Name: Pragmatic Change
Author: Mark Winter

As a busy leader...should I give a sh*t about your personal problems?

As a busy leader…should I really give a sh*t about your personal problems?

And more begrudgingly: Since when was it my job to be the therapist…? Do all these kids just lack resilience?!

I’m not making these questions up; as an elder millenial with lines blurred between social and professional circles…I’ve heard them all in the past fortnight. From frontline retail shop owner to Biotech CE.

So…do you? Yes - it’s surprisingly “life or death”. (I can back that up, read on)

You can’t fake it and you do have to figure out your own version of “how”.

Thoughts in article and app.pragmaticchange.com.au as your safe rehearsal space with my best attempt at an authentic AI version of me.

Change, LeadershipMark Winter7 July 2026Leadership, Management, AI, Change

Is it worth the struggle of being a manager?

Manager engagement has collapsed to 22% — yet managers are now the single biggest factor in whether AI adoption works. Is it still worth the struggle? Yes, but not the way it’s currently set up.

Leadership, ChangeMark Winter16 June 2026Leadership, AI, Management, Change

Don't squeeze harder. Free people up to move where they need to be.

I love the National Basketball Association (NBA) playoffs.

The best coaches know: at this point in the season, you can't squeeze your players any more. But what is our temptation as leaders, when the pressure is on and all eyes are on us?

I'm sad one of my all time heroes LeBron James is out. But I'm intrigued by what Mike Brown is building in New York. From being fired four times, to (in his first year with the team) making the Finals!

And now, on the cusp of success in a city with notoriously high expectations...he's making it all about the players.

I'm in my own 'playoff series' right now on a project. I just hope I've positioned us right for success.

What does it mean to lead complex change in 2026?

You know how I'm supposed to open a LinkedIn article. Especially one published on a Monday...who does that?!

Recognisable caricutures from the Boardroom. A leadership vignette. A clever mixture of intruige and just enough panic to make you keep reading...

Instead, I'm compelled to share a gem from my Evernote files, saved during my Masters at the University of Sydney in 2012.

It's from a British physicist named Mark McKergow. He coined a word using Japanese roots because English didn't have one for the concept he needed. It's 2026 and I keep coming back to it.

Because the way most organisations are approaching complex change right now lacks the substance that McKergow was writing about fourteen years ago.

So what does it actually mean to lead complex change in 2026?

49 conversations with Pragma, the AI clone of my professional self: two learnings from the data and a stuff up.

49 conversations with Pragma. 190 messages. Two learnings from the data: the first thing people present is rarely the problem, and specificity is the admission ticket.

Change, LeadershipMark Winter22 May 2026AI, Leadership, Change

Stay inside your budget by going outside your own boardroom.

The Planning Fallacy is the diagnosis. Reference Class Forecasting is the discipline. Why looking outside your own boardroom — at what actually happened to comparable projects — is the single best corrective to inside-view optimism.

Psychology is WEIRD...and that's a problem!

Psychology is WEIRD…and that’s a problem. Not a diversity problem. A validity problem. 96% of the psychological research your change frameworks are built on came from populations representing 12% of the world. Most of it was built on American college students. Then generalised to your manufacturing workforce. Your regional council. Your healthcare organisation. Your university with significant first-generation student populations. And when the frameworks produce mediocre results…we blame resistance. Poor sponsorship. Inadequate resourcing. It might simply be that the framework wasn’t built for these people.

Change, LeadershipMark Winter5 May 2026Change, Leadership, Frameworks, Research, Strategy

Your transformation will be remembered for two moments. Are you designing them?

What two moments will your transformation be remembered for?

Not the months of stakeholder engagement. Not the training rollout. Not the governance forums. Not even that beautiful documentation you’ve laboured over.

Over the long run: The emotional peak. And how it ended.

That’s what the research says. And if you’ve led (or been lead into…) a major change, I’d wager it matches your own memory too.

This is called the Peak End rule and applying it deliberately is one of the most underused lenses in change leadership.

There's a risk in your change programme that rarely makes it onto the risk register.

There's a risk in your change programme that rarely makes it onto the risk register. And if you've been watching the AI conversation lately...I can guarantee you've seen it! It's not a toxic leader, hostile stakeholder or external 'threat'.... It's someone capable and well-intentioned...but whose confidence has quietly outrun their calibration. It has a name. David Dunning and Justin Kruger documented it in 1999. Most importantly: before you look around the table and start spotting it in others, there's a quick game worth playing first.

Change, LeadershipMark Winter21 April 2026Change, Leadership, Decision-Making, AI, Strategy, AI Strategy

Most change programmes are still built for an organisation that no longer exists.

Most change programmes are built for an organisation that no longer exists.

The 2005 playbook: appoint a sponsor, hire a change manager, “do comms”, run training, go live…play a Kayne West track and declare success.

That model assumed stable hierarchies. Predictable timelines. Clear authority.

That 2005 world is largely gone. And not just because Kanye has lost the plot.

700 change practitioners across the globe just told us what’s actually coming.

In reading about it and writing this article, I realised I’ve been living it for 20 years…

Does your AI strategy have a coherence problem?

Most leadership teams can’t answer this question…without looking at a slide. Can your leadership team name your 3-6 distinctive capabilities? Then: does your AI investment map to those - or does it map to a desire to look like you’re keeping up? The Coherence Premium isn’t just a strategy concept. It’s the difference between AI that builds momentum and AI that quietly drains it.

Change, LeadershipMark Winter5 April 2026AI, Strategy, Change, Leadership

I got scared that AI would take my job. Then I read two things that changed everything.

I got scared that AI would take my job.

Which is mildly ironic...given I've spent 20 years helping leaders navigate exactly this kind of moment.

Even more ironic? The tool that scared me, has no emotions whatsoever.
There's something worth sitting with in that juxtaposition.

Then I got sent (by actual humans) two pieces of research that completely reframed what I thought I knew about the AI transition.

The headline finding: we've swapped the motor. We have not redesigned the factory. AI is wholly dependent on organisational change.

Transformation, Change, InnovationMark Winter26 March 2026AI, complexity, Change

The essential leadership concept behind why so many hyped AI projects are underperforming

There's an essential leadership concept behind why so many hyped AI projects are underperforming.

Your people don’t trust each other enough to share their data...or to do the work to create meaningful, high-quality data.
No trust = no data.
No data = no AI impact.

Let's get back to the bottom of the pyramid; here's Patrick Lencioni's perennial Five Dysfunctions of Team through an AI implementation lens

Change, Leadership, Org Development, TransformationMark Winter21 May 2025AI, Failure, Performance

Seeing red to learn: what my terrible stock picks taught me about change, innovation and leadership

Years ago in a bout of career boredom, I played the cursed game of picking individual ASX stocks because I thought I could "see the trends coming" and "beat the market"...

Much to the amusement of my Sydney based finance / wealth industry mates, I'm down 74% 😵

But I'm up infinitely in lessons about change, leadership and innovation 📈

Some of the best money I've ever spent!

Performance, ChangeMark Winter21 May 2025Change, change leadership, Leadership

The shared lie of the 'Magic Number' is destroying innovation in your organisation

The shared lie of the 'Magic Number' is destroying innovation in your organisation!

Embrace uncertainty, to the point where it is reflected in the business cases for genuinely innovative ideas.

Thanks to Tristan Kromer and Elijah Eilert from Innovation Metrics Podcast for the insights and inspiration!

InnovationMark Winter21 May 2025Innovation

The Quiet Influencers: Recognising the Subtle Change Champions in Your Organisation

I’ll admit it: I lost a couple of good hours each day this week to distraction.

Like many, I've been caught up in the “culture of personality festival” that is the US election cycle.

And yet for someone who thinks deeply and often about change and leadership...this spectacle is the opposite of how anything actually gets done. Real change is driven by consistent, low-fuss, purpose driven effort—usually from people who aren’t looking for the limelight.

Look beyond formal titles or outgoing personalities. Instead, notice who people trust with questions, who others go to for guidance, and who brings a steadying presence to the team.

An article on how Quiet Influencers are a vital part of change strategy, which also doubles as my own sublte ode to those types I've met along the way. Thanks as always...I won't tag you here, even though you deserve it!

Change, TransformationMark Winter12 November 2024Change

The Indisputable Numbers Behind the Value of “Why” in Organisational Transformation

“Every organisation I work with seems to be in a constant state of flux. They can't all be at Level 1 maturity! Does anyone know what they are doing yet?!"

This tongue in cheek musing by a topflight change manager, captures a common frustration across industries. It raises a critical question: does anyone get their transformation right...?

Somewhat recent research from Harvard Business School "Top 20 Business Transformations of the Last Decade" provides some compelling answers.

Organisations don’t just thrive because they adopt new technologies or pivot strategically. Instead, they do so by anchoring their transformation efforts in a powerful “Why”—a purpose that transcends profit. The numbers tell the story: purpose-driven transformations aren’t just aspirational; they deliver tangible results.

"What's the first step for me leading this complex change?"

"What's the first thing I should do for this complex change?"

It's seductive to think there's a "perfect" starting point... but complex change isn't linear—it's a web of intertwined processes and people.

A more effective question is, "What are all the relevant aspects of the change that I should consider?" Here's some shortcuts:

🌏 Think Holistically: Address multiple elements simultaneously rather than sequentially.

📊 + ❤️ Balance Data and Stories: Metrics tell you what's happening; stories reveal why and how.

🤩 Integrate Process and People: Technical solutions need human engagement to succeed.

Complex change demands both the head and the heart. By embracing this duality, you prepare yourself to navigate challenges with agility and authenticity.

Success isn't about a single step; it's about understanding the whole journey to lead with confidence and impact.

Change, LeadershipMark Winter18 October 2024Change, change management, change leadership

Children ARE change management: lessons from Fatherhood that I wasn't expecting

Certifications are great...but the best change management lessons come from life!

It strikes me that the patience that every parent requires, to continually emotionally regulate and whilst communicating simply and clearly...that's almost "unteachable" in a formal organisational change management sense. Not to mention the adept, multi-layered key messaging development that's required, ahead of 38 questions of "...why?"

Children ARE change management; every day has an element of 'newness' which comes with a from of 'demand'. It's mostly delightful, occasionally soul-destroying and pushes you to become a changed version of you.

In a truly blessed life, my two kids are the best thing that ever happened to me. In a happy coincidence for professional me, its the best lesson in change management I've ever had.

Having gratefully enjoyed a (multi-generational) Happy Father's Day yesterday, I sharpened my reflective thoughts into four personal favourites.

You don't have to be a Dad (or Mum / some form of carer) to relate to these. But if you are: keep going, you're doing great!

And if you aren't doing so great on that front...listen, watch and learn from your kids. They are living proof that change is innate to all of us, so you can improve too.

Change, Personal GrowthMark Winter2 September 2024Change, Personal Development

How To Know When Your Change Is DOOMED To Fail...

A change effort is doomed to fail when the key leaders of the change are arguing from a fixed position of what the 'future state' will look like.

They’ve already decided what the organisation "will be", and now the "change management" is simply getting everyone else on board. In essence, they are trying to win an argument.

And when leaders are focused on winning arguments, they’re not focused on solving the real problems that change management is meant to address.

Great leaders don't take charge and argue...they co-create care and accountability. The fundamentals of how to do that, are in this article.

#changeleadership

#changemanagement

#leadershipdevelopment

Change, LeadershipMark Winter20 August 2024change management, LeadershipComment