In today’s ever-evolving workplace, organizations are under more pressure than ever to create environments where employees not only stay, but thrive. The traditional model of “check your personal life at the door” is not just outdated — it’s detrimental. Dr. Angela Jackson, author of The Win-Win Workplace: How Thriving Employees Drive Bottom-Line Success, joined me on the Transform Your Workplace podcast to unpack what it truly means to build organizations where people — and businesses — flourish together.
From Burnout to Breakthrough
Angela didn’t write this book from an academic ivory tower. Her insights are deeply personal.
“I was the million-plus miler on American Airlines,” she told me, recounting her high-powered executive role at Nokia. But it all came to a halt, literally, after a car accident while rushing to her next meeting. “My busy life stopped in that moment. I was in physical therapy for months. And I had a lot of time to think about what work meant to me.”
That reflection became the seed of her book. She realized she’d spent years in what she calls a zero-sum workplace — where employees give everything and get little more than a paycheck in return. “I was willing to do whatever it took to advance. Come early. Stay late. But I wasn’t happy.”
The Zero-Sum vs. Win-Win Mindset
Angela draws a sharp contrast between outdated workplace norms and what she calls the win-win workplace. In a zero-sum environment, employees are replaceable. Personal matters are irrelevant. Rules are rigid and often arbitrary. Think of the blanket return-to-office mandates that ignore the real-life responsibilities remote work has allowed people to balance.
In contrast, win-win organizations operate from a different mental model: people matter, and investing in their well-being benefits the bottom line.
Angela explained, “These leaders aren’t just doing the ‘right thing.’ They’re doing the smart thing. Employee-centric policies have real ROI — increased productivity, better retention, lower turnover.”
How to Build a Win-Win Workplace
A key takeaway from Angela’s research is that leaders don’t need to overhaul everything at once. But they do need to shift their mindset and start somewhere — ideally by listening. “Every company will say they’re listening to employees. But if 48% of U.S. workers say their employer doesn’t care about them… clearly something’s broken,” she explained.
Angela’s first and foundational pillar? Center employee voice. That means:
- Ask employees what matters most to them
- Act on what you hear — and communicate what can or cannot change
- Bring employees into the thinking behind decisions, not just the results
She shared a powerful example from CHI Doors. A delivery driver had been using an inefficient GPS route for years. When management finally asked for feedback, he gave them a better route, which saved time, money, and stress. That small act of listening sparked a culture shift. “Employees began offering more ideas. The company even let them vote on building upgrades — one of which was installing central air, which boosted summer productivity.”
Listening is Just the Beginning
The win-win approach doesn’t stop at listening. It includes building humanistic relationships, recognizing intersectional identities, and designing benefits that actually reflect employees’ lives.
Angela shared a story of a veteran who nearly lost his job after chronic lateness — the result of a broken car and unreliable public transit. Only when a manager saw him sprinting from the bus stop and took time to ask did the truth come out.
“It was an eye-opening moment,” she said. “He’d been trained not to make excuses. But without that conversation, they would have lost a great employee.”
This is what Angela means by embracing the whole employee: their background, their challenges, their goals.
Reimagining Benefits and Ownership
Angela argues convincingly that outdated benefits packages are another symptom of a zero-sum model. One fast-casual restaurant chain gave all employees a 401(k) match, but no one used it. After asking why, the CEO learned that employees were more in need of emergency funds. So he redirected those dollars, helping employees in critical moments and increasing their loyalty tenfold.
Another company used a platform called Compt to let employees choose their perks — coffee, childcare, gym memberships. The result? Higher engagement and local economic impact, as most perks were spent in employees’ communities.
“When people use the benefits, they feel seen,” Angela told me. “And when they feel seen, they stay.”
Learning as a Retention Strategy
With all the buzz about AI and automation, Angela says we can’t forget about people. “Employees want to grow. They want to know what’s next — and how to get there.”
Whether it’s through tuition reimbursement, community partnerships, or even job shadowing across departments, companies that invest in learning see results. According to Angela, even offering learning opportunities can increase employee tenure by 30%.
And it doesn’t require a massive budget. “Small and mid-sized businesses are getting creative,” she said. “Local workforce boards. Government grants. Cross-training. It all adds up.”
The Ownership Mindset
One of my favorite parts of Angela’s book is her metaphor: renters vs. homeowners. Renters do the bare minimum to get their deposit back. Homeowners invest, improve, and care deeply about the future.
“That’s the kind of employee we want,” she said. “And you create that when you invite people to contribute, show them their voice matters, and follow through.”
She emphasized: it’s not a one-time suggestion box. It’s an ongoing, transparent conversation backed by action. The more organizations show they’re listening, the more employees will step up.
Measuring What Matters
You don’t need to guess whether this approach works. Angela advises companies to pick one pillar — say, benefits — and pilot a change. Measure usage, sentiment, and outcomes. Rinse and repeat.
“It’s like lean startup thinking,” she said. “Iterate until you find what works. And what works will look different for every team.”
Start By Listening
Dr. Angela Jackson’s book, The Win-Win Workplace, is a roadmap for a more sustainable and human future of work — one that doesn’t sacrifice performance for people, but unlocks both.
As she told me, “When people thrive, the business thrives. We have the data. We have the case studies. Now we just need the leadership.”
If you’re ready to build that kind of workplace, start by listening.
Learn More
To learn more or grab your copy of The Win-Win Workplace, visit readwinwinworkplace.com. And don’t miss the upcoming Win-Win Workplace Summit, May 5–6 in Chicago — with a 20% discount for Transform Your Workplace listeners.
Brandon Laws is a workplace culture and leadership enthusiast, host of the Transform Your Workplace podcast, and VP of Marketing and Product at Xenium HR.