Frequently Asked Questions
What is Pragma and how does it work?Pragma is an AI change advisor built on 20 years of practitioner experience. You type a change challenge — a stalled programme, a resistant sponsor, an AI rollout going sideways — and Pragma responds the way an experienced practitioner would. Not a textbook answer. Not a generic framework. Actual perspective on what's happening and what to do next.
It's built on Claude (Anthropic's AI), but the thinking behind it — the frameworks, the case study patterns, the things most change tools won't say out loud — comes from Mark Winter's two decades in the room where these decisions actually get made.
Who is this for?Broadly, anyone interested in the pragmatic approach to leading change.
Specifically, Senior leaders — MDs, COOs, programme directors — who are navigating a complex change and want a thinking partner they can access at 11pm on a Sunday without calling a consultant.
Change practitioners — change managers, project leads, transformation specialists — who want sharper thinking on the hard situations: the political ones, the stalled ones, the ones where the standard playbook isn't working.
If you're looking for a certification framework or a methodology to buy into, this isn't that. If you're looking for something that helps you think better in a real situation, this is exactly that.
Is this just ChatGPT with a change management hat on?No, and the difference matters. General AI tools know about change management in the same way a well-read graduate does — broad knowledge, no scar tissue. Pragma is calibrated to how Mark Winter specifically thinks about change: the frameworks he actually uses, the patterns he's seen across utilities, financial services, government, higher education and mining, and the things most practitioners only learn by getting it wrong a few times first.
The gap between "knows the frameworks" and "knows what actually happens" is where most change advice falls apart. Pragma is built to close that gap.
What can Pragma actually help me with?Complex change challenges: stalled programmes, resistant sponsors, AI transformation, team capability gaps, communicating in uncertainty, programme design, go-live risk. The kind of problems that don't have a clean answer but benefit enormously from sharper framing.
Pragma won't write your change plan for you. It won't give you legal or HR advice. It won't promise outcomes. What it will do is help you think more clearly about the problem you're actually facing — which is usually the most valuable thing in the room.
Is it free?Pragma Free gives you five messages per session — enough to work through a real question with depth. Pragma Premium (A$50 one-time, or A$9/month) gives you unlimited conversations, document upload so you can paste in your programme charter or stakeholder map, and saved sessions so you can pick up mid-programme over weeks.
Premium is in development. Express interest from within the app and you'll be first to access it.
Are my conversations private?Yes. Conversations are saved to improve Pragma's responses over time — Mark reviews them periodically to identify where the guidance could be sharper. Your conversations are not shared with third parties, not used for advertising, and not published anywhere.
The full details are in the Privacy Policy.
What's the relationship between Pragma and Mark Winter?Mark Winter built Pragma. It's his thinking, his frameworks, his 20 years of practitioner experience encoded into a tool. He reviews conversations, improves the underlying knowledge base, and uses what people are asking about to decide what to build next.
Pragma is not a replacement for working directly with Mark — it's a way to access his thinking when direct engagement isn't the right fit or isn't yet warranted. When it is, Pragma will tell you. You can book directly at markwinter.com.au.
Why "Pragmatic Change"?Because change management has never had a shortage of frameworks, certifications, or methodology. What it has always lacked is tools built around what actually works — in the real room, with real stakeholders, under real constraints.
Pragmatic Change is being built as a suite of practical tools for people doing that work. Pragma is the first. More are coming.
Will there be updates?Yes. Each time Mark publishes a new article the key ideas and principles are incorporated into Pragma. Furthermore, key models and research Mark engages with as part of his client work, are refined to be utilised by Pragma.
Moreover, Mark uses Pragma himself to augment his own thinking…so he’s invested!