Stop Being the Bottleneck: Keegan Sard on Delegation and Decision-Making

In this episode of the HabitStack Podcast, host Scott Ward interviews Keegan Sard, a fractional chief of staff based in Monaco who has been doing fractional work for 10 years. The conversation explores the critical difference between a chief of staff and a COO, and why chiefs of staff focus on the founder's priorities without P&L responsibility. They discuss why founders should hire fast and fire faster instead of endless interview rounds, and the distinction between executive assistants who manage calendars and chiefs of staff who make strategic decisions on the founder's behalf. Keegan explains decision playbooks for empowering teams without bottlenecking the founder, quick wins like eliminating payroll from the founder's plate and conducting calendar audits, and implementing the Ritz Carlton's $2,000 rule where every employee can spend money to fix problems without approval. They dive into why founders should include bad news in investor updates to get help before it's too late, the importance of listening tours in the first 90 days, and why anonymous feedback reveals customer insights that never make it up the chain.