Leading with Heart: Dr. Angela Jackson Of Future Forward Strategies On The Power of Authentic Women’s Leadership
An Interview With Pirie Jones Grossman
Trust Multiplies When You Lead with Transparency — Employees can spot inauthenticity from a mile away.
In today’s dynamic world, the concept of leadership is continuously evolving. While traditional leadership models have often been male-dominated, there is a growing recognition of the unique strengths and perspectives that women bring to these roles. This series aims to explore how women can become more effective leaders by authentically embracing their femininity and innate strengths, rather than conforming to traditional male leadership styles. In this series, we are talking to successful women leaders, coaches, authors, and experts who can provide insights and personal stories on how embracing their inherent feminine qualities has enhanced their leadership abilities. As part of this series, we had the pleasure of interviewing Dr. Angela Jackson.
Dr. Angela Jackson, a recognized authority on the future of work, is the CEO of Future Forward Strategies, a labor market intelligence firm focused on unlocking organizational potential through continuous learning and innovation. As a lecturer at Harvard University, her research redefines traditional human capital approaches, guiding leaders to embrace change and empower their teams. Dr. Jackson’s insights enable the creation of high-performing workplaces that boost employee engagement and productivity, driving sustainable growth and a competitive edge.
As a lecturer at Harvard University on leadership and organizational change and as the founder of Future Forward Strategies, a labor market intelligence and strategy firm, she collaborates with Fortune 500 companies, growth-stage startups, and policymakers, offering valuable research and insights into the ever-evolving landscape of work. Earlier in her career, Dr. Jackson held global operating roles with Viacom and Nokia, leading multimillion s P&Ls and driving significant year-on-year profitability increases. Currently, she serves as a board member and advisor to various public and private boards, including Arena Analytics, Guild Education, and Needham Bank.
Dr. Jackson is widely published in leading journals, including Fast Company, Fortune, Forbes, Newsweek, Harvard Business Review, and has spoken at numerous conferences including the Economist, Wall Street Journal, and TED conferences. Her forthcoming book, The Win-Win Workplace: How Thriving Employees Drive Bottom-Line Success, releases on March 11, 2025.
Thank you so much for joining us in this interview series. Before we dive into our discussion about authentic, feminine leadership, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
Thank you for inviting me to this conversation. My career has been shaped by one core belief: Work should work for everyone. Growing up in Beach Park, Illinois, I saw firsthand what happens when it doesn’t. My grandfather and our neighbors lost their jobs when the Chrysler factory shut down, and it devastated families. That experience fueled my mission — to help businesses build workplaces where employees and companies don’t just survive, but thrive.
Can you share the most interesting story that happened to you since you started your career?
I worked at MTV in the early 2000’s when Apple first launched iTunes — forever changing the music industry. Ironically, it could have been MTV that pioneered online music downloads. My colleague Jason Hirschhorn, now the CEO of REDEF, pitched the idea years before iTunes, but leadership dismissed it. They saw themselves as too dominant to need innovation.
Months later, you couldn’t walk through MTV without seeing employees carrying iPods. The lesson? If you ignore the voices of your own experts — whether they’re employees or customers — you risk missing the future.
What do you think makes your company stand out? Can you share a story?
Future Forward strategies stands out because we don’t just talk about workforce transformation — we measure it. We work with organizations to develop tangible strategies, track impact, and adjust in real time. A great example of this is our work with the Win-Win Workplace framework, which has helped companies rethink leadership, hiring, and employee engagement with data-backed insights.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- Curiosity — I ask a lot of questions. This has allowed me to spot trends early and push for innovation. For example, I recognized the potential of skills-based hiring years before it became mainstream.
- Resilience — The work of shifting mindsets isn’t always easy. I’ve had doors close on me, but I’ve learned that persistence often turns a ‘no’ into a ‘not yet.’
- Empathy — Understanding what employees and leaders need has been key to my work. A leader once told me they struggled with workforce retention, and through listening to both employees and managers, we discovered a simple but overlooked issue — workers needed more predictable schedules. That small shift dramatically reduced turnover.
Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.
In 2016, I made the difficult decision to step away from Global Language Project, a company I founded to create innovative language learning products. We had built strong brand recognition and were scaling internationally. By all accounts, it was a success.
But I had a realization — I thrive in the startup phase, building something from the ground up. I’m not a corporate operator. That self-awareness changed how I approached every opportunity moving forward.
The takeaway? There’s a difference between what you can do and what you’re meant to do. Success isn’t just about achievement — it’s about alignment.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a personal experience where embracing your unique leadership style, which might not align with traditional expectations, led to a significant positive impact in your organization or team?
When I founded my first company in 2009, I made a decision that raised a lot of eyebrows: I implemented an unlimited vacation policy. At the time, this was virtually unheard of outside of a few tech startups, and many people — including other business leaders — warned me that employees would take advantage of it.
“What if people just stop showing up?” “Won’t productivity take a nosedive?” “Aren’t you worried about abuse?”
But I wasn’t worried. I knew I was hiring people who were passionate about our mission and driven by purpose — not just a paycheck. My philosophy was simple: If I don’t trust my employees to manage their time responsibly, then I’ve hired the wrong people.
What happened next defied conventional wisdom. Instead of employees abusing the system, they self-managed their time off in a way that actually enhanced performance. No one disappeared for months at a time. No one took vacations at the expense of their team.
The policy quickly became one of the most beloved benefits of working at my company. During stay interviews — a practice where we regularly checked in with employees to understand what was keeping them engaged — unlimited PTO was consistently ranked as a top reason people loved working with us. The success of this policy wasn’t just about the number of vacation days available — it was about the culture of trust and autonomy it reinforced.
Too often, companies operate with a scarcity mindset when it comes to employee benefits. They assume that if they offer flexibility, workers will take advantage. But when you create an environment where people feel valued and respected, they don’t game the system — they take ownership of it.
In your journey as a leader, how have you balanced demonstrating resilience, often seen as a masculine trait, with showing vulnerability, which is equally powerful, but typically feminine? Can you give an example where this balance created a meaningful difference?
My motto is: You can do anything — but maybe not all at once.
Writing The Win-Win Workplace was one of the most intense challenges of my career. I was balancing business commitments, partnerships, and a rapidly shifting world. There were moments I had to acknowledge that pushing harder wasn’t the answer — pacing myself was.
Great leadership isn’t just about drive; it’s about knowing when to give yourself and your team grace. Sustainable success requires sustainable leadership.
As a woman in leadership, how have you navigated and challenged gender stereotypes, especially in situations where traditional male-dominated approaches are the norm? What strategies have you employed to remain authentic to your style?
As a woman in leadership, I’ve often walked into rooms where I was underestimated. My response? I don’t waste time proving people wrong — I focus on being excellent.
When I sense resistance, I don’t get stuck in frustration. I listen, I ask questions, and I keep showing up with high-caliber work. The truth is, if a space isn’t the right fit, you can leave — but when you lead with excellence, the right opportunities will find you.
How do you utilize emotional intelligence and active listening to create an inclusive environment in your team or organization? Could you share a specific instance where these qualities particularly enhanced team dynamics or performance?”
Recently, I had a conversation with a direct reporter who was speaking quickly, almost rushing through updates. Rather than letting it slide, I asked her to pause, take a breath, and check in. She admitted she was dealing with personal stress and wanted to impress me.
I told her she didn’t need to prove anything — she was already doing great work. The shift was immediate. She relaxed, and our conversation became a true dialogue rather than a performance.
That’s what real leadership looks like — not reinforcing hierarchies, but breaking them down so people can show up as their best selves.
What role has mentorship played in developing your authentic leadership style, and how do you communicate authentically to inspire and empower both your mentors and mentees?
Mentorship has been invaluable in my journey. I’ve been fortunate to have mentors who saw potential in me that I wasn’t even aware of. They challenged me with assignments that pushed me to my limits, making me uncomfortable and forcing me to stretch my skills. At times, I felt unsure — but those experiences became pivotal in shaping the professional I am today. I look back on them with deep gratitude.
Now, I pay that forward by supporting emerging leaders, encouraging them to trust their instincts rather than conform to outdated leadership norms. Recently, a mentee of mine stepped into a leadership role, and I reminded her to lead with authenticity. She did — and it paid off.
Mentorship isn’t just a one-way street. Reverse mentorship has taught me invaluable lessons, reminding me that leadership is about continuous learning. And even at my level, I still rely on mentorship and coaching from peers and those in positions I aspire to reach. You are never too experienced to learn and grow.
Based on your experience and research, can you please share “5 Ways Leading Authentically As A Woman Will Affect Your Leadership”?
- Trust Multiplies When You Lead with Transparency — Employees can spot inauthenticity from a mile away.
- Inclusive Leaders Build Stronger Teams — When you bring more voices to the table, you get better results.
- People Stay Where They Feel Valued — High engagement leads to high retention.
- Admitting What You Don’t Know Builds Credibility — Leaders who embrace learning unlock innovation.
- Sustainable Success Comes from People, Not Just Profits — The companies that thrive are the ones that invest in their people.
Are there potential pitfalls or challenges associated with being an empathetic leader? How can these be addressed?
Empathy without boundaries leads to burnout. Being an empathetic leader doesn’t mean saying yes to everything. It means setting clear expectations while still showing you care. I’ve learned that compassion and accountability go hand in hand that includes accountability for own health and well-being~
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂
The movement I would start is the one I’m leading now — The Win-Win Workplace.
I want leaders and employees alike to realize that a Win-Win Workplace isn’t just an ideal — it’s essential. This isn’t a “nice-to-have” or a dream for some distant future. It’s a business imperative that strengthens companies, employees, and economies alike.
On the cover of my book, there’s a rope — a powerful symbol of what this movement represents. I think of it like a bungee cord. Its strength doesn’t come from a single strand but from the way the threads are intertwined. That’s exactly how success in the workplace should look: strong, interconnected, and built on alignment between workers and the incentives that drive them.
A workplace where employees thrive isn’t just good for people — it’s the smartest strategy for business success.
How can our readers further follow you online?
Connect with me on LinkedIn, follow my work at thewinwinworkplace.com, and join the movement for better workplaces.
Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!
Leading with Heart: Dr Angela Jackson Of Future Forward Strategies On The Power of Authentic Women’ was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.