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Abstract: The article examines the delicate balance leaders must strike when cultivating personal relationships with direct reports. While friendly and empathetic relationships can foster teamwork, productivity, and morale, leaders must also maintain clear boundaries to avoid favoritism and compromising their authority and objectivity. The article explores strategies for establishing appropriate professional distance, actively listening to build understanding, facilitating team bonding through shared experiences, and promoting autonomy and growth through empowering leadership. By approaching interpersonal connections judiciously and for the right reasons, leaders can create optimal work environments where people feel understood, motivated, and able to excel to their fullest potential, strengthening overall organizational performance, cohesion, and well-being.
Working relationships within organizations can take on many forms. At their best, they foster teamwork, productivity and morale. However, cultivating personal friendships within a workplace power dynamic also poses risks that leaders must thoughtfully navigate.
Today we will explore how maintaining professionalism while also building understanding and trust with direct reports can help foster optimal work environments.
Establishing Appropriate Boundaries
All workplace relationships require clarity around boundaries (Rock & Jones, 2015). While friendliness and approachability are important virtues for leaders, it is crucial to maintain some degree of professional distance from those one manages. Complete openness in personal matters or socializing together outside work hours risks blurring lines and potentially enabling favoritism (Smith, 2017).
Set clear expectations that work conversations and decisions will remain professional in nature. Avoid discussing one's personal life in ways that could compromise objectivity.
Do not socialize privately with direct reports outside established team-building activities. Group lunches or occasional group outings after work hours can foster camaraderie while maintaining appropriate distance.
Consider personal or sensitive disclosures on a need-to-know basis only. Share just enough to build empathy and understanding without oversharing details that compromise a leader's authority or impartiality.
For example, as a mid-level manager at an ad agency, I make it a rule not to accept direct reports' social media friend requests or meet one-on-one for after-work drinks. However, I occasionally organize team pizza lunches or group outings, like going to see a new movie release together. This strikes a balance of friendliness and team-building while upholding boundaries.
Cultivating Understanding Through Active Listening
To succeed, leaders must know and understand their people. Yet maintaining distance risks missing important personal context that can impact work. Research shows leaders who make time for empathetic listening build greater rapport and motivate direct reports (Goleman, 2006; Kouzes & Posner, 2017). Regular one-on-one check-ins where both parties feel heard foster psychological safety that in turn improves performance, innovation and retention (Edmondson, 2018).
Schedule individual listening meetings regularly without an agenda to establish psychological safety. Ask open-ended questions and refrain from multitasking to give full attention.
Maintain empathy by paraphrasing what you hear and reflecting on each person's experience from their perspective. Avoid judgment and solve problems only if invited.
Share occasional self-disclosures judiciously to role model vulnerability, build understanding and strengthen the reciprocal nature of trust.
For example, as director of a nonprofit, I schedule monthly one-on-one "check-ins" with each staff member. I make it clear these are for open communication, not performance reviews. By actively listening without an agenda, our team has become more collaborative problem-solvers who feel empowered to innovate for our clients.
Facilitating Team Bonding Through Shared Experiences
Building cohesion among a diverse workforce requires forging bonds alongside professional relationships (Dutton & Heaphy, 2003). Research demonstrates shared positive experiences like accomplishing goals together or celebrating victories can increase affective commitment to an organization and its people (Matos et al., 2018). Yet these experiences must uphold boundaries while nurturing well-being.
Plan routine team-building activities where boundaries remain clear, such as group lunches to bond over shared organizational successes.
Consider occasional off-site outings as a group such as volunteer projects benefitting the community or attending a professional development seminar together.
During celebrations, maintain an even temper and professional conduct. Avoid over-socializing with any one person to the exclusion of others.
For example, as a hospital department head, my team cares deeply for patients but rarely celebrates achievements together. So after a record-breaking fundraising quarter, I organized a group dinner at a nice but casual restaurant for the whole team to bond over our shared success in serving the community. This strengthened our cohesion while avoiding friction.
Promoting Team Autonomy and Growth Through Empowering Leadership
Despite boundaries, leaders who invest in developing direct reports' skills and leadership see greatest returns (Gordon, 2017). When given leeway to problem-solve independently and learn from failures, people feel ownership over their work and grow into their best selves. Micromanaging or limiting risk-taking out of a misguided need for control fosters resentment and stifles motivation.
Assign stretch projects that push individuals outside comfort zones but provide support rather than close oversight.
Establish clear expectations and guardrails for projects rather than rigidly dictating tasks. Check in periodically for guidance, not scrutiny.
Celebrate failures that result from calculated risk-taking as learning opportunities, not punishments. View mistakes through a growth mindset of continuous improvement.
For example, as head of a tech startup's programming team, I give ambitious quarterly objectives but let individual engineers choose their own approaches and have autonomy to learn through trial and error. This has resulted in new sub-teams evolving and independently taking our products in exciting directions. Morale and creativity are high as people feel ownership over innovative solutions.
Conclusion
Cultivating positive personal relationships within a workplace power dynamic requires deft navigation. By establishing clear boundaries, actively listening with empathy, facilitating shared team experiences appropriately, and empowering autonomy through trusting leadership, managers can foster optimal working environments where people feel understood, motivated and able to excel to their fullest potential. When approached judiciously and for the right reasons centered around servicing organizational missions and developing individuals, connecting with direct reports on a deeper human level need not compromise professionalism and can significantly strengthen performance, cohesion, retention and overall well-being within organizations.
References
Dutton, J. E., & Heaphy, E. D. (2003). The power of high-quality connections. In K. S. Cameron, J. E. Dutton & R. E. Quinn (Eds.), Positive organizational scholarship: Foundations of a new discipline (pp. 263–278). Berrett-Koehler.
Edmondson, A. C. (2018). The fearless organization: Creating psychological safety in the workplace for learning, innovation, and growth. John Wiley & Sons.
Goleman, D. (2006). Emotional intelligence: 10th anniversary edition; Why it can matter more than IQ. Bantam Books.
Gordon, J. (2017). The power of positive leadership: How and why positive leaders transform teams and organizations and change the world. John Wiley & Sons.
Kouzes, J. M., & Posner, B. Z. (2017). The leadership challenge: How to make extraordinary things happen in organizations. John Wiley & Sons.
Matos, K., O'Neill, O., & Lei, X. (2018). Toxic leadership and the masculinity contest culture: How "win or die" cultures breed abusive leadership. Journal of Social Issues, 74(3), 500–528.
Rock, D., & Jones, B. (2015). Why people don’t change. NeuroLeadership Journal, 5, 1-7.
Smith, C. A. (2017). Boundary management: A grounded theory of the boundary processes affecting social identity work in manager-employee relationships. British Journal of Management, 28(3), 528–544.
Jonathan H. Westover, PhD is Chief Academic & Learning Officer (HCI Academy); Chair/Professor, Organizational Leadership (UVU); OD Consultant (Human Capital Innovations). Read Jonathan Westover's executive profile here.
Suggested Citation: Westover, J. H. (2025). Building Trust and Understanding: How to Cultivate Positive Relationships with Direct Reports. Human Capital Leadership Review, 19(2). doi.org/10.70175/hclreview.2020.19.2.6
