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What happens when jobs start changing faster than your org chart can keep up?In this episode of HR Nightmares, Lisa Leath and Amy Conway sit down with Lucy Wert, Head of HR at Pairwise, to talk about what modern HR leadership looks like when the business is moving fast, AI is changing how work gets done, and nobody has time to hide behind “that’s not my job.”Lucy shares her not-so-linear path into HR, starting with an economics degree, psychology and folklore minors, a rough job market, and a career that has taken her through financial services, startups, pharma, tech, and now agtech. Turns out, supply and demand, human behavior, and storytelling make a pretty useful HR toolkit.The conversation digs into one of the biggest challenges facing HR teams right now: how do you design roles and organizations when the work itself keeps changing?The group talks about hiring for curiosity and learning agility, why scrappiness matters, and how to spot candidates who naturally stretch beyond the boundaries of their job description. They also get into AI adoption, including why using the tools matters, why judgment matters even more, and why measuring logins probably tells you a lot less than whether employees are solving real problems differently.They also tackle talent planning without turning it into a once-a-year PowerPoint Olympics. Lucy shares how Pairwise uses talent reviews, career tracks, cross-functional committees, rotational opportunities, and ongoing conversations to develop employees and build flexibility into the organization.Plus, there’s a strong case for tying rewards not just to what people accomplish, but how they accomplish it. Because hitting your numbers while terrorizing everyone around you probably should not earn the exact same bonus.Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your podcasts, and join us next time for more straight talk from the front lines of HR on HR Nightmares.

What happens when jobs start changing faster than your org chart can keep up?

In this episode of HR Nightmares, Lisa Leath and Amy Conway sit down with Lucy Wert, Head of HR at Pairwise, to talk about what modern HR leadership looks like when the business is moving fast, AI is changing how work gets done, and nobody has time to hide behind “that’s not my job.”

Lucy shares her not-so-linear path into HR, starting with an economics degree, psychology and folklore minors, a rough job market, and a career that has taken her through financial services, startups, pharma, tech, and now agtech. Turns out, supply and demand, human behavior, and storytelling make a pretty useful HR toolkit.

The conversation digs into one of the biggest challenges facing HR teams right now: how do you design roles and organizations when the work itself keeps changing?

The group talks about hiring for curiosity and learning agility, why scrappiness matters, and how to spot candidates who naturally stretch beyond the boundaries of their job description. They also get into AI adoption, including why using the tools matters, why judgment matters even more, and why measuring logins probably tells you a lot less than whether employees are solving real problems differently.

They also tackle talent planning without turning it into a once-a-year PowerPoint Olympics. Lucy shares how Pairwise uses talent reviews, career tracks, cross-functional committees, rotational opportunities, and ongoing conversations to develop employees and build flexibility into the organization.

Plus, there’s a strong case for tying rewards not just to what people accomplish, but how they accomplish it. Because hitting your numbers while terrorizing everyone around you probably should not earn the exact same bonus.

Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your podcasts, and join us next time for more straight talk from the front lines of HR on HR Nightmares.

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YouTube Video UExXRnBuMF9zaTZyMVBBaTVKTVZZMWlHMW5JaXBpNmNwRS44QTY2MEEzNzBFQUJCMUQ2

Your Org Chart Can’t Keep Up with Lucy Wert | S5 EP7

Leath HR Group | HR Nightmares Podcast 7 hours ago

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Leath HR Group | HR Nightmares Podcast September 14, 2026 3:57 pm

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Leath HR Group | HR Nightmares Podcast September 14, 2026 3:50 pm

What does the future workforce actually think about careers, college, AI, and life after graduation?In this episode of HR Nightmares, Lisa and Beth sit down with Ruby Vogt and Ella Kober, two rising college sophomores with very different career paths and a surprisingly clear perspective on what comes next.They talk about choosing a major when you are barely old enough to know what you want for dinner, the pressure to have your entire career mapped out, study abroad adventures in Prague and New Zealand, and why having the right college adviser can change everything.The conversation also turns to AI. Ruby and Ella share how they are already using it in school, where they think it helps, and why there is still plenty of work that requires an actual human brain. For HR leaders wondering how the next generation will approach technology, communication, and the workplace, consider this your preview.Plus, there is plenty of discussion about social skills, good manners, college roommates, sorority recruitment, part-time jobs, parenting, parking tickets, Disney uniforms, and the apparent return of the mock neck.The future of work is not some far-off HR strategy exercise. It is already sitting in college classrooms, using ChatGPT, planning a semester overseas, and figuring out what kind of life it wants. And frankly, we think the future looks pretty good.Have an HR nightmare of your own? Submit it at LeathHRGroup.com for a chance to have the team tackle it on the show.We hope you enjoy this episode! Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your
podcasts, and join us next time for more straight talk from the frontlines of HR on HR
Nightmares.

What does the future workforce actually think about careers, college, AI, and life after graduation?

In this episode of HR Nightmares, Lisa and Beth sit down with Ruby Vogt and Ella Kober, two rising college sophomores with very different career paths and a surprisingly clear perspective on what comes next.

They talk about choosing a major when you are barely old enough to know what you want for dinner, the pressure to have your entire career mapped out, study abroad adventures in Prague and New Zealand, and why having the right college adviser can change everything.

The conversation also turns to AI. Ruby and Ella share how they are already using it in school, where they think it helps, and why there is still plenty of work that requires an actual human brain. For HR leaders wondering how the next generation will approach technology, communication, and the workplace, consider this your preview.

Plus, there is plenty of discussion about social skills, good manners, college roommates, sorority recruitment, part-time jobs, parenting, parking tickets, Disney uniforms, and the apparent return of the mock neck.

The future of work is not some far-off HR strategy exercise. It is already sitting in college classrooms, using ChatGPT, planning a semester overseas, and figuring out what kind of life it wants. And frankly, we think the future looks pretty good.

Have an HR nightmare of your own? Submit it at LeathHRGroup.com for a chance to have the team tackle it on the show.

We hope you enjoy this episode! Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your
podcasts, and join us next time for more straight talk from the frontlines of HR on HR
Nightmares.

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YouTube Video UExXRnBuMF9zaTZyMVBBaTVKTVZZMWlHMW5JaXBpNmNwRS43QzNCNkZENzIyMDY2MjZB

The Future Workforce Has Entered the Chat | S5E6

Leath HR Group | HR Nightmares Podcast August 27, 2026 12:00 am

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What happens when jobs start changing faster than your org chart can keep up?In this episode of HR Nightmares, Lisa Leath and Amy Conway sit down with Lucy Wert, Head of HR at Pairwise, to talk about what modern HR leadership looks like when the business is moving fast, AI is changing how work gets done, and nobody has time to hide behind “that’s not my job.”Lucy shares her not-so-linear path into HR, starting with an economics degree, psychology and folklore minors, a rough job market, and a career that has taken her through financial services, startups, pharma, tech, and now agtech. Turns out, supply and demand, human behavior, and storytelling make a pretty useful HR toolkit.The conversation digs into one of the biggest challenges facing HR teams right now: how do you design roles and organizations when the work itself keeps changing?The group talks about hiring for curiosity and learning agility, why scrappiness matters, and how to spot candidates who naturally stretch beyond the boundaries of their job description. They also get into AI adoption, including why using the tools matters, why judgment matters even more, and why measuring logins probably tells you a lot less than whether employees are solving real problems differently.They also tackle talent planning without turning it into a once-a-year PowerPoint Olympics. Lucy shares how Pairwise uses talent reviews, career tracks, cross-functional committees, rotational opportunities, and ongoing conversations to develop employees and build flexibility into the organization.Plus, there’s a strong case for tying rewards not just to what people accomplish, but how they accomplish it. Because hitting your numbers while terrorizing everyone around you probably should not earn the exact same bonus.Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your podcasts, and join us next time for more straight talk from the front lines of HR on HR Nightmares.

What happens when jobs start changing faster than your org chart can keep up?

In this episode of HR Nightmares, Lisa Leath and Amy Conway sit down with Lucy Wert, Head of HR at Pairwise, to talk about what modern HR leadership looks like when the business is moving fast, AI is changing how work gets done, and nobody has time to hide behind “that’s not my job.”

Lucy shares her not-so-linear path into HR, starting with an economics degree, psychology and folklore minors, a rough job market, and a career that has taken her through financial services, startups, pharma, tech, and now agtech. Turns out, supply and demand, human behavior, and storytelling make a pretty useful HR toolkit.

The conversation digs into one of the biggest challenges facing HR teams right now: how do you design roles and organizations when the work itself keeps changing?

The group talks about hiring for curiosity and learning agility, why scrappiness matters, and how to spot candidates who naturally stretch beyond the boundaries of their job description. They also get into AI adoption, including why using the tools matters, why judgment matters even more, and why measuring logins probably tells you a lot less than whether employees are solving real problems differently.

They also tackle talent planning without turning it into a once-a-year PowerPoint Olympics. Lucy shares how Pairwise uses talent reviews, career tracks, cross-functional committees, rotational opportunities, and ongoing conversations to develop employees and build flexibility into the organization.

Plus, there’s a strong case for tying rewards not just to what people accomplish, but how they accomplish it. Because hitting your numbers while terrorizing everyone around you probably should not earn the exact same bonus.

Submit your anonymous workplace questions at LeathHRGroup.com. Subscribe and share this conversation wherever you get your podcasts, and join us next time for more straight talk from the front lines of HR on HR Nightmares.

0 0

YouTube Video UExXRnBuMF9zaTZyMVBBaTVKTVZZMWlHMW5JaXBpNmNwRS44QTY2MEEzNzBFQUJCMUQ2

Your Org Chart Can’t Keep Up with Lucy Wert | S5 EP7

Leath HR Group | HR Nightmares Podcast 7 hours ago

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