
In this episode of The Sales Today Podcast I speak with Bryan Cassady, author of Generative Organization. His book looks at how people and AI can work better together inside a business.
The central idea is not about “using” AI but learning how to partner with it in the same
way you would with a colleague.
Brian explains why many leaders feel let down by AI.
The problem is not the technology itself but the way it is asked to work.
Just as you wouldn’t tell an intern to “go make a sale” without guidance, AI also needs clear direction and context.
Treated in the right way, it becomes more like a smart team member or even a muse that can spark new ideas.
We connect this way of thinking with sales practice. Just as salespeople partner with customers rather than trying to push them, the most effective approach with AI is to collaborate with it.
Brian shares how this can change the way salespeople prepare, research, and build proposals.
From shaping better questions, to testing different perspectives, to anticipating how different stakeholders might react, AI can raise the quality of every stage in the sales process.
We also explore the importance of mindset.
Seeing AI as a vending machine that spits out quick answers will keep you average.
Seeing it as a thinking partner that helps you clarify objectives, test ideas, and prepare for real conversations is where the real value lies.
Brian argues that AI can make everyone slightly above average, but it still takes excellent people to lead the process and ensure it is applied well.
Towards the end, we link Brian’s ideas to the VALUE framework for sales:
- Validate opportunities by checking if what you offer really matters to the customer
- Align your research and preparation with what drives their business
- Leverage better questions and sharper conversations
- Underpin your proposals with clear, customer-focused messages
- Evolve towards outcomes that prove real value
This is a lively conversation that blends practical sales thinking with a new way of looking at technology.
If you’ve ever wondered how to work with AI in a way that makes you stronger in front of your customers, this episode is worth your time.
--------- EPISODE CHAPTERS ---------
(00:00) - Collaborating With AI in Sales
(07:32) - Maximising Sales With AI Collaboration
(12:03) - AI Collaboration in Sales Conversations
(24:04) - Effective Sales Strategies With AI
(31:17) - Evolving Sales Strategies With Collaboration
Connect with Bryan https://www.linkedin.com/in/bryancassady/
Website: https://genorg.ai/
Follow me: https://linktr.ee/fredcopestake
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