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Strongly agree with this. Dates serve a critical goalpost in technical planning, yet they should be viewed as flexible (having a reasonable margin of error) and informed by tight & trust-driven feedback loops. I subscribe to Gantt charts as a planning tool, not a bible. Use it to empower development teams to plan and track execution, but don't use it for 0-margin accounting.

One anti-pattern in engineering management is shielding engineers entirely from timeline estimates. A CEO with limited runway, reporting to the Board, doesn't have such a luxury of infinitely elastic time.

Edit:

Note: dates should never be prioritized over value. If you're hitting dates and not delivering value then it won't do good for anyone. Product value should always be the function to optimize for, but rarely is it entirely independent of time.

"In preparing for battle I have always found that plans are useless, but planning is indispensable." - Dwight D. Eisenhower

Took me some years to fully internalize this, but I endorse it.

Related, when I was in school, I always took meticulous notes during class. But I never looked back at them.

I.e. Notes are useless, but note-taking is invaluable.

How funny, I took notes for a class to A/B test this and note taking ruined my ability to internalize data. When I wasn't taking notes, concepts would fly into my head as I'm writing an exam along with the associated memory (where I was sitting that day, whether it was bright out, where the lecturer was standing wrt board). When I took notes, I had all these notes and none of this would happen.

I used pen/paper. I also tried, separately, computer-based stuff and that ruined my ability to concentrate.

For me the note taking helped with the internalization process of linking the information with the memories of the professor talking about the lesson.

I think the key is to still allow your mind to wander and build the connections. I found I always had the best luck if I was a little distracted, but mostly paying attention.

Perhaps because the variations in attention helped to differentiate which information felt important vs what was just background noise.

Interesting. Ah well, the time has passed on that front.

agreed. i wanted to build something, and set myself a 90 (end of quarter) target. it really focused me on just doing what needed doing. my plan did not survive long, but i kept updating it to focus on what mattered. in the end i hit my abitary date, but i carried on tweaking for another 30 days before i was really happy. so reall a 33% overrun.

so having a date matters, just "dont do something stupid to hit a date" what i built: https://moca.computingarchitectures.com/en/~hello-world/

That's also one of my favorite quotes on the topic and have heard it phrased a few ways and variously ascribed [1] but definitely military where it's also said Generally that "all combat takes place at night in the rain and at the junction of four map sectors"

[1] https://quoteinvestigator.com/tag/dwight-d-eisenhower/

I'd probably generally disagree. Lose the date but sell the mission. Engineers that get lost in a world perfect is the enemy of good need to be reminded of the mission not stressed into cutting even more corners for the date.

Exactly. People are terrible at estimating things on long time scales. If an engineer isn't overly optimistic with estimates, management will force them to revise until they are. Unrealistic optimism despite heaps of evidence is a major human flaw. Adding pretend timelines is a stressful exercise in futility. But planning itself is not.

The example given is a strawman of a classic cigar-chomping executive whose philosophy comes largely from unskilled, fungible-labor economies.

I use this exact strawman to bounce ideas off of people and play devil's advocate.

He's such an integral part of my routine that I even gave him a name and a function: Richard Johnson, CEO of a pate factory.

> Now you've given every PM and sales guy carte blanche to throw whatever flavor-of-the-moment idea comes in their head.

YES! My current project has this issue. There is no deadline for my project beyond "urgent" (but so is everything else) and as a result, any request from a client gets approved. Client wants a button shifted slightly to the right? Approved. Comms wants the semi-colons gone? Approved.

For a supposedly urgent project, we are making no real progress week after week on functionality simply because urgent has no tangible meaning.

That's not solved by adding a date. That's solved by blocking feature requests. I'm in a project with the same problem, BTW. It's incredibly demoralizing.

Change Request == MONEY, and all prior deadlines extended. How much depends on the complexity required to perform the change... and figuring that out is a billable item too (please submit change requests in bulk to save).

I recently found myself in the position you described, to a T. And we did end up switching to scrum...

I've left that company after having been unable to fix the situation, which was ultimately a political problem; as you said, we had an "executive whose philosophy comes largely from unskilled, fungible-labor economies". Is this fixable, or is "leave" the only right answer?

No, "leave" is not the only answer. "Fire the executive" also works.

But to actually make that happen, there has to be someone with authority do actually do the firing, and that person needs to understand the problem...

The date is not important, the pressure it might create more so. But there are other things that create the pressure to get things done.

Natural pressure is the best: someone you care about suffers if you don't solve the problem, heating is broken and winter is coming, that family needs a place to stay etc.

The worst kind of deadline is completely arbitrarily set by someone who has no idea, because they thought promising early deadlines would make them look good and get them the contract.

This is a structural problem IMO, because freelancers usually don't make that mistake very often. If you manage someone elses time you can afford to become unrealistic.