By Yancy Wright
Introduction: The Friendship Conundrum at Work
As leaders, we spend the majority of our waking hours with our co-workers. It’s only natural to wonder: Why can’t we be friends with our employees or co-workers? For me, the answer is simple. I believe in creating real, meaningful connections at work. If I’m spending so much time with my team, I want to know them on a deeper level, to share trust and transparency. Without this, the workplace can feel superficial and disconnected.
Yet, many in leadership roles resist this approach. They argue that mixing friendship with authority can lead to blurred lines, especially when difficult decisions or feedback are required. However, I believe it’s possible to navigate this balance successfully with the right tools—namely, clear communication and defined expectations. Research shows that when employees have strong friendships at work, they are more engaged, satisfied, and productive. So, the real question is: How can leaders build meaningful relationships without compromising their professional responsibilities?
Number of Friends vs. Quality of Friends
Research into human relationships shows that we can maintain close relationships with around five to fifteen people, and up to one hundred fifty more casual acquaintances—this is known as Dunbar’s Number. In the workplace, it’s tempting to keep our interactions professional and distant, especially when managing large teams. But by prioritizing quality over quantity, leaders can cultivate relationships based on trust, vulnerability, and respect.
In fact, Gallup has found that employees who have a “best friend” at work are 36% more likely to feel engaged in their jobs. This engagement leads to 7% more customer loyalty and 12% higher profit. These are tangible benefits that leaders can harness by being open to forming deeper connections with their teams.
Friends at Work: The Challenges and Opportunities
It’s easy to see the potential pitfalls of being friends with your employees. There’s the risk of favoritism, the difficulty of maintaining boundaries, and the potential awkwardness of giving critical feedback to someone you’ve grown close to. However, I’ve found that these challenges can be managed with clear expectations and conscious communication.
The OKR (Objectives and Key Results) framework is one method that leaders can use to align their personal and professional relationships. OKRs are similar to KPIs (Key Performance Indicators), but they focus more on setting ambitious goals and tracking the progress toward them. Both KPIs and OKRs offer leaders and teams a way to maintain transparency, accountability, and alignment. For example, if a leader is friends with an employee, having clear OKRs can help ensure that any difficult conversations about performance are grounded in shared goals and measurable outcomes. This removes the emotional weight of these conversations, allowing them to be constructive and goal focused.
In my experience, the deeper the relationship, the more easily these conversations flow. There’s no need to tiptoe around issues when there’s mutual respect and clear expectations in place. Conscious communication tools—such as active listening, being fully present, and speaking openly about emotions—allow these relationships to thrive.
The Purpose of Friendship in Leadership
Beyond productivity, friendships at work serve a deeper purpose. Humans are wired for connection, and research shows that strong social bonds are linked to better health, longevity, and emotional well-being. When leaders foster genuine connections, they’re not just boosting engagement—they’re creating an environment where people feel seen, supported, and cared for.
Strong friendships at work can help reduce stress, increase collaboration, and even improve retention. Gallup has found that employee retention improves dramatically when workers feel they have a “best friend” at the office. Moreover, employees who are connected with their team are 27% more likely to report higher levels of organizational commitment. For leaders, these statistics offer a compelling case for building deeper connections at work.
Generational Approaches to Workplace Friendship
Different generations approach workplace relationships in unique ways. Generation Z and Millennials, who are more immersed in digital communication, often struggle with too many superficial connections. Gallup reports that many young workers feel isolated despite having large social media networks. Leaders in today’s workforce can address this by fostering more in-person interactions, ensuring their teams build authentic, face-to-face relationships. These friendships don’t just benefit the individual—they benefit the organization.
On the other hand, older generations, particularly those in leadership, often focus on smaller, higher-quality social circles. As people age, they tend to prioritize emotionally meaningful relationships, including those in the workplace. Socioemotional Selectivity Theory suggests that as we grow older, we become more selective about whom we spend time with, focusing on fewer, deeper connections. Leaders can harness this wisdom to create a more intentional, connected team culture.
Conclusion: The Leadership Lens on Friendship
Being friends with your employees as a leader is not without its challenges, but it’s also not impossible. With conscious communication, clear agreements, and the use of tools like KPIs and OKRs, leaders can navigate the delicate balance of being both a friend and a boss. Ultimately, it comes down to fostering trust, setting expectations, and maintaining transparency.
For me, the benefits of these relationships far outweigh the risks. A workplace built on mutual respect, collaboration, and genuine connection is not only more productive, it’s more fulfilling for everyone involved. By being intentional about the relationships we cultivate at work, leaders can build teams that are not only efficient but also deeply engaged and emotionally resilient.
Casa Alternavida was founded on the principle that there are healthier, “alternative” ways to balance life and work as a leader. One of those ways is to work with people you really enjoy being around and sometimes it requires learning better ways to communicate. We specialize in helping teams enhance collaboration by teaching conscious communication tolls that work. Teams walk away from our retreats with new excitement for their projects, practices to enhance communication, and a deeper appreciation for high performance collaboration. If you are a business that cares about your employees and wants to enhance your workplace culture, we are dedicated to providing alternative ways of building resilient leaders and teams.
(855) 850-0855
contact@casaalternavida.com
References
ThinkPotion. Dunbar’s Number and Social Media.
Gallup. Best Friend at Work & Employee Engagement.
Pollack Peacebuilding. Workplace Relationships and Job Satisfaction.
Leadership Fluent. OKRs and KPIs for Leadership.
Stanford Longevity Center. Social Connection and Longevity.
Senior Planet. Friendship in Old Age.
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