The Messy Middle: where planning meets execution
A collection of short reflections on the human side of software leadership, the unpredictable space between planning and execution. It explores how real progress happens in conversation, conflict, and collaboration, not in tidy plans or perfect processes. Each piece is written for engineering leaders who know that delivery isn't just about systems, it's about people.
Nov 07, 2025
Pressing pause for now
Nov 06, 2025
Seeing what drives our impatience
Nov 05, 2025
The patience test
Nov 03, 2025
Why patience matters at work
Oct 31, 2025
Small gestures create big shifts
Oct 30, 2025
The pressure conversation
Oct 29, 2025
You can’t make your people happy
Oct 28, 2025
Transforming dissatisfaction at work
Oct 27, 2025
Having an answer to the happiness question
Oct 24, 2025
Happiness isn’t a bonus
Oct 23, 2025
Why happiness feels hard at work
Oct 22, 2025
When being right would have made me wrong
Oct 21, 2025
A note to self about staying in conflict
Oct 20, 2025
Staying with conflict when others can’t
Oct 17, 2025
You can’t have learning without conflict
Oct 16, 2025
When the Tech Lead finally had room to think
Oct 15, 2025
Where to start when your team isn’t there yet
Oct 14, 2025
Everyone says they’re building high-performing teams
Oct 13, 2025
A clear path for escalation
Oct 10, 2025
Leader lines for toxic moments
Oct 09, 2025
Helping your team stay heard without heat
Oct 08, 2025
Owning what’s underneath
Oct 07, 2025
When anger wears a mask
Oct 06, 2025
Shifting the energy
Oct 03, 2025
Breaking the loop
Oct 02, 2025
The spiral of “Yeah, but…”
Oct 01, 2025
Who’s in the driver’s seat?
Sep 30, 2025
Fierce, not furious
Sep 29, 2025
The split-second flare
Sep 26, 2025
A small favour
Sep 25, 2025
The reluctant leader
Sep 24, 2025
Output or outcomes?
Sep 23, 2025
When managers mistake speed for progress
Sep 22, 2025
The cost of never asking why
Sep 19, 2025
Redefining progress
Sep 18, 2025
When work is no longer handed to you
Sep 17, 2025
When ‘I don’t know what to do’ is a step forward
Sep 16, 2025
When more gates make things less safe
Sep 15, 2025
No homework required
Sep 12, 2025
When safety creates helplessness
Sep 11, 2025
The release manager as shock absorber
Sep 10, 2025
When Code Becomes Real
Sep 09, 2025
The pain you don’t feel, you don’t fix
Sep 08, 2025
The hidden cost of fearing mistakes
Sep 05, 2025
Don’t let one mistake erase the whole picture
Sep 04, 2025
Why fixing weaknesses can backfire
Sep 03, 2025
The easy option is to write them off
Sep 02, 2025
Being let down is part of the job
Sep 01, 2025
Not good. Not bad. Context.
Aug 29, 2025
Why Personality Awareness Can Be Useful
Aug 28, 2025
More Than a Profile to Forget
Aug 27, 2025
Same Words, Different Worlds
Aug 26, 2025
Intent Is Invisible, Impact Is Real
Aug 25, 2025
The Rollercoaster We Don’t See at Work
Aug 22, 2025
The trap of thinking ahead
Aug 21, 2025
When questions close instead of open
Aug 20, 2025
Who are goals really for?
Aug 19, 2025
The strange life of goal setting
Aug 18, 2025
When the system, not the person, drives the behaviour
Aug 15, 2025
The Courage to Use Power (Even When You're Not Sure)
Aug 14, 2025
When the situation gives you power
Aug 13, 2025
The Responsibility of Influence
Aug 12, 2025
Power vs. Authority: Why the Distinction Matters
Aug 11, 2025
Let’s call it what it is
Aug 08, 2025
How to Get Your Team to Challenge You (Without Forcing It)
Aug 07, 2025
Psychological safety isn’t a team trait, it’s a leadership responsibility
Aug 06, 2025
What Power Feels Like (When You Don’t Have It)
Aug 05, 2025
Don’t make all the wrong moves
Aug 04, 2025
Caught in the middle? You're not alone.
Aug 01, 2025
The lead may set the tone. but the team holds It.
Jul 31, 2025
Wipe the slate?
Jul 30, 2025
When you inherit a performance issue
Jul 29, 2025
Growth is a thankless task
Jul 28, 2025
To read or not to read?
Jul 25, 2025
Leaning into the awkwardness
Jul 24, 2025
The method made sense, on paper
Jul 23, 2025
Carrying the responsibility without the confidence
Jul 22, 2025
The shift into management I didn’t see coming
Jul 21, 2025
Fix it. Flag it. Coach it. What kind of manager are you?
Jul 18, 2025
Is this really humanist, or just flatter?
Jul 17, 2025
When everyone waits for you
Jul 16, 2025
It only feels obvious after
Jul 15, 2025
“I’m disappointed” isn’t feedback
Jul 14, 2025
Being a manager means facing the emotional stuff—even if it’s awkward
Jul 11, 2025
“Agree to disagree” is a leadership moment, not an escape hatch
Jul 10, 2025
Why structured efficient meetings miss the point
Jul 09, 2025
Support That Sticks
Jul 08, 2025
When Delivery Becomes the Distraction
Jul 07, 2025
Consistency Without Sameness
Jul 04, 2025
When Nobody’s Watching, But Everyone’s Controlling
Jul 03, 2025
The Shifting Line of Support
Jul 02, 2025
When Trust Feels Like Abdication
Jul 01, 2025
Leadership as a responsive, relational act
Jun 30, 2025
The danger of too much alignment
Jun 27, 2025
We set the values
Jun 26, 2025
I don’t mind a bit of healthy skepticism
Jun 25, 2025
The difference between skeptical and stuck
Jun 24, 2025
Is it skepticism or just a no in disguise?
Jun 23, 2025
When silence hides something deeper
Jun 20, 2025
When support feels like scrutiny
Jun 19, 2025
When a check-in feels like a challenge
Jun 17, 2025
Leadership is just a story we tell
Jun 18, 2025
Leadership isn’t in the title
Jun 16, 2025
Leadership as system designer
Jun 13, 2025
It’s all just us, talking
Jun 12, 2025
All leadership sucks. But some of it is useful.
Jun 11, 2025
Growth warning: bruised ego ahead
Jun 10, 2025
Are You Preparing or Protecting?
Jun 09, 2025
The Emergence of Clarity
Jun 06, 2025
The Control Loop
Jun 05, 2025
The Developer’s Bargain
Jun 04, 2025
The Silent Room
Jun 03, 2025
The myth of the decisive leader
Jun 02, 2025
Not everyone who “saw it coming” actually did
May 30, 2025
How to change your mind without losing the room
May 29, 2025
When revisiting a decision becomes a trust issue
May 28, 2025
Making the call is just the start
May 27, 2025
When collaboration isn’t possible, someone has to decide
May 26, 2025
I used to think harmony was the goal
May 23, 2025
Why smoothing things over can break your team
May 22, 2025
How leadership teams turn into factions
May 21, 2025
Blame feels like leadership, but it isn’t
May 20, 2025
The go-live scramble no one could have predicted
May 19, 2025
Why smart plans still go sideways
May 16, 2025
Leadership happens from within, but that’s not the whole story
May 15, 2025
We remember the ship, not the conversations
May 14, 2025
You’re not outside the system. You’re in it.
May 13, 2025
Maybe politics isn’t a dirty word after all
May 12, 2025
Why “my door is always open” doesn’t work
May 09, 2025
Leadership lives in the messy moments
May 08, 2025
It’s all in the interactions
May 07, 2025
Where clarity meets care
May 06, 2025
It’s never too late to own it
May 05, 2025
If it feels fake, you’re doing it wrong
May 02, 2025
The myth of the professional robot
May 01, 2025
People should have thicker skin
Apr 30, 2025
Careful feedback isn’t soft. It’s serious
Apr 29, 2025
The smallest change that makes the biggest difference
Apr 28, 2025
A tool for when you want to get it right and say it right
Apr 25, 2025
What if your feedback is based on a story, not a fact?
Apr 24, 2025
You’re not under attack, but your brain thinks you are
Apr 23, 2025
That time I felt judged for someone else’s code
Apr 22, 2025
It sounds reasonable. So why does it shut people down?
Apr 21, 2025
The feedback you didn’t know you were giving
Apr 18, 2025
Being direct doesn’t make you a jerk. But this might
Apr 17, 2025
When safety is there, but it doesn’t feel like it
Apr 16, 2025
The time I argued against basic computer science
Apr 15, 2025
What I wish my first boss had known
Apr 14, 2025
The Slack facepalm that built more trust
Apr 11, 2025
The Hidden Reason Delegation Fails
Apr 10, 2025
You’re Not a Micromanager, You’re a Leader
Apr 09, 2025
Want to Delegate Better? Try Moving in Slow Motion
Apr 07, 2025
When Your Team Doesn’t See the Fake
Apr 08, 2025
Delegation Depends on What They See
Apr 04, 2025
The mistake that makes everything slower
Apr 03, 2025
When staying busy hides the real problem
Apr 02, 2025
Could Your Team Be Run by a Ham Sandwich?
Apr 01, 2025
The Moment I Wanted My Team to Shut Up and Just Do It
Mar 31, 2025
How to tell if they’re really with you—or just nodding along
Mar 28, 2025
No one said “no”, but the execution failed anyway
Mar 27, 2025
Silence isn’t the same as agreement
Mar 25, 2025
The Messy Middle (and why I’m emailing you again)
Mar 26, 2025
The Framework Isn’t Broken, Prioritisation Might Be