Why I'm Building a Flight Simulator for Tech Lawyers
How to cross the bridge from knowing the law to understanding the technology.
Every day, brilliant legal minds walk into tech companies and completely fail to communicate with the engineering teams building the future.
We all know the struggle. We try to advise on GDPR Article 32 (security of processing), but the engineering team is talking about cloud architecture, API endpoints, and ML pipelines. Traditional law schools are still teaching 20th-century theory for 21st-century problems. They teach you the law, but they leave you completely in the dark about the technical literacy.
In my work directing the Privacy Innovation Lab and running audits, I see this friction constantly. You can memorize all the data protection frameworks in the world, but if you don’t know how an AI system actually operates under the hood, how an API exposes sensitive data, or how a breach technically unfolds, you will always be a “theoretical lawyer” watching from the sidelines.
Companies no longer want theoretical lawyers. They want hybrid operators. They want professionals who grasp the legal risk, understand the technical architecture, and can sit in a room with developers without embarrassing themselves.
The Pushback: “It’s Not My Job”
Recently, I floated this idea in a community of privacy professionals. I suggested that lawyers need hands-on technical literacy. The response I got perfectly encapsulated the traditional, siloed mindset of our industry. One commenter wrote:
“My job involves telling people, ‘you need to make sure this data is secure’, and that’s the end of it. It’s up to the IT security guys to decide how to do that. They’re the specialists, and I don’t need to get involved... I’m not going to start creating work for myself that I’m not paid for.”
I completely respect the need for a separation of duties. We absolutely shouldn’t be the ones configuring firewalls or writing the actual security protocols.
But I view that hands-off approach as the exact reason so many modern compliance programs fail in practice. Relying blindly on the “IT guys” without speaking their language creates a wall. Legal becomes a compliance checkbox rather than a strategic partner.
Furthermore, I cannot count the number of times an official technical assessment stated one thing, but getting my hands dirty proved otherwise. Simply pulling up a basic Google Developer Console to check the actual network requests, or sitting side-by-side with DB admins to look at the SQL databases, frequently reveals data flows and exposures that were never declared in the official documentation.
If we just say “make it secure” and walk away, we miss all of those hidden risks.
It’s not about doing IT’s job for them; it’s about trust, but verify.
The Flight Simulator for Tech Lawyers
Learning to read network requests or understand a database isn’t doing IT’s job for free; it’s the exact skillset that makes a privacy professional irreplaceable tomorrow. The industry is rapidly shifting, and tech companies are actively seeking—and paying a massive premium for—hybrid professionals who can cross the bridge from “I know the law” to “I can operate in a technical environment.”
But how do you actually learn that? You wouldn’t trust a pilot who has only ever read a manual; you trust the one who has spent hundreds of hours in a flight simulator.
We need to apply that exact same methodology to law and compliance.
That is why I am building The Tech-Savvy Lawyer Lab
It is essentially an interactive flight simulator for privacy professionals. It puts you directly into simulated technical environments—like mapping a complex AI system’s data flow or responding to an unfolding data breach—so you can actually see how the tech operates under the hood. No boring seminars. Just hands-on, interactive technical workshops designed to give you the hat of a privacy engineer with a legal background.
The era of the theoretical lawyer is over. It is time to stop quoting regulations and start understanding the machine.
I just pushed the first interactive MVP module live. If you are ready to cross the bridge, you can test drive the simulator here:
https://compliancesim.com/