If you've started using agentic AI (Claude Cowork, Claude Code, ChatGPT's agent mode) on real files, there's a simple test worth knowing. The failure mode is invisible until it isn't. It's called the lethal trifecta, and an AI agent becomes genuinely risky when all three of these are true at once: it has access to private data, it's exposed to content you didn't write yourself, and it has a way to send data out. Here's what that looks like. You ask an agent to summarise a client's supplier invoices. One invoice is a PDF that arrived from a supplier you've never dealt with. Buried in it, in white text on a white background, is a line telling the AI to send the folder's contents somewhere else. You can't see it. The AI reads it perfectly, and complies. No alert. No error. The summary looks completely normal. All three legs were present: private data, an untrusted document, and an email connection to send through. You don't need to understand how the attack works. You need to be able to look at a setup and count to three. Two out of three is workable. Three is not. This is the one idea from the full Privacy and Security course in the Classroom I'd want every firm to know even if they read nothing else. It's not in the free guide, it's one of four extra chapters in the full course, alongside prompt injection, connecting AI to QuickBooks and Xero, and the 2026 rules for the UK, EU and US. Have you connected an AI agent to your email, files, or accounting software yet? What made you go for it, or what's held you back? 👇

A friend was raving about Krisp, the AI note taker. What he especially liked was it's ability to record in the background. No connection to Teams or Zoom required. No explicit permissions. He's an attorney so I was curious how he was handling consent. Regardless of the governing body's rules, recording conversations and meetings deserves transparency. He said he told the attendees that he was recording for personal use. If they were okay with recording, then he did so. Here's one the things that concerns me about these background recorders. What's to prevent someone from attending a meeting in your office and quietly recording it? Or imagine someone walking through your office with their note taker active. I'm not a doomsayer by any means. I've been in the technology world for more than 4 decades. AI has opened the door to possibilities we're never seen before. But with that comes the need for a level of awareness and responsibility we've never had to practice before either. How do you communicate your note taker policies to outside meeting attendees?

Uber disclosed that it burned through its entire 2026 AI budget in four months using Claude Code. This didn’t happen because a few developers went rogue. Quite the opposite. Uber’s technology teams were doing exactly what the company asked them to do. So how did Uber's budget overrun happen? The finance team did exactly what it had always done. It projected expenses based on the long-standing software pricing model — number of users x license fee = cost. For years, software was one of the easiest business purchases to understand. You bought it, put it to work, and seldom had to rethink what it should do. One tool had one job to do. The financial costs were simple to calculate: number of users x license fee = cost. AI is different. Using ChatGPT or Claude for chat usually falls within the fixed monthly fee. But when we start connecting AI with our everyday apps and expanding what AI can do, the math starts to get fuzzy. AI uses a consumption model similar to how our monthly electric bills are calculated. Instead of kilowatts, we’re paying in tokens. Different vocabulary but a similar concept. It’s important to consider what we want AI to do and how much we’re willing to invest.

AI note-takers are everywhere now. Plaud, Otter, Fireflies, Zoom AI Companion, Copilot. Most firms are using at least one. Here's the bit that catches people out. Somebody asked me recently about adding standing text to meeting invites ... "unless advised otherwise we will record this meeting". Reasonable instinct. It feels like you've covered yourself. But as consent, it fails. Under GDPR consent has to be freely given, specific, informed and unambiguous, through a clear affirmative action. Silence and inactivity don't count. So an opt-out isn't consent. Here's the link to the guide I created that shows how to fix this. What's interesting is that the same sentence works fine if you're relying on legitimate interests instead, because that needs transparency and a right to object rather than a yes. Same words. Different basis. Two practical things while I'm here. First, if you record in person with something like a Plaud ... turn the recorder on before you ask, and say that you've turned it on. Otherwise the one thing not captured is the agreement itself. Second, check your platform settings. Since January, Zoom makes every participant acknowledge the AI disclaimer before the meeting continues. Google Meet can require explicit consent before note-taking starts, but it's switched off by default. For video calls that solves most of the problem for you. So ... are you recording client meetings? And if you are, how are you handling consent at the moment? Honestly interested in how many people have thought about this 👇

I wonder if all this hype about AI replacing us is overlooking an important opportunity for us. • AI isn’t replacing experts. We’re joining the conversation at a different place. Expertise isn’t necessarily being replaced by AI. We’re simply joining a more mature, focused conversation. We’re not competing with AI to maintain our relationships. We’re using the skills that AI brings to complement how we already work with our clients. • The value of expertise is as important as ever. AI didn’t invent conversations. It has simply reminded us that our relationships started with human conversations. Over time the listening, asking questions, making time for thinking together was replaced by having the answer. • AI prepares us for better human conversations. Clients come to us when they’ve organized their thinking. They’ve asked the what-if questions that they weren’t able to say out loud yet. They allowed themselves to be vulnerable because AI gives them permission to share their thinking without judgment. 💡Idea: Encourage your clients to tell you about their experience with AI. The professionals who are curious enough to have a different conversation with their clients are the ones who will be valued, not replaced.