The "Anti-AI" Prompt: How to Force AI to Write Content That Actually Sounds Human

 

In a nutshell (TL;DR)...

Audiences are exhausted by generic, AI-generated text filled with corporate fluff and predictable clichés. To create a standout blog post, stop using vague tone adjectives like "friendly yet professional." Instead, use advanced prompting techniques—like stylistic constraints, linguistic profiling, and strict word bans—to force the AI to write with the variance, grit, and authenticity of a human author.

I have this feeling that we are entering into a new phase of "AI Fatigue"...

I wanted to find out if the concept of “prompt writing” or “prompt engineering” has changed somewhat since I started this blog in January 2026. I’ve read so many emails, posts and articles that I can start to see the signs of AI generated content by the first two sentences. I mean, it’s no secret that parts of my blog posts are generated by AI, but I do re-write huge swathes of it, either to make it more readable and it also helps me understand the research I’ve done too.

AI generated content tends to be grammatically perfect (with lots of inexplicable em dashes), flawlessly structured, but feels entirely devoid of life. It’s full of cliches like "delving deep," things being a "testament to innovation," and reminders that we live in a "fast-paced digital landscape." 

When every brand uses the exact same base models to generate content, the entire internet starts to sound like a mid-level corporate PR brochure.

If you want your blog to stand out, you have to actively break the AI's default habits. The secret isn't giving up on AI; it's changing how you prompt it.

The Problem with Vague Adjectives

When most people want a blog post to sound better, they stuff their prompt with descriptive adjectives:

"Write a fun, engaging, professional, but casual blog post about e-commerce trends."

To a Large Language Model (LLM), this is contradictory noise. The AI averages out those words and reverts to its safest, most sterilized default settings. Human writers don't write by thinking about adjectives. They have their own unique pacing, specific way of saying things, and stylistic nuances that make them, them. To get human-like output, you have to give the AI concrete operational rules, not feelings.

3 Tangible Techniques for the "Anti-AI" Prompt

Here’s a handful of thoughts to inject into your prompting routine that can possibly help strip away that robotic veneer:

1. Program "Burstiness" (Sentence Variance)

Unless you’ve not noticed, AI text is incredibly uniform. It loves to write sentences that are all roughly the same length, creating a rhythmic monotony that puts readers to sleep. Humans write erratically. We follow a long, complex thought with a short one. Like this. Sometimes those sentences are also incredibly long. You’ll notice this blog. Doesn’t have very long. Sentences. 

You can explicitly program this behavior into your prompts.

The Prompt Directive:"Vary your sentence structure using high burstiness. Alternate between long, explanatory sentences that build context and short, punchy sentences (under 5 words) that deliver impact. Avoid uniform paragraph lengths."

2. Implement a Strict Cliché Ban

AI models are trained on patterns, which means they default to the most common phrases on the internet. By creating a digital "swear jar" for overused AI tropes, you force the model to find more creative, authentic ways to express an idea.

• The Prompt Directive:"You are strictly prohibited from using the following words and phrases: 'In today's fast-paced world', 'delve', 'testament to', 'game-changer', 'revolutionize', 'tapestry', 'beacon', or 'in conclusion'. If you feel tempted to use these, rephrase the concept using simple, direct language."

3. Use Linguistic Profiling (The "Mirror" Technique)

The absolute best way to make an AI sound like a human is to give it a specific human to copy. Instead of asking it to guess what "casual" means, feed it a sample of your own writing—or text from an author you admire—and ask it to reverse-engineer the mechanics.

• The Prompt Directive:"Analyze the text sample below for its linguistic profile. Pay attention to vocabulary level, use of active vs. passive voice, how technical concepts are simplified, and the frequency of personal pronouns (I, we, you). Once analyzed, rewrite the draft below matching this exact linguistic profile."

Putting It Together: The Master Framework

The next time you sit down to draft a piece of content, bypass the basic text box and feed the AI a highly structured role.

Here is a comprehensive framework you can copy and paste:

Role: You are an elite developmental editor and ghostwriter known for a minimalist, direct, and engaging writing style.

Task: Rewrite the provided outline into a comprehensive blog post section.

Constraints:

• Tone: Grounded, practical, and candid. Speak like a helpful peer, not a rigid lecturer.

• Voice: Use active voice exclusively. Use personal pronouns (you, we) to connect with the reader.

• Pacing: Mix complex thoughts with sharp, sudden conclusions. Keep paragraphs to a maximum of three sentences.

• Formatting: Optimize heavily for scannability. Use bolding on key phrases to guide the reader’s eye, and break up dense data using simple bullet points or markdown tables where appropriate.

[Insert your raw notes/outline here]

By shifting your focus from what the AI writes to how it structures its thoughts, you transition from generating generic text blocks to crafting genuinely compelling narratives. The tool hasn't changed—but your boundaries have.

The Great AI Memory Bank: How Your Data Gets Consumed (and How to Keep It Private)

In a nutshell (TL;DR)

To secure your data, consider these strategies:

• Anonymization Pipelines: Replace sensitive identifiers with placeholders (e.g., [NAME]) before data leaves your network.
• Zero Data Retention (ZDR): Mandate that providers process prompts in memory only, without saving logs or using data for training.
• Local Models & Secure Orchestration: Keep data within corporate firewalls by running local models or utilizing secure protocols like MCP.
• Targeted Encryption: Encrypt or mask sensitive prompt segments, such as using unique emoji sequences, to keep text unreadable to the provider.

It's been two weeks since I last posted! But I am back after the day job got in the way with a major project and a tight deadline. Last post I talked about the dangers of copy and paste and how easily information can end up in the hands of the LLMs

Whenever we type a prompt into an AI assistant, it is easy to imagine our words vanishing into the digital ether the moment we hit 'send'. But Large Language Models (LLMs) have incredibly sticky memories. While it is easy to accidentally slip sensitive data into an AI tool, it is equally important to understand what the AI actually *does* with that information once it has it. 

LLMs are designed to consume, process, and generate text, which means treating them like a private diary or a secure vault can lead to unintended, and highly public, consequences. Here is a look at how your confidential information gets consumed and redistributed by AI, and the best practices you can use to keep your private data safe.

The Consumption and Redistribution Cycle

When you feed Personally Identifiable Information (PII) or corporate secrets into an external LLM, you are exposing that data to several hidden risks:

Data Logging and Storage

Many AI providers log user prompts to monitor for abuse, debug their systems, or improve their overall services. Once your confidential data is stored on a third-party server, it becomes vulnerable to unauthorized access or potential data breaches on the provider's end.

Training Data Contamination

The prompt you submit today could inadvertently become the training data of tomorrow. Even though some enterprise providers have strict policies, there is always a baseline risk that PII from user prompts might be absorbed to further train or fine-tune future versions of the models.

Output Leakage and Regurgitation

LLMs are known to memorize information from their pre-training phases as well as from prompts processed during active inference. This can lead to a phenomenon where the model unintentionally regurgitates your sensitive information verbatim in its responses to completely different users. In fact, the OWASP Top 10 for LLMs lists "Sensitive Information Disclosure" as a critical vulnerability, noting that poor input handling can cause models to leak PII, business strategies, or system credentials directly into the public domain.

Defending Your Data: Precautions and Safe Methods

Fortunately, you do not have to unplug your routers and swear off AI entirely. There are several highly effective precautions and architectural strategies you can implement to interact with LLMs safely:

1. Build Anonymization and Mapping Pipelines

The most practical defense is to scrub the data before it ever leaves your network. By using tools like Named Entity Recognition (NER), you can automatically identify sensitive entities and replace them with generic placeholders—for example, swapping a real name and email for `[FIRSTNAME]` and `[EMAIL]`. This allows the LLM to understand the context of the prompt without ever seeing the raw data. On your end, you keep a secure, temporary map of these placeholders. When the LLM replies, a mapping-based de-anonymization module simply swaps the real information back in, ensuring 100% accuracy without exposing the data to the cloud.

2. Demand Zero Data Retention (ZDR)

If you rely on cloud-based AI vendors, mandate a "Zero Data Retention" agreement. Under ZDR, the provider processes your prompt and immediately returns the response without writing your request to any persistent storage, training queues, or logs. The data exists only in memory for the exact duration of the API call, effectively shifting your risk profile from uncertain to bounded.

3. Utilize Local Models and Secure Orchestration (e.g., MCP Servers)

For the highest level of control, organizations can run fine-tuned, smaller language models entirely within their own corporate firewalls, ensuring data never leaves the internal infrastructure. When connecting AI to internal databases, utilizing secure architectural patterns like the Model Context Protocol (MCP) can help safely orchestrate how context is provided to the AI without exposing raw data to public endpoints.

4. Targeted Encryption

For highly regulated environments, researchers are developing targeted encryption techniques. This involves encrypting only the sensitive sub-parts of a prompt, sometimes even translating them into unique sequences of emojis (like *EmojiCrypt*), so the text remains unreadable to humans and providers, but retains enough structure for the LLM to process. While computationally expensive and complex to implement, it represents the bleeding edge of prompt privacyLarge Language Models (LLMs) pose significant security risks because they can unintentionally memorize and redistribute sensitive information, such as PII and corporate secrets. Primary dangers include unauthorized data logging, training data contamination, and output leakage where models regurgitate your data to others.

AI models are incredibly eager to learn, which makes them fantastic assistants but terrible secret-keepers. By adopting smart anonymization pipelines, demanding strict retention policies, and securing your integrations, you can enjoy all the productivity benefits of generative AI without accidentally donating your private data to the world.

The Clipboard Crisis: Securing the Modern Data Leakage Vector

In a nutshell (tl;dr)

The modern copy-paste function has become a major, often overlooked, vector for data exfiltration. As employees frequently use unmanaged personal accounts for Generative AI and messaging apps, corporate data is regularly moved outside secure environments. Because traditional security tools were designed to monitor file uploads rather than "file-less" text transfers, organizations must shift toward action-centric security, monitor browser activity, and restrict the use of personal accounts to protect sensitive information.

I totally missed out on last week’s post thanks to the day job and nearly missed it this week too! This week I was worried about how safe my personal or proprietary data was when passing it over to an AI to work with. How likely is it that this information is somehow leaked or made public? Here’s what I found out…

The Copy-Paste Crisis

We all use the copy-paste function without a second thought and the clipboard is our biggest blind spot. It is the ultimate productivity shortcut, saving us countless hours of retyping information. However, this simple, everyday action has quietly become the primary channel for data exfiltration in the modern workplace, completely bypassing traditional file-based security measures.

As we increasingly rely on artificial intelligence and cloud-based applications, the clipboard has transformed into a massive vulnerability. Here is a detailed look at how the "copy-paste crisis" unfolds, why it is so dangerous, and what organizations can do to protect their confidential data.

The Generative AI Black Hole

Generative AI tools have seamlessly integrated into our daily routines, and we are eagerly feeding them information to summarize, rewrite, or analyze. In fact, a staggering 77% of enterprise employees now paste data directly into GenAI prompts.

The core issue is not necessarily the AI itself, but how users are accessing it. Approximately 82% of the data pasted into AI tools comes from unmanaged, personal accounts. When employees bypass official corporate logins, IT and security departments lose all visibility. This turns "Shadow AI" activity into a massive blind spot for data leakage. Today, GenAI alone accounts for 32% of all corporate-to-personal data exfiltration, making it the number one vector for corporate data moving outside sanctioned environments.

Beyond AI: The Instant Messaging Trap

While AI gets most of the spotlight, instant messaging (IM) and chat applications represent another enormous vulnerability. A remarkable 87% of all instant messaging activity occurs on unmanaged, non-corporate accounts .

Because chat feels informal and conversational, users often let their guard down. Consequently, Chat and IM apps have become a major hotspot for sensitive data exposure, with 62% of users pasting Personally Identifiable Information (PII) or Payment Card Industry (PCI) data directly into these platforms.

Death by a Thousand Clicks

It might seem like pasting a quick snippet of text is harmless, but the sheer volume of these actions adds up to a significant security threat. On an average day, an employee makes about 46 copy-paste actions. While many of these transfers stay safely within corporate boundaries, an average of 15 pastes per day go to non-corporate accounts. Out of those, roughly four pastes contain sensitive PII or PCI data.

An employee pasting a few sensitive entries into ChatGPT each day might not trigger massive security alarms or generate large file logs, but every single instance increases the risk of a breach. Furthermore, employees are pasting corporate data into a surprisingly diverse range of destinations. Beyond just ChatGPT, top destinations for pasted data include developer platforms like Databricks and Snowflake, as well as websites like LinkedIn and DeepL. Exfiltration is highly unpredictable, driven by everything from innocent productivity shortcuts to competitive moves.

Why Traditional Defenses Are Falling Behind

The reason this copy-paste crisis has grown so severe is that traditional Data Loss Prevention (DLP) solutions were fundamentally designed for a different era. Legacy DLP focuses heavily on monitoring file uploads and centralized servers . They simply are not equipped to track "file-less" data transfers, like copying text from an internal document and pasting it directly into a web browser.

Taking Back Control of the Clipboard

To secure the modern workflow, organizations need to evolve their security strategies to match employee behavior.

Shift to Action-Centric Security

Security teams must move away from purely file-centric policies and embrace "action-centric" controls. Monitoring copy-paste functions and text inputs into prompts must become a first-class security priority.

Focus on the Browser

Because nearly every business workflow, from email to GenAI, now runs through the web browser, this is the environment where visibility and enforcement must be focused.

Ban Unmanaged Accounts

Allowing employees to use personal accounts for business-critical apps creates active shadow IT. Organizations should restrict the use of personal accounts for high-risk categories like AI and Chat, and enforce Single Sign-On (SSO) across all corporate logins to ensure activity remains visible and governed.

The clipboard might be the most overlooked tool in our software arsenal, but it is currently one of the riskiest. By understanding the flow of copy-pasted data and upgrading our security frameworks to monitor file-less transfers, we can enjoy the productivity benefits of modern SaaS and AI tools while keeping our private data exactly where it belongs.

Agentic Commerce: The Virtual Procurement Revolution

In a nutshel (TL;DR)...

Agentic AI is transforming B2B procurement by automating routine sourcing and negotiation, shifting operations from reactive to predictive purchasing, and leveraging structured data to allow human experts to focus on strategic oversight through a "Human-in-the-Loop" approach, ultimately reducing operational friction.

The B2B Revolution: Meet Your New Virtual Procurement Department

Earlier this year I posted about the rise of Agentic Commerce being the future of online shopping taking over the consumer experience. We imagined a digital assistant booking a flight to Barcelona or effortlessly picking out the perfect pair of trail running shoes for a weekend getaway. It is an exciting vision, but while consumer applications get most of the spotlight, a much quieter, and arguably much more impactful, revolution is taking place in the business-to-business (B2B) sector.

Welcome to the era of Agentic Commerce in B2B, where AI is moving from a simple data-crunching tool to an active, independent participant in your supply chain.

For years, B2B purchasing has involved a lot of heavy lifting: tracking down supplier catalogs, manually comparing specifications across sprawling spreadsheets, managing endless email chains for quotes, and reacting to sudden inventory shortages. Today, Agentic AI is stepping in to change that dynamic entirely, acting as a "Virtual Procurement Department" for trading and manufacturing companies.

From now on, when I talk about “AI Agents” I am referring to quite a number of software vendors that are offering this as a solution such as ORO Labs or LevelPath that have built their platforms from the ground up with artificial intelligence as the foundation, to the likes of Tropic that lean into AI for highly targeted areas of procurement, such as specialized software (SaaS) purchasing, contract intelligence, or complex e-auctions 

So let’s take a closer look at how platforms like this are transforming B2B commerce from a tedious chore into a highly predictive, streamlined operation.

Say Hello to Your Autonomous Sourcing Analyst

In the traditional B2B model, sourcing new components or managing supplier requests requires a significant amount of manual labor. Procurement teams spend hours sending out Requests for Quotations (RFQs), waiting for responses, and then lining up the data to make a choice.

With the introduction of Agentic Commerce, AI agents can take over this routine work. Instead of merely organizing data, these agents act like intelligent analysts. When a business needs a component, the agent can autonomously search through supplier databases, gather bids, and compare terms. It doesn't just look at the bottom-line price, either. The agent can evaluate lead times, review the supplier's quality history, and select the most cost-effective solution. It can even negotiate discounts within predefined rules and automatically approve orders that fall under specific budget limits.

Moving from Reactive to Predictive Purchasing

If you have ever had to deal with the headache of a sudden supply shortage, you know that reactive purchasing is stressful. Traditionally, businesses order new stock based on historical sales data and a little bit of guesswork, which often leads to either costly overstocking or frustrating "out of stock" scenarios.

Agentic AI shifts the paradigm from reactive to predictive. By analyzing historical data, current sales velocity, and market trends, AI agents can accurately forecast future demand. Furthermore, these agents can continuously monitor inventory levels and automatically trigger restocking orders at the perfect moment to prevent supply chain bottlenecks. The system knows not just what you need to order, but exactly when and in what quantity, ensuring operations run smoothly in the background.

Taming the Messy Supplier Data

Of course, for an AI agent to make smart purchasing decisions or negotiate with suppliers, it needs perfectly structured and accurate data. In the B2B world, supplier data is notoriously messy, often arriving in unstructured formats like massive PDFs or inconsistent spreadsheets.

To support an AI-based procurement platform, a Product Information Management (PIM) system acts as the critical intelligence hub. For an AI procurement agent to accurately analyze supplier bids, forecast demand, and execute purchases autonomously, it must base its decisions on flawless, highly structured data. They can even detect inconsistencies or missing attributes and populate them into the right fields. Ultimately, by guaranteeing that supplier records are accurate, consistent, and complete at the point of ingestion, an PIM system provides the trusted data foundation necessary for a B2B procurement platform to operate autonomously and reliably 

What Happens to the Human Experts?

With agents sending RFQs, negotiating prices, and monitoring inventory, it is natural to wonder where human professionals fit into this new landscape. The good news is that the rise of agentic AI is not about eliminating the procurement team; it is about elevating them.

This brings us to the concept of the "Human-in-the-Loop" (HITL). While AI agents are fantastic at analyzing data and executing routine purchasing tasks, they lack the nuanced judgment, ethical grounding, and relationship-building skills required for high-stakes decisions. In an agentic B2B environment, human experts transition from tactical execution (like manual data entry) to strategic oversight.

For example, an agent might handle 90% of routine supplier restocking autonomously. But if it encounters an unprecedented supply chain disruption, a wildly out-of-budget price hike, or a scenario that requires complex ethical reasoning, it is programmed to pause and escalate the issue to a human manager. Humans remain in control, defining the agent's objectives, setting the financial guardrails, and managing the exceptions.

A Smarter Way to Do Business

The B2B revolution powered by Agentic Commerce is ultimately about removing friction. By handling the drudgery of data processing, supplier negotiations, and inventory tracking, AI agents free up human professionals to focus on what they do best: building strategic partnerships, exploring new market opportunities, and driving innovation.

The future of B2B is predictive, highly automated, and incredibly efficient. And with a Virtual Procurement Department working tirelessly in the background, businesses can look forward to a much smoother ride.

Fortifying the Digital Vault: A Wee Guide to AI Privacy

In a nutshell (TL;DR)...

The widespread use of generative AI tools introduces major security risks for private and confidential company information. Sensitive data can leak when prompts are retained for logging/training, employees paste data into unmanaged "Shadow AI" accounts (the "Copy/Paste Blind Spot"), or malicious "Prompt Injections" trick the model. Consequences are severe, including regulatory fines (GDPR/HIPAA), data breaches, and loss of competitive advantage. To stay secure, organizations must:

• Anonymize sensitive data (PII) before using external LLMs.

• Prioritize vendors offering Zero Data Retention (ZDR).

• Banish "Shadow AI" by enforcing Single Sign-On (SSO).

• Upgrade to action-centric Data Loss Prevention (DLP) that monitors copy/paste actions.

Apply the principle of least privilege and keep a human in the loop for critical actions.

The AI Privacy Guide: How to Keep Your Confidential Data Safe in the Age of LLMs

The company I work for has drummed into me the perils of letting slip any confidential information when working with AI applications, but just how important is it? My employer specifically lists the AI applications we are allowed to use when working with confidential information, so it’s a really important thing to bear in mind. Let’s have a look at what the problems are and how we can protect ourselves, our customers and our employers…

Everyone is officially living in the era of Artificial Intelligence. From drafting emails to analyzing complex datasets, generative AI and Large Language Models (LLMs) have seamlessly integrated into our daily workflows. In fact, nearly half of all enterprise employees are already using these tools. But amid all this newfound productivity, there is a crucial conversation we need to have: how are we protecting our private data and confidential company information?

While AI assistants are incredibly helpful, treating them like a private diary or a secure company vault can lead to serious risks. Let’s break down exactly how sensitive information can slip through the cracks, what the consequences are, and the best practices you should adopt to stay secure.

How Does Confidential Information Actually Go Public?

When you type a prompt into an external LLM, that data is processed by a third-party provider. If you aren't careful, sensitive information can be exposed in a few common ways:

Logging and Training Contamination

Many AI providers retain user prompts for a certain period to monitor for abuse, debug their systems, or even train future versions of their models. If you paste confidential data into a prompt, it could end up stored on the provider's servers or, worse, replicated in the model's future outputs.

The Copy/Paste Blind Spot

A staggering 77% of employees paste data directly into generative AI tools, and the vast majority of this activity happens on unmanaged personal accounts. Because this bypasses official corporate channels, IT and security teams have no visibility into what is being shared, creating a massive "Shadow AI" blind spot.

Prompt Injections

Malicious actors can use "prompt injections", carefully crafted inputs designed to manipulate the AI's behavior to trick the model into revealing sensitive information. This can lead to the AI accidentally exposing personally identifiable information (PII), confidential business strategies, or even system credentials. I’ve made a note to dig deeper on this subject for a later post…

The Uncomfortable Consequences of Data Leaks

The fallout from exposing sensitive data to an LLM is rarely a minor hiccup. When PII or corporate secrets leak, the consequences can be severe.

Regulatory Penalties

Mishandling personal data violates strict data protection regulations like GDPR and HIPAA. Failing to comply with these laws can result in massive legal and financial penalties.

Data Breaches and Loss of Trust

If a customer service chatbot or an internal AI tool inadvertently reveals private user details or passwords, it can lead to full-scale data breaches. This erodes user trust and severely damages your organization's reputation.

Loss of Competitive Advantage

Exposing proprietary business data or intellectual property can directly result in a loss of your competitive edge in the market.

Best Practices for Handling Sensitive Information with AI

Fortunately, you don't have to abandon AI to keep your data safe. By implementing a few strategic best practices, you can enjoy the benefits of LLMs while minimizing your risk.

1. Anonymize Before You Analyze

Before sending a prompt containing sensitive data to an external LLM, scrub the text of any PII. You can use automated tools to detect and replace names, emails, and phone numbers with generic placeholders (e.g., swapping a real name for [PERSON] or [EMAIL]). This allows the AI to understand the context of your prompt without ever seeing the raw, sensitive data.

2. Demand "Zero Data Retention" (ZDR)

If you are procuring AI tools for your company, prioritize vendors that offer "Zero Data Retention" agreements. Under a ZDR policy, the AI provider processes your prompt and immediately returns the response without writing your data to any persistent storage, logs, or training queues. This ensures your data exists only in memory for the duration of the request. I think this is what my employer might have in place for the applications I am allowed to use.

3. Banish "Shadow AI" and Enforce SSO

Employees often use unmanaged personal accounts to access AI tools, completely bypassing enterprise security. To regain control, organizations must restrict the use of personal accounts for business-critical apps and enforce Single Sign-On (SSO) across all corporate logins.

4. Upgrade Your Data Loss Prevention (DLP)

Traditional Data Loss Prevention tools are heavily focused on file uploads, but today's sensitive data usually leaks when employees copy and paste text directly into AI prompts. Organizations need to shift to "action-centric" DLP policies that monitor file-less data transfers and enforce controls directly at the web browser level.

5. Keep a Human in the Loop and Limit Privileges

Finally, never give an AI unchecked autonomy. Apply the principle of "least privilege" by ensuring your AI applications only have access to the specific data sources they absolutely need. For high-impact actions, like modifying files or handling highly sensitive records, always require human approval before the AI can proceed.

AI is a powerful collaborator, but it is ultimately up to us to set the boundaries. By treating generative AI platforms with the same security rigor as any other enterprise tool, we can innovate quickly without putting our most valuable data on the line.

Next week let’s take a shifty at this “prompt injection” malarky and see how we can protect ourselves from that…