Using fake deadlines without driving your engineers crazy

The article would not be so controversial if it weren't outright saying "fake deadline". Of course you need a plan and a push, and stakeholders legitimately need (if only emotionally) some idea of when the builders will deliver. But on a charitable reading there are already terms for what it describes -- expected, target, soft date etc.

In my first engineering job out of college I was manipulated into working (on prem) into the early morning night, after I'd been there a few years. I couldn't help but think of that when I read

> If you think that a prototype might take a month, why not challenge the team to see what they can deliver by the end of the week? You will be surprised, and so will they.

Just being a kid and having my boss, a former professor I looked up to, expect that I could pull it off was enough. You have to be really careful "challenging" engineering reports like this -- need to actually use "see what you can do" language, NOT "deadline" (even if fake) for a 1mo->1wk timeline compression. He certainly acted surprised when I quit sometime thereafter. Hopefully he learned from the experience as well, I still appreciate my time there, just needed more experienced / realistic management.

I think we're talking past each other.

> I took a small company that was living contract to contract into a world where they started making millions in annual recurring revenue.

> There's no secret, magic bullet. All I did was make sure we were delivering progress at a regular cadence. Kept communication channels open. And tried to, but ultimately failed at, training the sales team to stop with the secret deadline negotiation

This is what I call hitting deadlines.

The industry is littered with software development teams that guessed when they could deliver something and failed.

If business can only depend on "this happens first, then that," well... they're either going to get lucky or fail.

It's just not how software development works. Knowledge work isn't a line in a Toyota factory. Scrum and agile all you want.

As someone else in another thread put it, you don't throw out your work just because it was delivered late. Knowledge is valuable regardless of how long it takes to acquire it.

> I think we're talking past each other.

Perhaps. I'm not saying that deadlines don't exist or shouldn't. I am saying that they're often unnecessary and most software teams can deliver value without them.

If you're in the embedded space there's no dodging deadlines. If you need to flash ROMs it could be months before you can do a release if you miss your deadline. You might not have enough money to survive until then.

If you're shipping boring, line-of-business enterprise SaaS you don't need deadlines. Customers want software that solves their problems and are happy with something that works for 80% and a steady rate of improvements over time. They want progress and milestones. There's nothing wrong with taking an extra week or month to reach the next milestone.

Where you get the "deadlines equal dollars," mentality in enterprise software is from the long sales cycle with the big price tags. A business is going to have reservations about dropping a few hundred thousand on a new software product. And so you end up with these negotiations between sales, management, and the software teams where you're lying about the deadlines to different parties in order to keep everything in line. I don't think that's a good way to go about it.

Especially when most of the time it's not even necessary. This was the finer point I was often finding myself in opposition to the sales folks with. Their reality was that deadlines are a negotiating chip they can't ignore. The software developers' reality was that any estimate about a deadline is completely made up of hopes, dreams, and unicorns. The easiest way to get people to work together, in my opinion and experience, is to cut out the lying and just be honest.

Some organizations like that, some don't. I went back into being an IC because I just can't operate at that level and keep my sanity/energy.

> I’ll go against the grain and say that fake deadlines are incredibly useful.

If everyone's on board with your definition of deadline and it always works that way, then sure yeah whatever I'm not going to argue the point.

But I'd argue the "fake" in "fake deadline" is admission to deliberately exploiting information asymmetry about where exactly a "deadline" sits between the "time box" definition of deadline and the "point when we stop working because the deliverable is now worthless" definition of deadline.