"No, it's less effort than that"

Did anyone ever get asked to simply make the estimate lower? Without any other context? That never happened to me, it sounds extremely immature.

Feedback that you don’t agree with the estimate on the other hand, happens all the time. This is a completely different thing than a hollow request for “lower plx”.

Good stakeholders often do have a good idea of how long time things take. Maybe they worked as dev before, or with other clients. Leaving the estimation exclusively for the well oiled hero-team with perfectly calibrated velocity and ponies coming out of their retrospectives, as the article portrays it, isn’t always ideal either. Some tasks are new and unknown to them too, and honestly not all teams are that perfect. There needs to be a two-way dialogue about scope contra timing.

TLDR - Yes, but from a crazy person.

Yes, in the most toxic place I ever worked. Gee, those are probably related, huh? The owner of the company was crazy. Not in a hyperbolic "oh yeah she's nuts" way but in a "she's either taken too much medication or not enough because she's unstable." Some of my favorite anecdotes, starting with one relevant to your comment:

1. After I provided an estimate of N weeks for a project, her response was "no it needs to be done faster than that." Okay, what features do you want to remove? What can be added after launch? "Everything is critically important and has to be available at launch, I thought it would take a day or two not weeks!" Finally she just wrote something about 80% of my original estimate and moved on. It took a week or two longer than I had originally estimated and it was fine.

2. Insisted on charging $10 instead of $9.99 because "the taxes get too complicated." Turns out rather than just using billing software like any sane person ca. 2010, she was using a calculator on her desk to figure out what clients owed and just typing that into an invoice and sending it. I bet 90% of our clients either overpaid or underpaid basically every bill by 1 cent due to her rounding in her head.

3. My favorite one ever was she was out on vacation one week, and while she was out we had some production issue over the course of a day and a half or so that was eventually resolved but she was cc'd on everything as she insisted. She pops into my office her first day back at like 8AM and says "I saw $THING wasn't working last week, everything's good now?" Yup. "Okay thanks!" and left. Comes in a few more times asking about $THING over the next hour, kind of weird but not unusual. Runs into my office frantic right before lunch "John Doe just emailed me, $THING is down!" Turns out she was just reading her Outlook top to bottom, so was gradually reading earlier and earlier emails. So in her mind $THING was totally fine and gradually slid into chaos as she read older and older emails.

That was an exciting few years, I have to say.

Oh yeah. Sales sets the ship date, which is 'set in stone' because of a trade show. PM makes a schedule that makes the ship date. PM shows the schedule to engineering and is told it's not possible. PM tells management what engineering said, and management tells the PM to make it work, we need to give sales what they need. Oh, and you can't add more engineering resources, the project isn't that important. PM tells engineering to 'make the schedule work' and we add time to some tasks, but then necessarily take time from other tasks. Then engineering starts the death march, with everyone dreading the inevitable escalation of complaints about the project being late. Start slipping schedule? Let's have a bunch of meetings to rearrange the schedule so we can pretend for a week that we're not behind and let the PM feel good when he gives the weekly update to management.

Of course there's blame on the engineering side of the table too. We chronically underestimate effort, not adding enough margin for unknown-unknowns. So we start working late. Sandbagging estimates. Telling the PM whatever he wants to hear just to end the meeting and get back to work.

Impossible schedules are toxic for people that care, and encourage apathy as a coping mechanism. If you put in a Herculean effort and ship on time you did what you said you were going to do, what, do you think you deserve a cookie or something? The other option is failure. Even if the PM or management isn't upset, engineers still feel the failure of not hitting a goal.

Engineers need to feel wins. Always shipping late because of impossible schedules means no project is a win, no matter how good the design is.

At a former job I found out after a couple years that impossible schedules was a business strategy by the c-level execs. It encourages engineers to work as 'efficiently' (i.e. as much) as possible. God forbid we clock out early because we're not stressed out about being behind. Learning that made me shift from caring to apathy. I left shortly after, but I wish I had stayed a bit longer, it might've been nice to have a job that I didn't care about so I could focus on other areas of my life.