January 2026 - Diary Of A CTO

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

Early in my career, I took “yes” at face value. Someone nodded in a meeting, agreed with the plan, and off we went. Over time, I learned that when people…

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…

Change Management Harmonisation Leadership

CTO Playbook for Unifying Multiple Product Versions: Part 2

A Step-by-Step Guide to Platform Convergence Step 1: Confirm That Unification Is the Right Problem to Solve Every successful unification starts with restraint. Not every organisation suffering from multiple product…

A senior technology leader guiding fragmented software platforms toward a single, scalable enterprise architecture.

Change Management CTO Playbook Leadership

CTO Playbook for Unifying Multiple Product Versions: Part One

A Familiar Moment at the Executive Table Most technology leaders eventually encounter the same uncomfortable chart. Several products, all recognisably related, yet none fully aligned. Each exists for a good…

A seasoned technology advisor calmly guiding executives through a difficult strategic discussion, capturing the tension between expertise and decision ownership.

Change Management Culture & Values Leadership

When your client won’t take your advice and what that really means

When your client won't take your advice, the sting arrives quietly. A polite nod appears, a noncommittal smile follows, and the decision moves in the opposite direction. After donkey's in…

A thoughtful technology leader stands at a crossroads of data streams, half illuminated, half in shadow, symbolising unseen assumptions in executive decision making.

Leadership Team

How CTOs Learn to See What They’re Missing

I have learned that the most dangerous problems rarely announce themselves. They sit quietly in the background, nodding along with our assumptions, reinforcing what we already believe. When results align…

A reflective technology leader balancing independence and responsibility while navigating the realities of Fractional CTO work.

CTO Playbook Development Leadership

Should You Become a Fractional CTO?

Becoming a Fractional CTO wasn’t part of any long-term career plan. I was made redundant, the market stalled, and senior permanent roles proved thinner on the ground than LinkedIn would…

A CTO reflecting at dusk, holding a notebook as mentor advice echoes years later

Culture & Values Growth Leadership

“Only Do What Only You Can Do”

I was privileged to have had an incredible mentor, I probably didn't appreciate him at the time, climbing the corporate ladder. I recall agonising about the sheer amount of work…

A senior technology leader observing subtle tension within a high-performing team during a quiet but consequential moment.

Culture & Values Leadership Team

Managing Quietly Toxic Employees: When Brilliance Becomes a Leadership Risk

After some time, you may learn that managing quietly toxic employees is one of the most uncomfortable (and most consequential) responsibilities a CTO, or any C-Suite Exec faces. Unlike overt…

salary negotiation, pay rise advice, asking for a raise, compensation strategy, career progression, executive pay, performance review, market salary, professional growth

Interviews Leadership

How to Get a Pay Rise: A Practical Guide to Being Paid What You’re Worth

I’ve learned that getting a pay rise has far less to do with asking nicely and far more to do with timing, evidence, and positioning. Early in my career, I…