INBOX INSIGHTS, June 18, 2025: When AI-First Goes Wrong Part 4, Helping AI Read Text with Markdown

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INBOX INSIGHTS: When AI-First Goes Wrong Part 4, How to Help AI Read Spreadsheets (2025-06-18)

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How to Build AI Partnerships That Actually Work: Your Implementation Roadmap

If you missed our analysis in Parts 1-3, catch up here. This week: your step-by-step roadmap to AI implementation that enhances human capability rather than replacing it.

After three parts analyzing what goes wrong, it’s time to build something better. Here’s your systematic approach to creating AI partnerships that make your organization stronger.

The 12-Month AI Partnership Roadmap

Based on Trust Insights’ proven methodology, successful AI implementation follows a structured quarterly approach that builds organizational capability while delivering measurable results.

Quarter 1: Foundation Building

Focus: Data and Purpose Alignment Your Key Actions:

Complete TRIPS analysis to identify high-impact use cases
Establish clear business objectives for each AI initiative
Conduct comprehensive data quality assessment
Build internal AI literacy through targeted training programs

What Success Looks Like: You have a prioritized list of AI opportunities, clean baseline data, and a team that understands how AI will enhance their work rather than replace it.

Quarter 2: Partnership Development

Focus: Human-AI Collaboration Design Your Key Actions:

Design workflows where AI handles initial tasks, humans add expertise
Establish quality standards and review processes
Launch pilot projects with AI advocates and skeptics
Create feedback loops for continuous improvement

What Success Looks Like: Small teams are successfully using AI tools to become more effective, with clear processes for human oversight and enhancement.

Quarter 3: Capability Scaling

Focus: Expansion and Integration Your Key Actions:

Scale successful pilots to broader teams
Integrate AI tools with existing martech systems
Develop advanced AI skills among power users
Establish governance guidelines for AI usage

What Success Looks Like: AI is integrated into daily workflows, people see measurable improvements in their work quality, and you have clear protocols for managing AI systems.

Quarter 4: Optimization and Evolution

Focus: Performance and Future Planning Your Key Actions:

Analyze ROI and organizational impact
Optimize human-AI collaboration based on learnings
Plan advanced AI capabilities for year two
Document best practices and lessons learned

What Success Looks Like: AI has become a natural part of how your team works, with measurable business impact and excited employees who see AI as their competitive advantage.

The 5P Implementation Framework

Each quarter should address all five elements of Trust Insights’ 5P framework:

Purpose: Clear connection between AI capabilities and business outcomes
People: Skills development, change management, and stakeholder engagement
Process: Workflow design, governance, and continuous improvement
Platform: Technology selection, integration, and infrastructure
Performance: Measurement, optimization, and ROI validation

Your 30-Day Quick Start

Want to begin immediately? Here’s your first month:

Days 1-7: Define your AI partnership value proposition using the Goal Alignment Worksheet
Days 8-14: Identify AI champions and conduct TRIPS scoring for potential use cases
Days 15-21: Design your first human-AI workflow with willing team members
Days 22-30: Launch pilot project and establish measurement framework

Building Sustainable AI Partnerships

The goal isn’t just AI adoption—it’s creating teams where humans and AI make each other better.

Successful partnerships look like:

Content teams using AI for research and drafts, then adding cultural expertise and strategic insight
Sales teams leveraging AI for data analysis while focusing human time on relationship building
Customer service using AI for information gathering while humans handle complex problem-solving
Marketing teams deploying AI for campaign optimization while humans drive creative strategy

The mindset shift: From “Can AI do this task?” to “How can AI help our people do this task better?”

Warning Signs vs. Success Signals

You’re building it wrong if:

People are worried about job security
Quality is declining despite automation
AI decisions can’t be explained or reviewed
Teams are working around AI tools instead of with them

You’re building it right when: – People are excited to try new AI capabilities – Work quality improves alongside efficiency – Domain experts are teaching AI systems – Innovation increases because routine work is streamlined

Get the Complete Implementation Framework

This roadmap overview gives you the strategic approach, but successful implementation requires detailed templates, checklists, and frameworks.

Download our complete AI-Ready Marketing Strategy Kit for:

Detailed quarterly planning templates
TRIPS scoring worksheets for opportunity assessment
5P implementation checklists
ROI calculation frameworks
Vendor evaluation criteria
Performance tracking templates

The kit provides everything you need to move from AI confusion to AI confidence.

Your First Step

Don’t wait for perfect conditions. Start with one small AI partnership this week:

Choose a willing team member
Identify one routine task that could benefit from AI assistance
Design a simple workflow where AI provides input and humans add value
Measure both efficiency and quality improvements

The companies that master AI won’t be the ones with the most sophisticated technology. They’ll be the ones that figure out how to make their people more capable, creative, and valuable.

Your organization can be the example others follow instead of the cautionary tale they avoid.

Next week in Part 5: Putting it all together – the organizational behaviors that separate AI success stories from AI disasters.

What is your first AI partnership going to be?

Reply to this email to tell me, or come join the conversation in our free Slack Group, Analytics for Marketers.

– Katie Robbert, CEO

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In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss the generative AI sophomore slump.

You will discover why so many businesses are stuck at the same level of AI adoption they were two years ago. You will learn how anchoring to initial perceptions and a lack of awareness about current AI capabilities limits your organization’s progress. You will understand the critical difference between basic AI exploration and scaling AI solutions for significant business outcomes. You will gain insights into how to articulate AI’s true value to stakeholders, focusing on real world benefits like speed, efficiency, and revenue. Tune in to see why your approach to AI may need an urgent update!

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

Last time on So What? The Marketing Analytics and Insights Livestream, we walked through transforming content types with generative AI. Catch the episode replay here!

This week on So What?, we’re starting our Summer Makeover series with podcast transcription and cleanup. Are you following our YouTube channel? If not, click/tap here to follow us!

Here’s some of our content from recent days that you might have missed. If you read something and enjoy it, please share it with a friend or colleague!

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In this week’s Data Diaries, let’s talk about another AI data format. Previously, we talked about how to convert CSV files (tables) into JSON (written language) to help AI better and more easily understand what our data means.

Document structure is something AI tools have been trained to recognize, so the more structured and formatted our documents, the easier it is for them to understand our intentions. Putting things in lists helps not only humans read data, but also AI.

Today, the gold standard for document structure is a format called Markdown. Markdown is a way to create structure within text, such as headings, subheadings, bold, italics, lists, and other forms of text markup. Unlike other formatting, however, Markdown is written in plain text itself.

Here’s an example. To make text bold in Markdown, we just use the plain text two asterisks in a row before and after the text:

**bold**

This tells a Markdown-aware application to render the text in a bold font.

Many popular tools like Hemingway, Joplin, and others can also read and write Markdown natively – but the secret is, any text file reader can read Markdown, because it’s just plain text. That in turn means your documents in Markdown will be readable in decades to come because there’s no proprietary, special format. It’s just plain text.

AI language models like the ones that power ChatGPT often will spit out Markdown as their native format. It’s the text format that’s easiest for them to understand – and as such, it can lend additional emphasis and structure to our documents.

If we want AI tools to most easily recognize our text and what we intend, formatting our documents as Markdown is the best way to do that. Markdown also saves space; PDF files can be 3-5 times as large as the same equivalent document in Markdown because it’s just plain text.

Want to convert a document into Markdown in a low-tech way? Load your document into Google Docs, go to the Download menu, and choose Markdown. It’ll make a Markdown file of your text. You can then drag and drop that Markdown file into a tool like ChatGPT or Claude and it’ll understand it – and better, it’ll recognize and understand the structure of your document easily, helping it generate better, more precise results.

Here’s a roundup of who’s hiring, based on positions shared in the Analytics for Marketers Slack group and other communities.

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Imagine a world where your marketing strategies are supercharged by the most cutting-edge technology available – Generative AI. Generative AI has the potential to save you incredible amounts of time and money, and you have the opportunity to be at the forefront. Get up to speed on using generative AI in your business in a thoughtful way with our workshop offering, Generative AI for Marketers.

Workshops: Offer the Generative AI for Marketers half and full day workshops at your company. These hands-on sessions are packed with exercises, resources and practical tips that you can implement immediately.

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