INBOX INSIGHTS, September 24, 2025: AI Skills Training, Process Documentation with AI - Trust Insights Marketing Analytics Consulting

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INBOX INSIGHTS: AI Skills Training, Process Documentation with AI (2025-09-24)

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How to Advocate for AI Skills Training

Today, let’s answer a reader question: “How do we convince executives and enablement leaders to invest in improving AI skills across the workforce?”

This is happening in organizations everywhere—executives are investing in AI technology while completely neglecting the human side of the equation. They love AI in theory, but they’re often blind to the fact that their people don’t know how to actually use it effectively.

Start with the Business Case, Not the Technology

When I work with teams trying to get executive buy-in for AI training, I tell them to flip their approach entirely. Don’t start with “We need AI skills training.” Start with “Here’s how our current skill gaps are costing us money and opportunities.”

Use the 5P Readiness Assessment from the AI Strategy Kit to document exactly where your team stands. This assessment evaluates your organization’s readiness across five critical dimensions: Purpose, People, Process, Platform, and Performance. When you can show leadership that 60% of your marketing team scores below a 3 on AI literacy, and connect that to slower campaign development or missed optimization opportunities, suddenly you’re speaking their language.

Connect Skills to Strategic Objectives

The Goal Alignment Worksheet is perfect for this. This tool helps you map your AI initiatives directly to specific business objectives, ensuring every AI investment has a clear strategic purpose. Take your organization’s current strategic priorities and map them against your team’s AI capabilities. If your company wants to increase personalization by 40% this year, but your team doesn’t know how to implement AI-driven content optimization, that’s a problem executives can understand.

For this, I recommend creating a simple visual (like a matrix) showing what your organization wants to achieve, what AI skills are required to get there, and where your current gaps exist. Make it visual. Make it obvious.

Quantify the Opportunity Cost

Nothing gets executive attention like lost revenue potential. Use the ROI Calculator to project what improved AI skills could deliver. This tool helps you quantify both the financial investment and expected returns from AI initiatives, translating operational improvements into dollars and cents. For example, if better prompt engineering could reduce content creation time by 30%, calculate what that means in terms of output capacity and cost savings.

But don’t stop there. Also calculate the cost of doing nothing. How much business could you lose to competitors who are leveraging AI more effectively? What opportunities are you missing because your team lacks the skills to execute?

Present a Phased Roadmap, Not a Wishlist

Executives hate open-ended training requests that feel like education for education’s sake. Instead, use the 12-Month AI Marketing Roadmap Template to show how skills development directly supports business milestones. This template helps you sequence AI initiatives across quarters while addressing all dimensions of successful implementation—from people development to platform integration.

Quarter 1 might focus on foundational prompt engineering tied to improving campaign development speed. Quarter 2 could tackle data analysis skills needed for better audience segmentation. Each phase should have clear business outcomes attached.

Address the Real Resistance Points

Let me be honest about what’s really happening in those executive meetings. Leaders are worried about training costs, time away from “real work,” and whether people will actually apply what they learn. They know you need the training, and they want you to have it. They are struggling to figure out how to make it work. This is where you can help. You need to address these concerns head-on.

Show them how the TRIPS framework can help prioritize where AI training will have the highest impact. TRIPS evaluates potential AI use cases across five factors: Time consumed, Repetition, Importance, Pain points, and Sufficient data availability. Demonstrate that you’re not asking for generic AI education, but targeted skill development that directly improves processes they care about.

Make it About Competitive Advantage

Frame AI skills as competitive intelligence. When your team can effectively use AI for market analysis, content optimization, and campaign performance prediction, you’re not just keeping up with competitors—you’re potentially leaping ahead of them.

The bottom line is this: executives will invest in AI skills when they see the direct connection between those skills and business results. Your job isn’t to convince them AI is important. Your job is to show them exactly how AI skills translate into the outcomes they’re already trying to achieve.

Stop asking for a training budget and start presenting skill development as the missing piece of their strategic puzzle. That’s when you’ll get their attention—and their investment.

Click here to get your free copy of the AI-Ready Marketing Strategy Kit

How are you making the case for more AI training? Reply to this email or join our free Slack group, Analytics for Marketers.

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In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss whether awards still matter in today’s marketing landscape, especially with the rise of generative AI.

You will understand how human psychology and mental shortcuts make awards crucial for decision-making. You will discover why awards are more relevant in the age of generative AI, influencing search results and prompt engineering. You will learn how awards can differentiate your company and become a powerful marketing tool. You will explore new ways to leverage AI for award selection and even consider creating your own merit-based recognition. Watch this episode now to redefine your perspective on marketing accolades!

Watch/listen to this episode of In-Ear Insights here »

Last time on So What? The Marketing Analytics and Insights Livestream, we analyzed our YouTube data with generative AI. Catch the episode replay here!

This week on So What?, we’ll be tackling a walkthrough of Microsoft Copilot. Are you following our YouTube channel? If not, click/tap here to follow us!

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In this week’s Data Diaries, let’s talk about breaking down a process. This is something that Katie advises all the time in things like our AI-Ready Strategist Course. One of my favorite tricks for doing this is, unsurprisingly, to use AI. Here’s how.

First, open the voice memos app or voice transcription app of your choice. It can be the free one on your phone – almost every phone has one. You can also use paid tools like Fireflies, Otter, etc. or even have a meeting by yourself in Zoom, Google Meet, etc. that can transcribe what you’re saying.

Talk through the process in question. Here’s a simple example from my morning routine:

Here’s my startup process for figuring out what content I’m gonna write on LinkedIn every day. First I go to LinkedIn and I scroll through my home feed for about three minutes. There’s some people I check in on, always, to see if there’s anything I need to repost from them, like any of the Trust Insights team. And then I look at the people I follow and see what it is that they’re writing about for the day. I also look at the suggested posts. What I’m specifically looking for are things that piss me off, especially around AI. Once I’ve found a post or two that I have something useful to contribute to, I then hop into my text editor, Joplin, and draft two to three really rough ideas using SuperKeet, my voice to text app. I write out the ideas and then toss them to generative AI, typically Gemini, and ask it to challenge my ideas and point out where I might be wrong. After a couple of rounds of adversarial debate, I finish writing the post and I post it. I then move the post to my queue folder for an AI agent to pick up and post to my WordPress blog automatically.

This process documentation alone is valuable, but next I take it to the best coding AI that I have access to – and it varies as time goes on, currently it’s Claude Opus 4.1 – and ask it to create a mermaid.js diagram. Here’s the prompt:

You’re a process optimization expert skilled at process flow diagrams. From this transcript, using Mermaid.js, create a process diagram that clearly illustrates the process. Diagram out the process; if something is unclear or you think information is missing, ask me to provide it. Be specific and clear so I know how to help you complete the diagram. Render the Mermaid.js code in the Canvas.

Here’s what it comes back with:

Now I’ve got the process documented in an easy to see fashion. What happens next?

One of the things that I do most wrong in documentation is that I forget things. There’s stuff I do that’s implicit or there’s stuff that I do that I forget about. By turning it into a process flow like this, I can see what’s logically missing.

Generative AI will also highlight things that are not apparent. Here’s what Claude had to say about my workflow:

Decision criteria: When you’re looking for posts that “piss you off,” what happens if you don’t find any on a given day? Do you have alternative triggers or do you skip content creation that day?
Reposting process: When you repost Trust Insights team content, is that a separate workflow or does it also go through the same writing/editing process?
AI debate rounds: How many rounds of debate typically happen with Gemini? Is there a specific threshold or criteria for when you consider the debate “complete”?
Content selection: Do you always respond to exactly 1-2 posts, or might you sometimes do more/fewer? What determines this number?
Quality checks: Is there any review or editing step between finishing the post and publishing to LinkedIn, or do you post immediately after the AI debate? WordPress posting: Does the AI agent post immediately or is there a schedule/timing component?

From here, I could provide new answers or refine my workflow, or I might just tell it nope, go with what we’ve got.

The key takeaway is that generative AI can be an incredible thought partner for clarifying our processes and understanding better what it is that we do and how we do it. Rather than suffer through trying to clarify our own thinking, we can use it as partner, critic, and adversary so that we understand best what it is that we do and clearly communicate it to others.

Almost every AI course is the same, conceptually. They show you how to prompt, how to set things up – the cooking equivalents of how to use a blender or how to cook a dish. These are foundation skills, and while they’re good and important, you know what’s missing from all of them? How to run a restaurant successfully. That’s the big miss. We’re so focused on the how that we completely lose sight of the why and the what.

This is why our new course, the AI-Ready Strategist, is different. It’s not a collection of prompting techniques or a set of recipes; it’s about why we do things with AI. AI strategy has nothing to do with prompting or the shiny object of the day — it has everything to do with extracting value from AI and avoiding preventable disasters. This course is for everyone in a decision-making capacity because it answers the questions almost every AI hype artist ignores: Why are you even considering AI in the first place? What will you do with it? If your AI strategy is the equivalent of obsessing over blenders while your steakhouse goes out of business, this is the course to get you back on course.

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