Best of Stay SaaSy — 2025

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   Stay SaaSy·52w

   Your Manager Is Not Your Best Friend

   Managers should avoid commiserating with their direct reports as it creates organizational toxicity, builds factions, and prevents other teams from improving. Instead of providing unconditional sympathy like a best friend would, effective managers need to ask clarifying questions, seek truth, provide perspective, and focus on constructive solutions. The key is to validate feelings without validating facts, remove disparaging language, and redirect conversations toward productive outcomes rather than allowing negative venting sessions.

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   Stay SaaSy·1y

   Judge Your Coworkers

   Encouraging judgment of coworkers' performance can enhance collaboration and accountability within teams. This is especially crucial in leadership roles or cross-functional groups. The post provides guidelines on how to productively evaluate peer performance, including the importance of private feedback, maintaining an awareness of peers' strengths and weaknesses, and fostering a culture of continuous learning and improvement.

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   Stay SaaSy·1y

   Managing People You Can't Fire

   Managers often face the challenging situation of needing to fire someone and getting blocked by their boss. This can stem from personal relationships, perceived harshness, lack of trust, or risk aversion on the part of the boss. Such situations can lead to significant frustration and even cause the manager to quit. The suggested solutions involve establishing clear protocols during the initial learning phase and then trusting the manager's judgment in firing decisions to foster trust and respect.

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   Stay SaaSy·33w

   How to Compete in SaaS

   Competing effectively in SaaS requires actively engaging with competitors rather than ignoring them. Success comes from delivering 'knockdown blows' that force competitors to retreat from overlapping markets by targeting their revenue operations and sales team morale. The key is persistence over cleverness: consistently winning deals to make competing against you a career liability for their sales reps. Competition escalates from marketing battles when you're strongest, to sales when moderately stronger, to product development when evenly matched. Companies that build quickly pose the greatest threat, especially desperate, founder-led startups willing to fight to the end.

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   Stay SaaSy·37w

   The Trauma You Need To Learn

   Learning from difficult experiences like firing employees and shipping bugs is essential for growth in management and engineering. Shielding people from the emotional impact of their failures prevents them from developing better judgment and practices. Managers who experience the full weight of firing someone become more careful about hiring and performance management. Engineers who directly engage with customers affected by their bugs develop stronger commitment to quality. Organizations should expose people to appropriate levels of discomfort from their failures rather than creating buffer systems that remove accountability and learning opportunities.

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   Stay SaaSy·47w

   Naming Software Teams

   Team names serve as contracts that define ownership and prevent mission creep in software organizations. A well-chosen name should be specific enough to block scope expansion while enabling efficient routing of questions and responsibilities. Broad names like 'Platform Team' attract unwanted work, while ambiguous names create confusion. Specific names tied to actual ownership (like 'Widget A Team') provide clarity and prevent territorial conflicts between teams.

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