glue more and more together until you have something big. In educational theory, it’s one of the big theories to help teachers be more effective. There’s also its inverse, deductive, where you take a big idea and decompose it, but that’s for another time. Alongside cognitive scaffolding is the equally important motivational scaffolding. To keep someone interested, to keep their attention these days, you need to show them early wins, early motivational boosts that reassure them and grow confidence in their abilities. Early wins, especially in a workshop, are so important to keep a person engaged in the material. Nothing’s worse in a workshop than starting out with 90 minutes of lecture and no chance to do anything. In the martial arts these days there are many, many colored belts before black belt and promotions and tests occur much more frequently, sometimes monthly now, because of this motivational scaffolding. In the old days when I was moving up through the ranks, it could take you a year or two between small belt promotions and five to ten years between big belt promotions like black belt levels. In today’s modern society, that’s not motivating to people. So having many more smaller promotions and belt colors keeps people motivated. And it’s that idea of motivational scaffolding that I bring into how I teach keynotes and especially workshops. My rule of thumb for a workshop is that you have to hit the first exercise within 20 minutes. If students don’t have their fingers on the keyboard in the first 20 minutes, the material isn’t organized well. It doesn’t have to be a big exercise and probably shouldn’t be, but it does have to flip them from passive receiver to active participant early. For a keynote or general session, there should be some kind of tangible “oh, I can try that out” within the first 15 minutes. So before the event, I take my outline and the material I want to cover and workshop it with my AI of choice, providing it a checklist of scaffolding techniques for it to choose from that I used deep research to distill. This way, I’m not making crap up, but drawing from a library of peer-reviewed instructional design papers from the last 5 years. I rearrange the material so that it’s scaffolded well from easy to difficult, from small to big, so that attendees get some early wins and build on them. Alongside, if I’m able to do so, I run a survey of registered attendees and ask them a simple, powerful question I learned from Stephen Hayes: “What one thing must you learn at this workshop to make it a resounding success for you?”, a variation of his reminder that we as participants should arrive at every learning opportunity with a burning question we absolutely must get the answer to. I ask people what their burning question is, then take that feedback and blend it with my second brain materials. Sometimes the survey results create a little last minute scramble. For example, with the LPA workshop, I got the results from the survey a week before the workshop, and the burning questions that attendees had were not at all what was marketed, what I and the LPA had advertised. Instead, the questions were along different lines about using AI in a more structured, scalable way, about diagnosing why they weren’t getting the results they wanted. The 163 slide deck I had created for the workshop immediately got shelved. That material would wait for another time. Instead, I took all the attendee feedback, analyzed it, and five days before the event, I created an entirely new workshop tailored to exactly what they asked for. You saw a piece of it in last weekend’s newsletter as I thought aloud about how prompting has changed in the last year with the advent of agentic models. That entire newsletter, plus some exercises, became the first 30 minutes of this week’s workshop. Why would I do something like that? Because the one job we have in the events industry is to give our audiences what they want. My martial arts teachers would say your job is to give audiences what they need, so we’ll interchange the two here. If the audience says they want burgers and I show up with sushi because it’s my favorite, I’m not serving the audience, I’m serving my own ego and needs. If I do my job, I show up with burgers. Now granted, if an organization requires the materials in advance for something like continuing education credit validation (which happens a lot with professional associations) then what’s promised is what has to be delivered - but the survey would also go out before that. Once I’ve got the slides and material worked out, I then create a Google Doc of the support materials, along with any support files zipped up and put on the Trust Insights website. Very often, especially for workshops, I’ll create support materials for a fake company, the Savory Oatmeal Company, so that attendees have a common dataset to work with and no one has to worry about attendees using confidential company data in a public/semipublic setting. The Google Doc, especially for workshops, is so important for attendees to have - it lets them copy and paste things like prompts or workflows without having to frantically type and keep up with what I’m saying on screen, and it makes for a great takeaway after the event. It’s always shared live, usually with an easy to remember redirect that stays persistent after the event and is the central hub for all the post-event resources, so attendees never have to remember where individual pieces are. One of the very tactical, practical things I do is make sure everything is named and numbered - exercises or segments are numbered and ordered in all the support materials. This makes it easier for me to remember where I am, and it makes post production a breeze. More on this in a bit. Part 3: How I Use AI During the EventWhen I set up for an event, especially a workshop, it looks like someone bombed a Best Buy. There’s wires, devices, batteries, cables, and gadgets everywhere. For workshops especially, I have my laptop set up along with my iPad as a second screen (super useful for staging), my DJI Mic Mini microphones wired in, my portable audio recorder running separately, my phone on a stand as the music player during exercises, plus cameras, tripods, etc. Bear in mind, speaking is not my full-time profession. I’m a data scientist; most of my time is spent on Trust Insights clients and client work. I don’t have a crew of 31 people, Gary Vaynerchuk-style, following me around, recording every moment, editing it into social-ready reels and clips. When you see full-time professional speakers on Instagram and TikTok walking through the airport, someone else is following them with a camera. Most of the time, it’s literally just me and a bag of gadgets. Everything I do throughout this process is a solo act - and I do this completely self-contained, without adding any burden for setup on the AV team (unless the venue has something like union rules that we have to collectively obey). On my laptop, I run OBS Studio to record my screen and the audio from the DJI mics, saving it as local file. I learned the hard way that using any kind of cloud service to do this is a very, very bad idea with venues’ wildly different, usually insufficient Internet services. Long ago, I tried using StreamYard to record a workshop. Never again. Streaming anything is a bonus but most often is impossible. During the event, all the devices are constantly recording and storing local files. When I teach a workshop, I usually split the recordings at each break and run TypeWhisper on the previous segment’s recording to get an early transcript, which I put into Gemini Notebook (formerly NotebookLM) as I go. This gives attendees the ability to use the Notebook at intermissions and ask questions if they missed something. They can catch up quickly on parts they missed or ask questions if I’m not around. If the room’s Internet supports it (and sometimes it really, really doesn’t), I’ll also start a Google Meet and invite attendees to connect to it. This gives attendees the ability to see what’s on my screen on theirs (since not all rooms and screens are easily visible), and also provides closed captioning/subtitles. If the room wifi doesn’t support it, I’ll run closed captions from my computer on screen. One of the other little things I do is use a command line app called Termdown, which puts a convenient countdown clock on screen during workshop exercises and breaks. This helps attendees know how much time they have left, keeps me on track, and makes post-production easier. Then, once I step off stage, my job is done, right? Nope. The moment I step off stage, it’s time for AI to take center stage. Part 4: How I Use AI After the EventOnce I’m off the stage, I have a pile of data to process - video, either from my phone (if it’s a keynote) or from my laptop screen (if it’s a workshop). If you’ve been following me for a while, this will be familiar territory - this is the content repurposing/transmedia content framework I’ve shared for well over a decade now. The videos go straight into Adobe Premiere, where I edit them to chop out any segments where I’m not speaking. This, especially for workshops, is so important to make the workshop videos much more condensed. Fully a third to a half of a workshop’s time is and should be dead air as attendees are working, doing exercises. That time is valuable during the workshop, but it’s unhelpful after, so I run speech detection in Premiere plus look for my on-screen countdown timer. I chop out all the breaks, then render the video of the event. That goes up as an unlisted video and into the attendees’ Google Doc (that way I don’t have to keep sending more emails to people afterwards, one is enough). For the most recent workshop I did at LPA, the recorded runtime with all the exercises and breaks chopped out was three and a half hours for a full-day workshop. Literally half the time was attendees doing hands-on work or taking breaks, which is the right pace because people need time to work through the material. Once the video is rendered, I then use TypeWhisper or Parakeet-MLX to create the subtitles file and raw transcribed text. SRT subtitles files are super important because they’re second-level timings of what I’m saying and when. That data helps AI and command line tools quickly find relevant pieces in the text later on. Remember how I said earlier that everything is named and numbered? This is why - AI tools can easily navigate a talk with good metadata. After the video is done, I use the ffmpeg command line tool to convert it to an MP3 audio file. This is for attendees to use later, if they want to listen rather than watch. Those SRT files? An agentic AI tool like Claude Code, ChatGPT Work, etc. can read the transcript and then splice the MP3 file programmatically into chapters for easy reference. One of the unique things about the MP3 file format is that it’s headerless, meaning that it can be cut up into pieces and each piece works independently. Once I have the text transcript, I pass that to AI to do an editing pass for what are called speech disfluencies. These are the common errors that show up in a transcript - doubled words, repeated interjections like “uh”, “um”, “you know?”, “right?” that we commonly accept in speech but are weird and jarring to read in the written word. The text transcript then goes into the Google Doc - and those same timestamps from the SRT file help break it up into chapters. Inside Gemini Notebook, I replace the day-of transcripts (which are raw and unfiltered) with the cleaned transcript, slides, and Google Doc contents so that the notebook can give more accurate answers from all the sources available. I’ll typically also automatically run all the major widgets inside so that there’s some good starting materials for attendees to use. The last part is a set of workflows I built specifically in Claude Code, a combination of command line tools, skills, and utilities that turn the transcript and captions into a full ebook. It takes each of my slides and programmatically renders each slide as a JPEG file, then injects the slides with the narration from the subtitles, with each major section of the talk or workshop as a chapter, and creates all the necessary front matter and other ebook essentials. When the flow is done, I have an ebook in both PDF and ePub formats that attendees can use in their favorite ebook reader. Depending on my contract, this may or may not be publicly available, too. For example, at my recent talk at Spotlight Summit, my contract explicitly stated I’d make the talk available for public distribution (since it was a 25 minute talk and not a full day workshop). From that event, I took the slides, transcript, video, and audio and put it in the Trust Insights Academy as a free resource. All these techniques scale to any event, from a private group session at a company retreat to the largest stages in the world. For example, at Spotlight Summit, I didn’t have time to do any hands on parts, not within 25 minutes. But I had plenty of time after I was on stage to derive the support materials needed and get them distributed right away. Attendees may not have had the opportunity to try things like prompts or workflows in realtime, but the support materials gave them that chance afterwards. At the upcoming MAICON conference in Cleveland, I’ll be teaching an all-new Build session where we have 45 minutes to have attendees build something in real-time. These techniques will be even more applicable at an event like that because we have so little time - the more I can prepare materials in advance, the better attendees’ outcomes will be. Here’s the wild part: I try to do all this, bandwidth permitting, within 24 hours of my stepping off stage. That’s never contractually required, but usually there’s time during travel to get all the editing and stuff done, especially since AI tools can dramatically speed up the processing. Why so fast? Partly because I will forget later on as regular work tasks flood my calendar once I’m back in the office, and partly because I want attendees to get the goods from a talk or workshop as quickly as possible to cement the impression in their minds of the value they received, of the knowledge they gained. This part’s so important, especially for the events themselves, whether it’s a company, an association, or a conference. After an event, stakeholders love to ask, “So what did we get for our money?” And often, attendees will cite some of the notes they took. On LinkedIn, I frequently see people refer to the one or two “golden nuggets” they took away from an event. Screw that. I want you going home with a fully-loaded ore cart. I want you to show your boss or CFO that you came home with armloads of stuff. If I do my job right, you get the irreplaceable live experience, yes. But you can show your boss:
Plus your own notes and experiences from your point of view. For every event that’s full-fee, this process is always included as part of my fee. The only thing you’re not allowed to do is resell it (that’s a separate license). I want your stakeholders to look at that pile of stuff and go, “okay, we clearly got our money’s worth, this event’s going to have a solid ROI”, which makes you look good, makes the organizers look good, and makes me look good. In turn, that means you’re likely to get approval to go to another professional development event or conference, which means that the conference industry continues to grow, and means that I’m more likely to get hired again. And because I used scaffolding, a significant part of the materials, especially early in the workshop, pass the “Monday morning” test - the day you’re back in the office, you should have something you can put into production immediately. For example, I showed a sales development technique at the LPA workshop that raised a bunch of eyebrows (in a good way) as I taught it and as attendees tried it. During the break immediately after, a half dozen people said they were already setting up their workflows to use it so that the moment they got back to the office, they’d have real results to hand to their sales teams. That’s the kind of success I want for you when you attend one of my events. Part 5: Wrapping UpGoing back to how my martial arts teachers teach, my approach has one more long-term benefit. If you so choose, you can take all those materials I provide and practice them, learn from them, build from them for months or years to come. There’s enough packed in these materials that you could spend a year easily mastering all the techniques and their infinite variations. If I never see you again, or I don’t see you for quite some time, you still have enough material from me to work on and grow from. For example, a friend of mine took my London workshop last year, one of the 25 lucky people who secured a spot in the room. Since that workshop, she’s grown a cottage consultancy with a handful of clients that pay her well for the value she delivers based on what she learned and put into practice afterwards, and is already having to hire to meet the demand for her growing business. She took what she learned and applied it rigorously. This approach also falls down if I skip the scaffolding part. That’s the hidden secret in this method - if I just assembled a list of techniques that had no connection to each other, it would be vastly overwhelming because you’d have no mental framework to build on. The talk, be it 25 minutes or two and a half days, would make little sense. The scaffolding is what glues it all together so that one item leads to the next. And let’s be clear, there’s an aspect of self-serving to this as well. If I do my job well, if I send you home with a ton of learning, then the next time there’s an event, conference, or in-house training where you’re wondering who to hire, my goal is for my name to be at the top of that list. This week, one of the attendees said that as soon as they saw who was speaking, they signed up because they took a workshop with me two years ago. My approach is not right for most speakers. It’s not right for some events. I willfully violate some speaking best practices, and I’m okay with those tradeoffs because I’m making them consciously. Most speaker guidance about how to structure talks and workshops is predicated on the idea that what you say in the room is the most important part and that your job is done when you walk off the stage. My approach is that while it’s important you have a positive, useful, productive experience in person, the support materials I create should keep giving you value long after we’ve both gone home. How Was This Issue?Rate this week’s newsletter issue with a single click/tap. Your feedback over time helps me figure out what content to create for you. Got More Feedback?๐ Please take my 6-question Reader Survey to tell me what you want! Here’s The UnsubscribeIt took me a while to find a convenient way to link it up, but here’s how to get to the unsubscribe.
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My Merch ShopI’ve been adding so much stuff that I’ve decided to bundle it all in what I call a Merch Shop, because otherwise there’s literally too much to keep track of and I run out of space in my own newsletter. So welcome to the Merch Shop! Courses:
Books: Skills for Claude and Agentic AI:
Subscriptions: On The TubesHere’s what debuted on my YouTube channel this week:
Advertisement: New AI For Writers Course“It’s not X, it’s Y!” “XYZ is the load-bearing feature here.” “XYZ is the entire argument. Everything else is incidental.” Does AI writing grind your gears? When you use it at work and it spits out dreck despite your best efforts, does that frustrate you? It’s not your fault - and believe it or not, it’s not AI’s fault either. It’s that great writing is inherently low probability, and AI is a probability engine that trades in high probabilities. In the new Trust Insights AI for Writers Course, I teach you how to use tools, analysis, data, and code to force AI to write much more like you, giving it measurable requirements that it can obey to give you what you want - writing that doesn’t sound like the Terminator went on a bender with a thesaurus. The course is 22 lessons and includes tools, skills, plugins, and how to use them all to generate the kind of writing you’d want to read, and retails for USD 397. ✍️ Claim your seat here and start making AI write the way you expect. Get Back To Work!Folks who post jobs in the free Analytics for Marketers Slack community may have those jobs shared here, too. If you’re looking for work, check out these recent open positions, and check out the Slack group for the comprehensive list.
Disclosure: I source these links from LinkedIn every week on the following criteria: New in the past seven days, Easy Apply on, remote roles, USA geography. How to Stay in TouchLet’s make sure we’re connected in the places it suits you best. Here’s where you can find different content:
Listen to my theme song as a new single: Social Good: Ukraine ๐บ๐ฆ Humanitarian FundThe war to free Ukraine continues. If you’d like to support humanitarian efforts in Ukraine, the Ukrainian government has set up a special portal, United24, to help make contributing easy. The effort to free Ukraine from Russia’s illegal invasion needs your ongoing support. ๐ Donate today to the Ukraine Humanitarian Relief Fund » Events I’ll Be AtHere are the public events where I’m speaking and attending. Say hi if you’re at an event also:
There are also private events that aren’t open to the public. If you’re an event organizer, let me help your event shine. Visit my speaking page for more details. Can’t be at an event? Stop by my private Slack group instead, Analytics for Marketers. Required DisclosuresEvents with links have purchased sponsorships in this newsletter and as a result, I receive direct financial compensation for promoting them. Advertisements in this newsletter have paid to be promoted, and as a result, I receive direct financial compensation for promoting them. My company, Trust Insights, maintains business partnerships with companies including, but not limited to, Amazon, Talkwalker, MarketingProfs, Agorapulse, The Marketing AI Institute, Spin Sucks, and others. While links shared from partners are not explicit endorsements, nor do they directly financially benefit Trust Insights, a commercial relationship exists for which Trust Insights may receive indirect financial benefit, and thus I may receive indirect financial benefit from them as well. Thank YouThanks for subscribing and reading this far. I appreciate it. As always, thank you for your support, your attention, and your kindness. Please share this newsletter with two other people. See you next week, Christopher S. Penn Invite your friends and earn rewards
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