High-Stakes Transformations with Allan Sampson

High-Stakes Transformations with Allan Sampson

From Tech Waka Podcast by Tech Waka Podcast

November 25, 2025 · 37 min · Season 1 · Episode 36

About this episode

Allan Sampson discusses the challenges of large-scale transformations and how to navigate them effectively.

Transformations don’t fail because of slide decks – they fail in the messy middle, where people are stressed, alignment drifts, and hard problems finally make their way to the top. In this episode, Jakub sits down with Allan Sampson, Executive General Manager – New Zealand at Gentrack, who has spent more than two decades leading large-scale software and business transformations in the energy and utilities sector. Allan shares what really makes transformation programmes hard: complex vendor–client dynamics, misaligned expectations, fragile governance, “watermelon” reporting, and the human reactions to sustained pressure. He talks through how he thinks about leaders, steady “followers”, and detractors on a programme, and what it takes to build trust and psychological safety without turning work into a comfort zone. You’ll hear practical ways to: Read what’s really going on beneath the project reports Build authentic leadership that people trust under pressure Navigate escalations, conflict, and clashing personalities Use the forming–storming–norming–performing model in real teams (including the often-ignored “adjourning” stage) Recognise and manage stress in yourself and your…

People in this episode

Host: Jakub

Guest: Allan Sampson

Topics covered

  • transformation
  • leadership
  • stress management
  • team dynamics
  • vendor-client relationships
  • psychological safety

Keywords

  • transformation
  • leadership
  • stress
  • team dynamics
  • governance
  • conflict resolution
  • psychological safety
  • vendor-client dynamics

Sponsors

Wires Uncrossed

Mentioned in this episode

Organizations: Gentrack

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