Automate the 80% Own the 20% (Cherryn-Paige Bissett) Notes To My Legal Self, Season 14, Episode 9

Welcome to Season 14, Episode 9 of Notes to My (Legal) Self. In this episode, host Olga Mack sits down with Cherryn-Paige Bissett, commercial attorney and Internal Commercial Counsel at LegalSifter, to explore how legal professionals can leverage AI without sacrificing human judgment. Together, they discuss the practical realities of contract automation, the role of playbooks, and why the most valuable legal skill in the age of AI is knowing when to step beyond the process and make a judgment call.With more than 20 years of experience as a commercial attorney, Cherryn-Paige has spent her career helping businesses navigate legal, operational, and commercial risk. As both a customer and now a leader within LegalSifter, she brings a unique perspective on how AI can help legal teams move faster, reduce contract noise, and focus on the issues that truly matter.Key insights from this episode:• Why lawyers should automate the routine 80% and own the critical 20%• How AI helps eliminate contract noise and improve consistency• The difference between applying a playbook and applying judgment• Why legal teams must balance commercial, operational, and legal risk• How to determine when a contract issue truly deserves escalation• The importance of understanding business objectives before negotiating risk• Why possibility and probability are not the same thing• How AI can accelerate contracting without replacing lawyers• The skills that will define exceptional in-house counsel in the years aheadWhether you're an in-house lawyer, legal operations professional, contract manager, or legal technology enthusiast, this episode offers practical insights into how legal teams can work smarter while delivering greater strategic value to their organizations.Takeaways:• Automate repeatable work so lawyers can focus on strategic decision-making• AI is most effective when guided by clear legal playbooks• Human judgment remains essential in complex negotiations• Strong lawyers prioritize the risks that truly matter• Understanding your business is critical to effective legal advice• The future belongs to lawyers who can combine technology with sound judgment• Possibility alone should not drive legal decision-making, probability mattersS U B S C R I B E!Want to be a guest on NTMLS or know someone who should be? Reach out! Self-nominations are acts of courage.Engage with us below, like, comment, and subscribe to follow the future of in-house law!Thank you for watching!Like, Comment, Subscribe and hit the bell so you never miss an episode!Subscribe to our channel: @NotesToMyLegalSelf#NotesToMyLegalSelf #LegalInnovation #ContractManagement #CommercialLaw #LegalOperations