Toxic Positivity Is a Leadership Strategy with Stephen Shedletzky

In this episode of "Actually I Can," host Lindsay Tjepkema sits down with leadership coach Steven “Shed” Shedletsky to unpack a piece of bad advice that taught him a powerful lesson about toxic positivity, organizational politics, and the importance of speaking up. Shed shares how he was once encouraged to coach a team member by deflecting an interpersonal problem with the advice, “Enough about them, let’s talk about you.” What sounded like a positive, forward-looking approach was actually a way of avoiding a difficult problem—and ultimately contributed to a valued team member being let go. Years later, Shed experienced the same tactic from the other side. When he raised concerns about leadership and morale, the conversation was redirected back toward him. Shed describes the experience as gaslighting and says it ultimately became part of what pushed him to leave. Lindsay and Shed explore what toxic positivity really looks like in leadership, why founders can fall into the trap of trying to fix people's emotions instead of listening to them, and how leaders can respond with compassion while still moving toward a bigger vision. They also tackle what to do when you're on the receiving end of unhealthy leadership. Shed introduces the idea of “Jedi leadership”—finding ways to influence ego-driven leaders without directly triggering their defenses—and explains why sometimes the most effective way to create change is to work within the system rather than fight it head-on. Shed shares a framework for healthier organizations built around mindset, actions, and systems, including the importance of consistent one-on-ones, creating genuine speak-up cultures, and designing systems that make empathy and psychological safety part of how a company operates. Because sometimes what looks like positivity is actually a strategy for avoiding the truth. What You'll Learn What toxic positivity really looks like in leadership How “positive” advice can become a way to avoid difficult conversations Why validating someone's emotions should come before trying to change their perspective How organizational politics and unhealthy power dynamics can silence concerns What to do when you're the person experiencing toxic leadership How “Jedi leadership” can help you influence defensive or ego-driven leaders Why founders need to recognize their own blind spots Why people should never be reduced to KPIs Shed's Mindset → Actions → Systems framework for organizational change Why consistent one-on-ones matter How to build a culture where people actually feel safe speaking up How leaders can turn empathy into an organizational system rather than an individual personality trait 📩 Subscribe to the newsletter 🔗 Follow Lindsay on LinkedIn 🔗 Follow Shed on LinkedIn 🌐 Learn more about Shed Inspires This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit humanbrandswin.substack.com