The Cost of Avoiding Hard Conversations

In this episode of The Ross Simmonds Show, Ross gets real about what culture truly is inside an organization. Spoiler alert: it’s not your values deck, your company retreats, or the catchphrases painted on your office walls. Culture is what your team experiences—and that starts with leadership.

Ross unpacks how the most problematic leadership habits quietly become the blueprint of a company’s culture. Through personal insights and actionable advice, this episode challenges leaders to reflect on their behaviors, confront their blind spots, and align their habits with the culture they aspire to create.

Key Takeaways and Insights:

1. Culture Is Practiced, Not Preached

- Culture isn’t your onboarding slide deck or a nicely printed poster—it's what your company does every single day.

- If you claim a value (e.g. empathy, growth, candor), but your actions contradict it, then it’s not part of your real culture.

2. Leadership Habits Define Team Norms

- “Your culture is a reflection of your worst leadership habits.”

- Leaders unintentionally shape culture through the behaviors and patterns they tolerate or exhibit.

3. The Toxic Impact of Avoidance

- Avoiding hard conversations or decision-making can silently simmer into dysfunction.

- Leaders need to have the courage to confront their personal weaknesses to positively affect culture.

4. Build Muscle Memory for Better Leadership

- If giving feedback or staying focused is hard, start building systems and routines that reinforce those behaviors.

- Example: “Pursue the awkward” moments to grow stronger in them.

5. Self-Awareness Is Crucial

- Ask critical questions as a leader: Am I consistent? Do I finish what I start? Am I a source of clarity or chaos?

- Teams watch leaders’ actions more than they listen to their words. Walk matters more than talk.

6. Cultivate Culture by Fixing Yourself First

- Introspective leadership is the foundation of thriving workplace culture.

- Practical step: Make a list of personal habits that are out of alignment with your company’s stated values and strategize ways to improve.

7. Leadership Isn’t About Titles

- You don’t need to be a CEO or founder to lead with intentionality.

- Cultural influence can come from any level within an organization—or your life.

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