Home/ Offline Sydney: What Happens When The Room Picks The Topics?

Offline Sydney: What Happens When The Room Picks The Topics?

NewsAmber Gladstone, 13 August 2026

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Run an unconference and you find out what's actually on people's minds. No set agenda, no keynote, just a room full of web folk deciding which topics matter to them most. At our latest AWIA Offline in Sydney, every topic that made the cut circled the same theme: AI, and what it's doing to our careers.

Here's where the conversation went.

Finding a role when the recruiter is an algorithm

Job hunting now often means getting past several layers of AI before a human sees your name. AI screens your CV. AI runs your virtual interview and records your answers. Then AI reviews the transcripts to decide who proceeds. (Yes, that's AI marking the AI's homework.) The thing is, a harder front door doesn't mean fewer ways in. The room kept coming back to two of them: your network, and building experience on your own terms, whether that's a side hustle or simply starting your own experiment.

The double-dip problem

One thread was more sobering. Qualified people are missing out on interviews for permanent roles, then watching those same roles reappear as contracts, with recruiters going back to review the people who were passed over the first time. One attendee had lived that for the past two years. It raises a fair question about wastage in recruitment, and who actually pays the cost of it.

Which skills will designers need most in five years?

Some answers were new: prompting AI well and knowing how and when to use new tech. Most skills were not new: A deep understanding of the problem you're solving. Systems thinking, which matters more as automation grows. Comfort with ambiguity. The ability to communicate across the organisation and tell a story people can follow. Sales skills to influence people and bring people on board. 

Where do juniors get their reps?

People used to build judgement through hundreds (or thousands) of hours of hands-on work. Much of that work is now automated. So where does the next generation build their experience? There was no tidy answer here. It’s a conversation the whole industry needs to keep having.

Thank you

The best thing about an unconference is that the agenda tells you where people’s heads are at. This one told us the industry is thinking hard about its people. Thank you to everyone who came, voted, and shared their stories. You can find photos from the evening here.

The evening was held at Canva Space, hosted by me (Amber Gladstone) alongside fellow AWIA Directors Lisa Railey and Alex Skougarevskaya, with support from Stephen at BugHerd and AWIA sponsors pay.com.au, Turn Left for Less and Fishr

If any of these conversations struck a chord, I'd love to hear your take: find me on LinkedIn, and keep an eye on AWIA's events page for the next Offline event in your city.

Written by: Amber Gladstone, Coach, Facilitator & Keynote Speaker | Founder, Progression


The Australian Web Awards are an initiative of the Australian Web Industry Association (AWIA), celebrating the best digital work across Australia for 21 years.

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