[HN Gopher] Why most product planning is bad and what to do abou...
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       Why most product planning is bad and what to do about it
        
       Author : ndneighbor
       Score  : 68 points
       Date   : 2025-10-02 19:34 UTC (3 hours ago)
        
 (HTM) web link (blog.railway.com)
 (TXT) w3m dump (blog.railway.com)
        
       | colonwqbang wrote:
       | Meandering post which struggles to get to the point.
       | 
       | The font is extremely thin which makes it unnecessarily hard to
       | read.
       | 
       | A lot of jargon and abbreviations also hinder understanding.
        
         | TuringTest wrote:
         | You can skip to the "The Four-Day Process" at the end to get
         | the gist.
         | 
         | But for people living in an organisation suffering from those
         | problems, reading how other solutions were tried and how they
         | failed is valuable, and it puts things in context of why the
         | recommended approach may work best.
        
           | stackskipton wrote:
           | As someone who has been at multiple organizations suffering
           | from planning hell, most of the time the solution is pretty
           | clear but outside factors prevent it.
           | 
           | Our Quarterly PI planning is nightmare but Sales wants to
           | sell the backlog so fighting is different business units
           | fighting over which items should be done and how fast they
           | are done.
           | 
           | It's generally employees meta optimizing for themselves
           | instead of larger business and business is too big for CEO to
           | figure out. Railways career page says they are a team of 27
           | so CEO/Founder/Whoever has vision in their head and keep
           | steering everyone towards that vision.
           | 
           | However, as Ops type, looks like could be interesting job.
           | _Digs further_
        
         | apsurd wrote:
         | You got downvoted but then I read some and you're not wrong.
         | 
         | I think we should call out bad writing assuming English is
         | their first language. Bad, lazy writing, doesn't respect the
         | audience.
         | 
         | > Instead of crowd sourcing the OKRs from the company and
         | bubbling them up per function.
         | 
         | First sentence under the heading "Good Ole Projects". This is
         | not a sentence.
         | 
         | edit: The charitable pov is that writing is very hard work and
         | writing and publishing anything is a net good. I wish for more
         | people to respect how hard writing is and also to take the time
         | to write well! So that's why that sentence bothered me.
        
           | ndneighbor wrote:
           | Author here, not my intent! My deepest apologies. English is
           | my first language but people do joke that they say I write
           | English like I learned it as a second language.
           | 
           | I have fixed the sentence fragment and connected the two
           | thoughts together. Thank you for keeping me honest.
        
             | apsurd wrote:
             | I just edited my comment! I do not wish to convey negative
             | energy toward something you made. I felt bad about it.
             | 
             | Also, I do care about writing, so thank you!
        
       | datadrivenangel wrote:
       | Weighted Shortest Job First with clear articulations of value is
       | the way. This problem driven development approach seems like a
       | decent take on that.
        
       | procaryote wrote:
       | Am I getting it wrong? It sounds like they're still doing
       | quarterly planning just with a different ritual?
       | 
       | I had hoped they'd realise quarterly planning is a bad premise
       | and asked themselves why they do it.
       | 
       | If you have a mature product where you add incremental features,
       | you don't need that plan because it's just an arbitrary block of
       | pretty fungible work.
       | 
       | If you're still looking for product market fit, that three month
       | plan wont last a week before becoming obsolete.
       | 
       | If you need to build a bigger thing that is only valuable once
       | it's all done, you A: need a project and B: probably don't
       | because it will fail.
        
         | ndneighbor wrote:
         | Hello there! Author there, and surprised/delighted with the
         | response. I don't think we had the issue with the cadence, the
         | quarter is arbitrary, but we think it gives us the ability to
         | just go heads down to focus.
         | 
         | With that said, one thing we did and I don't why we did it was
         | that we would "re-justify" why we would want to work on
         | something every three months which isn't great. There is a
         | world where if we had more eng. resources we could have more
         | people than problems and we could take stuff on board as it
         | arrives, but for us deciding on what to work on is a hard
         | decision.
         | 
         | I also agree that market fit is a key factor. I think Railway
         | was lucky that we didn't have to pivot the product 3 to 5 times
         | to get some latch.
         | 
         | What would be the post-quarterty planning process that you
         | would like to see?
        
           | __alexs wrote:
           | There is no world where you have more people than problems
           | because the more people you hire the more problems they
           | discover.
        
           | collingreen wrote:
           | > There is a world where if we had more eng. resources we
           | could have more people than problems and we could take stuff
           | on board as it arrives
           | 
           | I don't think this is a realistic world. The cavitation
           | surface area that spawns new bubbles of unvetted fresh ideas
           | grows as things are added. Adding eng resources to get more
           | done makes it grow faster and I don't think there is ever
           | such a thing as catching up.
           | 
           | tl;dr - deciding what to build (and what it looks like in
           | detail) will always be a critical and fundamental function of
           | product teams.
        
       | zer00eyz wrote:
       | Most planing is bad for two reasons that we never talk about.
       | 
       | 1. The wrong metrics: Ultimately the only metric that matters is
       | money. Is this saving us money, are we wasting money. Every
       | feature has a cost, and we are decent about tracking its
       | construction costs but not its operational costs. This matters
       | when you're paying for every iota of infra on AWS.
       | 
       | 2. No one ever gets promoted for ripping out a feature that costs
       | too much to run or doesn't retain customers, or is under used.
       | Heath of the product as a whole isnt always about growing the
       | business, sometimes it's about running it.
        
       | apsurd wrote:
       | "Focus on problems, not solutions" is pretty standard practice.
       | Seems like author cherry picks some abstract concept of "bigco"
       | and their process-driven planning. I guess.
       | 
       | Came here to say, I don't deny those anecdotes, but just as many
       | companies can and do intuit "what problem are we solving?" and
       | then come up with some potential solutions in meetings across
       | stakeholders. That's called planning. Time-box it and move on to
       | some face-reality testing.
       | 
       | Planning anything, in any way, is imperfect. Partly fed by over-
       | pontificating about the perfect way to plan!
        
       | lovich wrote:
       | I always found product planning went poorly because the bosses of
       | the people making the plans would make heads roll if you couldn't
       | draw them 7 parallel red lines, 3 of them being perpendicular,
       | and in green ink
       | 
       | They'd get a plan that made them happy in the moment, we'd
       | inevitably go off the rails in a few weeks but in a politically
       | satisfactory way. Mission accomplished would be declared and then
       | we'd start all over again next quarter/year.
       | 
       | That is unless you are working under the SAFe framework in which
       | case you cut out all that time wasted trying to execute on the
       | impossible plan and just doing constant rolling, planning of
       | planning
        
       | wrs wrote:
       | I must have missed something, because this seems to say you do
       | capacity and headcount planning and publicly commit to the work
       | _before you know how to solve the problem_? This seems like the
       | "draw the rest of the owl" part of this process...
        
         | ndneighbor wrote:
         | I am more than happy to add color here, I am sorry, I try my
         | best to write everything but my editor cuts as much as I add.
         | We also tend to hire really autonomous engineers who tend to
         | like just going off on their own to try to solve the issue.
         | 
         | There have been a few times where we would commit to the
         | problem, assign a DRI, and then find out midway that... no we
         | have to hire/consult our way out of the issue. I think that's
         | okay, we then look back at the retro to see what we missed.
         | 
         | If interested, I think we can blog about what happens when a
         | problem gets converted to an RFC and then we have more
         | engineering discussions with the stakeholders but the piece was
         | pushing a 10 min read time as it was...
        
       | 0xbadcafebee wrote:
       | > For most of my friends and colleagues at mature software
       | companies,         (randos at a company with a lot of money)
       | > there are usually three ways for an item of work to get put on
       | the board         (we assume that everyone should always do work
       | in the same basic ways and there's no reason to change the way
       | you work other than personal preference)              > Thats not
       | to say that every company is a disorganized mess or a
       | bureaucratic hell scape but         (no, no, they all are)
       | > and then at times get blindsided every now and then from a new
       | business priority or an incident         (your executive team is
       | disorganized and your operations are unstable; again, normal)
       | > we felt that reigniting the agile vs. waterfall armistice
       | needed to be torn up
       | 
       | Wait... what? This article _isn 't_ trading on clickbait tropes
       | about a black-and-white world for HN points? Ok, I'm listening.
       | > We implemented them faithfully, we all read the John Doer book
       | 
       | So you read the 2018 book that was written after a Silicon Valley
       | process used by mega-unicorns... but not the 1983 book that
       | process was based on? Foreshadowing? I'm going to call it and say
       | "they should've read Deming".
       | 
       | As a (lengthy) aside: planning is bad most places because most
       | people don't have multiple perspectives. Anyone _can_ have
       | multiple perspectives, but it requires both an interest in other
       | perspectives, and a means of communicating (and receiving) those
       | perspectives. Those are rare commodities.
       | 
       | Sales and executives set deadlines for objectives without talking
       | to the people who do the work. They don't have an accurate
       | perspective of the engineering (or other) departments. If they
       | knew there is no time, and they're crushing the morale of other
       | teams (and why that's _very important to avoid_ ), they wouldn't
       | commit to things when they don't know if it's feasible.
       | Similarly, when engineering gets word they have to throw out
       | their current work and rush to finish something else, and they
       | had the executive/sales perspective, this demoralizing slog might
       | not feel as bad.
       | 
       | Even within engineering, at every job I've had, splitting up
       | teams creates dysfunction. Engineers stop understanding the
       | entire system's architecture. They stop designing with the other
       | pieces in mind. Their perspective becomes a laser beam shot at
       | their own navels. This contributes to difficulty planning between
       | teams, and invents new problems that have to be planned around.
       | If they fully understood each other's perspectives, they wouldn't
       | have those issues.
       | 
       | Today nearly all online products are developed with a 2010s-era
       | "this is the _only way_ you can make software " mentality. Your
       | product is never finished, is constantly changing, re-
       | architected, etc. It's cargo cult. You don't have to develop this
       | way. You can make online products like physical products. But
       | because people today are incapable of thinking outside this
       | framework, planning is stuck in this bizarre world of only
       | considering a few quarters at a time. This wastes time and money
       | and creates more problems. Software architects, product owners,
       | and executives, force themselves into working in crappy ways, and
       | then struggle to find their footing.
       | 
       | This article is an example of people struggling to find footing.
       | Rather than deal with the fact that the way they're working is
       | causing them problems, they're instead focusing on how they can
       | _plan for_ the work that 's causing them problems. It's like
       | having a bum ankle while playing soccer, and rather than stop
       | running on the ankle, you're trying to figure out how you can
       | continue running on the ankle. Stop doing the thing that's
       | causing you problems.
        
         | YZF wrote:
         | This. I would also add that people are not
         | motivated/incentivized to have those different perspectives.
         | 
         | All of this is very much related to:
         | https://en.wikipedia.org/wiki/Conway%27s_law
         | 
         | Your software product is never finished is partly a reflection
         | of how you structured your organization. That is often the root
         | cause of your problem.
        
         | apsurd wrote:
         | Isn't software never being finished a unique trait of software
         | and therefore intentionally used as a value?
         | 
         | I get that never-done software tends to justify shitty
         | products.
         | 
         | But how would you suggest taking advantage of software's
         | features vs do you really recommend building it like a bridge?
        
       | florakel wrote:
       | Sounds Like you rediscovered the "opportunity solution tree"
       | (Teresa Torres) and were skipping a crucial step in product
       | management / UX which is product discovery. I would suggest not
       | to generalize your learnings by saying "why most product planning
       | is bad..." and rather use a more humble title "why our product
       | planning was bad and what we did about it".
        
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       (page generated 2025-10-02 23:00 UTC)