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In your experience, where do Product Managers usually get stuck the most? Any ideas on why that happens and what could help them get unstuck?

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I actually see 3 instances where folks tend to get stuck:

(1) from Senior -> Staff/Principal...this usually happens because there are only so many "big" product initiatives an org is doing at one time and you need to lead one of these successfully to get promoted to Staff/Principal...my advice on this front is to tackle cross-cutting (the gray area between product surfaces) problems and build advocates from multiple teams

(2) to Director - this jump takes from you from a functional lead (e.g. Principal PM) to a cross-functional leader (working between EPD, GTM, Finance, Legal, etc) - many people struggle with this transition because their entire career up to that point has been navigating a uniform ladder, and this transition is all about blurring scope and impact across functions

(3) to executive (VP+ level) - people struggle less to get here and more meeting expectations once they get the title, because it's more a mindset shift to orchestration over execution - it's hard to let go of the things that got you here but no longer serve you - doing a whole live, free, virtual webinar about this with an exec coach this Friday https://lu.ma/51t644j3

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Nice overview. Do you think there might be situations in which people skip a level? Like being able to tie business outcomes without being able to bet.

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Yes…

(1) sometimes you have a short stop to master a level

(2) sometimes you get an opportunity to show aptitude for multiple levels at the same time

(3) sometimes you show competency at the next level through shortcuts or storytelling…but eventually not having truly mastered a foundational skill comes back to bite you if you can’t coach others or connect the dots

tl;dr yes, but it doesn’t scale

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For someone who is not there yet but wants to start the journey - this is super insightful! Thank you for this!

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