Change in large organizations can often be treated as a strategic exercise: setting specific goals, outlining key priorities, and polishing the vision. Yet when the moment comes to put that vision into practice, the human reality proves far more complicated. Strategy is rarely what breaks down; people, alignment, and trust do.
This is where Aishani Gupta, director at Thoughtium, has built her career. A transformation consultant with nearly a decade of experience across healthcare, technology, and public policy, Aishani brings an approach that is as analytical as it is human. Her work insists that no strategy survives without people seeing themselves in it.
Aishani Gupta: A worldview that places people at the centre
Aishani’s career began in India with 91springboard, one of the country’s first coworking ventures. There, she helped scale operations from a single centre to a $150 million company serving thousands of members. That early exposure to growth taught her the mechanics of building systems at speed. But it was in the U.S., while pursuing an MBA at Babson College, that her philosophy of transformation began to crystallize.
While studying at Babson, Aishani collaborated with organizations such as the Toyota Mobility Foundation and the Massachusetts Executive Office of Elder Affairs. In one of her most defining projects, she led a design thinking initiative aimed at reducing the growing social isolation older adults faced after the COVID-19 pandemic. The state initially framed the problem as a technology challenge, focusing on expanding access to tools like telehealth services and public transit. Aishani’s team uncovered something deeper: the barriers were emotional, tied to dignity, independence, and the stigma of aging.
Reframing aging as a series of “living transitions” rather than a question of access to tools unlocked new solutions. Peer mentoring pilots, inclusive training designs, and policy recommendations were followed, embedded in the state’s Age Strong program, and reported in the 2020 Reimagine Aging annual report.
For Aishani, the experience was a key moment of clarity that showed her how transformation succeeds only when people, not just systems, are re-centred in the process.
Her work as a strategist: Listening for friction
That lesson now guides her first move in any organization: listening. At management consulting firm Thoughtium, Aishani pays attention not only to what is said in meetings but also to the subtle frictions that can prevent everyone from aligning behind a common goal. She describes transformation blockages not as issues linked to poor strategies but as deeper disconnects.
“Real transformation isn’t blocked by strategy,” she has said. “It’s blocked by disconnects: between leaders and teams, ambition and action, vision and buy-in — both emotional and intellectual.”
This listening-based approach has helped Aishani identify misalignments that others often overlook. For example, during her work with a leading genetic testing company, she was in charge of co-designing a customer experience playbook for an internal team of more than 400 employees. Made to make sure that the customer experience carried a consistent tone, the project merged messaging and leadership behaviours, ensuring executives and frontline staff were moving with shared clarity.
It was not just a rebrand, but an example of how, when done carefully, companies can work to align their internal workflows to turn strategy into lived behaviour.
From inclusion to integration
Another main factor Aishani takes into consideration is making sure strategy is a co-authored process. She believes the most sustainable change comes not from top-down directives, but from middle managers and teams who can recognize themselves and how their contributions can positively affect the performance of their company.
As an immigrant and woman of colour operating in traditionally white-dominant executive environments, Aishani understands the built-in power dynamics and invisible hierarchies that many corporate spaces have. That awareness shapes how she designs inclusive spaces: ensuring not only that voices are heard, but that those voices are integrated into the structures of strategy itself.
“Leading from within is about creating strategy from the inside out,” she reflects. “It draws on lived experience, collective intelligence, and the emotional truth of an organization.”
By shaping spaces where alignment develops naturally, Aishani focuses not on asserting the loudest voice, but on helping teams discover their own wisdom.
Turning resistance into insight
Finally, since the start of her career, Aishani has taken into account the resistance that can come with larger transformation. For many leaders, it is an obstacle; for Aishani, it is a signal. She recalls the Elder Affairs project, where the state’s proposed solution focused on expanding Zoom access and not much else.
Rather than rejecting the idea directly, she reframed the resistance as a way to propose more nuanced solutions. The real need was not technology, but emotionally intelligent design that affirmed older adults’ dignity and identity with tangible actions.
“One thing I’ve realized is resistance often works as a defence mechanism,” Aishani explains. “It disappears when leaders realize they’re being heard, they realize the respect they have remains, and they’re simply being re-engaged in the ‘why’ of the transformation.”
This approach, built on challenging assumptions without alienating stakeholders, has become one of her distinguishing traits. Aishani positions resistance not as a roadblock, but as data: evidence of what still needs to be surfaced before alignment can take hold.
A human standard for strategy
Aishani Gupta’s work is built on the belief that strategy cannot succeed unless it is humanized — connected to the lived realities of the people tasked with carrying it out. From scaling start-ups in India to advising global healthcare companies, her story is a demonstration of how transformation that lasts is built with open communication, mutual understanding, and co-authorship at the outset.
As organizations face more structural changes, Aishani represents a new kind of strategist, who understands that change sticks only when people see themselves in the story.
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