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Image of Sallyann Della Casa wearing a black dress and orange scarf and smiling.
From low-income schools to wealthy organizations, Casa identified that the gap in soft skills development continued to be a challenge. Photos courtesy: Sallyann Della Casa

Gender

How This Founder Is Using AI and Machine Learning to Teach Soft Skills at Work

‘You don't need to be an expert in anything to be able to create, it’s part of that impostor syndrome.’

“Your currency in the future for your employer is your ability to learn and shift and change,” said Sallyann Della Casa, the 41-year-old founder and Chief Identity Hacker at Gleac, a tech company that measures and develops soft skills for job seekers. Casa’s own ability to learn and change has been demonstrated by her five degrees in everything from urban planning to law and her trajectory from lawyer to author to now, a startup founder. 

Her life’s work? Teaching people the significance of soft skills, first through Growing Leaders Foundation, her non-profit and now through Gleac. Training technology to measure and develop human skills like negotiation and communication might seem strange to some, but there is a method behind the madness, Casa told Re:Set. Through a benchmark test, Gleac’s tech allows you to understand what soft skills are crucial to your job and where you currently stand on that spectrum. 

Very often, soft skills like critical thinking are viewed as “abstract,” so how do you teach a machine to quantify it? 

“I call those ‘umbrella skills’ and below that I built a taxonomy which are all these sub-skills. For example, communication —underneath that you have negotiation skills, persuasion, biases and there are sub-categories underneath that,” Casa said. The tech is able to go into job roles and journey map what skills you need to succeed. “So we’re able to quantify very specifically how much of those skills you need in a job role and in a particular industry and sector,” she said. 

Through machine learning, it is also able to show you how others, be it industry experts or peers, handle the same situation. “What it does is give a richness in feedback and coaching you would not have before because you’re not able to get all those people in the room all the time,” Casa said. 

An image of Sallyann Della Casa writing on a whiteboard.

Casa pointed out that women experience a lack of confidence especially in the workplace compared to men.

It was during her time as Head of People at Careem, a ride-hailing company based in the Middle East, that she began familiarizing herself with the tech knowledge she would need to take her journey to the next step. Today, Casa is one of only 4% of women globally who are sole inventors, for her patent-pending method and algorithm for measuring soft skills. “[Women] invent stuff all the time…but there’s a lack of confidence,” she said on why few women file patents. She pointed out that more often than not, women tend to be less sure about themselves and feel like they need to be “100% [ready] before putting our foot out there” with things like inventions and businesses. 

She added that investors have also mentioned that male founders sometimes ask for investment even before they’ve figured out their functioning compared to women who feel like they have to have all their bases covered. “You don’t need to be an expert in anything to be able to create, it’s part of that impostor syndrome,” Casa said.

“I cured myself of impostor syndrome by learning truly what I bring to the table.”

Like most women, Casa too is no stranger to experiencing impostor syndrome herself but believes she has changed since her 20s when she felt it the most. “I cured myself of it by learning truly what I bring to the table and…my ability to learn, there’s confidence now and it’s not even a fear anymore,” she said.

It has been an upward trek for Casa as a female founder with a limited background in tech. Her long list of degrees means that she’s well-respected in senior tech circles, but has faced trouble interacting with “junior level boys” especially in India who aren’t used to taking commands from a woman, she reflected. To handle this obstacle, she has more local management teams in place. 

Casa addressed the assumption that having an education from a prestigious university means that people understand soft skills better. “I was doing this work with incarcerated youth, at-risk youth [through Growing Leaders Foundation], I also worked with some of the wealthiest organizations in the world and the same problem kept popping up,” she said, citing that common issues like “non-engagement at work, not fitting into roles, people quitting jobs and people being in the wrong job,” all circle back to soft skills and the fact that most schools don’t work on developing them.

With the Growing Leaders Foundation, Casa has worked to incorporate soft skills in schools in places including Trinidad and Tobago, where she hails from. “I would come out of classrooms and have students asking me to autograph their bags and school shirts,” she said about her experience of teaching young people. At the time, Casa did not realize the impact that she was creating. In a school system that lauded academic prowess and “A and B students,” she was able to show them that their interpersonal skills were still valuable, she reflected. 


Also read: Navigation to Money Management: The Essential Life Skills Parents Are Teaching Kids


With a tool that measures your change, it’s difficult not to come face-to-face with the reality of your behaviour regularly. Her own tool revealed the gaps in her leadership skills. “In terms of my judgement and decision making, I’m very intuitive and sometimes that doesn’t work,” she said, adding that because of her constant rush to learn, she’s less patient with others and that can come across as being unempathetic.

 A coach works with Casa and the Gleac team, especially with some of the younger female employees who sometimes have trouble speaking up. Openly working on her own challenges puts her “in a vulnerable position” as a leader and founder, Casa said, but she emphasized the need for others to see that you’re on a learning curve as well. Talking about her trajectory, Casa has her sights set high as the soft skills revolutions starts picking up. “I want to be the region’s first female unicorn [startup founder],” she told Re:Set. 

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How This Founder Is Using AI and Machine Learning to Teach Soft Skills at Work