How can leaders turn disagreement into better decisions? Karan Yadav joins Felicia Shakiba to discuss productive friction, hiring people who learn and solve problems, and building teams that challenge ideas before committing to a shared direction.
Drawing on his experience at Apple, Workday and OrbitShift AI (a Sequoia backed company), Karan explores how leaders pressure-test ideas, use AI without losing originality, and make culture visible through everyday behavior. They also discuss coaching after customer calls, explaining the reasoning behind decisions, and ensuring quieter team members are heard.
Guest: Karan Yadav, Chief Operating Officer and Head of Americas at OrbitShift AI at the time of recording.
Host and interviewer: Felicia Shakiba.
CHAPTERS
00:00 Opening and introduction
00:28 Meet Karan Yadav
02:32 Friction in startups and large organizations
04:47 Scaling sales and marketing at OrbitShift AI
09:44 Why hiring becomes a search for familiar patterns
13:49 Encourage dissent, then commit together
16:52 Pressure-testing ideas: lessons from Apple
20:45 AI, productivity and human judgment
23:55 Using AI without losing your voice
25:19 Building a culture of creativity and disagreement
33:08 Leading change in established organizations
38:24 Coaching and two-way feedback after customer calls
46:21 Explaining intuition to remove decision bottlenecks
49:20 Making room for the quietest person
53:17 Connecting teams across cultures and locations
57:10 The cost of a culture of agreement
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