The Stretch – How to Stop Hating it Here

Hebba Youssef:
So, when I finally made it past season seven, I was like, guys I've lasted longer than Buffy the Vampire Slayer, my favorite show on TV.

Kevin Fyock:
We're gonna talk about feeling the unease of what's to come, but the things that need to change.

Hebba Youssef:
I do not want to have one more conversation about the future of work? I like really want people to be like, no, like we can never have that future if you aren't doing things today. 

Kevin Fyock:
And then also, what's in a podcast name?

Hebba Youssef:
My CEO did not want me to name it I Hate It Here. And I was like, please I need you to trust me. A lot of HR people might feel this way.

Kevin Fyock:
I'm incredibly excited again here at Transform in Las Vegas to have Hebba Youssef, the founder and host of I Hate It Here, and also the Chief People Officer at Workweek. Did I get that all right? 

Hebba Youssef:
Yes. All right.

Kevin Fyock:
Okay, I have to say too, this is like a Christopher Nolan movie in a way, right? 

Hebba Youssef:
Oh, ok!

Kevin Fyock:
Like Inception. It's kind of like a podcast in a podcast. 

Hebba Youssef:
Ok.

Kevin Fyock:
Because I'm the host of The Stretch. 

Hebba Youssef:
Yes.

Kevin Fyock:
You’re the host of I Hate It Here. 

Hebba Youssef:
I Hate It Here. Yep.

Kevin Fyock:
And I'm gonna be a guest on your podcast. 

Hebba Youssef:
Uh huh.

Kevin Fyock:
You're a guest on my podcast. There's a lot going on here.

Hebba Youssef:
There's a lot of podcasts. Should we be allowed to have mics? I don't know. 

Kevin Fyock:
I don’t think so. And we're done. 

Hebba Youssef:
And the episode is over everybody. Thank you for being here. We kicked them out.

Kevin Fyock:
Okay, so we had a chance to talk a little bit before. And actually, quite a bit before that, because being on your podcast, we’re gonna talk about women's health, which is near and dear to my heart. So, we'll stay away from that topic. 

Hebba Youssef:
Okay. 

Kevin Fyock:
And instead, we'll focus on maybe broader HR, maybe some benefit‑focused areas. 

Hebba Youssef:
Yes, okay. 

Kevin Fyock:
But I think something that I loved when we were talking is you have been in an HR and a people role for very big and very small organizations. 

Hebba Youssef:
Yep. 

Kevin Fyock:
So, like compare and contrast that for me.

Hebba Youssef:
Oh, it’s so fun. 

Kevin Fyock:
Yeah. 

Hebba Youssef:
When it's big the complexity with like every problem feels like times a million. 

Kevin Fyock:
Yeah. 

Hebba Youssef:
And when it's small, the complexity still feels times a million. Just like a different feeling. Same, same but different. At the big scale, it's like how do I communicate something across so many different people? And the small scale it's like how do I make this individual actually hear the thing I'm trying to tell them when I have to tell them five thousand times the same thing. 

It's so fun. I prefer small, to be clear. Because I'm like very much in my builder era where I'm like I want to build it, I want to do it, I need to experience it. When it's big sometimes you build it and then you have to like let it fly. And maybe I'm a little bit of a control freak. I don't want to let it fly.

Kevin Fyock:
Yeah, I think being a control freak at a small organization probably works a little better. Less bureaucratic nonsense.

Hebba Youssef:
Yeah. I'm like very open about being a control freak. I like talk about it all the time at work where I'm like I like things a certain way and I'm like trying to open up my mind up to like I will let them be different because we're like in the era of everything is different now. 

Kevin Fyock:
It's true. I am also a self‑proclaimed control freak, but only in like really bizarre areas. Like in many ways, I wish I could fly the plane.

Hebba Youssef:
Oh, I'm not like that. 

Kevin Fyock:
No? 

Hebba Youssef:
I'm just about it about HR.

Kevin Fyock:
About HR, okay. Not like transportation with jets.

Hebba Youssef:
No. I'm like very free spirit in other facets of my life and very intense about specific things in my life. The duality of women.

Kevin Fyock:
Okay, okay. Well maybe between the two of us we can control freak a lot together.

Hebba Youssef:
That's actually the next podcast we're gonna have. It's gonna be called control freaks.

Kevin Fyock:
That's right. Actually, I'll be flying a plane, and we'll do it from the cockpit.

Hebba Youssef:
I will not be there. I will be on the ground.

Kevin Fyock:
Okay, so big HR, small HR, what is your—at a small sort of company, what is your favorite thing you've ever done, maybe on behalf of the employees that that you work with?

Hebba Youssef:
Oh my God, what a good question. I'm like, wow, that was a really good one. My favorite thing I've done at small company. Okay, this is so corny, but like rolling out benefits that feel like it's actually meeting exactly what they want. 

Kevin Fyock:
Yeah. 

Hebba Youssef:
Because at a larger company I feel like you don't hear as much when you're doing a benefits rollout. It's just like here's our plan, here's everything. When you're at small company, I just feel like people are thankful for what you're doing. Yeah. So like every time we roll out benefits, employees will Slack me and be like, “Wow, this is so nice, thank you.” At a larger company, I feel like you get less acknowledgement for like certain things. And I feel like benefits is one of them.

Kevin Fyock:
You know what? It's a good point. Although I will say, counterpoint, at a big company, if it's the right benefit, I think you'll still get sort of those thanks, right? I think about things like—and not to delve too much into women's health, because we'll talk about that—family building, dependent care leave. Those are things that like are really meaningful to employees and make a difference in their day‑to‑day life. Like I'll share that my family, we had our children through IVF. Huge benefit that literally brought life to our family, right? And I remember thanking my employer for like having such a cool thing to offer to us.

Hebba Youssef:
So it's probably my favorite thing. I know it's corny to be like benefits, but it just feels different when you're doing it for like a small subset of people and you like know very much that this is going to impact their life. I don't—it feels like more, I don't know, authentic. And like a good feeling to hear from your employees like, “Wow, thank you for being so thoughtful about these things you're offering us.” And I do feel like at a larger scale, like sometimes you just don't get that. Because the benefits are expected to be great at a big company, whereas at a startup, people are like shocked when our benefits are good because they're like, “Wow. Startups don’t usually have this good of benefits”

Kevin Fyock:
It's funny too that like the concept of benefits, and I say this as somebody who is a benefits professional, has worked in this industry and adjacent industries for you know 20 years, we lose sight of like a benefit is supposed to be just that, right? We spend a lot of our times talking about like, you know, healthcare as a way to engage employees, but it's also a benefit. You know, time off as a way to, you know, drive resilience, but it's also a benefit. So it's just an interesting thread to pull on.

Hebba Youssef:
Yes. And I also think about sometimes in HR we get like lost in “the benefits are costing the company something.” And we forget to remember that it's like also adding so much to someone's life. And like that balance, I think—it feels really good to be able to give good benefits to our employees 'cause you're like, “Wow, I'm like significantly making their life better.” And I don't know. I always feel really good about it.

Kevin Fyock:
I think you should and I feel good about coming to work for that reason too. And I think when you find that intersection of benefit that's going to make someone's life better, but then also, yes, they cost something, but when you can impact the cost in a positive way for the employer, whether it's impacting productivity and impacting absenteeism and making someone catch cancer earlier than they otherwise would because you offered something to them, that's pretty cool.

Hebba Youssef:
Yeah. And I get to brag about it when I'm doing like offers and like recruiting people. I get to be like, “We have a really good benefits package. Let me tell you all about it.” Like even though we're a Series A startup, we have a 401(k) match. Like we have all these like really cool things to make your life better by working here. And I think that is also fun.

Kevin Fyock:
What what's your favorite benefit that you offer?

Hebba Youssef:
That's 401(k) match, honestly. I worked at a startup once that did not offer it despite us asking every single year, “Can we have a 401(k) match?” And it was not me that came up with the match. My CEO, like when I got to Workweek, he really cares about having good benefits. He is like an early, he was like father, he was like writing the benefits, he had just had a child, he was like, we have to have good insurance, we have to like help people save for their future. It's important to him. So, like when I got there, I was like, “Wow, this is so great. I just inherited like someone who really cares about the same things I care about and a really good benefits package.”

But I think 401(k) match can make just such a difference in people's life. And the fact that we get to offer and I've worked at other startups that don't, it feels really good that we're doing it.

Kevin Fyock:
So you are the host creator of I Hate It Here. 

Hebba Youssef:
Yes, I don’t hate it here, though.

Kevin Fyock:
No, you don't hate it here. Not specifically right here. 

Hebba Youssef:
No, we’re having fun here.

Kevin Fyock:
We're having a lot of fun. So you've had pretty varied conversations with different folks. Like what have you learned through those conversations? Like what sticks out for you from the folks that you've had on your podcast?

Hebba Youssef:
Yes. My God, so I've done twelve seasons.

Kevin Fyock:
Twelve! I'm on season three.

Hebba Youssef:
Well, you'll get there. That's my favorite season of Buffy the Vampire Slayer. That is my favorite show, Buffy. 

Kevin Fyock:
That's a great show. Okay. 

Hebba Youssef:
So when I finally made it past season seven, I was like, “Guys, I've lasted longer than Buffy the Vampire Slayer, my favorite show on TV.”

Kevin Fyock:
Also like that era of television was like some of the best. 

Hebba Youssef:
Dawson’s Creek. Charmed.

Kevin Fyock:
And like Clarissa Explains It All. Remember her little alligator?

Hebba Youssef:
Yes. That's so funny that you mentioned that 'cause I like made a Clarissa Explains It All reference at work. And I had to like explain it like and then obviously the older employees got it. Gen Z was like, “We've never heard of that.”

Kevin Fyock:
I showed my daughter an episode and her first question was like, “Can I get an alligator in my room?” It was like, you cannot in fact not. 

Hebba Youssef:
You cannot have that. Not at all.

Kevin Fyock:
And then she promptly went to ChatGPT and said, “How do I get an alligator in my room?”

Hebba Youssef:
Dad. Good use case for ChatGPT.  Yeah, “How do I convince my dad I want an alligator?” I'm gonna say it's smart. I should be doing that more.

Okay, my favorite thing I've learned from my guests. Okay, I think it's less that I've learned or something they've given me is like the confidence to be vulnerable in spaces that I maybe wouldn't normally.

And so I've like cried on multiple episodes. Because I like talk about serious things like grief. “The Cost of Motherhood” was a really interesting episode I did. I am not a mother, but I'm very cognizant of the tax it is on people to be mothers, the impact to their careers, to their wage earning potential. Mothers are leaving the workforce in waves. And so, my guests have given me so much like data, but also the ability to like be vulnerable in those moments when maybe I don't know something or I feel very strongly. Like I teared up on the motherhood episode thinking about my mother who didn't get to work. She was a stay‑at‑home mom, and I just don't want anyone to have to be forced into something because work doesn't support people and the choices they make. I don't know if that's a good way to answer.

Kevin Fyock:
That's a wonderful way to answer, right? Like, you know, we're here at Transform and everybody's talking about AI. It's all anybody talks about anymore, right? And sort of like what you're touching on is like the human element, like we can't lose sight of, right? If it's connecting to, yes, women in the workforce, or if it's connecting to like how we can all be better partners to each other. Like that, there's something special about that. And so, the fact that you're pulling away from your guests, like that's pretty awesome.

Hebba Youssef:
I love talking to people, yapping like my favorite pastime. 

Kevin Fyock:
Oh my gosh, me too!

Hebba Youssef:
So having a podcast is the most fun I could ever have. And every week I'm like, “Another episode? Yes. It's all about me.” No, but like also the guests I think are trying to change work. So we're like at Transform, yes, there's a lot about AI, but I do think there's a really good energy here, people being like, the old playbook is not working. 

Kevin Fyock:
Yes. 

Hebba Youssef:
Things have to change. Like COVID rocked us as a society and workplace. Now the rise of AI is also rocking us. Like we're gonna have to do massive workforce transformation.

So just being able to talk to HR leaders as they're navigating this like really hard time has been fascinating.

Kevin Fyock:
It has been fascinating. Okay, so what do you think is gonna be more impactful to sort of HR at large? COVID or AI?

Hebba Youssef:
AI.

Kevin Fyock:
You didn't even pause..

Hebba Youssef:
Sorry . AI is gonna be—okay. So I keep talking about AI like the introduction of email to the workplace. And instant message. Very different. And so now we all email each other 'cause it's normal or we Slack each other, whatever. AI I think is going to reshape how we do everything at work. And I think it's going to rock us in a lot of ways that like we should be rocked in. We've been doing things the same way for so long. Why?

And when we can automate some of the tasks that we need, when we can have generative and agentic AI embedded in all of our things, like could we actually spend more time doing better work? That's the future I'm excited for where I get to work on things that I'm really passionate about that also are interesting and unique problems for me to solve in my organization. I'm not excited about like doing or processing payroll.

Kevin Fyock:
Yeah.

That's weird. That does doesn't excite you.

Hebba Youssef:
I actually don't even do it, my direct report does it and if I had to do it I would cry. I'd like, I don't wanna do this anymore.

Kevin Fyock:
I talk to my clients about like the things that a machine could do. That’s a good example. Like I don't think any human being should be like, “Your deductible is five hundred dollars.” Like you can ask that question to a machine. So there's a lot of benefit to like not just upskilling but just driving efficiency so that—not that we can reduce workforce, but that we can free people up to do much cooler stuff.

Hebba Youssef:
And newer stuff. 

Kevin Fyock:
Yes. 

Hebba Youssef:
Stuff we don't even know, skills we didn't even know we were gonna need. 

Kevin Fyock:
Yes. 

Hebba Youssef:
I'm like, how fun. Right? But I think a lot of people are scared though because there's a lot of like fear content on the internet about AI, taking your job. And I'm just like, I feel like we could—I'm hopeful for the future. I'm scared but I'm also hopeful. 

Kevin Fyock:
Hebba, I agree with you. I'm quite optimistic, I would maybe even say bullish on the technology. I've been looking for like historical anecdotes that I could you know connect back. So email's a really good one. Creation of the World Wide Web, sorry, another one. Even like the automation of building the automobile. 

Hebba Youssef:
Yes. 

Kevin Fyock:
Like there's a lot of technology parallels that we can make here that should give a level of excitement rather than a level of pessimism.

Hebba Youssef:
The thing that excites me the most is I was like not in HR when email got introduced into the workplace. Not to age myself, but I was not. I was emailing. I was on instant messenger. I'm just kidding. 

Kevin Fyock:
You were on AIM. What was your profile name?

Hebba Youssef:
I am not telling you that! That's actually a question we have asked at a company‑wide level where we ask people like, “Share your AIM name,” and I was like, I will not be sharing that.

Kevin Fyock:
Did you at least have like an emotional quote in your profile?

Hebba Youssef:
Totally. I was like putting emo punk lyrics up all the time. I was on MySpace coding my like emo music like…

Kevin Fyock:
Well I'll just be vulnerable and I'll share that mine was KevFy123. But I had a second one. 

Hebba Youssef:
Okay. 

Kevin Fyock:
Which actually like you I won't share it. So…

Hebba Youssef:
I'm not sharing mine, sorry. It's not happening. 

Okay, but the thing that excites me the most right now is like I am in HR to potentially lead this like workforce transformation. I like love change management, very nerdy of me, but I think everything at its core is change management. A lot of problems at work are because they didn't manage the change correctly. So, if AI is just at its core a change management problem, and I get to maybe solve said problem and actually lead us through the transformation as the head of HR, that like really excites me. That feels really powerful in a way that I think is also fulfilling to me because I want to see the change happen well. I don't want to see it done poorly. So, I'm like very excited right now as well.

Kevin Fyock:
This is great. I love the excitement. Okay, so back to I Hate It Here. Well actually a specific question about the podcast name. How did you come up with…

Hebba Youssef:
Oh, “I Hate It Here?” 

Kevin Fyock:
Yeah. 

Hebba Youssef:
This is a really funny origin story at Workweek that we tell a lot to our employees because my CEO did not want me to name it I Hate It Here. And I was like, “Please I need you to trust me. A lot of HR people might feel this way.” And the second reason to the name is my worst fear is an employee comes to me and says, “I hate working here.”

Because then I feel like I have failed in my job as HR. I have not fostered an environment where that employee could thrive. I've not fostered an environment that I would be proud of. And I want to be proud of my work. Like, HR is my craft. I feel grateful that I get to do it. But also like I need to continue to hone this. Like an artist. I need to be like the Picasso of HR. 

Kevin Fyock:
Oh, I love that. 

Hebba Youssef:
But he was like kind of interesting artist.

Kevin Fyock:
Did he want you to call it, “I Love It Here”?

Hebba Youssef:
No, he was like, “Can you call it anything else?” And his reasoning was like, no top brand in the world has “hate” in the title. And I think a lot of people are gonna have a negative experience with the name. And I was like, I think it will resonate with so many people, and it will be wildly popular. He agreed to let me name it I Hate It Here. And when we launched the newsletter, it had 10,000 subs and it got a lot of love and now we're at almost 170,000 subscribers. And people love the name. They're like it's so funny, so cheeky.

I have like a very snarky, dry, dark sense of humor. So it works. It works.

Kevin Fyock:
You know, I'll say nobody gave me pushback on the name The Stretch for our podcast.

Hebba Youssef:
See? “I Hate It Here,” everyone was like, “Whoa, should we really call it that?” And then I was like, “Hey everyone, can we have serial killer letters for the logo?” And they were like, “What now?” And I was like, that's my vision. As if I am writing a murderer kidnapper's letter. I need it to say “I Hate It Here” in like newspaper letters. And they were like, “Okay. 

Kevin Fyock:
Have at it. 

Hebba Youssef:
Yeah, they were like, sure, we're not sure this is gonna work, but we'll see.”

Kevin Fyock:
Okay, so back to your guests. Back to also your role within HR, the different companies you work for. Maybe two balancing questions. One of like, what do you think the greatest opportunity is within maybe benefit‑specific within HR? Because I sit in our Health Solutions business. It's like, greatest opportunity? 

Hebba Youssef:
Okay. 

Kevin Fyock:
And then maybe, maybe it's the same way to ask the same question, but like, what is the most broken? Like what do we need to fix the most?

Hebba Youssef:
Such a good question. Greatest opportunity would be for HR leaders to really understand the cost of their benefits. I do feel like sometimes it's like very gray area where I'm like, “Ooh, I don't actually know what the cost is gonna be this year, I'm not aware, like I'm hoping for this kind of renewal, and like maybe they're utilizing it enough.”

I feel like there's a lot of gray area there, and I think that's an opportunity for HR to get really smart about the business. I always talk about how like we should understand the ins and outs of our business, the cogs. Like we don't need to be the CFO, but we need to understand how our business operates and what the costs are. And headcount is one of your biggest costs. You need to understand the impact that could have on an organization if one year you're hit with an increase that could decimate your entire cash flow. So, like that part I think is the biggest opportunity for us to get more clarity, more line of sight, and have more levers in place to understand what it's costing the company and be able to talk about it at an elevated level with our executive team. 

Kevin Fyock:
Totally agree with you. 

Hebba Youssef:
What was the other question? 

Kevin Fyock:
What is most broken?

Hebba Youssef:
Okay. Healthcare is very confusing. And I. Sorry, I feel like maybe I shouldn't out myself on this right now because I have a broker who explains healthcare to me every year and they're like, “You ask a lot of the same questions every year.” And I'm like, I just…

Kevin Fyock:
Because it’s not getting better.

Hebba Youssef: 
It's so confusing. 

Kevin Fyock:
Yeah, it is.

Hebba Youssef: 
If it's confusing for the employee and I'm in HR trying to make sense of it, Googling things, asking my broker the questions. Why is it so confusing?

Kevin Fyock:
Yeah, I mean. It’s a very valid question.

Hebba Youssef:
How can we simplify it not just for HR but for our employees? So our employees know, okay, this is what it is.

Kevin Fyock:
And believe it or not, it's actually gotten better in the past fifteen years, but that doesn't mean it it's where it should be at all.

Hebba Youssef:
I'm still confused.

I mean, my broker says I ask really good questions. Yeah. So I'm like…

Kevin Fyock:
Well that's good. Maybe you just keep asking the same questions because he's complimenting you.

Hebba Youssef:
But it feels very gray area. I'm like why I still have to ask these questions. Why why do I not know what my renewal is? Like why is it taking so long? How do I—can I get some more answers?

Kevin Fyock:
I know. And what's funny too is like back in 2010 with the passage of the Affordable Care Act, like I think that shined the light on how broken things were, but like at least people are talking about it, right? And there's a level of confusion, but I think there are tools that we now have that maybe we can access things a little bit better. 

Hebba Youssef:
Yes, for sure. 

Kevin Fyock:
Maybe that’s me being optimistic.

Hebba Youssef:
Yeah. That that's the part that I just feels broken though 'cause sometimes my friends are like, “I don't know what's going on. I'm just waiting for I'm waiting in fear for my renewal,” and I'm like, What do you mean? How do you not know? Can we get some line of sight? What's your utilization? Like, what does it look like?

Kevin Fyock:
The only time I'm cool among our friend group is around open enrollment 'cause they ask me questions about their benefits.

Hebba Youssef:
Love.

I'm also cool in my company then because my employees will ask me questions. I'll like, “Hey, that's a great question for our broker.” 

Kevin Fyock:
Could you put that in writing?

Hebba Youssef:
I'm literally like, “Please don't tell me anything about your medical choices. I don't want any of that's your personal—you please ask our broker, I should not know that. Thank you.”

Kevin Fyock:
Okay, Hebba. So this is this is a lot of fun. I have one final question for you. It's my crystal ball question. Okay around sort of where you see things in the next five to ten years. So you have—I know, cheesy question, right?

Hebba Youssef:
I don't even know where I'm going the next five minutes.

Kevin Fyock:
I know. Well that's why this is a stretch question, right? So you have lots of people on your podcast on I Hate It Here. What what do you think the type of conversations you're gonna have in five years, what are those gonna look like?

Hebba Youssef:
I do not want to have one more conversation about the future of work. I like really want people to be like, no like we can never have that future if you aren't doing things today. 

Kevin Fyock:
Oh, that's such a good point!

Hebba Youssef:
So like let's be tactical about today one baby step we can take to get to that. So like in five years, I still hope we're having interesting conversations about new ways to do things. 

Kevin Fyock:
But not the future of work. 

Hebba Youssef:
But not not like that. Like new but new and tactical. Yeah.

Kevin Fyock:
You're giving me so much to think about. I don't think I wanna talk about the future work any more.

Hebba Youssef:
I hate that phrase, it like makes me cringe 'cause I'm like we've been saying it for so long. Is—are we not in the—when are we finally

Kevin Fyock:
Like when is the future?

Hebba Youssef:
When like this this is—is this a Back to the Future storyline? Like what's going on?

Kevin Fyock:
Like we're not talking about the future of computing. Like we've we've been in the future of computing.

Hebba Youssef:
Yeah, but don't talk to me about the future of work and then be like, I'm gonna launch my annual performance review. I'm like, we've been doing annual performance reviews since literally World War Two. Come on. Let's do anything else.

Kevin Fyock:
Yes. Well said!

Well Hebba, this was so much fun.

Hebba Youssef:
So fun.

Kevin Fyock:
Hebba Youssef, the creator and host of I Hate It Here. This was awesome. Thank you so much for joining.

Hebba Youssef:
Thanks for having me.

Kevin Fyock:
And to our listeners, thanks so much for joining. Again, we're live here at Transform in Las Vegas and we're talking about all things workforce related. So thanks so much.

Hebba Youssef:
Killed it!