Revolutionizing DEI Conversations…For Everyone

Current DEI work has gotten very complicated. As a result, everyone – even the ‘woke’ and well-intentioned – is worried about looking foolish, being shunned or saying the wrong thing. No one feels safe to raise their hand, ask a question or admit they don’t know something. External forces and internal fear are making it harder and more complicated to connect with those around us.

The Solution: A Woke Wise LLM

AskLucky.ai is a conversational AI and connection coach to help you relate to others. These could be friends you have known for years, colleagues from work or complete strangers. Whatever the hard conversation is, AskLucky.ai is a friend you can’t offend, a counsellor who won’t judge and a wise elder who is always ready to guide you with understanding and care.

Modelled on the technology and safeguards behind AskEllyn.ai, AskLucky.ai is a supportive space to have hard conversations that you otherwise couldn’t. It is a confidential, safe and honest virtual space to share your worries about the changing world and find new ways to connect and learn with others.

AskLucky.ai, built on Gambit’s state-of-the-art conversational AI platform, integrates intentional risk mitigation strategies to ensure conversations remain positive, helpful and on track. The Language Learning Model (LLM) for AskLucky.ai will start with OpenAI’s platform with almost a dozen additional guardrails that identify and navigate away from harmful dialogue, ensuring discussions are honest, constructive and based on respect. Real-time monitoring and trained adaptive response mechanisms maintain a focus on learning and ongoing response refinement will grow from user interactions. In non-technical speak, AskLucky.ai is ready to take all the hurt, worry and confusion you have about a hard conversation and respond with acknowledgement, compassion and practical advice. 

Safe AI? We know that seems like a contradiction and it often is. Our commitment is to build a conversational AI that is unflappable, deeply insightful and capable of handling the nuances of DEI/mattering/belonging dialogue with grace and invitation. Maybe even a little humor. 

Some of the real-world questions we expect AskLucky.ai to hear and will be ready to help people think about: 

  • I was just called a racist!!!! WTAF?
  • My co-worker just changed their name in Slack from Steve to Stephanie and I have no idea how to react or what to say.
  • After a well-intentioned social post, my org is being labelled anti-semite and anti-Palestine!
  • My employer is organizing a pride event and people in my church are telling me not to go
  • Why do we need land acknowledgements at the start of EVERY meeting? Isn’t once a year enough?
  • I am the only hijab-wearing person in our office and it feels like everyone is scared of me
  • She touched my hair…again
  • That conversation was this close to insulting and they need to know why….
  • How do I ask for time off on holidays that no one else in my office celebrates? 
Lakhdeep Singh Dhaliwal

Who is Lucky?

Lucky is the name that many use for our project’s namesake,  Lakhdeep Singh Dhaliwal. Lucky is a DEI professional with over 20 years of experience and our Four Simple Words Diversity Champion. His wisdom, courage and ability to invite people into discomfort has helped thousands become more proximate to those around them. AskLucky.ai has been modelled on Lakhdeep’s Socratic approach to learning and is grounded in his compassion, his massive knowledge base and his empathy.  

For 20 years Lakhdeep Singh Dhaliwal has been building his leadership and experiences as a DEI (Diversity, Equity and Inclusion) professional. He has worked in large and small organizations across North America opening minds and hearts in classrooms, shop floors and board rooms. He is gifted in his ability to invite large and small groups into hard conversations about inclusion with grace, joy and humour. Through his knowledge, learning and curiosity, Lakhdeep’s focus has been to help organizations understand and reimagine power.

Case Use Examples

Childcare Worker

A rural childcare worker prepares to meet a Muslim family. Nervous about the conversation, they turn to AskLucky.ai for guidance on Islamic customs and advice about how to approach their first conversation. AskLucky.ai leaves them feeling confident and ready to welcome the family warmly.

High School Teacher

A teacher plans a lesson on Indigenous history in Canada and needs guidance on how to talk about the impact of residential schools that is respectful and accurate. AskLucky.ai helps them prepare an informative and engaging lesson, fostering a respectful classroom environment.

HR Manager

After an upsetting email was sent company-wide, a cis-gender HR manager wants to host a workshop on LGBTQS2+ inclusivity. They consult AskLucky.ai for advice on discussing gender diversity in the workplace. AskLucky.ai helps design a workshop that builds bridges and invites people to listen to one another.

Our Freemium-esque Model

Transforming How Companies Engage In DEI

At AskLucky.ai, we are committed to making DEI learning accessible to everyone. Our platform will always offer a free version, reflecting our mission to deconstruct power and build communities of service. This version will remain fully accessible and user-friendly, without collecting any personal data, ensuring privacy and inclusivity.

To sustain and expand our mission, we will offer customized versions of AskLucky.ai for medium and large-scale enterprises. These versions will integrate seamlessly with existing organizational DEI programs, enhancing them with our advanced conversational AI capabilities. By embedding company-specific policies, training and leadership content, we will co-create a bespoke DEI tool tailored to each organization’s needs.

Customized versions of AskLucky.ai will revolutionize enterprise DEI engagement, transforming static policies into dynamic, interactive learning experiences. This real-time and ongoing temperature check will give clients unprecedented data and insight into the thinking, worries and hopes of their teams. AI systems powered by AskLucky.ai will allow clients to transform DEI from emotionally driven and reactive initiatives to a reflective and data-driven function of their organization.

Revenue from these customized solutions will support the ongoing development of AskLucky.ai, ensuring we continue to offer free, high-quality DEI tools to all. Each bespoke version will proudly reference the AskLucky.ai brand, underscoring our commitment to fostering genuine curiosity and connection.

Built On Proven Technology

This is a case study based on an amalgamation of real-world stories | Navigating life’s toughest challenges often leaves us feeling lost at sea, especially when facing them for the first time. Such was the case for Kai, who confronted a reality she never imagined: her wife’s breast cancer diagnosis. Thrust into a whirlwind of medical terms, treatments, and the daunting task of emotional support, Kai found themselves grappling with fear and uncertainty. 

Seeking guidance, they turned to AskEllyn.ai, not as a tool, but as a confidante. “AskEllyn was a safe space to say I didn’t know anything. I was scared, worried, afraid I would do everything wrong and make this harder for my wife,” they shared. Through AskEllyn.ai, Kai found the clarity and support they desperately needed, learning that “the most important thing for me is to love my wife. I never could have gotten that clarity without the help of AskEllyn.ai.”

Kai’s story is a powerful illustration of the impact compassionate, AI-driven support can have on an individual’s journey through uncertainty. It showcases the potential of AskLucky.ai to guide users through not only personal crises but also the complex landscape of diversity, equity, and inclusion (DEI). By providing a safe, judgment-free space for exploration and learning, AskLucky.ai empowers anyone interested in navigating sensitive topics with empathy and understanding.

Empathy Engine will be built with our partners at Gambit Technologies in Waterloo and modelled after their revolutionary AI tool called AskEllyn.ai

The World Needs Your Philanthropic Investment

AskLucky.ai will be accessible 24/7 to anyone with web access in over 50 languages. We plan to promote it as a tool for individuals, businesses and organizations to reimagine their individual and collective DEI conversations. 

We estimate a spend of $1.1M to bring this to market:

  • $600k | Initial AI development including 60,000 interactions for year 1 – Gambit
  • $150k | 2nd year of interactions and additional development – Gambit
  • $235 | LLM coaching and guide rail development – Four Simple Words 
  • $100k | Branding and launch – Pearl Street

Intellectual Property Notice Be advised that the EmpathyEngine program, including but not limited to its current and future name, methodology, content, and structure, is the exclusive intellectual property of Pearl Street Communications Inc (Pearl Street) and our training division of Four Simple Words.  This program is presented for potential collaboration and implementation with your team, under the condition that its concepts, content, and strategies will not be copied, reproduced, or utilized in any form without the express written permission of Pearl Street. Unauthorized use of our intellectual property will be addressed under applicable laws to protect our rights and investment in creating this program.

We Are Ready To Reimagine DEI Conversations. Are you? 

The Team at Four Simple Words is called to do two things. Deconstruct power and build communities of service. It has only taken us 20 years to realize they are different sides of the same coin! While our past work has been meaningful, it has yet to reach the scale we know it must. Conversational AI has opened new opportunities for Four Simple Words to live out and amplify our purpose. AskLucky.ai is our gift — and responsibility — to the world to support and enable the very human need of belonging.

This project is a natural evolution of our work and a giant leap forward. We hear the audacity of helping build a tool like this and do so knowing it will be in partnership with minds, hearts and wallets that are bigger than our own. As the kids say, we are nerve-cited.

Lets talk about how your philanthropic capital can bring this project to life for leaders around the globe. You can find a copy of our pitch deck here and you can book a Zoom with us here.

519.496.2212 | [email protected]

519.580.9725 | [email protected]

FourSimpleWords.ca is the training and planning division of Pearl Street Communications Inc. Work agreements and invoices for DEI training and support will come from Pearl Street Communications Inc.

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