It can be hard to communicate a company’s priorities across all levels and divisions of the organization, but Twitter and Square CEO Jack Dorsey used an interesting technique — user stories.
Jack Dorsey, who co-founded Twitter and founded Square, has always been known for his unique approach to product development and team management. In a revealing insight into his leadership philosophy, Dorsey explains how storytelling became the cornerstone of how he ran two of Silicon Valley’s most influential companies. His approach transforms abstract product requirements into vivid, relatable narratives that every team member can understand and contribute to.
“One of the biggest things that has helped me is learning how to become a better storyteller and the power of a story,” Dorsey explains. “And by this I mean if you want to build a product and you want to build a product that is relevant to folks, you need to put yourself in their shoes and you need to write a story from their side.”
This approach goes far beyond traditional user personas or market research. Dorsey’s teams invested significant time in crafting what he calls “user narratives” — detailed stories that read like theatrical plays. “So we spend a lot of time writing what’s called user narratives of this user, or this person is in the middle of Chicago and they go to a coffee store in the middle of Chicago, and this is the experience they’re going to have. It reads like a play. It’s really, really beautiful.”
The power of this storytelling method becomes evident in how it streamlines complex organizational processes. “And if you do that story well, then all of the prioritization, all of the product, all of the design and all the coordination that you need to do with these products just falls out naturally because you can edit the story and everyone can relate to the story from all levels of the organization, engineers to operations, to support, to designers, to the business side of the house.”
For Dorsey, these stories weren’t just planning tools — they were living documents that evolved with the product. “So that story is very, very important for us and really constantly considering the story and what new twists and elements we need to add to this story are a pretty big deal for us as well. And we want to tell an epic story. We want to solve a really big problem. We don’t want to have a bunch of short stories strung together. We want one epic, cohesive story that we tell the world and both Twitter and Square are driving towards this goal.”
The implications of Dorsey’s approach extend far beyond product development methodology. By centering user narratives, he created a shared language that bridged technical and business teams, ensuring that everyone from engineers to executives could contribute meaningfully to product decisions. This technique likely contributed to both companies’ ability to maintain focus on user experience while scaling rapidly. At Twitter, this manifested in features like the timeline and real-time updates that made complex social interactions feel intuitive. At Square, it translated into payment solutions that turned complicated financial transactions into simple, story-driven experiences for small business owners. As more tech companies struggle with alignment across growing teams, Dorsey’s storytelling framework offers a compelling alternative to traditional product management approaches, suggesting that the most powerful organizational tool might be the oldest one humanity has: a well-told story.