AI-powered · Trained on Andrew's thinking and experience
Ask Outrider
A conversation before the conversation.
Outrider Technology Consulting is a Melbourne-based advisory practice led by Andrew Hill. Ask Outrider is an AI trained on Andrew's professional thinking, experience and approach — built for leaders who want to explore whether Outrider is the right fit before committing to a real conversation.
Before you start
What this is — and what it isn't.
Ask Outrider is not a generic chatbot. It's trained specifically on Andrew's professional knowledge, methodology, the situations Outrider works with, and the philosophy that underpins every engagement.
That means it can have a substantive conversation about your situation. It can tell you how Outrider would approach a problem like yours. It can give you an honest assessment of whether what you're dealing with sounds like a strong fit — or whether it doesn't.
It won't pretend to be Andrew. It won't tell you what you want to hear. And if the conversation suggests Outrider isn't the right fit for your situation, it will say so — clearly and without hedging.
If at any point you'd rather talk to Andrew directly, that option is always open.
Request a callback →How it works
Start anywhere. The AI will find the thread.
There's no right way to begin. Ask about your situation. Ask about Outrider's approach. Ask the question you'd want answered before picking up the phone.
The conversation is designed to reach a conclusion — not just exchange information. After a natural arc of discussion, Ask Outrider will offer an honest assessment: whether your situation sounds like a strong fit for Outrider, what a first engagement might look like, and what the logical next step is. You've come this far. There's nothing to lose by going a little further.
Andrew Hill
Principal, Outrider Technology Consulting
Twenty years in technology delivery and business management. Cross-domain thinker. Business-problem-first approach to technology and AI.
This AI is trained on Andrew's professional knowledge and experience. It doesn't have access to confidential client information. Conversations are not stored or shared. For complex or sensitive matters, request a callback.
Request a callback →
Ask anything about your technology situation or how Outrider works.
Rather talk directly?
Andrew answers his own calls.
If you'd prefer to skip the AI and have a direct conversation, that's equally valid. There's no gatekeeping at Outrider — when you reach out, you reach Andrew.
Ask Outrider is an AI trained on Andrew's professional knowledge and experience. It doesn't have access to confidential client information. Conversations are not stored or shared. For sensitive matters, request a callback and Andrew will be in touch directly.