Start with problems, not AI - #13
This week I’ve been writing about AI and money. Stripe and OpenAI now let ChatGPT shop for you, but the incentives are misaligned. The second your AI agent starts pushing sponsored products, trust is gone. Before we even trust AI to write emails, should we really be giving it our credit cards?
From Summer to Autumn, I'm now back in the UK
I’ve been working with a global enterprise, helping them turn an existing business into a new product. Even a small lift in their success metrics would be huge.
I ran a workshop with them and sensed immediate misalignment. Many stakeholders start by painting a big vision instead of digging into the real problems customers face. It sounds exciting, but it often misses the mark. The truth is it’s far more powerful to talk to customers every week, uncover their struggles, and build directly around those insights.
Jason Fried captures this mindset well in It Doesn’t Have to Be Crazy at Work. He recently explained why Basecamp doesn’t use roadmaps. To him, a roadmap is a relic, a snapshot of what you thought back then. Instead, he prefers asking every few weeks, “what’s worth working on now?" It’s a builder’s perspective, not a corporate promise.
Thought for you: where in your own work are you talking tech headlines and relying on a roadmap of “what we thought then” instead of asking "what’s worth doing now?"
Thank you for your attention,
Ross
Note: If you fancy a chat about any of this content, why not email me and we'll set something up?
