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In-Ear Insights: How to Manage Microsoft Copilot Cowork Costs
Jun 24, 2026
Unknown duration
In-Ear Insights: Enterprise AI 101
May 27, 2026
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In-Ear Insights: Setting up Agentic AI For Success Part 1, Job Descriptions
May 6, 2026
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In-Ear Insights: Updating Mental Models and Old Knowledge
Apr 15, 2026
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In-Ear Insights: AI And the Future of Work in 2026
Apr 8, 2026
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
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| 6/24/26 | ![]() In-Ear Insights: How to Manage Microsoft Copilot Cowork Costs | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the release of Microsoft Copilot Cowork and its hidden financial implications for your business. You’ll learn how to calculate potential costs by categorizing your daily tasks into light, medium, and heavy workloads. You’ll discover how to apply the 5P framework to prevent runaway AI spending in your organization. You’ll identify specific strategies to optimize your workflows by separating planning from execution. You’ll explore how command-line tools can help you maintain efficiency without burning through expensive credits. 00:00 – Introduction 03:15 – Categorizing AI tasks 08:45 – The shock of the credit-based bill 14:20 – Applying the 5P framework for cost control 19:10 – Using planning to save money 25:30 – Call to action Watch this episode now to learn how to keep your enterprise AI costs under control before you start using Microsoft Copilot Cowork. Use the free Trust Insights Microsoft Copilot Cowork Cost Calculator! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-how-to-manage-microsoft-copilot-cowork-costs.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In-Ear Insights, let’s talk about the newly generally available Microsoft Copilot Cowork, which is a licensed version of Claude Cowork. So Katie, you have spent a lot of time with Claude Cowork. You teach for Smarter X for their AI Academy on all the different uses of Claude Cowork. You’ll be doing an entire workshop at the Marketing AI conference on the Claude ecosystem and stuff like that. So when you hear that now Microsoft, the largest enterprise AI deployment system, has made effectively a copy of Claude Cowork available, what comes to mind? Katie Robbert: Endless opportunities. I have never met someone who is like, “Yay, Microsoft.” And we’ve talked about why a lot of companies are tied into Microsoft and a lot of it comes down to security and privacy. Chris, you have a whole series on enterprise AI, so enterprise AI not being the size of the company, but really more of the security and governance requirements needed. Microsoft as a workforce software, Microsoft 365, tends to check the most of those boxes, which is why so many large companies or companies in general tend to be tied into Microsoft. Which also means what we hear is, “Well, I can’t use Claude or I can’t use OpenAI, I can only use Copilot. I want all the bells and whistles that I’m seeing you guys talking about.” Very quick anecdote. My husband, who I’ve mentioned numerous times, is not a technology person—that is not the nature of his job—was lamenting that the new version of Microsoft is hiding all the replies to his emails from the entry-level user to the expert user. I don’t know anyone who enjoys using Microsoft, but I’m hoping now that this little bell and whistle is something that could bring people around on the users. Because Claude Cowork has been such a literal game changer for the way that I operate. The amount of things that I can get done that I couldn’t get done before because I’m just one person is infinite. Just the other day, I’ve always done the company financial projections—it’s very laborious. I have a spreadsheet, I have to check numbers from four or five different places. That’s something that Cowork can now not only help me with, but build an interactive dashboard for. And it’s lik | — | ||||||
| 5/27/26 | ![]() In-Ear Insights: Enterprise AI 101✨ | Enterprise AIAI strategy+4 | — | Microsoft CopilotTrust Insights | — | Enterprise AIAI strategy+5 | — | — | |
| 5/6/26 | ![]() In-Ear Insights: Setting up Agentic AI For Success Part 1, Job Descriptions✨ | agentic AIjob descriptions+4 | — | Trust Insights | — | agentic AIjob descriptions+4 | — | — | |
| 4/15/26 | ![]() In-Ear Insights: Updating Mental Models and Old Knowledge✨ | professional knowledgetechnology shifts+5 | — | agentic AITrust Insights | — | mental modelsknowledge decay+5 | — | — | |
| 4/8/26 | ![]() In-Ear Insights: AI And the Future of Work in 2026✨ | future of workartificial intelligence+4 | — | AITrust Insights | — | AIfuture of work+4 | — | — | |
| 3/25/26 | ![]() In-Ear Insights: Virtual Versions, Digital Twins, and AI Clones✨ | virtual versionsdigital twins+4 | — | digital twinAI clone+2 | — | digital twinAI clone+5 | — | — | |
| 3/18/26 | In-Ear Insights: Balancing Authenticity In An AI Automated World✨ | authenticityAI automation+5 | — | Trust Insights | — | AIautomation+5 | — | — | |
| 3/11/26 | ![]() In-Ear Insights: Measuring and Improving AI Proficiency✨ | AI proficiencymeasuring AI impact+4 | — | Trust Insights | — | AI proficiencyquality in AI+4 | — | — | |
| 3/4/26 | ![]() In-Ear Insights: Switching AI Providers, Backup AI Capabilities✨ | AI providersbusiness continuity+3 | — | OpenAIAnthropic+1 | — | AIbusiness continuity+5 | — | — | |
| 2/25/26 | ![]() In-Ear Insights: How to Turn Plans into Results✨ | planningexecution+3 | — | Trust InsightsAnalytics for Marketer Slack group+2 | — | Q1 plansgenerative AI+3 | — | — | |
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| 2/18/26 | ![]() In-Ear Insights: Cognitive Offloading, Deskilling, and The Impact of AI✨ | AIcognitive offloading+3 | — | Trust Insights | — | AIcognitive offloading+5 | — | — | |
| 2/11/26 | ![]() In-Ear Insights: Project Management for AI Agents✨ | Project ManagementAI Agents+3 | — | AI agentsTrust Insights+1 | — | AI managementproject management+3 | — | — | |
| 2/4/26 | ![]() In-Ear Insights: OpenClaw and Preparing for an Agentic AI Future✨ | autonomous AI agentsautomation+4 | — | OpenClawMaltbot+3 | — | autonomous AIautomation+4 | — | — | |
| 1/28/26 | ![]() In-Ear Insights: Durable Skills in the Agentic AI World | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the critical staffing decisions leaders must make in the age of autonomous AI. You will learn the four key options organizational leaders must consider when AI begins automating existing roles. You will identify which essential durable skills guarantee success for employees working alongside powerful new technologies. You will discover how to adjust your hiring strategy to find motivated, curious employees who excel in an AI-augmented environment. You will gain actionable management strategies for handling employees who need encouragement after repetitive tasks become automated. Tune in now to understand how AI changes the modern workforce and secure your company’s future talent. Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-durable-skills-in-age-of-agentic-ai.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In Ear Insights, one of the biggest questions that everybody has about AI, particularly as we’re seeing more automation capabilities, more autonomous capabilities. Last week we took a look at Claude Code, both on the Trust Insights podcast and on the live stream. Katie, you and I did some pretty cool stuff with it outside of that for our own company. Here’s the big question everybody wants an answer to—at least people who are in charge. And I want to hear your answer to this because I have an answer that’s a terrible answer. The answer is this. With the capabilities of AI today, and as they’re growing and becoming more autonomous, do I as a leader—do I hire, retrain, or outsource, or figure out the fourth category? Replace with AI? Hire, retrain, outsource, replace with AI. So, Katie, when you think about the people management at any company with that big 800-pound gorilla in the room called AI, how do you think about this? Katie Robbert: To borrow a phrase from Christopher S. Penn, it depends. And you knew I was going to say that. It really depends on what the responsibility is. So for those of us in the service industry—consulting—we have clients, customers. There’s still an expectation of human-to-human contact and relationship management, client services, really. So that I feel like unless that expectation goes away, which there’s a reason you’re in that industry in the first place, that I don’t see being able to replace. But then when you go behind the scenes, there’s a lot of tasks that can be automated, and that’s what you and I were working on at the end of last week. And so that to your question of, well, if the person is only just talking to the clients, why do I need someone full time? It really, again, it really | — | ||||||
| 1/21/26 | ![]() In-Ear Insights: Applications of Agentic AI with Claude Cowork | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the practical application of AI agents to automate mundane marketing tasks. You will define what an AI agent is and discover how this technology performs complex, multi-step marketing operations. You will learn a simple process for creating knowledge blocks and structured recipes that guide your agents to perform repetitive work. You will identify which tools, like your content scheduler or website platform, are necessary for successful, end-to-end automation. You will understand crucial data privacy measures and essential guardrails to protect your sensitive company information when deploying new automated systems. Tune in now to see how you can permanently eliminate hours of boring work from your weekly schedule! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-agentic-ai-practical-applications-claude-cowork.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In Ear Insights, one of the things that people have said, me especially, is that 2026 is the year of the agent. The way I define an agent is it’s like a real estate agent or a travel agent or a tax agent. It’s something that just goes and does, then comes back to you and says, “Hey, boss, I’m done.” Katie, you and I were talking before the show about there’s a bunch of mundane tasks, like, let’s write some evergreen social posts, let’s get some images together, let’s update a landing page. Let me ask you this: when you look at those tasks, do they feel repetitive to you? Katie Robbert: Oh, 100%. I’ve automated a little bit of it. And by that, what I mean is I have the background information about Trust Insights. I have the tone and brand guidelines for Trust Insights. So if I didn’t have those things, those would probably be the biggest lift. And so all I’m doing is taking all of the known information and saying, okay, let’s create some content—social posts, landing pages—out of all of the requirements that I’ve already gathered, and I’m just reusing over and over again. So it’s completely repetitive. I just don’t have that more automated repeatability where I can just push a button and say, “Go.” I still have to do the work of loading everything up into a single system, going through it piece by piece. What do I want? Am I looking at the newsletter? Am I looking at the live stream? Am I looking at this podcast? So there’s still a lot of manual that I know could be automated, and quite frankly, it’s not the best use of my time. But it’s got to get done. Christopher S. Penn: And so my question to you is, what | — | ||||||
| 1/14/26 | ![]() In-Ear Insights: Processing Survey Data With Generative AI | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss analyzing survey data using generative artificial intelligence tools. You will discover how to use new AI functions embedded in spreadsheets to code hundreds of open-ended survey responses instantly. You’ll learn the exact prompts needed to perform complex topic clustering and sentiment analysis without writing any custom software. You will understand why establishing a calibrated, known good dataset is essential before trusting any automated qualitative data analysis. You’ll find out the overwhelming trend in digital marketing content that will shape future strategies for growing your business. Watch now to revolutionize how you transform raw feedback into powerful strategy! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-processing-survey-data-with-generative-ai.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In Ear Insights, let’s talk about surveys and processing survey data. Now, this is something that we’ve talked about. Gosh, I think since the founding of the company, we’ve been doing surveys of some kind. And Katie, you and I have been running surveys of some form since we started working together 11 years ago because something that the old PR agency used to do a ton of—not necessarily well, but they used to do it well. Katie Robbert: When they asked us to participate, it would go well. Christopher S. Penn: Yes, exactly. Christopher S. Penn: And this week we’re talking about how do you approach survey analysis in the age of generative AI where it is everywhere now. And so this morning you discovered something completely new and different. Katie Robbert: Well, I mean, I discovered it via you, so credit where credit is due. But for those who don’t know, we have been a little delinquent in getting it out. But we typically run a one-question survey every quarter that just, it helps us get a good understanding of where our audience is, where people’s heads are at. Because the worst thing you can possibly do as business owners, as marketers, as professionals, is make assumptions about what people want. And that’s something that Chris and I work very hard to make sure we’re not doing. And so one of the best ways to do that is just to ask people. We’re a small company, so we don’t have the resources unfortunately to hold a lot of one-on-one meetings. But what we can do is ask questions virtually. And that’s what we did. So we put out a one-question survey. And in the survey, the question was around if you could pick a topic to deep dive on in 2026 to learn about, what would it be. Now keep in mind, I didn’t say ab | — | ||||||
| 1/7/26 | ![]() In-Ear Insights: What is Generative Engine Marketing (GEM)? | In this week’s In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss generative engine marketing, or GEM, the AI equivalent of SEM. Just as SEO became GEO, so too is SEM likely to become GEM. Learn what it is, how it might manifest, and what you should be considering. Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-what-is-generative-engine-marketing-sem-gem.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In-Ear Insights. Welcome back. Happy new year. It’s 2026. I have just begun to realize as I was cleaning out my pantry over the holidays, oh yeah, all these things expire in 2026. That’s this year. A lot happened over the holidays. A lot of changes in AI. But one thing that hasn’t happened yet but has been in discussion that I think is—Katie, you wanted to talk about—was SEO for good or ill, sort of centered on this GEO acronym, Generative Engine Optimization, and all of its brethren: AIO and AEO and whatever. SEO’s companion has always been SEM, also known as Pay Per Click marketing, and that has its alphabet soup like rlsa, remarketing lists for search ads, and all these acronyms, part of the paid version of search marketing. Well, Katie, you asked a very relevant… Katie Robbert: …question, which was, when is GEM coming? So as a little plug, I’m doing a Friday session with our good friends over at Marketing Profs on GEO and ROI, which I have to practice saying over and over again so I don’t stumble over it. But basically the idea is what can B2B marketers measure in GEO to demonstrate their return on investment so that they can argue for more budget. And so what we were talking about this morning is that GEO is really just an amped up version of brand search. If you know SEO, brand search is a part of SEO. And so basically it’s like how well recognized is my brand or my influencers or whatever. If I type in Katie Robbert or if I type in Trust Insights, what comes back? And so all of the same tactics that you do for branded search, you do for GEO plus a little bit more. So it’s the same end result, but you need to figure out sort of where all of that fits. So I’ll go over all of that. But it then naturally progressed into the conversation of, well, part of brand search is paid campaigns. You pay money to Google AdWords, if that’s still what it’s called, or whatever ad system you’re using, you put money behind your branded terms so that when someone’s looking for certain things, your name comes up. And I was like, well, that’s the SEM version of SEO. When are we getting the paid version of GEO? So basically GEM, or whatever you would want to call it, the way that I k | — | ||||||
| 12/17/25 | ![]() In-Ear Insights: 2025 Year In Review | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the massive technological shifts driven by generative AI in 2025 and what you must plan for in 2026. You will learn which foundational frameworks ensure your organization can strategically adapt to rapid technological change. You’ll discover how to overcome the critical communication barriers and resistance emerging among teams adopting these new tools. You will understand why increasing machine intelligence makes human critical thinking and emotional skills more valuable than ever. You’ll see the unexpected primary use case of large language models and identify the key metrics you must watch in the coming year for economic impact. Watch now to prepare your strategy for navigating the AI revolution sustainably. Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-2025-year-in-review.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s *In-Ear Insights*. This is the last episode of *In-Ear Insights* for 2025. We are out with the old. We’ll be back in January for new episodes the week of January 5th. So, Katie, let’s talk about the year that was and all the crazy things that happened in the year. And so what you’re thinking about, particularly from the perspective of all things AI, all things data and analytics—how was 2025 for you? Katie Robbert: What’s funny about that is I feel like for me personally, not a lot changed. And the reason I feel like I can say that is because a lot of what I focus on is foundational, and it doesn’t really matter what fancy, shiny new technology is happening. So I really try to focus on making sure the things that I do every day can adapt to new technology. And again, of course, that’s probably the most concrete example of that is the 5P framework: Purpose, People, Process, Platform for Performance. It doesn’t matter what the technology is. This is where I’m always going to ground myself in this framework so that if AI comes along or shiny object number 2 comes along, I can adapt because it’s still about primarily, what are we doing? So asking the right questions. The things that did change were I saw more of a need this year, not in general, but just this year, for people to understand how to connect with other people. And not only in a personal sense, but in a professional sense of my team needs to adopt AI or they need to adopt this new technology. I don’t know how to reach them. I don’t know where to start. I don’t know. I’m telling them things. Nothing’s working. And I feel like the technology of today, which is generative AI, is creating more barriers to communication than it is opening up communication channels. And so that’s a lot of where my head has bee | — | ||||||
| 12/10/25 | ![]() In-Ear Insights: What Are Small Language Models? | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss small language models (SLMs) and how they differ from large language models (LLMs). You will understand the crucial differences between massive large language models and efficient small language models. You’ll discover how combining SLMs with your internal data delivers superior, faster results than using the biggest AI tools. You will learn strategic methods to deploy these faster, cheaper models for mission-critical tasks in your organization. You will identify key strategies to protect sensitive business information using private models that never touch the internet. Watch now to future-proof your AI strategy and start leveraging the power of small, fast models today! Watch the video here: https://youtu.be/XOccpWcI7xk Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-what-are-small-language-models.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s *In-Ear Insights*, let’s talk about small language models. Katie, you recently came across this and you’re like, okay, we’ve heard this before. What did you hear? Katie Robbert: As I mentioned on a previous episode, I was sitting on a panel recently and there was a lot of conversation around what generative AI is. The question came up of what do we see for AI in the next 12 months? Which I kind of hate that because it’s so wide open. But one of the panelists responded that SLMs were going to be the thing. I sat there and I was listening to them explain it and they’re small language models, things that are more privatized, things that you keep locally. I was like, oh, local models, got it. Yeah, that’s already a thing. But I can understand where moving into the next year, there’s probably going to be more of a focus on it. I think that the term local model and small language model in this context was likely being used interchangeably. I don’t believe that they’re the same thing. I thought local model, something you keep literally locally in your environment, doesn’t touch the internet. We’ve done episodes about that which you can catch on our livestream if you go to TrustInsights.ai YouTube, go to the Soap playlist. We have a whole episode about building your own local model and the benefits of it. But the term small language model was one that I’ve heard in passing, but I’ve never really dug deep into it. Chris, in as much as you can, in layman’s terms, what is a small language model as opposed to a large language model, other than— Christopher S. Penn: Is the best description? There is no generally agreed upon definition other than it’s small. All language models are measured in terms of the number of tokens they were trained on and the number of parameters they have. Parameters are basically the number of combinations of tokens that they’v | — | ||||||
| 12/3/25 | ![]() In-Ear Insights: AI And the Future of Intellectual Property | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the present and future of intellectual property in the age of AI. You will understand why the content AI generates is legally unprotectable, preventing potential business losses. You will discover who is truly liable for copyright infringement when you publish AI-assisted content, shifting your risk management strategy. You will learn precise actions and methods you must implement to protect your valuable frameworks and creations from theft. You will gain crucial insight into performing necessary due diligence steps to avoid costly lawsuits before publishing any AI-derived work. Watch now to safeguard your brand and stay ahead of evolving legal risks! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-ai-future-intellectual-property.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn: In this week’s In Ear Insights, let’s talk about the present and future of intellectual property in the age of AI. Now, before we get started with this week’s episode, we have to put up the obligatory disclaimer: we are not lawyers. This is not legal advice. Please consult with a qualified legal expert practitioner for advice specific to your situation in your jurisdiction. And you will see this banner frequently because though we are knowledgeable about data and AI, we are not lawyers. We can, if you’d like, join our Slack group at Trust Insights, AI Analytics for Marketers, and we can recommend some people who are lawyers and can provide advice depending on your jurisdiction. So, Katie, this is a topic that you came across very recently. What’s the gist of it? Katie Robbert: So the backstory is I was sitting on a panel with an internal team and one of the audience members. We were talking about generative AI as a whole and what it means for the industry, where we are now, so on, so forth. And someone asked the question of intellectual property. Specifically, how has intellectual property management changed due to AI? And I thought that was a great question because I think that first and foremost, intellectual property is something that perhaps isn’t well understood in terms of how it works. And then I think that there’s we were talking about the notion of AI slop, but how do you get there? Aeo, geo, all your favorite terms. But basically the question is around: if we really break it down, how do I protect the things that I’m creating, but also let people know that it’s available? And that’s. I know this is going to come as a shocker. New tech doesn’t solve old problems, it just highlights it. So if you’re not protecting your assets, if you’re not filing for your | — | ||||||
| 11/12/25 | ![]() In-Ear Insights: Sales Frameworks Basics and AI | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss essential sales frameworks and why they often fail today. You will understand why traditional sales methods like Challenger and SPIN selling struggle with modern complex purchases. You will learn how to shift your sales focus from rigid, linear frameworks to the actual non-linear journey of the customer. You will discover how to use ideal customer profiles and strong documentation to build crucial trust and qualify better prospects. You will explore methods for leveraging artificial intelligence to objectively evaluate sales opportunities and improve your go/no-go decisions. Watch this episode to revolutionize your approach to high-stakes complex sales. Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-sales-frameworks-basics-and-ai.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. **Christopher S. Penn – 00:00** In this week’s In Ear Insights. Even though AI is everywhere and is threatening to eat everything and stuff like that, the reality is that people still largely buy from people. And there are certainly things that AI does that can make that process faster and easier. But today I thought it might be good to review some of the basic selling frameworks, particularly for companies like ours, but in general, to help with complex sales. One of the things that—and Katie, I’d like your take on this—one of the things that people do most wrong in sales at the very outset is they segment out B2B versus B2C when they really should be segmenting out: simple sale versus complex sales. Simple sales, a pack of gum, there are techniques for increasing number of sales, but it’s a transaction. **Christopher S. Penn – 00:48** You walk into the store, you put down your money, you walk out with your pack of gum as opposed to a complex sale. Things like B2B SaaS software, some versions of it, or consulting services, or buying a house or a college education where there’s a lot of stakeholders, a lot of negotiation, and things like that. So when you think about selling, particularly as the CEO of Trust Insights who wants to sell more stuff, what do you think about advising people on how to sell better? **Katie Robbert – 01:19** Well, I should probably start with the disclaimer that I am not a trained salesperson. I happen to be very good with people and reading the situation and helping understand the pain points and needs pretty quickly. So that’s what I’ve always personally relied on in terms of how to sell things. And that’s not something that I can easily teach. So to your point, there needs to be some kind of a framework. I disagree with your opening statement that the biggest problem people have with selling or the biggest mistake that people make is the segmentat | — | ||||||
| 11/5/25 | ![]() In-Ear Insights: Account Management in the Age of AI | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the essentials of excellent account management and how AI changes the game. You will discover how to transition from simply helping clients to proactively taking tasks off their to-do list. You will learn the exact communication strategies necessary to manage expectations and ensure timely responses that build client trust. You will understand the four essential executive functions you must retain to prevent artificial intelligence from replacing your critical role. You will grasp how to perform essential quality checks on deliverables even without possessing deep technical expertise in the subject matter. Watch now to elevate your account management skills and secure your position in the future of consulting! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-account-management-in-age-of-ai.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. **Christopher S. Penn – 00:00** In this week’s In Ear Insights, Trust Insights is a consulting firm. We obviously do consulting. We have clients, we have accounts, and therefore account management. Katie, you and I worked for a few years together at a PR firm before we started Trust Insights and managed a team of folks. I should clarify with an asterisk: you managed a team of people then to keep those accounts running, keep customers and clients happy, and try to keep team members happy. Let’s talk about what are the basics of good account management—not just for keeping clients happy, but also keeping your team happy as well, to the extent that you can, but keeping stuff on the rails. **Katie Robbert – 00:51** The biggest thing from my experience, because I’ve been on both sides of it—well, I should say there are three sides of it. There’s the account manager, there’s the person who manages the account manager, and then there’s the account itself, the client. I’ve been on all three sides of it, and I currently sit on the side of managing the account manager who manages the accounts. If we talk about the account manager, that person is trying to keep things on the rails. They’re trying to keep things moving forward. Typically they are the ones who, if they choose, they can have the most power, or if they don’t, they have the least power. **Katie Robbert – 01:38** By that I mean, a good account manager has their hands in everything, is listening to every conversation between the stakeholders or the principals and the client, is really ingesting the information and understanding, “Okay, this is what was asked for. This is what we’re working on. This is discussed.” Whatever it is they don’t understand, they take the initiative to find out what it means. If you’re working on | — | ||||||
| 10/29/25 | ![]() In-Ear Insights: How to Create Effective Reporting | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss effective reporting and creating reports that tell a story and drive action using user stories and frameworks. You will understand why data dumping onto a stakeholder’s desk fails and how to gather precise reporting requirements immediately. You will discover powerful frameworks, including the SAINT model, that help you move from basic analysis to crucial, actionable decisions. You will gain strategies for anticipating executive questions and delivering a clear, consistent narrative throughout your entire report. You will explore innovative ways to use artificial intelligence as a thought partner to refine your analysis and structure perfect reports. Stop wasting time and start creating reports that generate real business results. Watch now! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-how-to-create-effective-reporting.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn – 00:00 In this week’s In Ear Insights, it’s almost redundant at this point to say it’s reporting season, but as we hit quarterly ends, yearly ends, things like that, people become reflective and say, “Hey, let’s do some reports.” One of the problems that we see the most with reporting—and I was guilty of this for the majority of my career, particularly the first half—is when you’re not confident about your reporting skills, what do you do? You back the truck up and you pour data all over somebody’s desk and you hope that it overwhelms them so that they don’t ask you any questions, which is the worst possible way to do reporting. So, Katie, as a senior executive, as a leader, when someone delivers reporting to you, what do you get and what do you want to get? Katie Robbert – 00:51 Well, I would start to say reports, like the ones that you were generating, hate to see me coming. Because guess what I do, Chris, I ask a bazillion questions, starting with so what? And I think that’s really the key. As the CEO of Trust Insights, I need a report that tells me exactly what the insights and actions are so that I can do those things. And that is a user story. A user story is a simple three-part sentence: As a Persona, I want so that. If someone is giving me a report and they haven’t asked me for a user story, that’s probably step one. So, Chris, if I say, “All right, if you can pull the monthly metrics, Chris, and put it into a report, I would appreciate it.” Katie Robbert – 01:47 If I haven’t given you a user story, you need to ask me what it is, because that’s the “so what?” Why are we doing this in the first place? We have no shortage of data points. We have no shortage of informat | — | ||||||
| 10/22/25 | In-Ear Insights: Generative AI for Marketers at MAICON 2025 | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the stark reality of the future of work presented at the Marketing AI Conference, MAICON 2025. You’ll learn which roles artificial intelligence will consume fastest and why average employees face the highest risk of replacement. You’ll master the critical thinking and contextual skills you must develop now to transform yourself into an indispensable expert. You’ll understand how expanding your intellectual curiosity outside your specific job will unlock creative problem solving essential for survival. You’ll discover the massive global AI blind spot that US companies ignore and how this shifting landscape affects your career trajectory. Watch now to prepare your career for the age of accelerated automation! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-maicon-2025-generative-ai-for-marketers.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn – 00:00 In this week’s In Ear Insights, we are at the Marketing AI Conference, Macon 2025 in Cleveland with 1,500 of our best friends. This morning, the CEO of SmartRx, formerly the Marketing AI Institute, Paul Ritzer, was talking about the future of work. Now, before I go down a long rabbit hole, Dave, what was your immediate impressions, takeaways from Paul’s talk? Katie Robbert – 00:23 Paul always brings this really interesting perspective because he’s very much a futurist, much like yourself, but he’s a futurist in a different way. Whereas you’re on the future of the technology, he’s focused on the future of the business and the people. And so his perspective was really, “AI is going to take your job.” If we had to underscore it, that was the bottom line: AI is going to take your job. However, how can you be smarter about it? How can you work with it instead of working against it? Obviously, he didn’t have time to get into every single individual solution. Katie Robbert – 01:01 The goal of his keynote talk was to get us all thinking, “Oh, so if AI is going to take my job, how do I work with AI versus just continuing to fight against it so that I’m never going to get ahead?” I thought that was a really interesting way to introduce the conference as a whole, where every individual session is going to get into their soldiers. Christopher S. Penn – 01:24 The chart that really surprised me was one of those, “Oh, he actually said the quiet part out loud.” He showed the SaaS business chart: SaaS software is $500 billion of economic value. Of course, AI companies are going, “Yeah, we want that money. We want to take all that money.” But then he brought | — | ||||||
| 10/15/25 | ![]() In-Ear Insights: How to Make Conferences Worth the Investment | In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the worth of conferences and events in a tight economy. You will learn a powerful framework for evaluating whether an expensive conference ticket meets your specific professional goals. You will use generative artificial intelligence to score event agendas, showing you which sessions offer the best return on your time investment. You will discover how expert speakers and companies create tangible value, moving beyond vague thought leadership to give you actionable takeaways. You will maximize your event attendance by demanding supplementary tools, ensuring you retain knowledge long after you leave the venue. Watch this episode now to stop wasting budget on irrelevant professional events! Watch the video here: Can’t see anything? Watch it on YouTube here. Listen to the audio here: https://traffic.libsyn.com/inearinsights/tipodcast-how-to-make-conferences-worth-the-investment.mp3 Download the MP3 audio here. Need help with your company’s data and analytics? Let us know! Join our free Slack group for marketers interested in analytics! [podcastsponsor] Machine-Generated Transcript What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for listening to the episode. Christopher S. Penn – 00:00 In this week’s *In Ear Insights*, let’s talk about events, conferences, trade shows, workshops—the gamut of things that you could get up from your desk maybe, go somewhere else, eat hotel chicken, and enjoy speaking. The big question is this, Katie: In today’s absolutely loony environment, with the economic uncertainty and the budgets and all this and that, are events still worth it? This is a two-part question: Are events still worth it for the attendees, and are events still worth it for companies that want to generate business from events? Katie Robbert – 00:50 It’s a big question. And if our listeners are anything like me, it takes a lot to get them to put on real pants and actually leave the house—something that isn’t sweatpants or leggings or something like that—because you’re spending the time, the resources, the money to go out and actually interact with other people. In terms of an attendee, I think there can be a lot of value, provided you do your homework on who the speakers are, what their expertise is, what they’re promising to teach you in the workshop or the session or whatever the thing is. The flip side of that is it can be worth it for a speaker, provided you know who your audience is, you can create an ICP, and provided you are giving value to the audience. Katie Robbert – 01:54 So if you’re a speaker who has made their whole career on big ideas and thought leadership and all that’s fine, people have a hard time buying something from that and saying, “I know exactly what it is I need to do next.” So there is a time and place for those speakers. But for an attendee to really get value, you need to teach them something. You need to show them how to be very tactical, be very hands-on. That’s where an | — | ||||||
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