Know when not to escalate
Early in my time leading a legal team, my instinct on a hard call was to escalate it — get cover, share the risk, let someone more senior own the outcome. I learned the cost of that habit the slow way. Every escalation upward teaches your team that hard calls live above them, and it teaches executives that you are a conduit, not counsel. A team that watches its leader pass every difficult decision upstairs stops making difficult decisions at all.
So I set a simple threshold: escalate only when the decision exceeds your authority, creates enterprise risk you cannot own, or needs a call only a senior leader can make. Everything else, you decide, you write down why, and you report the outcome. Executives trust the counsel who brings them solved problems and only true exceptions — not the one who brings them every problem. Owning the call at your level is not recklessness. It is the job you were hired to do.
When a platform makes and sells the product, it is no longer just a platform
Earlier this month a federal judge in Ohio sent Amazon to a jury trial over its Merch on Demand service, and the reasoning is worth more attention than the headline. Weekend Warrior Clothing, a small apparel company, alleges that third-party creators uploaded copies of its designs to the service, producing roughly 560 accused listings and more than 20,000 orders between March 2020 and February 2025. Judge Douglas R. Cole denied Amazon summary judgment on direct and vicarious copyright claims, while dismissing the contributory claim.
The distinction turns on how much Amazon actually does. It does not just host uploads: it creates the listings, sets the price, identifies itself as the seller, and manufactures and ships the product when someone orders. Judge Cole compared that to a print shop that advertises copies in its window and takes a cut of each sale — at some point, the shop stops being a passive provider and becomes the seller. Add that Amazon's system flagged Weekend Warrior's infringement notices as fraudulent and routed later emails to the trash, leaving its DMCA safe harbor for trial as well, and the lesson is plain: control is the price of the business model. The more hands-on you are in making and selling, the less the passive-platform defense will carry you.
Read the IPWatchdog report:
https://ipwatchdog.com/2026/10/15/judge-says-amazon-must-face-direct-vicarious-copyright-claims-over-merch-demand-products/
The rule I drilled into every legal team I led: never just say no
Twenty plus years leading high-functioning legal teams at top tech companies taught me that the fastest way for an in-house lawyer to become irrelevant is a one-word answer. "No" ends the conversation. So the rule on my team was simple: if you can't approve something as proposed, you owe the business the version you can approve. "Yes, if you…”
It works because it keeps counsel in the room where decisions actually get made. A business team that gets a "no" stops asking questions and starts working around you. A business team that gets a "yes, if" brings you the next one earlier. Saying no is easy. Shaping the yes is the job.
Trademark law just walked into the AI lab
Generative AI is no longer just a copyright story. In Getty v. Stability AI, a federal court refused to dismiss Getty's Lanham Act claims over AI-generated images bearing distorted Getty watermarks — holding that AI outputs can be "goods" under trademark law and can confuse consumers about source. Brand owners: your enforcement playbook now extends to model outputs, not just counterfeit listings.
The fastest legal teams I've seen all do one thing
They ask the business team this question early: "What does winning look like, and when does it have to happen?" Most legal bottlenecks aren't legal problems — they're undefined success criteria. When the business can't describe the win, counsel can't calibrate risk, and everything becomes "urgent." A two-minute question at the start saves two weeks at the end.
Navigating Inconsistencies Without Defensiveness
When you suspect a colleague or partner is withholding information, aggressive confrontation only triggers defensiveness. Instead, neutrally label what you observe, ask open-ended "what" questions, and allow comfortable silence. Giving people space to explain themselves reveals the truth much faster. Read an investigator's guide to difficult workplace conversations: Fast Company.
Breaking Strategic Deadlocks Through Action
Forecasting upcoming disruption is not enough if leadership teams remain stuck in endless analysis. When groups stall on complex challenges, break the gridlock by sharing costs, launching small joint pilot tests, and naming a clear decision tie-breaker. Action beats continued debate. Read how to break strategic deadlocks: Inc. Magazine.