This is a great response, Chad! Thanks for the thoughts and for sharing the Steve Blank article, which I had not read before.
It’s a really key insight that the reason why we end up with launch dates & timelines is because we try and create a “contract” of sorts that can serve as the compromise between the expectations of different stakeholders. What’s interesting is that each stakeholder is bringing their own cognitive biases to the table — customers overestimate how much they need certain things, the planners underestimate how much work there is to do, the builders underestimate how long it will take, and the financial stakeholders overestimate the impact they expect to see. So, that “launch contract” is usually a mix of over promising and under delivering. The same problem exists with agile, but to a lesser extent because each time window is much narrower and there’s less variability as a result.
To your point though, it’s interesting to think about the financial factor in particular— how do you better align short execution windows with longer measurement ones? That question ties into a topic I’m looking forward to writing about, which is the lack of financial rigor in typical project/product development; that is, thinking about topics like marginal cost/benefit, opportunity cost, forecasting, etc. as part of the agile process. If we did a better job of thinking through a financial lens when planning/executing/measuring these agile cycles, especially by partnering with financial/strategic partners, I wonder if there’d be more trust in the effectiveness of a less rigid approach? It’s easier said than done, and a bit hand wavy, but I think there might be something to that line of thought.
