Elevate L&D
What is your philosophy on training beyond the executive level?
Rachel Cossar and Katie Sheketoff convert on the topic of personalized training beyond the executive level in the workplace. Katie Sheketoff has a distinct focus at Elevate Labs and is looking to empower a much broader range than typically considered, stretching beyond the typical executive. Traditional emphasis is on leadership development focusing on executives, the thought being that changes instigated at the top trickle down. However, Sheketoff believed that change needs to happen immediately at all levels, due to the demanding environment we currently occupy. She highlights two data points that support this view. Firstly, a study by Gallup indicated that 70% of turnovers are related to people’s managers, suggesting that the action, engagement and enthusiasm about an organization at the frontline is coming from their individual managers. The second data point looks at Google’s Project Aristotle which studied the performance and innovation of different teams, finding that the most effective were those whose leaders created an environment of psychological safety where people are unafraid to take risks or make mistakes. Furthermore, Sheketoff discusses the significant role AI has been playing in elevating the learning of managers and is seeking ways to use it to improve teams. Rachel Cossar contributes to the discussion by linking their focus at Virtual Sapiens manager training to this. She observes that people are often promoted into managerial roles based on their individual contributor performance, which may lead to a gap in supporting the behaviors required to handle people, particularly communication. She sees a huge value in giving people a safe space to practice communication. In the conclusion, Katie Sheketoff emphasizes the issues with the common approach of bringing in a once-off manager trainer, underlining the need for opportunities for managers to practice and apply their skills in a safe space for feedback.
How do you structure your programs at Elevate Labs to support larger groups of leaders?
On discussing their program structuring and how it supports groups of leaders, Katie Sheketoff from Elevate Labs mentioned beneficial aspects such as ‘just in time learning’ and ‘psychological safety’. They wanted to provide practical resources and tools for those transitioning into managerial roles. To work towards this, they created demand courses and monthly core courses focusing on leading high-performing teams. Targeting challenges and issues that managers might face, they plan to release a course next month focusing on managing conflict and underperformance. With Katie sharing that conflict on teams and underperformance is a common struggle for managers, this course will help tackle real conversations and create an environment where high performers feel valued and heard. In their plans for next year, they aim to launch diverse courses on communication, influence, managing diverse and virtual teams. Rachel Cossar points out that Elevate Labs’ approach is interesting, addressing the benefits of their courses. While they are figuring out if they should go directly into companies or continue offering public access to their courses, one potential plan of action in mind is a subscription model with partnerships with companies that can offer their employees access to their public courses alongside potential customized add-ons. Working through questions and challenges during their 10-month journey working on this project, Katie expresses enthusiasm and excitement for what they’ve learned and are still figuring out in the future of work. Keywords: executive presence, virtual presence, hybrid workplace thought leadership, Innovation and AI.
What lessons have you brought with you from the world of hospitality ?
Rachel Cossar and Katie Sheketoff discussed their unique backgrounds in hospitality and revealed significant insights they’ve gained from their experiences. Rachel found hospitality to be a microcosm of the broader society, dealing with different people daily. Katie, formerly with Marriott, believed individuals without specific backgrounds or education could still engage with leadership concepts successfully. She emphasized simplifying the language for everyone to understand, without dumbing down the content. Katie, deeply invested in leadership development, found huge value in people from diverse contexts interacting and learning from each other. Both believe managers at the future of work should be of service to their organization’s betterment at a hybrid workplace. They stressed the need for people to feel heard and to be of service to others, which transcends cultural, political, and religious barriers. Rachel related these insights to her ballet background and how receiving opportunities could help an individual maximize their potential with the right support and coaching, echoing the sentiment of executive presence in a virtual space. The conversation emphasized the role of a manager, highlighting the importance of understanding potential from an inside-out perspective rather than an imposed high potential tag, hinting at innovation and AI’s future roles.
What has most surprised you so far in your journey as a founder?
In this discussion, Rachel Cossar chats with Katie Sheketoff about her surprising findings as a founder. Katie shares her initial misconception about the roles of sales and marketing in her venture. While she expected sales to dominate her role, she discovered how much time, effort, and energy marketing requires. She also discussed how important it is to have a clear and consistent story for effective marketing. Katie candidly admits the struggle of defining vision, mission, values for her startup, and the necessary balance between her personal beliefs and the business’s market and future outlook. Interestingly, Katie shares the unexpected drawback of having a business; the lack of guidance that comes with being your own boss. Despite these surprising revelations, the journey has been one of joy, terror, and constant learning. Katie’s story provides insights into the future of work, executive presence, virtual presence, and the hybrid workplace thought leadership, which is essential in this era of Innovation and AI.
Transcript
Rachel Cossar: Everyone, and welcome to another episode of Conversations in the Future of Work. I am your host, Rachel Kasser, and I am very pleased to welcome Katie Shekhetov on the show today, and we’re gonna be diving into all things L&D. So, Katie, welcome.
Katie Sheketoff: Hello. It’s so great to be here. Thank you so much for taking the time.
Rachel Cossar: If you don’t mind just sharing a little bit about your background and what you’re up to now?
Katie Sheketoff: So I am the founder of Elevate Labs. We started earlier this year, so very early in our journey. Elevate Labs is an organization dedicated to elevating leadership across various industries, from frontline managers to the C-suite. What makes us unique is our focus on lower- and mid-level managers.
This comes from my background in leadership development across multiple sectors. I started in nonprofits, working both domestically and internationally—in Ukraine, Romania, Egypt, Rwanda, Malaysia, and beyond. Over the last six years, I led global leadership strategy at Marriott, where we realized that while we were doing great work with senior leaders, we weren’t reaching our 200,000 frontline leaders. That experience inspired Elevate Labs and our mission to reach leaders at all levels.
Rachel Cossar: That’s so interesting. You mentioned that Elevate Labs focuses on empowering a broader range of leaders beyond executives. Can you share your philosophy on leadership training beyond the top level?
Katie Sheketoff: Traditionally, leadership development focuses on executives under the belief that change trickles down. While that has value, today’s organizations don’t have the luxury of waiting for change to cascade. We need transformation at all levels—now.
Two data points drive my approach. First, Gallup found that 70% of turnover is related to managers. Engagement and retention start with frontline leadership. Second, Google’s Project Aristotle found that the most effective teams are those with leaders who foster psychological safety—environments where people feel safe to take risks and learn from mistakes.
So, organizations that want to thrive must prioritize managers who create environments where people want to show up, innovate, and take risks. That’s the foundation for Elevate Labs—supporting managers who lead in this new environment. Recently, we’ve also explored how AI can support this development—not just in productivity but in learning, reflection, and self-improvement.
Rachel Cossar: I completely agree. Many people become managers because they were strong individual contributors—not because they were trained to manage people. There’s such a skills gap there. Communication is a huge piece of that. At Virtual Sapiens, we’ve seen that creating safe practice environments for communication skills really resonates with managers.
Katie Sheketoff: Absolutely. Too often, companies bring in someone for a one-day training, and while those can be great, they don’t allow for ongoing practice or feedback. That’s why we structure learning over several weeks—with opportunities to apply and reflect.
Like Virtual Sapiens, we focus on giving people safe spaces to practice real scenarios—delegation, feedback, communication—so they can try, fail, and learn without consequences. That’s where true behavioral change happens.
Rachel Cossar: How do you structure your programs? Do you mostly work with groups of leaders?
Katie Sheketoff: Yes, our programs are open to the public. We designed them for just-in-time learning, especially for new managers promoted from individual contributor roles who suddenly need management skills.
We offer a monthly core course, Leading High-Performing Teams, tailored to first-time managers. We’re also expanding into focused programs like Managing Conflict and Underperformance, Communications & Influence, and Managing Diverse and Virtual Teams. Our goal is to reach people when they need support the most—and create spaces for shared learning and psychological safety.
Rachel Cossar: That makes sense. Do you also sell directly into organizations, or are all your programs open to the public?
Katie Sheketoff: We’re still exploring. Public diversity of experience is incredibly valuable, but we also want to partner with companies through subscription models—sending cohorts through public programs while layering on customized options for senior leaders. We’re ten months in, learning fast, and evolving every day.
Rachel Cossar: I love that. Shifting gears—your background in hospitality must have given you powerful insights. What lessons did you carry forward from that experience?
Katie Sheketoff: So many! From a large-scale, global perspective, I learned two key lessons. First, before Marriott, I worked mostly with highly educated white-collar professionals. When I moved into hospitality, I realized the assumption that leadership development requires advanced education is false.
We wrote all training materials at a sixth-grade reading level—but instead of dumbing down content, we simplified language and elevated the ideas. The results were incredible. Frontline employees—housekeepers, engineers—were diving into emotional intelligence, psychological safety, and strategic decision-making. It proved people are capable of far more than we often expect when we communicate clearly and believe in them.
Second, cross-context learning is incredibly powerful. A front desk manager in New York and a housekeeping supervisor in Cincinnati might face very different challenges, yet learn deeply from each other’s perspectives. That’s why we prioritize diverse cohorts.
Hospitality also taught me that people want two things: to be heard and to be of service. Those principles underpin our work. Managers are, above all, in service to their people and organizations—and that starts by truly listening.
Rachel Cossar: That resonates so much. People often rise to the occasion when given the right support. It reminds me of my ballet background—how dancers from the corps could step into principal roles and excel when given opportunity and coaching. The same principle applies to leadership.
Katie Sheketoff: Exactly. Potential starts from within. I recently wrote in ATD Magazine about how the concept of “high potential” is flawed—it’s often defined externally. We should instead ask: What do people want? Motivation and desire drive growth far more than labels. With the right coaching, people can exceed expectations.
Rachel Cossar: That’s such a great insight. Switching topics—now that you’re a founder, what’s surprised you most about entrepreneurship?
Katie Sheketoff: Everything! But most of all, the difference between marketing and sales. I assumed sales would be the focus, but marketing has taken much more time and energy. It’s not just about telling the story—it’s about having the right story and believing in it.
Also, the myth that being your own boss is freeing—sometimes you just wish someone would tell you what to do! It’s exhilarating and terrifying in equal measure, but so rewarding.
Rachel Cossar: I can completely relate. It’s a mix of humility and growth, learning through every challenge.
Katie Sheketoff: Exactly.
Rachel Cossar: Katie, thank you so much for joining us and sharing your expertise. It’s inspiring to hear how Elevate Labs is rethinking leadership development. How can people follow your work?
Katie Sheketoff: The best place is LinkedIn—either the Elevate Labs page or my personal profile. We regularly share articles, blog posts, and updates about upcoming programs. Our website, elevatelabsleadership.com, also has our newsletter signup and event schedule. And if you want to try a Compass Session, you can register for $1 with the code virtualsapiens.
Rachel Cossar: Amazing. Thanks so much, Katie. And thanks to our audience for joining. We’ll see you next time.