this is work 746 big conversations every leader needs to have (awkward chats, talented jerks + why 1:1s matter)
Nov 23, 2025
Rowan Dredge, a leadership practitioner known for enhancing communication and team capabilities, dives into critical yet often avoided conversations for leaders. He and Shell tackle the importance of clarity in communication and the necessity of one-on-ones to boost engagement. They discuss the challenges posed by 'talented jerks' and how leaders can balance high standards with psychological safety. Rowan emphasizes adopting discipline over mere desire for growth and the power of asking questions to foster engagement.
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Leader As Dealer In Context
- Leaders must be dealers in context who simplify complexity for their teams.
- Clear, timely context prevents drowning in busy work and sideways energy.
Communicate The Next Step
- Give people the end goal and the single next step rather than overwhelming detail.
- Time your communication so the team receives the right information at the right moment.
Maps Gave Instructions Too Early
- Shelley describes a drive to Sydney where maps gave instructions too early and caused wrong turns.
- The story illustrates how premature information can overwhelm and confuse decision-making.
