Digital transformation rarely fails because of technology. It fails because of people, structures, and misaligned expectations. 

Amel Gaily is joined by Sacha Helfenstein (Transformation advisor) and Juhana Ovaska, IT Manager at Anora, to unpack why so many digital transformation initiatives derail, even when projects appear “green” on paper. 

Together, they explore the real difference between technical readiness and business readiness, why change management is underestimated, and how contracts, trust, and organizational silos quietly undermine long-term value. From horizontal vs. vertical complexity to early warning signs of failure, this conversation offers grounded, experience-backed insights for leaders navigating complex change. 

If you’re planning, leading, or recovering a digital transformation, this episode will help you rethink what success truly means — and how to keep momentum alive. 

You walk away with: 

• A clearer definition of what failure really means in transformation 

• Practical warning signs that appear long before projects collapse 

• Insight into why “go-live” is not the finish line 

• A new way to think about scope, contracts, and complexity 

• Concrete advice for keeping business value front and center 

Perfect for: 

• CIOs, CDOs, CTOs 

• Digital, IT, and transformation leaders 

• Enterprise and mid-market decision makers 

• Anyone leading complex change initiatives 

Topics covered: 

• What digital transformation failure really looks like 

• Technical readiness vs business readiness 

• Change management and expectation alignment 

• Organizational silos and internal resistance 

• Trust, contracts, and partnership dynamics 

• Early warning signs and recovery strategies 

Digital transformation doesn’t fail suddenly. It fades when vision, trust, and alignment are lost. The good news? Those signals are visible if you know where to look.

🎧 Simplifiers is the podcast that cuts through the complexity of digital transformation to reveal what works. Created by Solteq, hosted by Amel Gaily, and built for anyone who believes clarity beats complexity — every time. 

#DigitalTransformation, #ChangeManagement, #BusinessTransformation, #EnterpriseIT, #Leadership, #DigitalStrategy, #TransformationFailure, #AgileMindset, #TechAndBusiness, #CustomerValue