Katherine von Jan (KVJ), CEO and Co-founder of Tough Day and a longtime innovation leader across Lotus Development, IBM, Salesforce, and multiple startups, joins Bob to trace a career built on one consistent thread: putting culture and human potential at the center of technology. The conversation covers the perils of workforce surveillance AI, why "human in the loop" has become a nearly meaningless phrase without real definition, and how KVJ's Human Positive Company framework gives organizations a way to evaluate whether their AI and culture choices are actually earning trust. They dig into the ethical review process that killed a risky Salesforce AI project (and the better one that replaced it), how KVJ's earlier startup RadMatter tackled bias against non-Ivy League candidates, and what her team learned about great management while building the AI behind Tough Day. It's a wide-ranging, practitioner-level conversation about responsible innovation, moral leadership, and what it actually takes to build AI people can trust. Keywords: human-centric AI, responsible AI, AI governance, workforce surveillance, human in the loop, AI ethics, Human Positive Company framework, Tough Day, Tuffy, RadMatter, Salesforce, IBM, Lotus Development, Irene Greif, talent acquisition, hiring bias, quality of hire, employee trust, ethical review, red teaming, collective intelligence, workplace culture, moral leadership, AI slop, skills-based hiring, retention Takeaways: KVJ's path from anthropology and Lotus Development (working for Irene Greif) through IBM, Salesforce, and now Tough Day traces one consistent thread: technology in service of culture and human potential "Human in the loop" is losing meaning as a governance concept; every stage of a workflow, like a recruiting funnel, is a decision point that either includes or excludes real human judgment Workforce surveillance AI, tools that flag "risk" signals across email, Slack, and HR systems, is a dangerous use case that erodes trust rather than building it Responsible innovation requires research and ethical review before deployment, not just fast iteration; Salesforce's own attrition-prediction AI backfired until it was redesigned into a re-recruiting tool instead KVJ's Human Positive Company framework evaluates organizations across three pillars: workforce ingenuity, positive-sum prosperity, and the ethical and humane use of AI RadMatter, her earlier startup, aimed to give overlooked and non-Ivy-League students visibility with employers, a problem that still shapes bias in AI-driven hiring today Building AI that reflects an organization's values starts with defining those values clearly and creating a real process, not just a poster on the wall, for employees to raise concerns Great management often looks like curiosity, asking more questions before offering answers, a pattern KVJ observed directly while researching how to train Tough Day's AI Quotes: "A coalition is designed to go solve something." - KVJ "You don't just go build the app. You build the research first." - KVJ "A lot of organizations have values written on the wall and that's as far as it goes." - KVJ "We're getting AI slop, and we're getting process slop, and we're getting application slop." - KVJ "Every employee is responsible for understanding, what am I complicit in?" - KVJ "Human in the loop is almost meaningless at this point. What is the loop? And where is the human in said loop?" - Bob Chapters: 00:01 Welcome and introductions 01:00 KVJ's path into tech: anthropology, Lotus Development, Irene Greif, and IBM 08:09 The strange LinkedIn deactivation and the leap to Salesforce 12:26 Comparing culture and tools across IBM, Salesforce, and beyond 15:13 Early social network analysis and today's AI parallels 18:32 Where to draw the line: what AI should do, not just what it can 21:27 Workforce surveillance AI and the danger of thinning out the workforce 25:47 Responsible innovation and human-positive AI 29:34 Inside the Human Positive Company framework 33:32 Measuring what matters: retention, morale, and moral leadership 37:05 Rethinking human in the loop across the recruiting funnel 38:26 RadMatter and surfacing overlooked talent 43:26 Building governance: ethics committees and guardrails 47:06 Training Tough Day's AI on values, culture, and what research reveals about great management 57:20 Closing thoughts and a call to action KVJ: https://www.linkedin.com/in/kvonjan Tough.Day: https://tough.day For advisory work and marketing inquiries: Bob Pulver: https://linkedin.com/in/bobpulver Elevate Your AIQ: https://elevateyouraiq.com Substack: https://elevateyouraiq.substack.com
