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Why overplanning makes projects fail?

sanju.sh

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Re: Why overplanning makes projects fail?

#11

Post by intelVISA »

steveBK123 wrote: post #6

Serendipity is real and hugely important to innovation. 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 Agil…

Sounds like a layer of management that doesn't understand the works below, or the vision above, and has to maintain value theater.

Re: Why overplanning makes projects fail?

#12

Post by spikey_sanju »

csours wrote: post #5
spikey_sanju wrote: post #2

Why do some of our best ideas come out of nowhere? This post talks about how planning too much can kill creativity, and why greatness often shows up when you least expect it.

The scariest and most exciting words are "That's funny ..." --- 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) https://www.americanscientist.org/article/thats-funny

Exactly. 'That's funny…' is when you realize you were looking at it wrong all along...

Re: Why overplanning makes projects fail?

#13

Post by steveBK123 »

intelVISA wrote: post #11
steveBK123 wrote: post #6

Serendipity is real and hugely important to innovation. 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 Agil…

Sounds like a layer of management that doesn't understand the works below, or the vision above, and has to maintain value theater.

You just described median middle manager behavior.

Re: Why overplanning makes projects fail?

#14

Post by jiggawatts »

“It’s too hard to change the plan now.”

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.

Re: Why overplanning makes projects fail?

#15

Post by spikey_sanju »

Here are a couple of Reddit threads on accidental inventions. It’s wild how small, unexpected moments led to some of the biggest discoveries ever. Uncertainty has its own kind of magic—it can spark the best ideas.

- 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_...

Re: Why overplanning makes projects fail?

#16

Post by Nina1000 »

This is a great reminder of how unexpected success often comes from things we don’t plan for. Focusing too much on perfection can sometimes limit creativity, but you can’t just sit back and wait for things to happen either. It’s all about balance.

Re: Why overplanning makes projects fail?

#17

Post by spikey_sanju »

Nina1000 wrote: post #16

This is a great reminder of how unexpected success often comes from things we don’t plan for. Focusing too much on perfection can sometimes limit creativity, but you can’t just sit back and wait for things to happen either. It’s all about balance.

This is the whole point of the post...

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.

Re: Why overplanning makes projects fail?

#18

Post by perrygeo »

I've noticed one obvious commonality to failed projects: the plans are made in a vacuum of information, before data is gathered. This leaves land mines everywhere in the execution path, leading to big risks and large error bars on estimates.

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!

Re: Why overplanning makes projects fail?

#19

Post by dkarl »

steveBK123 wrote: post #6

Serendipity is real and hugely important to innovation. 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 Agil…

Same here, I've never worked at a place that did too much planning. However, I've been at a lot of places that wildly overvalued plans.

"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.

Re: Why overplanning makes projects fail?

#20

Post by spikey_sanju »

jiggawatts wrote: post #14

“It’s too hard to change the plan now.” 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.

"It's too hard to change the plan now"

+1 Agreed. Plans fail when sticking to them matters more than adapting...

TBH, the best plans know when to shift.

Flexibility > Rigidity

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