Stressful leadership meetings are a common problem for startups and high-growth companies, often due to data-related challenges. The author, who was VP of BizOps and then VP of Customer at a real estate technology company, learned these lessons the hard way and wants to share them with others. The four main data-related reasons for leadership meeting failures are: (1) the "spaghetti stack problem" where teams pull data from siloed systems and SaaS tools, (2) the "old dog, new tricks" problem where companies invest in a modern data stack but still struggle to trust their data, (3) the "multiple sources of truth" problem where multiple teams maintain their own data sets, and (4) the "air traffic control" problem where coordinating data from multiple sources is challenging. To address these issues, companies can invest in a modern data stack, educate and communicate with their teams, build scalable processes, and use tools like Zapier and AirOps to streamline their data management.