The CTO Playbook

66: CTO Playbook: Leading Change Without Chaos — Giorgia Prestento

The CTO Playbook

Show Notes

Logic alone won’t land; people react to change emotionally.

Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.  In this episode, I sit down with Giorgia Prestento, a behavioral scientist and author of The Change Maze. She’s here to show why change so often derails and how CTOs can lead through it with clarity and confidence.

We break down why rational explanations fall flat, the different speeds leaders and teams move at, and how losing control sparks uncertainty and anxiety. A call center story shows how rewarding quick answers without customer outcomes skews behavior. A Hong Kong example proves that “ask your line manager” messaging failed culturally, so we rewrote it to a nominated peer contact. A pre-mortem setup surfaces blind spots by declaring the project failed and collecting reasons before execution. We run through an eight-step playbook from purpose and alignment to blind spots, impacts, resistance, indicators, validation, and finally execution.

You’ll Learn:

The reason logic-only change pitches backfire What happens when leaders move faster than teams The link between the metric you reward and the behavior you get What it feels like to run layoffs twice The reason pre-mortems work What happens when you don’t set indicators early The link between purpose, alignment, and smoother execution What happens when a key trainer is missing The damage of losing clarity at the top

Timestamps:

[00:00] Introduction [05:18] Why logic fails when leading change [10:42] The emotional side of resistance and uncertainty [15:56] How leaders move faster than their teams [20:11] The blind spot that halted a global SAP rollout [26:27] Why bad metrics destroy good behavior [31:03] Cultural barriers that derail transformation [36:49] The pre-mortem method for spotting hidden risks [42:08] The eight-step change playbook

Resources Mentioned:

Master the Change Maze by Giorgia Prestento | Book

Giorgia offers a short assessment 'Leaders: Are You Change Ready?' You will gain valuable insights across the categories of Leadership Style, Change Expertise and the Readiness of your organisation. It takes less than 3 minutes. You get readiness scores in a personalised report. Plus a digital copy of her book, Master the Change Maze. Click here to get started.

You can connect more with Giorgia on LinkedIn.

Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

More from The CTO Playbook

Oct 20, 2026

Most leaders treat impostor syndrome as something they need to overcome. But what if the belief that you're not good enough is actually serving a purpose?

Oct 13, 2026

AI has made building software dramatically faster. The problem is that the rest of the engineering system hasn’t caught up.  AI agents can now produce code, tests, documentation, migrations, and pull requests at a pace most engineering organisations weren’t designed to handle. But when everything around code review accelerates, review becomes the bottleneck. Pull requests pile up, reviewers spend more time reconstructing intent, and experienced engineers can end up reduced to repeatedly saying yes or sending work back for fixes.

Oct 6, 2026

AI adoption is getting easier for everyone. The harder question is whether you're using it to optimise the game you're already in, or to build a position that changes the game.

Sep 29, 2026

AI isn't just changing how engineers work. It's forcing technology leaders to rethink what makes management valuable.

Sep 22, 2026

Quantum computing may not be breaking your security today, but the decisions you make now could determine how exposed your organization is when it does. Conor Deegan explains why CTOs need to start preparing before Q Day arrives.

See all episodes →