CTO Playbook Archives - Diary Of A CTO

CTO reviewing defragme.net personality platform interface on laptop in modern office setting focused on leadership development

Building defragme.net Without Putting People in Boxes

There is a particular vulnerability in releasing a personality tool into the world when you built it yourself. The product carries your thinking, your assumptions, and your quiet convictions about…

Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion

CTO Playbook Strategy Team

How You can run a Stop, Start, Continue Exercise

A Stop, Start, Continue exercise is a simple retrospective method for getting focused feedback from a team, group, or individual. Purpose It helps answer three questions: What should we stop…

Change Management CTO Playbook Culture & Values

Diary of a CTO: On Stop, Start, Continue

A leadership team can maintain respectable performance metrics and still sense that something essential has softened at the edges, as diaries fill, initiatives progress, and conversations maintain their familiar rhythm…

Boardroom with ERP dashboard on laptop representing executive-led ERP implementation under time pressure; modern enterprise systems planning in a leadership setting

Change Management CTO Playbook Leadership

The Six-Month ERP Implementation. Can It Be Done?

The instruction doesn't land gently.Someone, usually well-intentioned, says we need a new ERP. They then pause, as if offering a kindness, and add that it must be done in six…

A quiet boardroom moment where confident decisions are made — and unintended consequences begin.

CTO Playbook Culture & Values Leadership

Five leadership mistakes that destroy companies

There is a comforting myth in business that companies are felled by dramatic external forces. For example, regulation changes overnight, startup appears from nowhere, technology shifts beneath our feet. However,…

A composed leader bringing clarity and calm to a senior team discussion.

CTO Playbook Leadership

12 Signs You’re Working With a True Leader

At some point in most organisations, the word leader becomes strangely weightless. It appears everywhere, job titles, competency frameworks, investor decks, yet often explains very little. Everyone is labelled a…

A CTO navigating multiple board-level responsibilities, symbolised by overlapping leadership ‘hats’ in a modern boardroom setting.

CTO Playbook Leadership

The 12 Hats of a CTO: What the Role Really Demands at Board Level

The most persistent misunderstanding about the CTO role at board level is that it is, at heart, a technology role. This misunderstanding is rarely voiced out loud. It appears instead…

Abstract lines dissolving into a connected network, illustrating how organisational boundaries blur under real-world pressure.

CTO Playbook Industry Leadership

Understanding Business Boundaries Are Illusions

The most comforting thing about a boundary is that it looks solid. It has a name, a box, a budget code, and, if you are very lucky, a PowerPoint slide…

Dave P, freight tech leader and AI innovator

AI CTO Playbook Leadership

AI Trends for 2026: How Embedded Intelligence Will Redefine Supply Chain Leadership

I was recently interviewed by SCM Executives, who specialise in senior supply chain leadership roles, as part of their campaign exploring AI trends and leadership as we look ahead to…

A composed CTO guiding executives through a difficult decision, balancing authority, empathy, and long term trust.

CTO Playbook Leadership Stakeholders

The CTO Playbook for Saying No Without Burning Political Capital

The quiet risk of agreement The longer you sit in a CTO role, the clearer one truth becomes. Saying yes is often more dangerous than saying no. Bad ideas rarely…