Finding the right question to ask is the biggest challenge. Without it, 85% of your user research will be useless. Richard Buchanan, 9/22/17 Stanford Law + Design Summit.


Don’t ask negative questions or ask them in a spirit of advocacy. See 5 Common Questions Leaders Should Never Ask (Warren Berger) (What’s the problem?; Whose fault is it?; Why don’t you do it this way?; Haven’t we tried this already?; What’s our iPad?) Compare The Secret Phrase Top Innovators Use (Warren Berger) (How might we?).

(3) HiPPOs

As technology has spread, so have opportunities to move past the standard partnership and its over reliance on human HiPPOs (highest-paid person’s opinion), and to move toward more data-driven decision making. The data show that companies that do this usually have an important advantage over those that do not.

A. McAfee & E. Brynjolfsson, Machine, Platform, Crowd: Harnessing Our Digital Future,  p. 60. See HIPPO Explained.


Research in many different fields points to the same conclusion: it’s exactly because incumbents are so proficient, knowledgeable, and caught up in the status quo that they are unable to see what’s coming, and the unrealized potential and likely evolution of the new technology. This phenomenon has been described as the “curse of knowledge” and “status quo bias,” and it can affect even successful and well-managed companies.

A. McAfee & E. Brynjolfsson, Machine, Platform, Crowd: Harnessing Our Digital Future,  p. 23. See The Curse of Knowledge,  See also, Richard Buchanan, 9/22/17 Stanford Law + Design Summit (Institutions are hard to change because they are trapped by their own success.) Recognize your circumstance.


Businesses and in-house teams hire “counsel,” while many law firms hire (and staff cases with) “attorneys” and lawyers.” To counsel someone is to advise them. See Blacks Law Dictionary (Counsel), A lawyer is a person learned in the law. See Black’s Law Dictionary (Lawyer),  and Wikipedia (Lawyer). Words matter. See also Good Leaders Don’t Use Bad Words (Michael Schrage).


Products (think of this as being something made by humans — documents, advice, etc.) must be useful, usable and desirable. Focus on desirability to get beyond lawyer’s egos. See Richard Buchanan, 9/22/17 Stanford Law + Design Summit.


Enterprise AI is not about big data, it is about small data. Think about how you are labeling your data (e.g., meta-data) to enable machine learning and other AI technologies. Engineering the future of AI for businesses (Ruchir Puri) [Separately, consider that most of our content is stored in PDFs.]


Taxonomy design and management is like gardening. Thoughtful system design and data labeling requires planning and active management across systems. See Four Challenges in Taxonomy Management (Agnes Molnar).


In order to get the productivity and effectiveness benefits of technology & AI, you need to (re)design your processes. Integrate some of the principles of design thinking into your approach: understand the customer, work collaboratively, and iterate and experiment. The Rise of Cognitive Work (re)design (Tom Davenport). See also The State of Legal Design: The Big Takeaways of the Stanford Law + Design Summit (Margaret Hagan)


Look for those who have a strong motivation to excel in the pursuit of challenging goals, along with the humility to put the group ahead of individual needs; an insatiable curiosity that propels them to explore new ideas and avenues; keen insight that allows them to see connections where others don’t; a strong engagement with their work and the people around them; and the determination to overcome setbacks and obstacles.

21st-Century Talent Spotting (Claudio Fernández-Aráoz) See also CLOC Legal Operations Career Skills Toolkit.