In this interview, HDI Top 25 Thought Leader and SupportWorld Live speaker Anthony Orr shares insights on the future of IT leadership, emerging trends and the skills professionals need to thrive. Check out the Q&A below for his take on IT and business alignment, AI-driven leadership, digital transformation and more. Want to learn even more from Anthony? Join him this May 18-22 in Las Vegas for SupportWorld Live. Save $200 on your registration with the code SWNEWS.
If you weren’t in IT, in what other career could you see yourself thriving?
Athony: If I weren’t in IT, I could absolutely see myself thriving as a doctor. I deeply resonate with the idea of directly helping people improve their lives, whether through healing, guiding them toward better health or simply offering comfort during tough times. Much like IT, being a doctor is about solving complex problems, but instead of working with systems and data, it’s about understanding the human body and the emotions that come with it. Whether IT or medicine, my driving force remains the same: making a positive impact and helping others thrive. We should think of IT careers as such, with value realizations that we help people, organizations and their customers. This is why I am also a practicing hypnotherapist.
What’s the first step IT leaders should take to bridge the gap between technology and business effectively?
Anthony: The first step IT leaders should take to bridge the gap between technology effectively and business is aligning IT initiatives with business goals. This requires a deep understanding of the organization’s strategic objectives, challenges, and opportunities. IT leaders must go beyond technical knowledge and become active partners with business stakeholders, speaking their language and prioritizing outcomes that drive business value.
As a mentor and advocate for continuous learning, how do you inspire teams to embrace innovation and best practices?
Anthony: As a mentor and advocate for continuous learning, I inspire teams to embrace innovation and best practices by fostering a culture of curiosity, collaboration and empowerment. The basic approach is:
1. Lead by example: I actively demonstrate a commitment to learning by staying updated on industry trends, sharing insights and experimenting with new tools and approaches. When teams see leaders embracing innovation, they are encouraged to do the same. At the same time, it inspires people to become thought leaders.
2. Encourage psychological safety: I create an environment where team members feel comfortable sharing ideas, asking questions and making mistakes. Innovation thrives when people know they can take calculated risks without fear of judgment.
3. Provide growth opportunities: Offer access to resources such as training programs, workshops, certifications and mentorship opportunities. I also encourage peer-to-peer learning, where team members can share their expertise with others.
4. Align innovation with impact: I help teams see how adopting best practices and innovative approaches directly contributes to achieving business goals and solving real-world problems. Always showing the “why” behind the change creates motivation.
5. Celebrate successes and learn from failures: Recognizing and rewarding innovative efforts reinforces a continuous learning mindset. At the same time, analyzing setbacks as growth opportunities ensures that teams feel encouraged to improve.
What emerging trends do you think will redefine IT leadership over the next five years?
Anthony: The next five years will likely bring significant shifts in IT leadership as emerging trends reshape how leaders strategize, manage and execute. Here are some key trends that I believe will redefine IT leadership:
1. AI and Automation as Core Drivers
• IT leaders will need to move beyond being implementers of AI to become strategic enablers. Leveraging AI for predictive analytics, decision-making and operational efficiencies will become a critical skill.
2. Focus on Digital Resilience
• As cybersecurity threats grow more sophisticated, IT leaders will need to prioritize building systems that are not only secure but also resilient. Proactive threat detection, real-time response mechanisms and robust recovery plans will become central. Including overall improved Identity and Access Management (IAM).
3. Improving IT as a Business Driver
• IT leaders will increasingly take on roles as business strategists, ensuring technology decisions directly align with and drive business outcomes. They’ll need to work closely as a team with other C-suite executives to integrate IT into their overall organizational strategy.
4. Empathy-Driven Leadership
• The rise of hybrid work models and the growing emphasis on work-life balance will demand empathetic leadership. IT leaders must foster inclusive and flexible environments that prioritize employee well-being while maintaining productivity.
5. Experience and Data-Driven Decision Support
• IT leaders will need to champion the democratization of data across the organization, ensuring it’s accessible and actionable for all departments. Developing data literacy and governance frameworks will be a top priority. Including using data to justify opinions based on experience. This is improved system thinking and decision support.
For IT professionals aspiring to lead digital transformation, what skills should they prioritize developing?
Anthony: IT professionals aspiring to lead digital transformation must develop technical, strategic, operational and leadership skills.
- Strategic Vision and Business Acumen: Digital transformation foundation is about aligning technology with business goals. IT leaders must understand the organization’s objectives, market dynamics and customer needs.
- Change Management: Digital transformation disrupts workflows, roles, and processes. IT leaders must guide organizations through these changes while minimizing resistance, including the people side of organizational change management (OCM).
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Data Analytics and Insights: Data, Information, and Knowledge are the backbone of digital transformation. Leaders must harness data, information, and knowledge to make informed decisions, identify trends and measure ROI, including adopting AI.
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Technical Expertise in Emerging Technologies: Leading transformation requires understanding how to implement and leverage technologies such as AI, cloud computing, IoT and blockchain.
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Customer-Centric Mindset: Digital transformation aims to enhance customer experience. Leaders must focus on delivering value, personalizing customer journeys and overall experience for customer success.
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Leadership and Emotional Intelligence: Strong, people-focused leadership is essential for successful transformations. Emotional intelligence (EQ) helps build trust and inspire teams. Without trust, you can only manage teams, not lead.
- Collaboration and Cross-Functional Communication: Digital transformation involves multiple departments. To ensure success, IT leaders must collaborate with marketing, sales, HR, and operations. Enterprise Service Management (ESM) is not just a technology solution.