Leadership Development

Leadership Development

Leadership insights for PMs and Technical Leaders who refuse to be order-takers. The Project Pirate take on strategic leadership and real value.
05
Mar
A worn vinyl record on a turntable, label reading "Project Pirate Records - 99 Problems, Side A

I Got 99 Problems But the PMO Ain't One (hit me!)

Why projects don't die from governance - they die from lost belief. In 2003, Jay-Z gave us one
5 min read
25
Feb
Cargo ship sinking in fog on calm waters

The Silent Shipwrecks, Part 2: Emptying the Coffers

In "The Silent Shipwrecks, Part 1: Mediocrity is the Slow Death to Obscurity", we explored how organisational cultures
9 min read
17
Feb
Cargo ship disappearing into fog on calm waters.

The Silent Shipwrecks, Part 1: Mediocrity is the Slow Death to Obscurity

While sailing the high seas of complex IT delivery, I watched a team make a "strategic" decision that
7 min read
05
Jan
Mountain ranges layering into distance at dawn, demonstrating continuous peaks beyond peaks

Blessed by Mountains: Why the Hardest Paths Lead to the Truest Self

A 2026 reflection on leadership, resilience, and why enduring challenge shapes the leaders who last. There's a mountain
6 min read
18
Dec
Ship crew jettisoning cargo crates into stormy seas at night, illuminated by Japanese lanterns with Bonenkai text

Bonenkai: The Anti-Pattern to "Lessons Learned"

Why strategic forgetting might be more valuable than one more retrospective Every winter, before the long crossing, Captains face a
8 min read
02
Sep
Blue jellyfish with flowing tentacles against dark background, representing the lingering effects of hindsight

The Sting of Hindsight: Shaping those Critical Moments

How nine words can transform team dynamics when deadlines loom. The Universal Human Experience There's a feeling every
6 min read
19
Aug
Chess pieces in impossible positions on a board - thinking beyond conventional strategy

Six Impossible Things Before Breakfast: The Leader's Guide to Revolutionary Thinking

Why, sometimes I've believed as many as six impossible things before breakfast." - Lewis Carroll, Through the Looking
5 min read
13
Aug
Project Pirate - Gunpowder barrel with protective cover against stormy sea, symbolising strategic restraint

Keep Your Powder Dry: The Art of Measured Leadership in Stormy Seas

When the cannons are firing and the deck is chaos, the Captain who keeps their powder dry is the one
7 min read
29
Jul
Book depicting withdrawals and deposits as a ledger to be balanced.

Relational Capital: The Currency of Sustainable Delivery

Why the strongest crews are built on trust, not compliance The Moment of Truth There's a moment every
10 min read
13
Jul
Harbour image at sunset showing departures and arrivals at the dock side.

It's Always Someone's First Day & Someone's Last Day

The profound leadership lesson hiding in a poolside conversation The Pool Revelation Sometimes the most profound insights emerge from the
4 min read