Episode 186 - Hebba Youssef (Founder & creator of I Hate it Here & Chief People Officer at Workweek)

Listen to our recent episode with Hebba Youssef, Founder & creator of I Hate it Here & Chief People Officer at Workweek.

We talked about the work they're doing to elevate their managers to the next level, why the CEO and Chief People Officer dynamic is challenging, and whether there has been scope creep for the CPO role.

If you don't have time to listen, read the highlights below. ??

1. Getting managers to the next level is what keeps Hebba up at night ???

Hebba talked about the impossible job of being a manager, especially in a 65-person startup.

She shared a funny story about her CEO's take on her views about managers. "My CEO was like, 'You just don't think anybody would be a good manager.' I told him, 'False. I do think people can be good managers, but it's an impossible job.' It's hard enough anywhere, but in a startup where each manager also has their own workload? Forget about it."

Hebba got real about the struggles:

• Balancing being a good employee and a good manager
• Executing all your work while managing others
• Setting realistic expectations for new managers

She admitted, "I've been managing teams for almost a decade, and I still think I'm just an average manager. If it's this tough for me, imagine someone who's been at it for six months."

Here’s the kicker: people aren't naturally good at key managerial tasks like giving feedback, talking performance, handling compensation questions, and saying no. "Now we’re in this workplace where we're all exchanging pleasantries instead of getting better at our jobs."

So, how is she tackling this?

Hebba has a game plan:

• Bi-weekly 30-minute training sessions: Every other Friday, she leads a quick, impactful training.
• Themes: She aligns with her CEO and COO on hot topics, or she picks her own.
• Recent sessions:Hiring process improvementsTeam culture inspired by basketball coaching strategies (think managing Jordan, Pippen, Rodman, and the Bulls)
• Feedback loop: She asks managers what they want training on, working to build trust.

If she had endless funds? Hebba would hook every manager up with an external coach. But for now, she’s focused on these bite-sized, actionable trainings to level up her team.

2. Has the scope of the Chief People Officer role gotten too big? ??

Her big question for all Chief People Officers: "Has our job gotten too big?"

There are massive and varied responsibilities that come with the role. "I have to do so much. And that's not just at an early-stage startup. If you think of your average CPO at a global company, we touch so much, and it's one of the most interdisciplinary fields," she said.

She broke down the wide-ranging skills required:

• Understand the finances of the business
• Know what motivates and develops people
• Have critical conversations and navigate tough situations
• Plan for layoffs and communicate about them effectively
• Be an expert in hiring and understanding different profiles
• Manage the expectations of a constantly changing community
• Constantly think about the tech stack to push the team forward

"It's a skill set that’s so wide that a lot of CPOs are stretched too thin. And I just want to be honest, we're not all good at everything. It's impossible. I can't be good at everything. I'm not. There are my weaknesses," she admitted.

3. The CEO & CPO relationship can be really difficult ??

Hebba recently did a quick search in her community, Safe Space, to see how often "CEO" was mentioned. In just 90 days, it came up over 300 times. She says it’s because the CPO-CEO relationship can be really difficult.

To illustrate, she gave us a peek into her relationship with her CEO. She said, "My CEO and I clash on some things, which is actually good—it means we have a healthy conflict based on trust and respect. A lot of startup CEOs are there because they had killer ideas, not necessarily because they're great leaders. That can make things tricky."

She also put a spotlight on the complexity of HR, saying, "HR isn't just about fun events; it's a deeply regulated field. We have to be on top of laws in every state and country we operate in. Some CEOs think HR is a cakewalk, but it's not. We need to know the laws and how they impact the business."

Hebba shared more about their disagreements, adding, "Adam and I often butt heads, especially on communicating departures. I push for transparency, while he likes to control the narrative. Our different perspectives lead to some interesting conversations, like our first impressions of each other and the hurdles of working together. It was pretty wild to interview my CEO and straight up tell him, 'You're annoying me today.'"

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Hebba's definition of a Modern People Leader ??

"Somebody who is empathetic, curious, and honest. I feel like a lot of business communication gets tricky and we lose a lot when we are dishonest about what's actually at play. So, I think being really honest and communicative is key."

The career advice Hebba would give to her 22-year-old self ??

"I would tell myself to ask more critical questions and listen carefully. I was really scared to ask questions, but I think there's so much power in asking them. Also, really listening to what people have to say is crucial because so much is in between the lines. Back then, I was afraid to ask questions. I would just do things without asking why."

Go listen to the full episode: Apple | Spotify

See you next week!

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