Real-time coaching that turns difficult management moments into trust-building opportunities. The question AskLucky helps managers ask: How do I show up when things are hard?
AskLucky is a conversational AI that delivers practical coaching to managers when they need it most: in the messy, human moments where leadership can either build trust or lose people. We’re seeking a founding partner to co-create this breakthrough solution.
Better Leadership. Lower Turnover. Higher ROI.
Shitty Boss Moments cost your organization time, money, and trust. In fact, the math is brutal and the opportunity is massive. Only 21% of employees globally are engaged at work and manager behavior accounts for 70% of the difference in team engagement (Gallup, 2025)
AskLucky is a conversational AI that delivers practical, real-time coaching to managers when they need it most: in the messy, human moments where leadership can either build trust or lose people. AskLucky is ready for its next leap: moving from concept to product.
Most managers want to do the right thing. But good intentions aren’t enough when you’re facing a tough conversation with 10 minutes before your next meeting. Without real-time support, even strong managers can miss opportunities to build trust. Small missteps add up: frustration grows, engagement drops, good people leave.
Coaching When It Actually Counts
Traditional training builds foundational knowledge and establishes shared language. But when the workshop ends, managers still face tough moments that no slide deck can cover. AskLucky provides real-time, in-the-moment coaching that helps leaders apply what they have learned, stay aligned with values, and show up when it matters most. AskLucky builds on your existing leadership programs to create a powerful one-two punch: bigger leadership capacity + stronger everyday execution.
| Traditional Training | Traditional Coaching | AskLucky | |
|---|---|---|---|
| The Question It Answers | What should I know? | How can I improve? | What do I do right now? |
| When It Helps | Building foundation | Developing mastery | Applying in the moment |
| The Learning | Concepts and frameworks | Reflection and refinement | Just-in-time guidance |
| Who Benefits | Everyone present | Individuals | Everyone, anytime |
| The Gap It Fills | Knowledge | Capability | Confidence |
AI Built By A Good Human, for Good humans
Lucky, called Lakhdeep Singh Dhaliwal by his mom when he is in trouble, is the heart and soul of AskLucky.ai. With over 20 years of experience as an inclusion champion, Lucky’s wisdom, courage, and infectious joy have helped thousands discover the power of mattering. He has a rare talent for inviting people into challenging conversations with grace and humour. His Socratic approach to learning (grounded in compassion, empathy, and genuine curiosity) is the foundation of AskLucky.ai.
Help Shape The Future of Leadership Coaching
AskLucky is ready to be built. We are looking for partners ready to invest $200k and provide access to a small group of managers who will help us build, test, and refine AskLucky in real workflows. This is not just a pilot. It is a capital investment in a breakthrough solution designed to reduce turnover, strengthen engagement and make leaders better where it matters most.
We are seeking organizations ready to:
- Help test and shape AskLucky inside their real workflows.
- Provide financial investment to accelerate product development.
- Become early champions and co-creators of a new category of leadership enablement.
