TL;DR
Shitty Boss Moments cost your organization time, money, and trust. 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.
Where Better Leadership Begins
Mattering Impacts Your Top Line
AskLucky helps managers transform messy, human leadership moments into evidence that people matter, which is a direct path to lower turnover, higher engagement, and better results.
- Only 21% of employees globally are engaged at work (Gallup, 2025).
- Manager behavior accounts for 70% of the difference in team engagement (Gallup, 2025).
- $438 billion is lost globally each year due to declining engagement (Gallup, 2025).
- Half of employees are actively looking or open to a new job right now (Gallup, 2025).
Where training ends, AskLucky begins
Traditional training is important: it fosters foundational knowledge, establishes a shared language, and cultivates long-term leadership capacity. But when the workshop ends and the real work begins, managers still face tough, messy moments that no slide deck or playbook 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 | AskLucky Real-Time Coaching |
|---|---|
| Builds foundational knowledge | Helps apply it in real situations |
| Teaches frameworks and tools | Offers just-in-time guidance |
| Happens in dedicated settings | Happens in the flow of work |
| Strengthens long-term capacity | Supports everyday action |
| Optional or required | Voluntary, judgment-free support |
| Retrospective learning | In-the-moment help |
Listen to a NoteBookLM summary of our goals for AskLucky.ai
Listen to a NotebookLM conversation about why mattering is the missing link in so many workplaces, and how AskLucky.ai is transforming everyday challenges into moments of real leadership.
Meet Lucky
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—forms the foundation of AskLucky.ai’s personality and interaction style.
FAQ’s
Why are organizations excited to use AskLucky?
Because it gives managers the confidence to handle tough moments, without adding more work. Organizations that can offer managers immediate support will have fewer fires to put out, reduce HR workload and equip leaders who show up with more care and clarity.
What makes AskLucky different from other leadership tools?
AskLucky works when the moment is happening. It is judgment-free, practical, and designed to fit into the real flow of work — no workshops required. Importantly, it doesn’t tell people what to do. It invites them to reflect then respond.
Who is Lucky?
Lucky is Lakhdeep Singh Dhaliwal — an experienced and successful leadership coach and diversity champion whose wisdom, courage, and humor have helped thousands navigate hard conversations. AskLucky is inspired by his approach: compassionate, practical, and fearless in the moments that matter most. This is not just software — it is decades of lived leadership experience, built into a tool to help managers rise to the challenge.
Is AskLucky only for “problem managers”?
Not at all. AskLucky is for every leader who wants to improve a little, every day. It is a tool for growth, not punishment. In addition to reducing sitty boss moments it helps good managers become great ones.
How does AskLucky protect privacy?
AskLucky is designed with privacy at its core. No personal user data is collected or stored, and no login is required. AskLucky learns from patterns, not from tracking individuals, ensuring every conversation is private, safe, and judgment-free.
Can AskLucky support multilingual teams?
Yes. AskLucky currently works in over 20 languages. It is not just translation — it is designed to understand cultural nuance, helping you deliver consistent, human-centered leadership support across geographies.
What’s inside AskLucky’s knowledge base?
AskLucky draws on decades of workplace wisdom, leadership research, and practical experience. We blend insights from global thinkers, changemakers, and cultural leaders with Lakhdeep’s expertise to help managers not just “interact,” but lead in ways that make people feel seen, valued, and engaged.
Does AskLucky integrate with our HR systems?
Yes. AskLucky connects with your HR platforms (HRIS, LMS, performance systems) using secure APIs, giving managers personalized, context-aware guidance without disrupting existing workflows. It can also provide aggregated insights back to HR leaders to share meta-insights and trends.
Can AskLucky support a multi-lingual team?
Absolutely. AskLucky.ai is built to support diverse, global teams. Our platform currently offers support in over 20 languages, with more being added regularly. It not only translates content but also understands cultural nuances, ensuring that communication is both linguistically accurate and culturally appropriate. This capability allows for consistent HR support and engagement across your entire organization, regardless of geographical location or language preferences.
How is AskLucky different from a chatbot?
AskLucky is not a chatbot — it is a real-time coaching tool. While a chatbot spits out formulaic answers, AskLucky helps leaders navigate complex, emotional moments with practical, human-centred guidance. It is designed to build leadership confidence, strengthen trust, and improve decision-making.
How does AskLucky know what to say?
AskLucky combines cutting-edge AI with the best of human leadership wisdom. It is trained on decades of knowledge in inclusion, leadership, and culture, enhanced by your organization’s policies and values. Most important: it is designed to guide, not replace, human judgment.
What kinds of moments does AskLucky help with?
Everything from giving feedback, to navigating team conflict, to showing support when someone is struggling. AskLucky is there in the moments that matter — when leadership is tested, and trust is on the line.
Build With Us
AskLucky is ready for its next leap. We are seeking a group of forward-thinking organizations to partner with us to develop our MVP and shape the future of real-time leadership support.
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.
AskLucky.ai will be built with our partners at Gambit Technologies in Waterloo and modelled after their revolutionary AI tool called AskEllyn.ai
Transform Moments That Matter
If you are ready to build the future of leadership culture, we would love to talk. Book a time to connect to see how AskLucky.ai can change your top line and organizational culture.
519.496.2212 | [email protected]
519.580.9725 | [email protected]
FourSimpleWords.ca is the training and planning division of Pearl Street Communications Inc. Work, partnership and IP agreements for AskLucky will be established through Pearl Street Communications Inc.