In Conversation: Alison Rand on Finding Sense in Design Leadership

The author of Sentido shares how instinct, empathy, and systems thinking can reshape leadership for a more human future. 

In an industry that often rewards speed over depth, Alison Rand is making a case for slowing down, thinking in systems, and leading with heart. From her time shaping design strategy at SAP and Automattic to co-founding Forty Fifty, a social health platform for women navigating midlife, Alison has consistently challenged the boundaries of design leadership. 

In this conversation with Digital Digest, Alison reflects on the evolving role of systems thinking, her upcoming book Sentido, and why operational empathy isn’t just a buzzword, but a foundation for building sustainable, inclusive cultures. Through both her corporate experience and community-focused ventures, she offers a clear, deeply human framework for how design leaders can navigate complexity without losing their voice. 

As a woman in leadership, you’ve navigated the structure of enterprises and the chaos of startups. What have these extremes taught you about designing systems that hold up under pressure? 

Alison: Both enterprises and startups carry equal parts chaos and structure, just dressed differently. In enterprises, process creates a veneer of order, while startups operate in raw, unfiltered turbulence. What I’ve learned is that smaller organisations often lean on loyalty to the founder, while large ones disperse focus across efficiency and silos. As companies scale, decision-making can become messy, often driven by mismatched problems, solutions, and participants. The key to designing resilient systems is trust. Leaders who rush in with rigid models fail, while those who listen, learn, and build relational trust create systems that bend without breaking. Structures succeed when leaders prioritise people, ensuring voices are heard and contributions recognised, rather than chasing perception or control. 

At SAP, you built a Center of Excellence from scratch. How did you turn systems thinking into something teams could rally around? 

Alison: Building the CoE required urgency and trust-building in equal measure. I began by listening deeply across product lines, many with conflicting goals. From there, we established verticals, design systems, user insights, inclusion, brand, and operations, that created best practices to scale. My role was to connect the dots horizontally and vertically, ensuring operations supported each discipline with shared objectives. Alignment with leadership was vital, but so was managing across, building relationships, piloting projects, and securing proof points of success. Once small wins were visible, they multiplied. Systems thinking became a shared framework not because it was imposed, but because people saw it working in practice. 

Through your venture Forty Fifty, you’re redesigning support for women in midlife. What gap were you seeing in tech or healthcare that led to its creation? 

Alison: The gap was both personal and systemic. Losing my mother to breast cancer at 16 gave me an early awareness of how thin support structures for women can be. Statistically, midlife women make up nearly 65% of the U.S. female population, yet healthcare and workplace systems rarely reflect their needs. Menopause is gaining visibility, but midlife encompasses far more, identity, reinvention, grief, and resilience. Many of us were told we could “have it all,” only to discover the toll of broken systems and persistent bias. Forty Fifty was born to honour these realities, creating support that speaks to both physiological and emotional truths. Its mission is to design communities and services that make women feel less isolated and more empowered to thrive in midlife. 

Empathy is often cited but rarely operationalised. What does it look like when companies truly embed it into their culture and systems? 

Alison: Too often empathy is reduced to a buzzword, stripped of meaning. To operationalise it, leaders must show up with presence and vulnerability, building trust not through fear or control, but through courage. At Forty Fifty, we model this by co-creating with the people we serve, ensuring growth is evidence-based and human-centred. Brands that embed empathy succeed because people believe in their intent and integrity. For me, it’s about resonance, how a leader or organisation shows up for people in ways that feel authentic. Patagonia is a strong example: mission-driven, transparent, and committed to practices that endure. True empathy in systems is less about soft gestures and more about consistent alignment between values, actions, and outcomes. 

Systems thinking can be messy, especially in practice. How do you bring clarity without flattening complexity? 

Alison: Systems are inherently complex and grow more so with time. My approach is rooted in living systems, looking to nature for lessons in mutualism and regeneration. Sentido argues that instincts, shaped by lived experience, are essential in discerning signal from noise. Strategic foresight adds another layer, encouraging us to identify patterns that repeat across time and context. Designers are especially well-suited for this work: making the complex clear, extracting opportunities, and knowing what to subtract. Clarity doesn’t mean overexplaining; it means surfacing the essentials and letting the rest fall away. As John Maeda said of my work: “The best leaders don’t force change; they reveal it.” That’s what clarity in complexity looks like. 

Your upcoming book blends memoir with leadership guidance. Why did you choose this hybrid form, and how does it reflect your approach to leading? 

Alison: The idea began during coaching, when I reflected on my life milestones and realised how deeply they shaped my leadership. Growing up multiethnic in New York, navigating unfamiliar spaces, and relying on “street smarts” gave me a strong sense of emotional intelligence. Writing Sentido allowed me to connect those experiences with the leader I’ve become. The memoir elements bring honesty, loss, identity, resilience, while the leadership guidance translates them into actionable insights. For me, leadership isn’t just about frameworks; it’s about instinct, authenticity, and care. This hybrid form reflects that balance: systems and strategy informed by lived experience. 

Sentido explores instinct as a quiet driver of leadership. How do you turn instinct into influence in environments that weren’t built for you? 

Alison: Instinct is a compass, but it needs self-awareness and emotional maturity to translate into influence. As women, we’re often taught to dismiss our instincts, yet they’re one of our clearest guides. The key is responding rather than reacting, creating trust by remaining curious, patient, and observant. Language also matters, framing change as “iterative” rather than “transformational” can reduce resistance. Influence grows when instinct is paired with empathy, observation, and pacing. Even in spaces not built for us, listening deeply and trusting our intuition helps us shift dynamics and open doors. 

You’re currently studying Foresight alongside your consulting work. How does that shape how you design for ambiguity and long-term impact? 

Alison: Foresight gives me tools to stay comfortable with uncertainty while still grounding decisions in evidence. It encourages research, scanning for signals, and recognising patterns that repeat over time. Instead of rushing to solutions, I can hold space for possibilities, asking not just “what’s happening now?” but “what could emerge?” This approach makes me more deliberate and expansive in my leadership, balancing today’s needs with tomorrow’s opportunities. Authors like adrienne maree brown remind us that love, purpose, and generosity can guide strategy as much as data. Foresight isn’t just tactical, it fuels radical imagination, which is essential for designing systems with lasting impact. 

DesignOps is often underestimated as just delivery. What needs to shift for more teams to see it as a strategic growth layer? 

Alison: DesignOps needs a rebrand. It’s not just execution, it’s the discipline of marrying strategy with delivery. At SAP, I structured my team around two sides: Service Enablement (service design, programs, data, strategy) and Culture & Practice (the experience of designers themselves). Together, they balanced people and process, strategy and execution. DesignOps at its best is human-centred change management. The shift we need is education, helping organisations see that design isn’t a bottleneck but a growth engine. When leaders recognise that design operators are building both systems and cultures, DesignOps can step into its rightful place as a strategic lever. 

Inclusive systems don’t just include people, they shift power. What does inclusive systems leadership look like in your view? 

Alison: True inclusion isn’t about adding diversity into old structures, it’s about questioning whether those structures allow belonging at all. Too often, DEI efforts are surface-level: resource groups, slogans, or mandates that fade when challenged. Inclusive systems leadership holds complexity, distributing power across many voices instead of concentrating it. It’s about servant leadership, listening deeply, noticing the invisible forces that shape people’s experiences, and removing barriers. It’s also about rethinking language and slowing down change so it feels sustainable. Inclusion is not just representation; it’s transformation. Systems evolve when difference is treated not as an afterthought, but as the force that makes them thrive. 

You’ve worked across design, strategy, operations, and now FemTech. What’s the first signal you look for when entering a new system? 

Alison: I always begin with listening. My first 90 days in any new role are about understanding, not imposing. Too many leaders rush in with “my way,” which only adds complexity. In Sentido, I describe this rhythm as Explore, Test, Wander, and Emerge. It starts with curiosity, mapping the system, listening to voices, and watching what rises above the noise. From there, hypotheses can be tested, often through meandering but intentional exploration. Over time, the true signals reveal themselves. Entering a system is less about immediate fixes and more about creating space for discovery, so solutions emerge authentically. 

Hybrid work has reshaped how teams connect or drift. What small interventions make a big difference in distributed cultures? 

Alison: Hybrid work is valuable when it’s intentional. In-person time should create connection, not just stack meetings. I’ve seen companies fund quarterly off-sites where teams choose a location and spend meaningful time together. The experience felt like a retreat, building bonds that translated into stronger day-to-day collaboration. Even in hybrid settings, leaders must design moments that matter, from how an off-site is structured to how a single meeting feels. Priya Parker’s The Art of Gathering reminds us that connection is about purpose, not formality. The question for leaders is: how do you create experiences that foster belonging, not just attendance? 

Storytelling and system-building might seem unrelated, but not in your work. How do you use narrative to build stronger systems and more human teams? 

Alison: For me, systems and storytelling are inseparable. Mapping a system, its players, history, and direction, creates threads that need coherence. A narrative arc helps weave them together into something people can follow and believe in. Storytelling isn’t about oversimplifying; it’s about making complexity digestible. I use frequency and variation, telling the story in different ways, to skeptics and supporters alike, until it sticks. The real power comes when people see themselves in that story. When they feel heard, they move from resistance to partnership. At its best, storytelling transforms systems because it humanises them, aligning data with meaning. 

Many mid-career women are navigating quiet reinvention. What would you say to someone leading while still figuring it all out? 

Alison: Reinvention is both daunting and liberating. Midlife often forces truth-telling: what do I want, what no longer serves me, and what am I too tired to fight? My advice is to map your life milestones and pull the threads, they reveal what matters most. For me, reconnecting with tactile work like sculpting and living closer to nature has informed my leadership as much as any corporate role. Reinvention doesn’t separate personal from professional; it integrates them. Women should embrace that softer power, trusting that leading while “figuring it out” is not weakness, it’s a pathway to more intentional leadership. 

With Sentido launching this month, it lands in a moment of redefinition. What impact do you hope it makes for leaders, teams, or even one reader? 

Alison: I hope Sentido shifts how we value talent and intelligence. Too often, systems reward conformity over creativity. My book argues for the power of organic intelligence, the instincts and lived experiences that shape who we are. For younger generations, especially those forging nontraditional paths, I want this book to be a guide that validates their voices. For leaders, I hope it inspires a move from individual power to collective strength. In a world full of uncertainty, I believe we’re on the edge of a new renaissance, one fuelled by imagination, empathy, and resilience. If even one reader feels seen and emboldened, Sentido will have done its work. 

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