EPISODE · Nov 24, 2025 · 1H 8M
S10 E5: Shooting the Sh*t With My Direct Report with Madison Montgomery
from I Hate It Here · host Hebba Youssef
Okay, friends…this episode is pure fun (okay, a little usual chaos too) in the best way, because I sat down with my actual direct report, Madison Montgomery, who confessed ON AIR that she has never listened to my podcast. And honestly? Fair. We talk generational gaps (including the infamous “generational shits” typo I will never emotionally recover from) and the magical Venn diagram that forms when an HR Millennial and a Gen Z truther try to get work done together. It’s lowkey unhinged, but I hope some of you have this much fun with your own direct reports! Teamtailor is the fun, intuitive ATS that candidates actually like and recruiters don’t dread opening on Monday mornings. Create branded career sites, automate the boring stuff, and give candidates the hiring experience they dream of — without burning out your team. Check them out here. 0:01:34 - Hebba Prepares to be Questioned 0:10:09 - Things People Ops Leaders Get Wrong Early in Their Career 0:19:13 - Inheriting Madision as a Direct Report 0:25:39 - How Hebba’s Management Style Evolved Over the Years 0:37:07 - Things Hebba Has Learned From Madison 0:47:10 - Rapid Fire Questions And if you love I Hate It Here, sign up to Hebba’s newsletter! It’s for jaded, overworked, and emotionally burnt-out HR/People Operations professionals needing a little inspiration. https://workweek.com/discover-newsletters/i-hate-it-here-newsletter/ And if you love the podcast, be sure to check out https://www.youtube.com/@ihateit-here for even more exclusive insider content! Follow Madison: LinkedIn: https://www.linkedin.com/in/madison-montgomery14/ Follow Hebba: YouTube: https://www.youtube.com/@ihateit-here/videos LinkedIn: https://linkedin.com/in/hebba-youssef Twitter: https://twitter.com/hebbamyoussef
What this episode covers
Okay, friends…this episode is pure fun (okay, a little usual chaos too) in the best way, because I sat down with my actual direct report, Madison Montgomery, who confessed ON AIR that she has never listened to my podcast. And honestly? Fair. We talk generational gaps (including the infamous “generational shits” typo I will never emotionally recover from) and the magical Venn diagram that forms when an HR Millennial and a Gen Z truther try to get work done together. It’s lowkey unhinged, but I hope some of you have this much fun with your own direct reports! Teamtailor is the fun, intuitive ATS that candidates actually like and recruiters don’t dread opening on Monday mornings. Create branded career sites, automate the boring stuff, and give candidates the hiring experience they dream of — without burning out your team. Check them out here. 0:01:34 - Hebba Prepares to be Questioned 0:10:09 - Things People Ops Leaders Get Wrong Early in Their Career 0:19:13 - Inheriting Madision as a Direct Report 0:25:39 - How Hebba’s Management Style Evolved Over the Years 0:37:07 - Things Hebba Has Learned From Madison 0:47:10 - Rapid Fire Questions And if you love I Hate It Here, sign up to Hebba’s newsletter! It’s for jaded, overworked, and emotionally burnt-out HR/People Operations professionals needing a little inspiration. https://workweek.com/discover-newsletters/i-hate-it-here-newsletter/ And if you love the podcast, be sure to check out https://www.youtube.com/@ihateit-here for even more exclusive insider content! Follow Madison: LinkedIn: https://www.linkedin.com/in/madison-montgomery14/ Follow Hebba: YouTube: https://www.youtube.com/@ihateit-here/videos LinkedIn: https://linkedin.com/in/hebba-youssef Twitter: https://twitter.com/hebbamyoussef
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S10 E5: Shooting the Sh*t With My Direct Report with Madison Montgomery
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