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A weird thing in my personal experience is that executive leadership often wanted as much specificity and accuracy as possible in technical estimates, but for anything that was pure business or marketing strategy they all relied on the stack ranking and napkin math you've illustrated here. It's as if they think computers = math and all things measurable to the nth degree, whereas their own domain was more creative, subject to head winds and network effects and therefore naturally forgiven for being far less precise. Perhaps it's on us to dispell the myth that engineering projects somehow need to be planned and priced 10x more accurately than any other sort of project. It's unfair to hold tech leaders to a level of accountability that other departments don't adhere to. I wonder if anyone else can attest to this phenomenon oor whether I have just worked for orgs who were doing it wrong? 🤔

I did once get my invitation to future business strategy meetings revoked after I blurted out "Wait a second, those numbers on the whiteboard are totally made up! They don't even reflect our budget. How is that okay?". Woops.

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Yeah I think, as you're pointing out, a key point is that stuff like Sales & Marketing plans are often seen as subject to many external factors, while Eng projects are seen as "under our control internally", so you're expected to hit the timeline. Of course, there are still tons of unknowns in the estimates even on the Eng side...

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