Why overplanning makes projects fail?
sanju.sh
sanju.sh
That said, I've worked exactly 0 jobs that had too much planning in 20 YOE. However I worked lots of jobs with over-measuring. Constant check-ins, syncs, status meetings, team wide weeklies, etc. Measuring every step we take before we take the next one, but no vision as to wear this journey is supposed to actually lead.
This presents its own danger, and Big Agile Industrial Complex is the current manifestation of this problem.
I think its a micro-optimization that creates a macro problem.
We did not get from the Wright Brothers to a Boeing 777 with lots of minute check-ins and week-long visions of micro deliverables along the way.
You DO get improvements applying that process to say- churning out the current plane on the factory floor in a 25% more efficient manner, step by step. Not a lot of planning for what 6 months looks like there.
So one needs to match the type of problem they are solving with the correct amount of vision & planning.
"Plans are useless, but planning is indispensable."
The culprit is usually someone who sees their job as checking boxes off a list. In extremely complex situations, box-checkers can be valuable to help ensure that nothing falls through the cracks, but everything goes to shit when you elevate people like that to any position involving the word "manager." Project manager, product manager, people manager -- it's a disaster to try to reduce these jobs to checking boxes. Immediately they'll start to say things like, "Why did we spend so much time creating a plan if we're not going to follow it?" They'll create deadlines for finalizing plans and insist that everything after the deadline has to robotically follow the plan. They see their job as 80% making sure every box on the plan is ticked and 20% stopping you from doing anything there isn't a box for. If they do that and the project fails, they point fingers at people for not adding all the right boxes to the project plan according to the schedule for making boxes.
Good planning isn't about checking boxes. It's about forcing yourself to consider all aspects of a project, crystallizing your plan at a certain point in time, and periodically reconsidering and re-crystallizing your plan on a cadence that makes sense for the project.
This ends up inversing all of the agile Manifesto.
* Individuals and interactions over processes and tools
* Working software over comprehensive documentation
* Customer collaboration over contract negotiation
* Responding to change over following a plan
This is a bad assumption for the agile premise in many large non tech orgs. Many cases internal tech tools just do not have users with this mindset.
Here’s what I wanted, why isn’t it already this way, go fix it, stop showing me stuff that isn’t done yet.
Or the other flavor where every touch point changes their feature of the week such that you are always behind what they actually want.
It’s entirely possibly to iterate such that no one is happy with delivery.
As you learn, the scope of the plan must change.
As you plan, you reduce the scope of what you may learn.
Example: We are migrating legacy code to new hosting with a small change. The plan is straightforward and simple. As we progress through migration we learn about unsupported dependencies and bad code practices in the legacy code, so we have to replan.
Previous comment: https://news.ycombinator.com/item?id=41183984
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If you don't address budget when you talk about planning, you are missing the biggest problem.
Instead of course correcting to any new data, failed projects tend to double down on the process. Even as more information comes to light, it gets systematically ignored in favor of "sticking to the plan". This is the death of software.
Of course I've seen projects that have basically no plan at all beyond the 2 week sprint. It's not the presence or absence of a plan that hurts, it's about the quality of the plan. Duck tape and prayers don't constitute a plan either.
We need a tight feedback loop between planning and experimentation. Otherwise planning goes off the rails with bad assumptions, and experiments can go off the rails chasing new technology for its own sake. A planning process without a data-gathering period and an iteration loop to refine the design isn't software engineering!
A good heuristic in the absence of a detailed high level plan is "work on the highest risk things first".
Have you seen a very detailed plan yet very flexible release date mixed together?
You can run into this with certain types who want to talk through every possible eventuality in their head they have imagined, so they can feel like they have control of outcomes. Of course the stuff that happens in life is none of the things they imagined.
When you let things flow instead of sticking to a rigid plan, you end up finding better ideas. It’s like the pressure’s off, and the real work happens naturally. That freedom makes everything more productive ;)
- What was invented by accident?https://www.reddit.com/r/AskReddit/comments/ygqwwl/what_was_...
- What is the best accidental invention?https://www.reddit.com/r/AskReddit/comments/1cajrnr/what_is_...
Casually leaving out the vast effort of a whole team of people to develop the drug:
https://www.sciencemuseum.org.uk/objects-and-stories/how-was...
Fleming gets the credit, but Florey and a whole team of people of other people did the hard work.
Success rarely comes from what we aim for—it’s often about timing & flow. Perfection can hold us back, but staying open leads to breakthroughs.
Few irl examples:
1. Spend hours perfecting a video, 100 views. Post a raw clip, and it goes viral.
2. A polished product flops, but a scrappy weekend tool takes off.
3. A masterpiece gets ignored, but a casual sketch goes viral.
4. A failed dish turns into the next food trend.
Don’t wait for perfect. Keep creating, stay open, and let the unexpected happen.
P.S. Success is personal. But if you aim for something and it doesn’t happen, that’s a failure in that context.
That one sentence alone is enough to explain the failures and I’m not even accounting for the very real cost overheads of planning.
Don’t try to change this! You can’t convince a PM that their job is not needed, their pay depends on it being a necessary function and they will fight dirty to protect that income no matter what.
+1 Agreed. Plans fail when sticking to them matters more than adapting...
TBH, the best plans know when to shift.
Flexibility > Rigidity
A project started a year ago, planning an infrastructure (cloud IaaS) deployment of a complex product 12 months into the future.
Now, there is a turnkey software service (SaaS) version of the product that covers the same features and more for less money and takes literally seconds to spin up.
They're stuck in the mud trying to work around complex network routing, split-DNS, and other issues with the IaaS solution. They're going to spend months applying workarounds to problems that don't need to be solved because the SaaS version has none of those problems. They're already starting to talk about getting MFA and SSO integrated Q1 next year even though the SaaS uses MFA+SSO by default.
It's incredible how much inertia these things build up, and how much time, effort, and money is wasted "sticking to the plan" even if those plans are invalidated by changes to reality.
If the project manager simply said "let's rip up the plan and use the SaaS", they'd instantly make themselves redundant and might actually be let go when their contract is up for renewal. If they keep "fighting the fight" to make a bad plan succeed, then they're the hero and will be gainfully employed for the foreseeable future.
It's not just that the plans are too rigid. It's not just that you don't know enough to plan in that much detail. It's that the planning takes time that you could be doing something useful with.
Note well: I am not advocating for no planning. I am against over planning.
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The most exciting phrase to hear in science, the one that heralds new discoveries, is not “Eureka” but “That’s funny...” —Isaac Asimov (1920–1992)