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Executive Summary

Hey everyone, thank you for joining us as we embark on an incisive journey with Lou Carter on this episode of The Leader Show. Our guest today is Robert LoCascio, the CEO of LivePerson. Headquartered in New York City, LivePerson is an internationally recognized technology company specializing in the creation of conversational commerce and AI software. 

With that said, lets delve into the insights that Robert shares and what makes LivePerson a Most Loved Workplace®.

Robert Shares Strategies for Cultivating a Positive Company Culture

Lou commends Robert LoCascio’s successful tenure as CEO of LivePerson, expressing interest in learning about how he has created a positive company culture. Lou then asks Robert to share his experiences and strategies.

Robert responds by acknowledging that cultivating a positive company culture is a continuous process. He refers to his board members who are culture-focused CEOs, including Fred Mossler (previously with Zappos) and Jill Layfield (former CEO of Backcountry). 

He reveals that 11 years ago when the company had around 400 employees, he decided to establish core company values, a process that took nearly eight months and involved input from the entire company. This process culminated in a three-day retreat in Israel where the proposed values were scrutinized and ultimately voted on, with the requirement of 98% approval.

The values adopted included being an owner, helping others, and creating meaningful connections. To further these values, they also transformed their physical workspaces by removing walls and cubicles to foster connection, centered their meetings and events around connection before content, and incorporated training focused on these values.

On that note, Robert emphasizes the uniqueness of LivePerson’s culture, describing it as a blend of connection and entrepreneurship. He notes that those who thrive in the company are both connected and entrepreneurial. Over time, they’ve added another value, “Dream Big,” to further cultivate this culture.

Aligning Customer Experience with Internal Culture

Next, Lou observes that LivePerson, like many loved workplaces, aligns what it provides to its customers with its internal culture. Robert confirms this, noting that the company’s aim for meaningful connections mirrors what its software offers. He refers to this alignment between customers, products, and company culture as a “golden thread,” contributing to its status as a “Most Loved Workplace.”

Robert then goes on to share his inspiration for creating such a company culture, which he attributes to Tony Hsieh and Zappos. After watching a profile of Tony Hsieh on a morning show 11 years ago, when Zappos was rated the top company to work for, he decided to visit the company’s headquarters in Las Vegas. 

Witnessing their unique culture based on “delivering happiness” deeply impacted Robert, making him realize how different LivePerson was and setting a high bar for what he wanted his company to achieve. Despite the progress the company has made over the years, he admits that it is still far from reaching that high bar, underscoring his ongoing commitment to improving the company culture.

Navigating the Challenges: Balancing Growth, Remote Work, and Cultural Alignment at LivePerson

Moving on, Lou asks Mr. LoCascio about potential improvements to reach the high bar he has set for LivePerson. The latter identifies the company’s dynamism, due to its growth and transition from chat technology to messaging and AI, as a key challenge. Balancing the demands of business development with nurturing a positive company culture is a complex task.

Robert recognizes the difficulties in maintaining culture, especially with the influx of new employees and the shift to remote work. Typically, a lot of cultural understanding is transmitted through physical office settings, where employees can observe behavior, meeting styles, and office layouts. However, with the shift to remote work, it’s harder to instill these cultural elements.

He also mentions difficulties in assessing whether potential hires are a cultural fit during virtual interviews. As a solution, Robert is considering the creation of a cultural competency grid to better define and impart the essence of LivePerson’s culture to its employees. This new approach will be necessary as the company adapts to the remote work landscape.

LivePerson’s Collaboration with Equal AI for Culture and Hiring

After that, Lou questions Robert about the role of unconscious bias and its impact on hiring and maintaining culture, particularly in the current context of remote work. 

Robert highlights the work LivePerson is doing with Equal AI, an organization aimed at eliminating unconscious bias in machine learning and algorithms. It provides training and certification to companies, helping them identify and counteract unconscious bias within their systems and culture. 

Robert details the concept of unconscious bias, explaining it as a physiological mechanism rooted in human evolution. Bias is, in essence, the brain’s effort to conserve energy by making automatic decisions about individuals based on preconceived notions.

Acknowledging the expanding role of technology in daily life, Robert mentions the potential of this bias to be transposed into digital environments like the ‘metaverse.’ He argues that it’s critical to ensure that, as technology scales and becomes more integrated into everyday life, it doesn’t perpetuate or exacerbate harmful biases. Instead, the goal is to enhance the positive elements of AI while mitigating its potentially harmful effects.

Learning from Mistakes: Robert Approach to Hiring and Cultivating Internal Talent

Lou probes Rob on his biggest mistake as a leader and how he rectified it. Robert candidly admits that the biggest mistake he’s made as a leader is hiring the wrong people for senior roles, especially those who don’t fit the company’s culture.

Robert distinguishes between managers and leaders, highlighting that leaders bring about exponential change while managers maintain existing systems. He mentions that it’s essential for newcomers to understand the company culture before trying to implement their own structures or frameworks. Otherwise, they can pose a detrimental impact on the organization, especially if they do not respect or align with the existing culture.

Despite these setbacks, Robert remains optimistic, stating that his recent learning is to nurture internal talent rather than hiring senior leaders from outside the organization. He emphasizes the importance of developing a strong ‘farm team,’ fostering the growth of existing employees into leadership roles. 

Lastly, Robert acknowledges that at certain stages of growth, hiring from outside might be necessary, but at LivePerson’s current scale, internal leadership development is his focus.

Authenticity as a Cornerstone: Robert’s Emphasis on Cultural Fit and Individual Growth

Moving on, Robert shares his insights about the crucial role of authenticity in the workplace, stating that people come to work at LivePerson because they feel they can be themselves and grow. He expresses his concern for individuals who have to fake their personalities to survive in certain company cultures.

On that note, Robert recalls when he used to hold meetings with all new hires to discuss the culture and history of the company. During these meetings, he could usually identify individuals who didn’t fit with the company’s culture. He illustrates this with an anecdote about a new employee who physically distanced himself during a group session, which clashed with LivePerson’s culture of connection. 

This individual had come from a company known for its far from ideal culture, which further emphasized for Robert the importance of cultural fit over skills alone when hiring.

Striking a Balance Between Personal Comfort and Organizational Alignment

Continuing the discussion, Robert emphasizes the struggle of balancing personal comfort with organizational alignment. He shares his experience as a CEO, admitting that he has often felt uncomfortable with individuals who don’t align with the company’s culture, even though they are good people.

Despite being the founder and CEO, he sometimes tolerates this discomfort, hoping that the individuals will change or that he might be missing something about them. He mentions his podcast, “Over the Wall,” which delves into the psychology of being an entrepreneur and a leader.

He concludes that he’d rather work with a team that cares for the business and fits the culture, even if they don’t necessarily succeed. He suggests this approach eliminates the need for political maneuvering (“jiu-jitsu”) within the company. He concludes by acknowledging that he might not see the full impact of these cultural misalignments on the rest of the organization.

The Power of Shared Beliefs and Servant Leadership: Fostering Growth in Organizations

Lou posits that real growth in a company occurs when everyone within the organization is dedicated to serving the customer and the company. He critiques the philosophy of some founders who believe that no one will ever love the company as much as they do or work as hard as they do, which he views as destructive leadership. Lou argues that a company can’t grow significantly without a shared belief in a greater goal.

Robert supports this perspective with a story about a retiring CEO who left his company in a better state than when he assumed the role. He admired the CEO’s belief that you should always leave a place better than when you arrived and continue learning no matter where you are. He ties these principles back to the concept of servant leadership

According to Robert, being a servant leader involves making the “home” better, whether that refers to the customer experience, the team, or the company as a whole.

Lou and Rob go into much greater detail throughout this conversation.

Thank you for listening!