I Hate It Here S10 E5: Shooting the Sh*t With My Direct Report with Madison Montgomery
Nov 24, 2025
In this lively discussion, Madison Montgomery, an early operator at Workweek and direct report to the host, shares her candid insights about generational workplace dynamics. They dive into the fun chaos of collaborating across HR Millennials and Gen Z perspectives, revealing the amusing reality of their working relationship. Topics like micromanagement evolution, the importance of finding common ground, and memorable team moments add depth to their chat. Plus, expect some playful banter over pop culture favorites!
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Design Structured Hiring From The Start
- Build fair, structured hiring processes from day one to level the playing field for candidates.
- Implement structured interviews so referrals and favoritism don't replace merit-based hiring.
Swap Annual Reviews For Regular Feedback
- Replace annual performance rituals with continuous feedback practices like Feedback Fridays.
- Use frequent, lightweight feedback to reduce emotional load and make performance discussions useful.
Do Fewer Things Exceptionally Well
- Avoid overcommitting early in People Ops; focus on one to two clear goals instead of everything at once.
- Prioritize scope to prevent burnout and allow time to celebrate achieved milestones.