INBOX INSIGHTS, September 10, 2025: You Get What You Pay For, Small Data Breaches - Trust Insights Marketing Analytics Consulting

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INBOX INSIGHTS: You Get What You Pay For, Small Data Breaches (2025-09-10)

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You Really Do Get What You Pay For

Last week, my dog walker spent exactly ten minutes with my dog. She took her outside, gave her quality attention, checked her water, and headed out. The bill? $25.

For a moment, I felt that familiar sticker shock. Twenty-five dollars for ten minutes of work? That math made my brain hurt a little. But then I stepped back and reconsidered what I was actually paying for.

I’m paying for her experience with large breeds who can be… enthusiastic. Georgia is overly enthusiastic at times and 150 lbs of muscle. I’m paying for her background in pet safety and emergency care. I’m paying for the peace of mind that comes from knowing my dog is with someone I trust completely—someone who won’t panic if something goes wrong.

In other words, I’m paying for expertise. And you know what? It’s reassuringly expensive.

The “Reassuringly Expensive” Principle

My business partner Chris has this phrase about sushi being “reassuringly expensive.” When you’re about to eat raw fish, you don’t want the cheapest option on the menu. You want confidence that someone with serious skills prepared your meal, that the ingredients are top-quality, and that the restaurant follows strict safety protocols.

The price tag becomes a reliable signal of quality, care, and expertise.

This principle applies far beyond sushi or pet care. Right now, it’s especially relevant in the world of business consulting and digital transformation. (And trust me, I’ve seen enough transformation projects go sideways to know the difference good expertise makes.)

The AI Expert Explosion (And Why You Should Be Cautious)

Here’s what’s happening in the market right now: Everyone is suddenly an “AI expert.” People who discovered ChatGPT a few months ago are now offering consulting services on artificial intelligence strategy. The market is flooded with inexpensive options and overnight experts.

I get the appeal of a bargain—who doesn’t love saving money? But when you’re making decisions that could transform your entire organization, the discount option carries some serious risk.

What Makes Something Worth the Investment

When I’m evaluating any service or expertise (and I’ve done this more times than I care to count), here’s what justifies a higher investment:

Time and Experience

Years of trial and error, with real lessons learned from failures
Pattern recognition that comes from seeing similar challenges across multiple organizations
The ability to anticipate obstacles before they derail your project (this one’s huge)

Proven Track Record

Documented results with real companies facing real challenges
Case studies that demonstrate depth beyond surface-level success stories
References who will actually pick up the phone and give you honest feedback

Depth of Knowledge

Understanding of fundamental principles, not just whatever’s trending this month
Ability to adapt strategies when technology evolves (because it absolutely will)
Strategic thinking that connects tools to measurable business outcomes

Ongoing Support

Confidence that your investment will deliver lasting value
Someone who will tell you honestly what won’t work for your specific situation
Available guidance when implementation gets complicated (not if, when)

Why Our Course Represents Strategic Value

I’m going to be direct here: our new digital transformation course carries a significant price tag. And frankly, that makes me a little uncomfortable to talk about. But that investment reflects something specific.

We’re not teaching you how to use AI tools—I’m not an AI expert, and I don’t pretend to be. What we’re teaching is how to prepare your organization for digital transformation, whether that involves AI or whatever technology comes down the pipeline next.

This distinction matters because tools change rapidly. I’ve watched countless “revolutionary” technologies come and go. But the fundamentals of process optimization, team dynamics, and organizational change management? Those stay remarkably consistent.

I’ve spent over twenty years working in process optimization, operations, team building, and organizational behavior. I’ve watched companies succeed spectacularly and fail miserably at transformation projects. I’ve made my share of mistakes, learned from them (sometimes the hard way), and developed systems that consistently deliver results.

That experience—those sometimes painful lessons—represents the real value of the investment.

The Reality of True Expertise

Here’s something that genuinely makes me squirm: I really don’t like calling myself an “expert.” The word feels presumptuous, even after two decades doing this work.

But I am confident in my experience. The systems I’ve developed and refined. The patterns I’ve learned to recognize. The mistakes I’ve made and (hopefully) won’t make again. The organizations I’ve successfully helped transform.

This knowledge didn’t just appear overnight. It’s the result of years of focused work, continuous refinement, and plenty of learning moments that weren’t exactly fun at the time.

Your Strategic Evaluation Framework

The next time you’re considering any significant service investment, use this evaluation process (I wish I’d had this checklist years ago):

Assess the True Value

What exactly am I purchasing? (Skills, experience, peace of mind, or simply a low price?)
What’s their documented track record with challenges similar to mine?
How long have they been doing this specific type of work?
What support do they provide when implementation gets messy?

Questions to Ask Any “Expert”

Before making your decision, ask potential consultants or service providers these specific questions. Their responses will tell you everything you need to know:

Experience and Background

“Can you walk me through three specific projects similar to mine and the actual results you achieved?”
“What’s the biggest mistake you’ve made in this type of project, and what did you learn from it?”
“How long have you been doing this exact type of work?” (Not adjacent work—this specific expertise)

Approach and Methodology

“What’s your process for projects like mine, and how do you handle unexpected challenges?”
“Can you provide references from clients who faced similar challenges to ours?”
“What would you need to learn about our organization before proposing a solution?”

Ongoing Value

“How do you ensure the changes stick after the project ends?”
“What ongoing support do you provide during implementation?”
“What would you tell me if you thought your solution wasn’t right for our situation?”

Pay attention not just to their answers, but to their confidence level, specificity, and willingness to discuss failures and limitations. The best consultants I’ve worked with are refreshingly honest about what didn’t work.

The Bottom Line

Sometimes the most expensive option isn’t the best choice. But often, a higher price reflects genuine value: proven experience, documented results, and the confidence that comes from working with someone who has been doing this work long enough to know what actually works (and what doesn’t).

Your business transformation is too important to entrust to the lowest bidder. Look for the option that’s reassuringly expensive—where the price reflects real value, proven experience, and the peace of mind that comes from working with someone who has the depth to guide you through the inevitable challenges.

The right investment in expertise today can save you significantly more in avoided mistakes, faster implementation, and sustainable results. (And fewer late-night calls wondering why nothing is working the way it’s supposed to.)

What are you willing to invest in experts? Reply to this email or join our free Slack group, Analytics for Marketers.

Interested in learning more about our new AI-Ready Strategist Course? Sign up at trustinsights.ai/aistrategycourse

– Katie Robbert, CEO

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In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss how to identify a true AI expert amidst a crowded market.

You will discover the crucial difference between someone who knows what to do when things go right and a real expert who navigates challenges when things go wrong. You’ll learn key questions to ask and red flags to watch for when evaluating potential partners for your AI initiatives. You will understand how to assess value beyond just cost, ensuring your investment leads to sustainable results. You’ll gain confidence in making informed decisions, protecting your projects from inexperienced advice and costly mistakes. Tune in to empower your strategic choices and find the right expertise for your business.

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In this week’s Data Diaries, let’s talk about cheerleaders and data breaches.

My wife and I often take our dog for a walk in the local parks and ball fields, especially on the weekends when school isn’t in session and it’s not as busy. We’re members of the local “Keep {City} Beautiful”, so you’ll often find me walking around with one of those long handled claw devices to pick up trash from the ground.

This past weekend, we found a binder in the dugout of one of the baseball fields along with copious used water bottles. Upon closer inspection, it said Fall Cheerleading 2025 on it. Around the binder was its contents, scattered a bit.

On closer inspection, I looked in horror at what I had found. Yes, there were some cheerleading cheers and formations and things of no particular interest to me. But amidst that pile of papers were the medical records of every member of the local high school cheerleading squad, along with their names, dates of birth, contact information, home address, parents and guardians, their prescrptions and allergies, their medical conditions and disabilities, you name it.

It was the physical embodiment of the second worst kind of data breach: protected health information.

In the world of data security there are five levels of data sensitivity and privacy:

Public: non-protected information like published blog posts
Sensitive: basic PII (personally identifying information), business information like emails, proposals, etc.
Confidential: information like trade secrets, source code, things that could cause real economic damage
Restricted: protected health information (PHI), GDPR-protected data, account numbers, things that could cause not only economic damage but real harm
Classified: government and government adjacent secrets, the kind of data that usually leads to jail time if you’re caught with it

That binder of information fell under level 4, restricted information. That information, if it fell in the wrong hands, would cause serious economic and even physical harm to the people whose data was compromised.

On Monday, once school reopened and cheerleading practice was back in session, we walked the binder back over to the cheerleading coach and told them what we had found, including the condition it was found. It took a good ten minutes of explaining what a data breach even was for them to understand, at least partially, the consequences of what had happened. Every student on that cheerleading squad whose information was in that binder needs to be notified and their parents notified. They need to be on the lookout for things like identity fraud and other data related criminal activity.

The key takeaway from this story is that data breaches don’t have to be big and don’t have to be caused by large corporations for there there to be real, serious, lasting harm to individuals – especially students, children in our care. We all have an obligation to protect the data we are entrusted with, whether we’re a Fortune 10 or the local cheerleading squad.

This is doubly important in the age of AI when it seems like people just put whatever data they want into AI tools with nary a look at the privacy policy or terms of service on those tools. Where is your data going? How well cared for is it? What policies and procedures are in place to deal with the data breach if it happens?

The best time to consider this was when you first came into receipt of the data. The second best time is now.

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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