Startups run on hustle, speed, and sacrifice, but what if everything you’re building is quietly burning out the people you’re counting on most?
In her new book Love Works, leadership expert and former executive Kelly Winegarden Hall flips the script on startup culture. Drawing from a career in corporate boardrooms and gritty startup trenches, she makes a bold case: leading with love, not fear of survival, is what makes your startup scalable and sustainable.
In this interview, Hall shares what leading with love is about, how it drives performance, and why it helps founders sleep soundly at night.
Grit Daily: Your leadership philosophy has been forged in high-stakes environments, from corporate boardrooms to resource-strapped startups. When did you realize that love isn’t a liability, but a business asset?
Kelly Winegarden Hall: In 2017, I was the chief commercial officer in a fast-growing, private equity-owned company. After we sold the business to the next investors, the CEO asked me to resign. I really liked the business and the team, but she had someone else in mind for the role. I had to respect that; she had the right to choose her team for the next phase of growth.
I was a hot mess for weeks after that disruptive life event, as it was the first time I’d been on “that side” of a layoff. With a hole in my heart and a deeply bruised ego, I enrolled in a weeklong residential program called the Hoffman Process. I credit The Hoffman Institute and their unusual retreat with helping me transition from believing that love is difficult, finite, and destined to end to understanding that love is abundant, everywhere, and flowing freely when we let it.
Once I realized love is the magic flowing through every relationship we have—with ourselves, our friends and families, our colleagues, animals, and nature — it became quite easy to enjoy the love in my life.
The more I brought that love with me, including to work, every challenge became easier to tackle, and winning was only satisfying if everyone benefited in some way.
Grit Daily: Everyone benefiting sounds like nirvana, especially in startups fueled by speed, scarcity, and survival. What do you say to founders who hear the word “love” and assume it’s a luxury they can’t afford?
Kelly Winegarden Hall: To get past scarcity and survival, founders need their people operating at peak performance. But this only happens when people feel seen, safe, and supported. Leading with love truly isn’t a luxury. It’s how you unlock the energy and potential already within your teams.
When your people feel psychologically and physically safe, they’ll truly bring their best to work and choose, of their own free will, to do whatever it takes to get through the day’s highs and lows.
To love a colleague is to see them wholly: their skills, interests, and motivations. To treasure them as adults who are giving you their time and effort, knowing they have other options. To encourage managed risk-taking and course corrections after failure.
It’s so much easier to learn, pivot, and persevere when we’re at ease, feeling our leader’s hand on our back and trusting that we’re in this together.
In contrast, when dis-ease is present, whether that’s fear, anxiety, distrust, blame, shame, or worry, costs rise. Time gets wasted as people double- and triple-check their work. Turnover ticks up, driving hiring and onboarding costs skyward while slowing progress and innovation. Sustained stress leads to higher healthcare costs, lost productivity, and endless turnover.
Startups are full of risk and challenges, so paying attention to employees’ well-being and inviting people to bring their whole selves to work isn’t “too much.” It’s mission-critical.
Grit Daily: In your book, you make the argument that love isn’t soft. What’s a real-world example where love saved or supercharged a team?
Kelly Winegarden Hall: It’s challenging to maintain psychologically safe spaces when everyone brings different backgrounds, styles, communication preferences, conflict-resolution skills, and management approaches. Your teams might cruise along for a while, but we all get tested when deadlines and results are on the line. That’s where love can be the difference-maker.
Here’s an example: Two of our teams at Niaga were working to prove a new technology. At the same time, our pilot production line needed them for high-priority partner product launches. Eight colleagues, who generally appreciated and respected one another, fell into chaos as pressure mounted. This eventually spiraled into full-fledged breakdowns.
As the “Head Coach” of the organization, I set up a two-hour video call to unpack what everyone was experiencing. Together, we moved past surface-level frustrations and into the assumptions, pain, and blame that were driving the conflict.
A former mentor used to say, “Sunlight is the best disinfectant,” and I couldn’t agree more! Once people saw one another’s distress, they immediately recommitted to radical transparency, fierce inclusion, and restoring trust. Within days, the team was reconnected and back on track, for each other and our partners.
Grit Daily: You often remind founders that trust is a two-way street. That includes encouraging leaders to “focus on outcomes, not hours.” Why is this mindset so hard to adopt? What tips can you offer?
Kelly Winegarden Hall: Most of us have grown up in societies shaped by 40-hour workweeks and 24/7 operations. In our minds, the amount of time we spend at work reflects the type of employee we are. For generations, we’ve held the belief and expectation that “more hours” meant “more committed.”
However, if we step back and pay attention, we can see that there have always been people who complete their assignments and tasks early, while others require more time to achieve the same results.
Some people are social at work and use regular hours to connect and fraternize. Others focus intensely and deliver results in a fraction of the time. There’s no perfect way to work, and there’s nothing wrong with a 32-hour week or an 80-hour week if people are satisfied, energized, and meeting their goals.
At Niaga, half of our team worked 0.8 or 0.9 schedules, meaning they had one day off every week or every other week. Other teammates were freelancers and contractors working part-time while serving different clients. I honestly never noticed which hours or days people worked, as they were all committed to their teams and honored their promises to one another and the business plan. They flexed their hours as needed.
If anything, I had to check in with our part-time workers when I saw emails and calendar invites appearing on Saturdays and Sundays to make sure they weren’t feeling pressured or behind. Each time, they assured me they felt best when they used a little weekend time to stay organized while things were quiet at home.
Grit Daily: You’ve talked a lot about shaping culture at scale. But you also pay close attention to “microclimates,” the small, often overlooked dynamics on individual teams. What’s one thing a founder can do this week to shift a microclimate from fear to trust?
Kelly Winegarden Hall: When a founder has done a good job laying out the organization’s mission, purpose, and plan to win, and the culture is generally strong, safe, and satisfying for most members, struggling teams will stand out like a neon sign. These are the microclimates I pay close attention to, where fear, friction, or fatigue can quietly take hold.
My advice? When teams are in distress, falling behind, or drama is escalating, stop and explore what’s happening without assuming you already know.
For instance, you might ask the team to pause and spend an hour together to explore how the work is going without mentioning the actual project or deliverables. This space isn’t for troubleshooting. It’s for connection, understanding, and exploring how people are feeling, if their needs are being met, and where gaps or challenges are contributing to tension, fear, or anxiety.
If the team can’t shape a path forward on its own, bring in a coach or trusted leader to listen, care, release drama, repair and restore trust, and revisit priorities.
Genuinely caring about your people isn’t about creating a perfect, cozy culture. It’s about carving out a safe space for people to bring their authentic selves, passionate convictions, and strong opinions to the table.
Yes, dissolving drama takes time and energy, but it brings teams back to safety and higher performance again and again.
Grit Daily: You’ve led remote, part-time, and cross-cultural teams, and they’ve thrived. What’s the biggest myth about modern work you’d like to shatter?
Kelly Winegarden Hall: The biggest myth I’d like to take a sledgehammer to is the assumption that those with C-level titles and fat paychecks know the most and have superior intuition. The “I know the most because I’m up here, and I’m paid to make decisions for you and about you, so trust me” type.
In a traditional, top-down, triangular work structure, executives will give everything they have (and more) to shower everyone below them with their energy, charisma, and effort. Employees in this system may admire, appreciate, and adore the inspiring leaders at the top, but they probably don’t feel known, seen, heard, or celebrated themselves.
Compare this with a circular structure, where leaders have shifted from commanders to coaches. They use their experience, wisdom, and energy to attract great talent and activate employees’ energy. These leaders are humble enough to realize no individual has all the answers: breakthroughs can come from anyone, anywhere, at any time. They provide safe spaces, sounding boards, and resources to enable and empower teams. They lead with transparency, welcome feedback, and insist on truth through the best and worst of times.
Everyone is at the pinnacle of their experience on any given day. Whether we are 25 or 75 years old, we have all the experience, education, and skills we’ve gained so far. If we accept that people are generally trying to do the right thing and can be counted on to do what they say they’ll do, falls and failures are simply learning opportunities to do better tomorrow. Adults can be trusted to act like adults when we treat them like adults.
The best news? When we connect, collaborate, and care for each other, we not only deliver consistently and improve continuously, but we also end up with friends for life.
Grit Daily: Let’s talk capitalism. Your book asks a bold question: Can capitalism survive without compassion? What answer have you landed on?
Kelly Winegarden Hall: Without compassion, capitalism doesn’t go away, but it also doesn’t leave the world better for future generations. Unfettered, investor-centric capitalism will continue to drive the divide between the top 10% and the bottom 90%. The wealthiest among us, who already have more than anyone could ever spend in a precious, short lifetime, will expand their abundance and collect their wins while entire communities struggle.
Many wealthy individuals are great philanthropists, so the 1% and 10% can do a lot of good. I’d argue, though, that the world is a better place when everyone has access to education and employment, allowing them to provide for themselves and their loved ones. With full participation in the workforce, households can cover basic life needs and have discretionary funds for play and pleasure, as well as savings to weather a rainy day.
There’s enough food, water, and opportunity for all 8 billion of us to thrive while we’re here on this planet. Through compassionate capitalism and loving leadership, companies can be responsible to their employees, customers, and the communities in which they reside. We can manage natural resources for our great-great-grandkids. We can innovate and shift overconsumption. We can care and share until everyone is healthy, at ease, and enjoying their time in this amazing and beautiful world.
Grit Daily: If you could put one sentence on every founder’s wall, what would it be?
Kelly Winegarden Hall: I see you, I love you, and it is my pleasure to serve you.
Grit Daily: Is there anything you’d like to add that we haven’t talked about?
Kelly Winegarden Hall: The world is as divided, volatile, and chaotic as it’s ever been. People are showing up to work holding more tension, more separation, and more dis-ease than ever. It’s more important today to ensure our workplaces are safe, empowering, and fueled by shared purpose.
We hold the power to be at ease, in our own love, and to offer that love and compassion at every opportunity. Over time, we’ll receive back everything we give and more! At the end of our lives, it’s our relationships that have created the most joy and value. So, please gift yourself the pleasure and fun of creating value wherever you go. I call it Living L.A.R.G.E.: living with love, abundance, respect, gratitude, and equality.
Thank you for this opportunity to share, and I wish you the very best!
