What are your biggest project management challenges?

As a product person, what are your biggest project management challenges? Somewhere in the “agile good, waterfall bad” conversation, certain fundamentals got left behind and I’ve seen great people held back by not having these basic tools in their kit. I’m working on a piece (“A crash course in project management for product managers”), where I hope to cover the basics in a lightweight way that’s relevant to product people.


I would say getting estimates from devs and giving visibility to stakeholders on the status of items without having a flood of meetings


Oh I am looking forward to this piece, Wayne; something I have thought up writing for my essay at some point from the project managers POV working with PMs.

This was a big change for me when I joined a big company and suddenly having to work with Product Managers. One thing I saw was that some PMs were very territorial and actively kept project managers out of technical or product exploration discussions because they felt it would hinder the process if we suddenly started asking “is it doable questions too early”. Sometimes what sounds wicked awesome isn’t always right or achievable given the constraints. Don’t run from constraints, use them as an asset to shape your product direction.


Stakeholder management + cross-functional visibility and alignment. I (think) I’m abnormal in that I enjoy this aspect of the job but it’s still a challenge at every startup I’ve been at - especially now that we’re all remote.


Looking forward to the article! My prior company transitioned to Scrum Agile after having no declared development framework the first few years. With the change all our project and program managers were either let go or asked to work as a scrum masters. This meant all the project management work fell on the PMs who were already filling in gaps in both UX and product marketing. What made this so challenging was that several PMs lacked this skillset (myself included) and it was critical as there were a lot of dependencies on internal / external teams based on how we were structured. I did my own crash course on project management and partnered with others with strengths in this area but the gap was never really addressed by product leadership. Our execution did not improve and the company wasn’t able to win business from competitors. A third of the company was let go over a month ago as a result. I suppose this is a cautionary tale of why not to ignore this problem.


That sounds horrible, @Michael. This is what I absolutely dislike about the dogmatic approach to agile. You can’t just read the Agile Scrum guide, fire all the project managers or think - we just need scrum masters now. This is genuinely a huge problem and something I know even the agile community have been trying to address. Agile is about a mindset and not prescription. When implementing agile you have to goals:

  • Faster and simplified decision making
  • Better information flow and knowledge exchange

That is literally it. Waterfall fails at both of these. If a company thinks agile is all about 2wk sprints and scrum masters, surprise, its a LOT simpler than that


@Karan, Yeah, neither of those things were accomplished. I wonder if would’ve been less dogmatic without the influence of Agile consultants. Design and data science were a complete afterthought in this implementation. I agree with the notion of agile being a mindset and not a prescription. We were probably more agile before if you follow this definition. Fortunately I got out before they implemented SAFe


@Michael, OH GOD. SAFe. Do not even get me started on that hocuspocus that is SAFe. I genuinely believe everyone has the capacity to be successful Project Managers - its not hard but with all these methodologies and hype, we ruin a lot of it.


This generated a much better conversation than I could’ve imagined! Definitely has my gears turning. I will be sure to share my final post when it’s ready.

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@Nathan - did you ever wind up writing this post on Project Management for Product Leaders? Or @Karan the essay you suggested on your transition to Technical Project Management?
My goal: to better understand what good project management looks like (vs. the corporate-speak/certification overload that a google search yields). I would love to hear how Product leaders who thrive on strategy and vision, learn and implement the necessary techniques to be effective Project Managers.
(adding this to the broader thread since when I searched for “project management” only found this one, which while applicable, is about a year old).

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