How Leaders Think with Kenny Lange How Cary Matthews Thinks About Difficult Conversations for Stronger Relationships
Nov 19, 2025
Cary Matthews, Managing Partner at Opal Partners Group, brings his wealth of experience from Fortune 100 companies to the table. He dives into the challenges leaders face when having difficult conversations, highlighting how fear and insecurity can derail relationships. Cary emphasizes the importance of trust in delegation and accountability. He shares insights on empowering employees and nurturing mutual trust, while distinguishing intentional delegation from abdication. Tune in for actionable advice on building stronger teams and fostering growth.
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Trust Is The Root Leadership Problem
- Trust underlies most leadership issues like delegation, accountability, and loyalty.
- Cary Matthews sees trust as the core problem he helps companies solve.
Conversation Defines The Relationship
- The conversation itself defines the relationship between people.
- Cary Matthews warns that avoiding hard talks means you don't actually have the relationship you claim.
Push Through The First Eight Seconds
- Start hard conversations even if the first 7–8 seconds feel awful.
- Kenny Lange challenges leaders: don’t let brief discomfort wreck your team or cost you A players.
