Why Gregory Hold of Hold Brothers Capital Says Onboarding Defines Long-Term Retention

A strong onboarding experience builds connection, confidence and clarity. A weak one breeds uncertainty and disengagement. Retention isn’t built solely through policies. It begins the moment someone joins and is defined by how genuinely they’re welcomed into the culture. Gregory Hold, CEO and founder of Hold Brothers Capital, understands that onboarding is more than orientation. He believes it’s the company’s first real demonstration of its culture in action. The first weeks are not for training, they’re about trust. 

When employees feel connected early on, they adopt the company’s values more quickly and contribute more confidently. The first 90 days create the emotional and cultural foundation that influences engagement for years to come. Intentional onboarding, through mentorship, clear communication and shared experiences, turns those early days into lasting commitment.

Why the First 90 Days Matter

The first 90 days shape how employees interpret their roles, their teams, and the organization’s values. This period defines expectations, builds habits, and determines whether new hires feel included or isolated. During this time, employees decide whether they can see a future with the company. When onboarding is structured, supportive and authentic, new hires transition smoothly and build early momentum. When it’s rushed or inconsistent, confusion sets in, and with it, disengagement.

Employees who experience effective onboarding are far more likely to stay and succeed within the organization. The early days of employment shape how people perceive leadership, culture and opportunity. Effective onboarding creates trust, clarifies purpose, and helps employees see the value of their contributions. In short, onboarding is about alignment.

Culture Begins on Day One

Culture is not taught through handbooks; it is experienced through everyday interactions. From the first welcome email to the first team meeting, each moment communicates the company’s values in practice. When transparency, communication, and care are part of the culture, they naturally show up during onboarding. Employees quickly recognize whether leadership is approachable, whether feedback is genuinely encouraged, and whether collaboration feels authentic.

Gregory Hold of Holds Brothers Capital mentions, “High-performance teams aren’t just skilled. They are emotionally strong, adaptable and able to execute consistently, even when conditions aren’t ideal.” Onboarding plays a central role in shaping those qualities. It provides employees with the context, relationships and confidence they need to adapt quickly and perform effectively in high-pressure situations. When the process emphasizes communication, empathy and shared goals, teams build the foundation for long-term stability and trust.

Effective onboarding reflects an organization’s core values and working style. New employees benefit when they are paired with mentors, included in team discussions from the outset, and encouraged to contribute their ideas from the start. This process creates early connections, accelerates learning, and supports long-term engagement.

The Role of Connection in Early Retention

Human connection is the most powerful tool for retention. New employees who establish relationships with peers and leaders early on tend to feel more engaged and less likely to leave. Connection gives people a sense of belonging and serves as a psychological anchor, turning uncertainty into motivation. When employees feel seen and supported, they begin to associate the organization with stability and trust, which strengthens commitment from the start.

Leaders play a critical role in making this happen. Facilitating introductions, encouraging mentorship, and promoting regular team interactions create a sense of community that lasts beyond onboarding. Even small gestures such as a conversation with a manager, a check-in from a colleague, or recognition after a successful first project can make a lasting impression. These moments communicate that every employee matters, and that their contributions already have value.

Designing Onboarding with Intention

Effective onboarding is not a single event. It’s a structured journey that blends education, engagement and empowerment.

1. Establish clarity early. Employees should leave their first week understanding not only their job responsibilities, but also how their work ties into the company’s mission. Clear expectations eliminate guesswork and build confidence.
2. Provide access to leadership. Early exposure to senior leaders demonstrates transparency and inclusion. It shows that communication is valued and that every role contributes to the company’s vision.
3. Assign mentors or peer partners. Mentorship accelerates learning and creates a personal connection to the organization. It gives new hires a trusted resource for questions, feedback and support.
4. Create feedback loops. Onboarding shouldn’t be one-way. Asking new employees for input shows that their voices matter, and helps improve the process for future hires.

The Cost of Missed Opportunities

Poor onboarding has a ripple effect. When employees start without proper guidance or connection, their engagement drops quickly. They may question whether they made the right choice, and productivity can take months to recover.

Turnover in the first year is often linked to weak onboarding. Employees who feel disconnected or overwhelmed early are more likely to leave within months. Replacing them costs far more than investing in a strong onboarding process from the start.

Mentorship and Mobility: Extending the Onboarding Experience

The best onboarding programs extend beyond the first few weeks. Ongoing mentorship and clear growth pathways help maintain engagement long after the initial phase.

When new hires see a future within the organization, their confidence turns into commitment. Regular check-ins, development conversations, and performance feedback sustain that connection. Onboarding blends seamlessly into professional development. Mentors continue working with new hires throughout their first year, making sure that support doesn’t end once orientation does. 

The First 90 Days Define the Next 900

The first three months of employment create a blueprint for everything that follows. When employees experience clarity, connection and care during the onboarding process, they carry those values forward in their work.

Gregory Hold of Hold Brothers Capital recognizes that effective onboarding is a leadership responsibility, not just an HR process. Structured onboarding builds confidence, clarifies expectations, and connects new employees to the company’s mission from the start. When the first 90 days are personal, purposeful, and participatory, new team members develop relationships, understand performance standards, and engage more quickly with the culture.

The way a company greets its people shapes how long they stay, how deeply they engage, and how strongly they contribute. When onboarding is done well, it becomes more than a starting point and signals a lasting commitment to support and growth.