EntreLeadership Should I Take on a Leadership Role Again? (I Failed Last Time)
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Feb 4, 2026 Luis, owner of a contracting business now running remotely from Guatemala, asks about leaving operations in his team’s hands while doing mission work. Cole, part-owner of a growing property management company from Springfield, debates whether to leave to rescue his father’s struggling trucking firm. They discuss weighing long-term tradeoffs, diagnosing failing businesses, and leading remotely with trust and clear rhythms.
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Young Leader Faced Resistance Before
- Tyler failed earlier as a young leader when an older rep resisted his authority and trust couldn't be built.
- He plans to lead again but wants practical ways to avoid the prior breakdown.
Run Short Regular One-On-Ones
- Set a regular one-on-one rhythm (weekly or biweekly) to serve and correct your team.
- Use that time to learn personal context, remove blockers, and course-correct performance early.
Not Every Relationship Is Fixable
- Some people simply won't accept authority because they don't believe you're worthy to lead.
- That's often not fixable by changing your behavior, so identify it quickly and adjust.