The human side of leadership

Boxers & Briefs Podcast #8: Self awareness creates better leaders with Debbie Gregory

In an era where workplace dynamics are rapidly evolving, effective leadership has become more crucial than ever. Debbie Gregory, founder of Positive Direction and leadership consultant with 25 years of global operational leadership experience, shares valuable insights into what makes a great leader and how to create psychological safety in the workplace.

“Who you are is how you lead,” says Debbie, emphasising that leadership development must start with self-awareness. This fundamental principle underlies her holistic approach to leadership development, which integrates professional growth with personal development and home life.

Creating psychological safety

The cornerstone of effective leadership lies in creating an environment where employees feel safe to bring their whole selves to work. “People need to feel safe when they come into a workplace,” Debbie explains. “If you’ve got someone that can actually really take those risks, they’re going to come up with new ideas and feel comfortable to put in the extra effort.”

The absence of psychological safety can lead to concerning outcomes:

• Anxious and underperforming employees who stay out of fear
• Talented individuals leaving the organisation
• Eroded confidence that affects future career choices

The marks of poor leadership

Debbie uses a powerful metaphor to describe toxic leadership: “A bad leader is someone that snuffs others’ candle out to make their shine brighter.” Some key indicators of poor leadership include:

• Underdeveloped emotional intelligence
• Working in isolation (‘lone wolf’ mentality)
• Refusing to listen to others
• Believing they have all the answers
• Lacking vulnerability
• Demonstrating excessive ego

The distinction between managing and leading

While managers focus on tactical and operational aspects – the ‘who, what, when, why’ of processes and guidelines – leaders take a different approach. “A leader actually leads,” Debbie notes. “They’ll paint the vision for someone, they’ll connect those dots that we talked about. They encourage, they stretch, they challenge, they care for their people – I mean genuinely care for the people, not because it’s a job.”

Debbie identifies several key trends shaping the future of leadership:

Technology and artificial intelligence: While technology continues to advance, Debbie emphasises that this doesn’t diminish the need for human leadership. Instead, it heightens the importance of emotional connection and human-centred leadership.

Geographical connectivity: With remote work becoming common, leaders must find new ways to maintain team connections and culture. This might mean more frequent, shorter interactions rather than traditional lengthy meetings.

Generational diversity: Today’s workplace spans five generations, from the ‘silent generation’ to Generation Z. Each brings different expectations and values, requiring leaders to adapt their approach accordingly.

Social responsibility: Modern employees increasingly choose organisations based on their sustainability and social responsibility credentials, requiring leaders to demonstrate genuine commitment to these values.

Developing better leaders

Debbie recommends several key practices for leadership development:

Self-reflection: One of her most powerful recommendations is scheduling regular ‘balcony time’ – dedicated meetings with yourself for reflection and strategic thinking. “If you did nothing else, have a one-on-one regular meeting with yourself,” she advises. This isn’t about dear diary entries but purposeful reflection on leadership goals and performance.

Feedback and growth: Leaders should be willing to seek feedback and help when needed. “It’s amazing when you do ask for help,” Debbie notes. “People will actually give you so much more than you ever realise.”

Connecting people to purpose: Great leaders help team members understand how their work contributes to larger goals. This connection to purpose is crucial for engagement and motivation.

Addressing leadership challenges

When facing challenges or conflicts, Debbie recommends getting closer to the issue rather than avoiding it. She references a Harvard Business Review article suggesting that personality clashes are best addressed by moving closer to the person and remaining curious about their perspective.

Contrary to common belief, Debbie argues that taking on a leadership role doesn’t necessarily require sacrifice. Instead, it requires clarity about priorities and boundaries. “A really good and true leader actually just knows where to put their energy, where the priorities are,” she explains.

For those considering leadership positions, Debbie recommends:

• Having thorough discussions about expectations upfront
• Being honest about areas where you’ll need support
• Seeking mentorship
• Setting clear boundaries
• Maintaining regular self-reflection practices

The future of leadership requires a more human approach than ever before. Despite technological advancement – or perhaps because of it – the need for emotional intelligence, genuine care, and psychological safety in leadership continues to grow.

“Start with yourself,” Debbie advises. This means regular self-reflection, continuous learning, and a commitment to creating an environment where others can thrive. True leadership isn’t about having all the answers but about creating conditions where teams feel safe to innovate, contribute, and grow.