Why most business owners lead like it’s 1990 (and what it’s costing you).

Leadership isn’t a single quality but rather a blend of many. While no individual possesses every talent required for leadership, everyone has the capacity to develop a unique combination of skills that make them an extraordinary leader. Yet many family business owners remain trapped in outdated leadership approaches that limit their growth potential. 

The leadership evolution most have missed 

The way we think about leadership has transformed dramatically in recent decades. Back in the 1990s, leadership was all about being in charge—having a clear hierarchy and calling the shots from the top down. Today’s most successful businesses have abandoned this model for something far more effective. 

The hierarchical, directive leadership style that dominated the 20th century has given way to a more empowering, collaborative, and authentic approach in the 21st century. It’s no longer about being the loudest voice in the room—it’s about being authentic, listening to your team, and creating an environment where everyone feels like they’re part of something bigger than themselves. 

This shift is particularly relevant for family businesses, where leadership styles often reflect founding personalities and may persist across generations without deliberate reconsideration. 

The stark contrast in leadership approaches 

Consider how leadership characteristics have evolved over time. Where command and control once reigned, authentic leadership now flourishes. Hierarchical management structures have been replaced by empowering approaches that distribute decision-making. Leaders, once defined by charismatic personalities, now drive purpose throughout their organisations. 

The motivation has shifted too—from self-interest toward what serves the institution best. Experience is no longer measured by the perfect CV but by learning through challenges. Time horizons have extended from quarterly thinking to genuinely long-term vision. Perhaps most significantly, emotional intelligence has surpassed raw IQ as leadership’s greatest strength, while validation now comes from intrinsic contribution rather than external recognition. 

Most family business owners can quickly identify where their leadership style falls on this spectrum. Those still operating from outdated paradigms are increasingly finding themselves at a competitive disadvantage, particularly when it comes to attracting and retaining top talent. 

The hidden costs of outdated leadership 

Continuing to lead like it’s 1990 takes a heavy toll on your business. Staff engagement weakens when people don’t feel valued or heard, leading them to invest minimal effort rather than bring their full creativity and commitment. Teams become misaligned without a clear purpose and shared values, pulling in different directions, wasting resources, and creating friction. 

Great initiatives fail not because they’re flawed but because teams lack the motivation and clarity needed to implement them effectively. The workplace culture often turns toxic, creating environments of fear, competition, and blame rather than collaboration and innovation. 

Today’s employees, particularly younger generations, simply won’t tolerate outdated leadership styles, leading to expensive recruitment cycles as staff turnover increases. The best candidates research company culture before accepting positions and actively avoid organisations with reputations for outdated leadership. 

Innovation stagnates when people fear suggesting ideas or challenging the status quo, causing businesses to miss crucial opportunities for improvement and growth. Internal dysfunction inevitably affects customer experience, regardless of how well it’s hidden. These factors collectively erode margins, creating financial pressure that further reinforces controlling leadership behaviours. 

The qualities of future-ready leaders 

Modern leadership that drives business success centres on authenticity and emotional intelligence. While each leader develops their own style, certain qualities consistently appear in effective 21st-century leaders. 

Integrity forms the foundation—doing what’s right, even when challenging, builds trust through consistent ethical behaviour. This pairs with genuine self-awareness and understanding of one’s own capabilities, limitations, and emotional patterns, which allows for continuous improvement. 

Effective leaders today empower their teams, giving them the tools, authority, and support needed to excel rather than micromanaging their efforts. They demonstrate humility by celebrating others’ successes rather than seeking the spotlight and readily acknowledging when they don’t have all the answers. 

Authenticity manifests as the courage to be genuinely yourself rather than projecting an artificial ‘leadership persona.’ This connects with empathy—understanding and connecting with team members’ experiences, challenges, and perspectives on a human level. 

Resilience shows in how leaders navigate and learn from setbacks rather than being defined by them. Accountability completes the picture, as modern leaders take ownership of both successes and failures without deflecting responsibility. 

Boss vs. Leader: The fundamental choice 

There’s a profound difference between being a ‘boss’ and being a true leader. The best leaders inspire their teams to rise to challenges, while bosses merely demand compliance. Where bosses direct, leaders show by example. Bosses claim to know everything, while leaders demonstrate continuous learning. The boss creates followers, but the leader develops more leaders within the organisation. 

This distinction becomes particularly critical in family businesses, where leadership style directly influences succession planning and the business’s ability to transition between generations. When team members experience only directive bossing rather than development-focused leadership, they remain perpetually dependent rather than growing into potential successors. 

The language that signals your leadership style 

What you say and how you say it reveals your leadership approach. Simple phrases like “I agree” acknowledge others’ ideas and show you value their input. Saying “Let’s get started” motivates the team to take action together rather than issuing commands. Using ‘we’ instead of ‘I’ emphasises teamwork and collective effort, building trust and alignment throughout the organisation. 

Asking “How can I help?” offers support and shows you care about the team’s success, not just your authority. Admitting mistakes with a sincere “I’m sorry” demonstrates vulnerability and builds credibility. Telling someone, “I trust you to handle this”, empowers them by showing confidence in their abilities. 

These subtle language shifts signal profound differences in mindset that team members instantly recognise and respond to, often transforming engagement and initiative without any other systemic changes. 

Finding your authentic leadership style 

Not all leadership styles are identical, and effective leaders adapt their approach depending on the situation and the people they’re working with. The common thread is authenticity—leading in a way that reflects your genuine values and strengths rather than adopting an artificial persona. 

Some leaders inspire transformation through vision, communication and intellectual stimulation. Others take a servant approach, prioritising team needs and focusing on growth and wellbeing. Many emphasise authenticity, bringing genuineness and transparency to every interaction. The most adaptable practitioners adjust their style based on specific contexts and the development level of individual team members. 

The most effective family business leaders often blend approaches, maintaining consistent values while flexing their style to address different challenges. Finding your authentic voice as a leader means aligning your approach with both your natural strengths and your business’s current needs. 

Making the shift 

Evolving your leadership approach isn’t about personality transplantation but rather intentional growth. Begin by seeking honest feedback—create safe channels for team members to share how your leadership impacts them. Rather than attempting wholesale transformation, focus on modifying a single leadership habit that would most benefit your team. 

Finding a leadership community can accelerate your development. Connect with other business owners making similar journeys who can provide perspective and accountability. Create reflection rituals by scheduling a regular time to evaluate decisions and interactions against your leadership ideals. 

Many family business leaders find that investing in coaching provides momentum for change. An external perspective can identify blind spots and provide structured development that might otherwise take years to achieve through trial and error. 

This evolution must be deliberate and strategic. Leadership development should be explicitly integrated into your business strategic plan, not treated as a separate initiative. Without a formal plan that articulates your company’s direction, even the most evolved leader will struggle to align their team. A comprehensive strategic plan serves as both your roadmap and communication tool—allowing leaders to clearly show where the company is headed and how everyone contributes to that journey. When leadership development becomes a strategic priority, it creates a powerful feedback loop: better leadership improves strategy execution, while clearer strategy enhances leadership effectiveness.

Leadership is a journey of continuous growth, self-reflection, and intentional action. By developing qualities aligned with today’s business needs, adopting an authentic approach, and learning from experiences, you can transform both your leadership effectiveness and your business outcomes. 

Ready to evolve your leadership approach?  Contact Bill at Gilligan Sheppard to explore how leadership coaching can help you build a more engaged team and a more profitable business. Email bill@gilshep.co.nz or call +64 21 126 9017 to start your leadership evolution. meeting. That’s what makes us human, and that’s what makes our content worth reading.