3 min read
Avoiding Stupidity at Work
“It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”
--Charlie Munger
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2 min read
In-House Legal In A Doom Loop?

There is an expression that comes from design thinking that goes something like "Every system is perfectly designed to get the results it gets." If that holds true, then the system that In-house Legal finds itself inside of must have been designed by...
3 min read
mot-r Fails to Secure $75 Million in Series N/O Funding to Revolutionize Legal Service Operations

January 17, 2025 — Toronto, ONmot-r, a proudly old-fashioned and customer-focused provider of contract tracking, workflow, and dashboard solutions for the legal industry, announced today that it has not raised $75 million in a Series N funding round. The...
5 min read
Avoiding the Post-DMS Pit Of Despair

The mandate of this blog is to help people avoid making the same old bad decisions when it comes to legal technology and legal operations. It has been inspired by Charlie Munger’s quote, “It is remarkable how much long-term advantage people like us have...
4 min read
Avoiding LegalTech Stupidity: The Hidden Curse of Technical Debt

The mandate of this blog is to help people avoid making the same old bad decisions when it comes to legal technology and legal operations. It has been inspired by Charlie Munger’s quote, “It is remarkable how much long-term advantage people like us have...
5 min read
Avoiding LegalTech Stupidity: Adapt or Suffer

The mandate of this blog is to help people avoid making the same old bad decisions when it comes to legal technology and legal operations. It has been inspired by Charlie Munger’s quote, “It is remarkable how much long-term advantage people like us have...
2 min read
One Loop or Two?

I've written previously about the effective application of the OODA loop to legal operations, and also where it doesn't apply. While it is a very useful tool in the right context, it is insufficient without being an embedded component in a learning...
3 min read
From Fighter Pilots to General Counsel: Using The OODA LOOP

I had the good fortune to attend a session at Alternative Events’ Tech Summit where Andrew Cooke, General Counsel at TravelPerk, was speaking. While the content of all the sessions at the Summit was excellent, Andrew surprised me by referencing John...
2 min read
The Best LegalTech Stack is No LegalTech Stack- part II

Now with the preamble out of the way from Part I, let's drill down into the LegalTech Stack issue.
2 min read
The Best LegalTech Stack is No LegalTech Stack - part I

I'm fortunate that next week I'll be attending the Alternative Events In-House Technology Summit in the UK. I'm looking forward to seeing some old friends and making some new ones (assuming the coffee will be strong and plentiful enough to counteract the...