Leading in the Age of AI: Dessalen Wood on Hybrid Work, Culture & Change

Leading with Curiousity and Courage

The world of work is changing faster than ever. Leaders today are expected to adapt to hybrid models, embrace AI, and guide their teams through unprecedented change, all while maintaining culture, connection, and performance.

On this episode of The Next Moves, host Joe Diubaldo sat down with Dessalen Wood, Chief People Officer at Syntax, to explore what it really takes to lead in this new era. Syntax is a global leader in managed cloud, ERP, and IT services—powered by over 2,800 employees around the world—helping enterprises modernize, secure, and scale their mission-critical applications.

A Career Rooted in People and Possibility

Dessalen’s leadership journey has always been shaped by curiousity about people. From early roles in HR to senior leadership positions, she has consistently looked at the human side of business: what motivates people, how they respond to change, and how leaders can unlock their potential.

Her perspective is that organizations succeed when they focus on people first. Technology, strategy, and operations matter, but without engaged and empowered people, they can’t deliver results. This people-first mindset is what led her to join Syntax, a global IT services provider, where she is responsible for aligning culture, people, and organizational growth.

Hybrid Work: More Than a Location Debate

While many companies still struggle to define hybrid and remote policies, Dess sees the issue differently. It’s not about where people work. It’s about whether leaders are creating environments of trust, accountability, and connection. She explains that hybrid models can only succeed when leaders are intentional:

• Trust first, measure later: Productivity can’t be judged by time in a seat.
• Connection is a strategy: Leaders must deliberately create opportunities for employees to engage with each other and the organization’s purpose.
• Flexibility is now table stakes: Employees expect a degree of autonomy over when and how they work.

For Dessalen Wood, the real question isn’t “should we be hybrid?” but rather “how can we build a culture where people feel connected, regardless of location?”

AI and the Future of Leadership

Artificial intelligence is no longer a futuristic concept – it’s here, reshaping the workplace in real time, and Dess believes AI presents both opportunities and challenges for leaders. On one hand, AI can:

• Automate repetitive administrative tasks, freeing HR and leaders for more strategic work
• Provide faster access to insights, enabling better decisions
• Support employees with tools that enhance efficiency and creativity

But Dessalen also highlights the responsibility that comes with it: leaders must apply AI ethically, transparently, and thoughtfully. For her, the goal isn’t replacing human work but enabling more meaningful human impact. Leaders who embrace AI as a partner, not a threat, will position their organizations for success.

Culture in a Digital-First World

Culture has always been critical, but in today’s digital-first environment, it takes even more intentional effort to maintain. Dess stresses that culture isn’t created in boardrooms or strategy documents – it lives in everyday interactions and behaviours. Her advice:

• Celebrate often: Recognize achievements, big and small, to keep people connected.
• Tell the story: Remind employees of the organization’s mission and why their work matters.
• Design for belonging: Create touch-points where employees feel included and valued, no matter where they work.

Leaders who underestimate the importance of culture risk losing not just employees, but also innovation and performance.

The Takeaway

Dess closed with a challenge: leaders must embrace possibility, not just process. Whether it’s adopting AI, navigating hybrid work, or building culture, the leaders who succeed will be those who see change as an opportunity to grow. When asked about her top advice for executives today, Dessalen Wood is both simple, yet legendary, as always:

• Stay curious: Ask questions, seek out new ideas, and keep learning.
• Be courageous: Make bold decisions, especially in uncertain times.
• Never stop adapting: The pace of change isn’t slowing down – resilience and adaptability are now core leadership skills.

For Dessalen, leadership is less about having all the answers and more about creating the conditions for people to thrive in ambiguity.

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