Only about 12% of family businesses successfully transition to a third generation. Most fall short not because of a lack of commitment, but because continuity is treated as a future challenge, instead of an ongoing discipline.
As R.W. Holmes approaches its 50th year in business, the firm is now operating in its third generation of family leadership. Founded in 1976, the company has remained one of Massachusetts’ largest independent commercial real estate brokerage firms by focusing on long-term stability, disciplined leadership, and a culture built to endure market cycles. That experience offers several lessons relevant to family-owned businesses planning for longevity.
Retention starts with consistency and trust. One of the most effective retention tools is stable leadership. Under President Garry Holmes’ more than 30 years of leadership, R.W. Holmes has remained profitable through multiple real estate cycles. Consistent decision-making, clear expectations, and transparency reduce uncertainty and allow employees to focus on building long-term careers rather than reacting to constant change. That stability is reflected in employee tenure. The average employee at R.W. Holmes has been with the firm for approximately 25 years, underscoring a shared culture of trust, accountability, and long-term commitment.
Culture matters. Collaboration is emphasized across the organization, with an expectation that employees share knowledge, support one another, and contribute beyond individual roles. Hiring decisions are made deliberately and only when there is capacity to properly train and mentor new team members. Cultural fit is weighed as heavily as technical skill, recognizing a strong culture is difficult to repair if compromised.
Equally important is treating employees as people first. Flexibility during major life events, recognition for contributions, and meaningful appreciation reinforce loyalty and trust over time.
Client continuity follows an advisory mindset. Many R.W. Holmes client relationships span more than 30 years. That continuity is driven by an approach that prioritizes long-term advice over short-term transactions. The firm often works with clients well before a transaction occurs, helping them understand market conditions, timing, and strategic options. This positions the firm as a trusted advisor.
Leadership transitions should be phased, not rushed. One of the most common mistakes family businesses make is equating readiness with tenure rather than demonstrated capability. Preparing the next generation begins long before formal titles change.
I joined this firm nearly nine years ago after starting my career in consulting at Ernst & Young. My early years were focused on learning the core business, rather than assuming leadership immediately. I began by drafting annual company goals and strategic initiatives, which were refined collaboratively and then implemented under oversight. Early initiatives were intentionally low risk and measurable, such as introducing marketing efforts, implementing new technology, and launching internal reporting tools. My responsibilities expanded to include hiring, mentoring brokers, and organizational planning.
In parallel, I was given exposure to broader leadership decisions by participating in meetings related to financials, benefits, executive hiring, and strategic partnerships. This allowed my leadership skills to develop.
Family business continuity is rarely achieved through a single handoff. Longevity is built through intentional leadership choices, disciplined preparation, and a culture designed to outlast any one generation.
