Skip to content

Diary Of A CTO

  • Home
  • About
  • CTO Accelerator
  • Tap Tap Move
  • Subscribe To Diary Of A CTO!
  • Contact
Top Stories
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
Chief technology officer leading a strategic technology discussion in a boardroom setting, illustrating the difference between managing operations and providing executive leadership
The Difference Between Managing and Truly Leading
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
How You can run a Stop, Start, Continue Exercise
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
Diary of a CTO: On Stop, Start, Continue
A professional developer meal featuring sausages for software developers to boost cognitive focus.
Sausages: A Nutritional Foundation for Software Developers
A professional executive reflecting on when a CTO should walk away from their current role.
When a CTO Should Know When to Walk Away
Why Emotional Intelligence Still Beats Authority
The New Leadership Test: Can You Build Trust While Rolling Out AI?
Managing Engineers to Build More Agile Logistics Systems
10 Leadership Theories for CTOs (Without the Fluff)
10 Leadership Theories for CTOs (Without the Fluff)
Using Codex and Claude to Tackle the Engineering Backlog
Why Engineering Culture Fails During Rapid Scaling
Board level executives examining Corporate Sustainability Due Diligence Directive compliance data and value chain risk dashboards in a modern boardroom setting
The Corporate Sustainability Due Diligence Directive
The High-Performing Paradox: Managing Elite Engineers Without Breaking Your Culture
The AI Orchestrator: Shifting from Code Writing to System Verification
The Legacy TMS Data Trap: Why Your Freight Forwarder Software is Hiding the ESG Data You Need
Walking the AI Tightrope: Innovation Without Chaos
The Innovation Tightrope: Mastering AI Without Breaking the Business
A senior executive stands in a modern glass-walled office overlooking a city skyline at dusk. Digital dashboards glow on a large screen behind them, displaying global maps, performance graphs, and real-time analytics. The leader holds a tablet showing key metrics while diverse team members join via video screens from different countries. The atmosphere conveys focus, international collaboration, and strategic clarity.
Leading Without Guesswork: Mastering Data-Driven Decision-Making Skills in a Complex Global World
an impact leader at a team briefing
Leading for Impact: The Practical Playbook for Modern Leaders Who Want to Matter
Senior executives in a quiet boardroom discussing leadership challenges; empty corporate office corridor symbolising talent attrition; leadership meeting room after hours representing disengagement of top performers
10 Leadership Cock-Ups That Quietly Drive Top Talent Away
7 C’s of Leadership
The 7 C’s of Leadership: A Practical Framework for People Who Actually Want to Lead
Executive leadership team reviewing SWOT analysis matrix during strategic planning session in a corporate boardroom
Why I Love SWOT Analysis
Boardroom with ERP dashboard on laptop representing executive-led ERP implementation under time pressure; modern enterprise systems planning in a leadership setting
The Six-Month ERP Implementation. Can It Be Done?
Executive offsite meeting room with leadership team seating and flipchart; corporate strategy away day in a neutral conference venue; senior executives gathering for quarterly offsite discussion
The Executive Offsite Where Everything Is Already Decided: A CTO’s View
A quiet boardroom moment where confident decisions are made — and unintended consequences begin.
Five leadership mistakes that destroy companies
Calm leadership in action: clarity, trust, and progress without theatre.
10 Signs You’re a Leader People Want to Follow
A composed leader bringing clarity and calm to a senior team discussion.
12 Signs You’re Working With a True Leader
A short, focused prioritisation meeting where trade-offs are made explicit and decisions stick.
How to Run a Development Prioritisation Meeting in 15 Minutes
“An executive development roadmap showing clear focus, visible trade-offs, and intentional restraint.”
Prioritising Development Work Is Mostly About What You Decide Not to Care About
A quiet boardroom with empty chairs, performance dashboards glowing while no one speaks.
When Leadership Hides from Performance Management
Senior executives in a boardroom discussion, illustrating confident leadership tempered by collective judgement.
Intelligence Gets You There. Humility Keeps You There.
A CTO navigating multiple board-level responsibilities, symbolised by overlapping leadership ‘hats’ in a modern boardroom setting.
The 12 Hats of a CTO: What the Role Really Demands at Board Level
A group in a meeting room may look like a team—but without shared consequence, it’s just proximity.
A group of people sharing a room isn’t a team
A quiet boardroom with empty chairs and a single notebook, suggesting that decisions are shaped by narratives long after meetings end.
Wise leaders understand the power of stories
“Executive communication training: where confidence often arrives before clarity.”
Neuro-Linguistic Programming: When Confidence Is Mistaken for Competence
Abstract lines dissolving into a connected network, illustrating how organisational boundaries blur under real-world pressure.
Understanding Business Boundaries Are Illusions
Dave P, freight tech leader and AI innovator
AI Trends for 2026: How Embedded Intelligence Will Redefine Supply Chain Leadership
A modern IT team balancing system stability, complexity, and organisational expectations behind the scenes.
What’s the Right Amount of IT Staff for Your Company?
A silent boardroom moment where ambitious technology plans collide with a fixed IT budget.
When the IT Budget says No
A technology executive standing slightly apart in a boardroom as strategy discussions unfold around them.
Moving from Head of Tech to CTO
A garment label with a QR code being scanned, revealing verified ESG and supply chain data layered over textile textures.
Digital Product Passport: Why Textile Transparency Is Finally Becoming Real
A thoughtful executive pauses during a meeting as others nod, capturing the tension between spoken agreement and unspoken doubt.
When people say yes, but they really mean no
A composed CTO guiding executives through a difficult decision, balancing authority, empathy, and long term trust.
The CTO Playbook for Saying No Without Burning Political Capital
resilient technology teams
CTO Playbook for Unifying Multiple Product Versions: Part 2
A senior technology leader guiding fragmented software platforms toward a single, scalable enterprise architecture.
CTO Playbook for Unifying Multiple Product Versions: Part One
A seasoned technology advisor calmly guiding executives through a difficult strategic discussion, capturing the tension between expertise and decision ownership.
When your client won’t take your advice and what that really means
A thoughtful technology leader stands at a crossroads of data streams, half illuminated, half in shadow, symbolising unseen assumptions in executive decision making.
How CTOs Learn to See What They’re Missing
A reflective technology leader balancing independence and responsibility while navigating the realities of Fractional CTO work.
Should You Become a Fractional CTO?
A CTO reflecting at dusk, holding a notebook as mentor advice echoes years later
“Only Do What Only You Can Do”
A senior technology leader observing subtle tension within a high-performing team during a quiet but consequential moment.
Managing Quietly Toxic Employees: When Brilliance Becomes a Leadership Risk
salary negotiation, pay rise advice, asking for a raise, compensation strategy, career progression, executive pay, performance review, market salary, professional growth
How to Get a Pay Rise: A Practical Guide to Being Paid What You’re Worth
An incoming CTO shaping clarity and direction through a carefully considered technology strategy document.
Writing Your Incoming CTO Strategy Document
A reflective CTO stands alone in a quiet boardroom, overlooking an unfinished strategy diagram—capturing the moment of honest leadership after a failed initiative.
CTO Playbook: Handling the Quiet Failure of a Strategic Initiative No One Wants to Admit Didn’t Work
A thoughtful CTO balancing technical insight with strategic leadership in a modern executive setting.
How Technical Do You Have to Be to Be a CTO?
Redesigning the invisible structures that shape how tech teams actually work.
Org Design Exercises for a Struggling/Growing Tech Team
A reflective view of global engineering collaboration, symbolising the strategic balance between in-house focus and outsourced scale.
When It’s Right to Consider Outsourcing or Offshoring
Digital transparency and sustainability intersecting across a modern global supply chain.
ESG in the Supply Chain: A CTO’s View from the Engine Room
A stark boardroom wall with peeling corporate values posters, revealing a raw, handwritten list of real behaviours underneath.
Company Values Honesty: Why Some Values Exercises Are Fiction
A thoughtful leader aligning priorities and strategy during a focused executive conversation.
Managing Upwards: The Quiet Skill That Separates Trusted Leaders from Busy Managers
“Leadership in the quiet aftermath of an acquisition, where trust is built before systems are integrated.”
CTO Playbook: Navigating Acquisition
Using the Headway app to capture ideas in small moments throughout a busy day.
Why I Use the Headway App
A calm but focused one-to-one conversation, capturing the human side of performance management.
Performance Management
A living map of global logistics in motion, showing the hidden complexity behind everyday supply chains.
Why the Logistics Industry Is Different to Any Other Industry
A CTO reviewing the hidden architecture of software, VM and CAL licensing beneath a modern enterprise infrastructure.
Licensing: The Hidden Architecture Beneath Your Technology Stack
A modern technology leader balancing multiple leadership styles while guiding a diverse team through complexity and change.
Leadership Styles: Why the Best Leaders Never Stick to Just One
A CTO stands at a crossroads between a crumbling custom-built system and a stable off-the-shelf platform, symbolising the build vs buy decision.
When to Stop Digging: The Dilemma of Build vs Buy
A practical CTO playbook on building trust when inheriting a fragmented or broken tech team, based on real-world leadership experience.
CTO Playbook: Building Trust as an Incoming CTO
How to fix first-line support by clearing legacy tickets, enforcing triage, using Jira properly and separating support from development work.
Why Your Helpdesk Is Not a Graveyard for Unfinished Work
Shipping less but finishing more helps technology teams improve focus, reduce delivery risk, and ship higher-quality software with greater predictability.
Shipping Less but Finishing More: The Discipline Most Technology Teams Avoid
Why trust, not process or tooling, is the real constraint when scaling technology teams, and what CTOs can do to fix it.
Trust Is the Real Scaling Problem in Technology Teams
How to prepare for your next CTO role, focusing on leadership mindset, business impact, decision-making and executive readiness.
How to Prepare for Your Next CTO Role
A PRINCE2 Practitioner explains project management methodologies, clarifying how PRINCE2 governs projects while Agile and Waterfall guide delivery.
Project Management Methodologies: What Actually Works in the Real World
ISO 27001 explained through real-world experience implementing it in a global logistics company, focusing on leadership, risk and operational resilience.
Implementing ISO27001 Inside a Global Top 20 Logistics Company
Why harmonisation often outperforms standardisation in global organisations, enabling alignment, flexibility and better outcomes across regions.
Why Harmonisation Can Beat Standardisation in Global Organisations
Learn how Lean Six Sigma helps organisations identify outliers, reduce harmful variation and turn process anomalies into lasting improvement.
Using Lean Six Sigma to Identify and Address Outliers: Turning Noise Into Insight
Leadership debt explained from a CTO perspective, exploring how hidden leadership decisions quietly compound risk, slow execution and weaken organisations over time.
Leadership Debt: The Invisible Risk on Your Balance Sheet
Why helpdesk triage is essential for prioritising issues, reducing stress and turning a busy support team into a calm, effective and trusted service function.
Why Triage Is So Important on the Helpdesk: The Difference Between Control and Chaos
resilient technology teams
Building Technology Teams That Can Survive Leadership Change
busy teams, leadership effectiveness, team productivity, high performance teams, technology leadership, delivery focus Synonyms: effective teams, outcome-driven teams, high-impact teams, focused teams
The Difference Between Busy Teams and Productive Ones: A Leadership Problem, Not a Capacity Problem
Servant leadership explained from the perspective of a seasoned CTO and CEO, exploring why putting people first drives stronger teams, better technology outcomes and sustainable business growth.
Servant Leadership: Why Putting People First Has Always Been My Leadership Philosophy
Learn how to land your next CTO role by showcasing strategic vision, leadership, and business acumen. Discover practical tips on positioning, networking, and preparing for executive-level interviews.
Navigating the Path to Your Next CTO Role: Lessons from the Frontline
roadmap implementation, software testing practices, agile adoption, developer workflow optimisation, change management, process improvement, team productivity, workflow discipline
Unlocking Team Potential: How to Drive Adoption
work-from-home productivity, remote team management, flexible working benefits, employee autonomy, hybrid work culture, trust-based management, remote collaboration, output-focused leadership
From Hours to Outcomes: Why Trusting Remote Teams Drives Real Productivity
software testing value, business analysts in technology teams, delivery team structure, scaling engineering teams, CTO leadership, digital delivery effectiveness
Why “Just Hire More Developers” Is Usually the Wrong Answer
developing technology teams, scaling engineering teams, CTO leadership, tech team culture, engineering management, digital transformation leadership, high performing tech teams engineering team development, technical capability building, team transformation, technology leadership, delivery team growth
From Inherited to High-Performing: Building a Technology Team That Actually Works
Agile development, Agile transformation, Scrum framework, Lean software delivery, Agile teams, iterative development, Agile vs Waterfall, continuous delivery, product-led development
Why Agile Still Wins: A CTO’s Perspective on Building Technology That Actually Delivers
Why harmonisation beats standardisation after acquisition, enabling global booking visibility, stronger cyber security and better outcomes for freight companies.
Harmonisation as a Strategy, Not a Compromise
Title: The Week Before the Failure: A CTO’s Diary on Why Digital Transformations Collapse Before They Even Begin
Why Digital Transformations Collapse Before They Even Begin
Title: When AI Meets the Corner Office: A CTO’s Diary on What Really Helps – and What Quietly Makes Life Harder
When AI Meets the Corner Office: What Quietly Makes Life Harder
Inside the Architecture: A CTO’s Diary on Building a Platform from Scratch
Inside the Architecture
The 90 day plan
Welcome!
CTO reviewing defragme.net personality platform interface on laptop in modern office setting focused on leadership development
Posted inCTO Playbook Development EQ

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…
Read More
Chief technology officer leading a strategic technology discussion in a boardroom setting, illustrating the difference between managing operations and providing executive leadership
Posted inCTO career advice Development Engineering Leadership

The Difference Between Managing and Truly Leading

The board had asked for reassurance. Revenue tracked to plan, delivery milestones held, attrition remained within tolerable limits, and the dashboards glowed with that reassuring shade of green that tempts…
Read More
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
Posted inCTO 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…
Read More
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
Posted inChange 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…
Read More
A professional developer meal featuring sausages for software developers to boost cognitive focus.
Posted indeveloper diet nutrition productivity

Sausages: A Nutritional Foundation for Software Developers

Discover how sausages provide a practical nutritional foundation for software developers, focusing on efficiency, protein, and cognitive support.
Read More
A professional executive reflecting on when a CTO should walk away from their current role.
Posted inCareer Development CTO career advice Engineering Leadership

When a CTO Should Know When to Walk Away

Discover the critical signs a CTO should walk away from a role to protect their career, mental health, and professional reputation.
Read More
Why Emotional Intelligence Still Beats Authority
Posted inAGILE EQ Leadership

Why Emotional Intelligence Still Beats Authority

Managing a room full of brilliant, senior engineers requires a specific set of tools that you won't find in a standard management handbook. Historically, many leaders relied on the weight…
Read More
The New Leadership Test: Can You Build Trust While Rolling Out AI?
Posted inAGILE AI Leadership

The New Leadership Test: Can You Build Trust While Rolling Out AI?

Every tech leader I speak with lately is facing the same massive pressure to integrate artificial intelligence into their workflow. The board wants results, the market expects innovation, and the…
Read More
Managing Engineers to Build More Agile Logistics Systems
Posted inAGILE Leadership Legacy

Managing Engineers to Build More Agile Logistics Systems

Managing engineers to build more agile logistics systems often feels like trying to fix a plane while it is mid-flight. The logistics industry operates around the clock, meaning any technical…
Read More
10 Leadership Theories for CTOs (Without the Fluff)
Posted inAGILE Leadership Team

10 Leadership Theories for CTOs (Without the Fluff)

Most leadership advice for CTOs feels like it was written by someone who has never had to debug a production outage at 3 AM. It is often filled with corporate…
Read More

Posts pagination

1 2 3 … 10 Next page

Recent Posts

  • Building defragme.net Without Putting People in Boxes
  • The Difference Between Managing and Truly Leading
  • How You can run a Stop, Start, Continue Exercise
  • Diary of a CTO: On Stop, Start, Continue
  • Sausages: A Nutritional Foundation for Software Developers

Archives

  • April 2026
  • March 2026
  • February 2026
  • January 2026
  • December 2025

Categories

  • AGILE
  • AI
  • Career Development
  • Change Management
  • Cost Control
  • CTO career advice
  • CTO Playbook
  • Culture & Values
  • Customers
  • Data
  • developer diet
  • Development
  • Due Diligence
  • Engineering Leadership
  • EQ
  • ESG
  • Executive Resignation
  • Free Course
  • Global
  • Growth
  • Harmonisation
  • Industry
  • Interviews
  • ISO27001
  • Leadership
  • Learning
  • Legacy
  • Licensing
  • M&A
  • nutrition
  • Outsourcing
  • Performance
  • PRINCE2
  • Process
  • productivity
  • Project Management
  • protein
  • Six Sigma
  • software developers
  • software development
  • Stakeholders
  • Strategy
  • Support
  • Sustainability
  • Team
  • Technology Management
  • TMS
  • Toolkit
  • Uncategorised
You May Have Missed
CTO reviewing defragme.net personality platform interface on laptop in modern office setting focused on leadership development
Posted inCTO Playbook Development EQ

Building defragme.net Without Putting People in Boxes

Posted by davep 16 April 2026
Chief technology officer leading a strategic technology discussion in a boardroom setting, illustrating the difference between managing operations and providing executive leadership
Posted inCTO career advice Development Engineering Leadership

The Difference Between Managing and Truly Leading

Posted by davep 15 April 2026
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
Posted inCTO Playbook Strategy Team

How You can run a Stop, Start, Continue Exercise

Posted by davep 9 April 2026
Executive team conducting a structured stop start continue exercise in a boardroom with clearly labelled whiteboard sections and active leadership discussion
Posted inChange Management CTO Playbook Culture & Values

Diary of a CTO: On Stop, Start, Continue

Posted by davep 8 April 2026
Copyright 2026 — Diary Of A CTO. All rights reserved.
Scroll to Top