Picture yourself pasting a signed NDA into ChatGPT to “speed up” a summary. Feels harmless. It isn’t.
That single habit is the kind of move that keeps cybersecurity pros up at night. So we sat down with Darien Maples, co-founder and CEO of TechBesties and a 16-year veteran of the cybersecurity industry, to get her real rules for using AI without leaking the one thing that actually matters: your data.
Darien leads technical integrations and alliances at an ethical hacking company, and she builds AI integrations for a living. Below are her AI security best practices, pulled straight from her day-to-day work and condensed into rules you can use today.
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Contents
- 1 What should you never paste into an AI tool?
- 2 Should you treat every AI tool the same?
- 3 How should you handle a tool you stopped using?
- 4 How do you verify what AI gives you?
- 5 Where do you draw the line on what AI can do?
- 6 What security mistake do beginners make most?
- 7 What are the three non-negotiables before you roll out AI?
- 8 What will people wish they’d been careful about in a year?
- 9 The one takeaway: your data is the gold
- 10 Frequently asked questions
- 11 Bio
What should you never paste into an AI tool?
Start here, because this is the line that protects everything else.
“I would never want to put any type of legal agreement, strategy, deal terms, anything like that within those tools,” Darien says. She handles NDAs and technical agreements all day, and they stay out of every chatbot she touches.
Her reasoning is simple. “I see AI as a powerful collaborator externally. But at the end of the day, there’s data that can be put into this that can be utilized or exposed in some kind of way.”
So what does she feed it? Structured ideas. Team collaboration. Workflows and strategy brainstorms. “That’s a really great way to build strategy and build those teams to make you stronger,” she says. The split is clean: ideas go in, secrets stay out.
Should you treat every AI tool the same?
No. And treating them all as one bucket is a beginner mistake.
Darien sorts her tools by power and purpose. “I use a lot of ChatGPT more for my personal, my branding, my messaging. Claude I use in my business; that has amazing coding. The inputs are more controlled.”
Her advice: put each tool in its own bucket and decide what kind of work belongs there. Claude, Gemini, and ChatGPT are all powerful, she notes, and that power cuts both ways. “If you’re really trying to build content and workflows and data handling, there is some high risk of vulnerabilities if you’re using such powerful tools.”
One reframe she wants everyone to remember: the chatbot is the front door, but a giant company sits behind it. “Gemini is Google, Claude is Anthropic, OpenAI is ChatGPT, and these companies are facing risks and hackers every day.” If you’re new to comparing these tools, our guide to the best AI tools to improve your workflow is a solid starting point.
How should you handle a tool you stopped using?
Don’t just log out and forget it. “Unused tools are a silent risk,” Darien warns.
Her routine is practical. “I always delete saved prompts, sometimes files, and conversations, depending on how deep that information is.” Because her work involves API access and integration building, plenty of accounts simply aren’t needed anymore, and dead accounts are exposure waiting to happen.
She also builds a weekly cleanup into her calendar. “Go through your data and what you’re doing and see what you can remove.” Then review the history with one question in mind: “What am I doing that could put myself at risk?” Spot the pattern, then stop repeating it.
How do you verify what AI gives you?
Darien has the best metaphor we’ve heard for this. “I treat AI as a self-checkout.”
You know the scene. You’re scanning your own groceries, something errors out, and an employee has to walk over and fix it. “That happens to me every day,” she says. “I’m like, no, that’s wrong. Let me fix this.”
AI output sounds confident even when it’s flat wrong. “There’s some accuracy the tools will think is completely correct, and it’s wrong,” she explains. So she cross-checks facts against her own company knowledge and the real world every time. The error might be in the tone, the data, or the info, but the fix is always the same: a human sanity check before anything ships to a client. This is exactly why coding and technical fundamentals still matter even as AI gets better.
Where do you draw the line on what AI can do?
“AI is here to help us and collaborate, but you should never trust it,” Darien says. “Treat it as someone reviewing your work, that added assistance. Never allow it to make final decisions.”
That rule gets stricter the more is on the line. If you have revenue, clients, and security obligations, every output should be fact-checked by your team. “Replacing human judgment should never be a part of what these tools are.”
She’s especially protective of one underrated asset: your voice. “Don’t let it take away how you speak. Soon we’re all going to be saying the same things and sounding like a robot.” She works with nearly every cybersecurity company and keeps spotting copy that feels recycled. “I’m like, wait, didn’t I write that?”
What security mistake do beginners make most?
One word: oversharing.
When a company rolls out a new AI tool, excitement takes over. “Everyone gets so excited and they overshare data,” Darien says. “Company documents, client documents, internal workflows, how the whole company works, everything that has some type of legal NDA tied to it. They’re throwing it in there.”
The motive is innocent. People want to build a template or map their day fast, so they dump everything in. “But what they’re doing is ignoring the risk of it all.” In competitive fields, that exposure can hand rivals your playbook. “Your competitors will gain that knowledge and be like, oh, that’s what you’re doing?”
Her fix is refreshingly old-school: “Try to really use your human brain first before just plugging it all in.” Building that judgment is a skill, and structured cybersecurity and security courses are a great way to develop it.
What are the three non-negotiables before you roll out AI?
If you’re about to give an entire team access to AI tools, Darien says three things come first.
- Data awareness. “Know what’s sensitive versus what’s safe to expose.” Every business has contact details, agreements, clients, and strong data that others want. Map yours before anything goes near a prompt.
- Tool awareness. Understand exactly what you’re using and what it connects to, from your CRM to your email to your integrations. “Understand what you’re using within your business.”
- Human oversight. “Start with yourself first. Always review, validate the output.” The skills that made you successful before AI are the ones that keep you safe now.
And keep a backup plan. Tools get shut down, prices rise, companies fold. “Like a calculator, if it runs out of battery, you’ve got to do one plus one on your hand.” If you want a structured way to build these AI skills, explore our AI courses and learn to use these tools responsibly.
What will people wish they’d been careful about in a year?
“It’s going to be the data,” Darien says without hesitation. Data leakage, over-automation, and lost authenticity top her list.
People are already learning to spot machine-made work. “You can see comments now and people are like, oh, that’s AI. We’re seeing the brand voices in what people prepare, and it’s not genuine anymore. It’s just filtered.”
Her closing note balances enthusiasm with caution. “I love AI, and I definitely use it. But in a year we have to be careful of the data, the over-automation, and the authenticity of who we are as people.”
The one takeaway: your data is the gold
If you remember nothing else from Darien, remember this. You are the IP. Your data is the asset. Use AI as a sharp, tireless assistant, but never let it become the decision-maker, the source of truth, or your voice.
Want to build the judgment behind these habits? A guided path beats trial-and-error. You can start a free trial and work through real courses on AI and security, or read our beginner-friendly breakdown of what AI tools are and how they work. Either way, lead with your human brain first.
Frequently asked questions
What should you never paste into an AI tool like ChatGPT?
Never paste legal agreements, NDAs, deal terms, technical contracts, client documents, or sensitive internal data. Cybersecurity expert Darien Maples warns that anything you enter can be stored, used, or exposed. Stick to structured ideas, brainstorms, and workflow strategy instead of confidential information.
How do you verify information that AI gives you?
Treat AI like a self-checkout: it works, but it errors and needs a human to fix it. Cross-check every fact against your own company knowledge and the real world before using output with clients or publishing. AI often sounds confident even when the data or tone is wrong.
What are the three non-negotiables before a business adopts AI?
Data awareness (know what is sensitive versus safe to share), tool awareness (understand exactly what tools you use and what they connect to), and human oversight (always review and validate AI output yourself before relying on it). Skip these and you risk leaking critical business data.
Should you delete AI accounts you no longer use?
Yes. Unused AI tools are a silent security risk. Delete saved prompts, files, and conversations, and remove accounts you no longer need, especially those with API access. Build a weekly routine to review your data and clear anything that creates unnecessary exposure.
Is data leakage the biggest AI risk to watch?
According to Darien Maples, data leakage tops the list, alongside over-automation and lost authenticity. Every chatbot connects to a major company facing hackers daily, so what you share is never fully private. Protect your data, keep human judgment in the loop, and preserve your own voice.
Bio
Darien Maples is the Co-Founder and CEO of TechBesties, a 501(c)(3) nonprofit dedicated to making technology education more accessible through mentorship, community, and career development. With more than 15 years of experience in cybersecurity, strategic partnerships, and go-to-market leadership, she has built programs that connect aspiring and early-career professionals with the resources, relationships, and opportunities needed to succeed in tech.
Driven by a passion for expanding access to technology careers, Darien has dedicated her career to helping others break into and thrive in the industry. Through TechBesties, she is building a global community where education, mentorship, and meaningful connections empower the next generation of technology professionals.
