"HR is not your friend." And other unconventional insights from Jessica Winder, the self-professed 'Quit Queen'

In Leaders in Learning, we sit down with industry leaders and explore their lives and experiences to uncover the learning principles, key moments, and common threads that shape careers, businesses, and journeys. Through these collective stories, we'll piece together the bigger picture of what it means to be a leader in learning.

We’ve been searching for leaders who think differently, aren’t afraid to challenge conventional wisdom, and have fresh opinions and unique stories to tell. Our latest guest delivers all this and more.

In episode 5, we talk with Jessica D. Winder, a seasoned HR professional with unconventional yet profoundly insightful views on organizational behavior.

Jessica’s known for her trademark statement, “Burn traditional HR to the ground.” So you can bet she’s got some fiery takes. If you want a fresh and modern perspective on Human Resources and People Operations—this is it. Jessica weighs in on everything from workplace culture to DEI&B efforts to job hopping to the disconnect between what employees want (and what employers think they need) and everything in between. 

Get it all in the full episode, or read on for the key takeaways.

HR is not your friend. (But they are on your team)

Perhaps one of the boldest opinions Jessica shared was her position on the modern HR-employee relationship. With equal parts candor and coyness, she claims, "HR is not your friend." 

Um....what? 

According to Jessica, this is one of the biggest misconceptions in the industry. “I don’t know why people would want that. You don’t say that Finance or Marketing or Sales is your friend. Why do I need to be your friend?” She makes a valid point. Nowhere in the job description does it say HR has to be your friend. (Fire you? Yes. Friend you? No.) 

What about the employees-as-a-family analogy? Her reaction to this one is nothing short of visceral. “Ugh. Hate it!” she laughs.

"Saying that your employees are your family is the biggest cringe moment. Because they're not! I am not your family."

So, how does she define the HR-employee relationship? 

“What’s wrong with saying we’re a team?” Absolutely nothing. A group of (unrelated) people working together with a collective focus on achieving common goals is a perfectly fitting (and more accurate) analogy.  

It might not be HR’s job to be your friend or your family, but Jessica believes it is their job to understand the employee experience. If you ask her, the best way to do that is to live it. For her, that meant going on late-night ride-alongs with technicians when she worked with the world’s biggest crime scene cleanup company, and working alongside staff in the store when she was in retail. Because “how do you understand what employees are going through and how are they going to respect you if they think you don't even know what they’re talking about?”

This hands-on approach helps Jessica understand the daily challenges and realities employees face. More importantly, it fosters empathy, mutual trust, and respect, laying the foundation for a productive HR-employee relationship that allows her to serve and support employees far better than simply befriending them ever could. 

And that’s important—especially when it comes to development and growth. (Unsurprisingly, Jessica has an unconventional POV on this.)

Growth isn't a zero-sum game

In Jessica’s experience, many organizations have a zero-sum mindset where they view employee growth in the context of immediate business needs. If a skill isn't directly applicable to an employee's current role, it's seen as a loss rather than an investment. This baffles Jessica, who asks, “Why wouldn't you want your people to grow?!”  

In most organizations, there’s a disconnect in development.

“Part of the problem is there's a gap between what leaders think employees need and what employees actually want to learn.”

When she asks employees what they want to learn about, they usually say project management or change management (which are things they can use in their personal lives). But then, when she goes “to ask the leadership team, they're like, ‘We’re going to do a session on communication skills.’” And, as she points out, those are two very different things.

It’s on this note that Jessica introduces the concept of a talent destination: “You want the people at your organization to be better because they worked at your company.” But it takes big-picture thinking to invest in someone’s growth knowing they may leave. Despite this, a talent destination still invests in learning and development for its employees and helping them grow.

When asked what she thinks the role of learning is within an HR team, Jessica stresses that “it needs to be someone's full-time job—not just an additional responsibility for HR business partners.” When L&D is integrated into all HR practices, employee development becomes as important as other HR functions. And, because someone is specifically tasked with developing and implementing learning programs, they align with both employee interests and organizational goals. More importantly, rather than perpetually being pushed to the bottom of an HR business partner’s to-do list, programs actually get implemented, so employees can learn, grow, and eventually go. (And they will go. In Jessica’s words, “Nobody’s meant to stay anywhere forever.”)

Job hop to the top

What does the self-professed Quit Queen think about job hopping? She’s all for it!

"If something is not serving me. I will quit."

She might be one of the few HR leaders who think job hopping is good—for employees and employers alike. She explains, “I’ve had several jobs where I knew instantly this is not for me. I'm not the right person to solve this problem. So I quit and I went to another job. Everywhere I've gone, I've moved up. It's been very strategic.” As she puts it, she’s “job-hopped to the top.”

Some of Jessica’s peers cling to the outdated notion that an employee has to be somewhere for at least two years for the company to see an ROI. Jessica disagrees.

"I don't think you have to be somewhere for five, ten years to make an impact."

An opinion that has garnered pushback from her peers on LinkedIn. “They're like, ‘Absolutely not. You need to stop telling people this.’“ In response, she challenges them: “Someone works somewhere for two years and you got nothing out of it? That's not realistic unless they were underperforming. Clearly something’s wrong with your onboarding program or your leaders if you’re not able to set someone up to deliver value.”

There’s still a bit of a stigma associated with job hopping. It’s often perceived as a lack of loyalty on the employee’s part or a lack of retention on an employer’s part. But Jessica encourages us to look at it from a new perspective. For employees, it allows them to take their career development into their own hands. For employers, it comes back to the concept of being a talent destination. They can use employees’ willingness to make a move to attract high-quality candidates. 

From a business/HR perspective, Jessica acknowledges the potential impact this can have from a long-term culture perspective. When high volumes of people—especially the high performers—quickly leave the organization, “you're losing historical context.” 

That said, if you’ve got a mass exodus on your hands, you might want to spend less time fixating on context and more time fixing your culture.

Which brings us to our last key takeaway…

Dismantling disingenuous DEI&B efforts

Our conversation turns to culture—or rather, the appearance of it.

Jessica shares the following: “In most companies I've joined, the HR team is the most diverse, most inclusive team. And I find that fascinating. This is the team that's representing the values. But no other department is doing this. That's a call out that I have not figured out yet, but it's happening.” 

Regardless of which team is the most (or least) diverse, her experience highlights the sometimes superficial nature of culture. To drive the point home, she says, "Tell me who the exceptions to the rules are, and I can tell you what the culture is."

The same goes for Diversity, Equity, Inclusion, and Belonging (DEI&B) efforts. Jessica weighs in on how many DEI&B initiatives post-2020 failed to create meaningful change.

“If DEI&B is separate from everything else in the business, if it was not embedded into everything that you're doing—and I mean everything—and if money was not involved in holding people accountable, it was never going to work.”

She adds, “If you were able to easily dismantle it, it was fake, because how can you dismantle something that was supposed to be part of everything you were doing?”

This point underscores the importance of embedding DEI&B principles into every aspect of a company’s operations. It’s not enough to have standalone programs; instead, DEI&B should influence decision-making processes, leadership development, and even financial accountability. This holistic approach ensures that diversity and inclusion are not just buzzwords but fundamental elements of the organizational fabric.

We spent a lot of time talking about the professional side of things, but Jessica ends the conversation on a personal note with a reminder for us all:

"You are so much more than your job. That's been a hard lesson for me to learn, that my worth is so much more than my job or my title."

Speaking of more, there are plenty more insights, modern views on HR and People Ops, and infectious laughs in the full-length episode. And, if you have more thoughts, let us know in the comments.

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