Robert Ambrogi Blog
Ben M. Schorr, one of the leading experts in the use of Microsoft products in legal practice, has joined Affinity Consulting Group LLC, one of the top companies in the U.S. providing strategic business and tech-implementation consulting for law firms and legal departments.
Starting today, Schorr is joining a new innovation strategy team at Affinity, focusing on the practical application of generative AI tools and Microsoft 365 technologies in law firms.
Schorr has spent over 30 years bridging Microsoft’s productivity tools with the unique needs of legal professionals, most recently at Microsoft, where he had been senior content program manager since 2016, creating and managing content to help customers get the most out of Microsoft Office and Microsoft 365.
In May, Microsoft eliminated Schorr’s position, as part of layoffs that affected 6,000 employees.
From Microsoft MVP to Employee
Schorr’s departure from Microsoft comes after eight years with the company, where his role involved creating content and user experiences to help customers maximize Microsoft 365 and artificial intelligence tools, with a particular focus on cybersecurity applications.
Prior to joining Microsoft as an employee, Schorr had been a Microsoft Most Valuable Professional (MVP) for 20 years, initially recognized for his Outlook expertise and later becoming the first OneNote MVP in 2003.
In an interview this morning, Schorr told me that, even before he got that “somewhat surprising” news that his position was being eliminated, he had considered what companies he might want to join as his next move, and Affinity was at the top of the list.
Debbie Foster, CEO of Affinity, said that when Schorr reached out to her, she immediately thought, “Microsoft’s loss could be Affinity’s gain.”
Bridging Legal and Technology
Schorr’s expertise stems from over 30 years in legal technology, including nearly eight years as director of information services at Damon Key Leong Kupchak Hastert, a prominent Honolulu law firm.
Following that role, he co-founded Roland Schorr & Tower, a consulting firm with offices across the western United States that specialized in helping law firms maximize their technology investments.
A prolific author, Schorr has written multiple books for the American Bar Association, including The Lawyer’s Guide to Microsoft Outlook, The Lawyer’s Guide to Microsoft Word, Office 365 for Lawyers, and OneNote in One Hour for Lawyers.
He was also a contributing author for technology publications and served as part of the “Ask the Exchange Pros” team for Windows Server System magazine.
The AI Implementation Challenge
In our conversation this morning, Foster identified a key problem among law firms that Schorr’s expertise makes him well-suited to address: Purchasing AI tools but struggling to implement them effectively.
“I read a post on LinkedIn yesterday that talked about AI being the new Peloton,” Foster said. “People buy it but they don’t actually use it.”
Schorr emphasized the importance of managing expectations around AI implementation.
“Most of the time when I talk to somebody, legal professional or otherwise, who’s tried AI and been disappointed, it’s usually because they thought it was going to be a flying car,” he said. “They thought it was just going to be a big green button that said practice law.”
Instead, Schorr advocates for realistic expectations about AI’s current capabilities. “In most cases, it’s saving people 30 minutes a day, 45 minutes a day, an hour a day,” he explained. “That’s meaningful, that’s important. It’s only disappointing if you thought it was going to save you eight hours a day.”
A Tool-Agnostic Approach
While Schorr brings deep Microsoft expertise to Affinity, he said that his approach to consulting will be to focus on the best tool for the job rather than be platform-exclusive.
While Microsoft Copilot excels at tasks like summarizing emails and comparing documents within the Microsoft 365 ecosystem, other AI tools might be better suited for specific applications like legal research, he said.
“I can ask Copilot to do legal research and it will try to do it, and it may even do it okay in many cases, but it’s just not really the best tool for that,” Schorr said. “I would use an AI that’s configured for legal research.”
New Innovation Strategy Team
At Affinity, Schorr has joined a new innovation strategy team focused on practical applications rather than theoretical demonstrations. Foster said the team will help firms address the challenge they often face of seeing impressive demos but then struggling to translate that into actual workflow improvements.
“There is no translation from sitting in a Zoom meeting or in a conference room and watching a demo of a product and then sitting down at your own desk and doing the next thing,” Foster said.
The team will focus on helping firms make incremental changes that build comfort and confidence in new approaches rather than attempting wholesale workflow transformations.
Foster described the strategy as helping lawyers make small changes that compound over time.
“How do I take small things that I do and integrate generative AI so I start to believe myself there’s a different way,” she said. “Because then I, as the lawyer, start asking questions: ‘Wait, that thing that used to take me three hours, I am able to do better in an hour. What about this next thing, how do I do that differently?’”
Creating Believers
Schorr’s move to Affinity represents a return to direct client consulting after his tenure at Microsoft. Foster said the move will be particularly valuable for creating “believers” in new technology approaches, explaining that successful AI implementation requires people who are passionate about working smarter.
“You’ll never get ROI from generative AI unless you have believers that there’s a better way to get work done,” Foster said. “And so you should focus on your believers if you want ROI from generative AI.
“That’s one of the things that I love about Ben, is that Ben has a passion for working smarter — and showing people how you can work smarter helps you create believers.”