Great article. When I worked at $OldJob, the leadership wanted an unsolved, research-grade problem solved in a few months. They demanded estimates, then refused to accept estimates beyond their timeline, then tried to hold people "accountable" for missing the estimates. Of course it was a mess, and of course we failed to hit our goals, and of course many many people burned out.
But I noticed that some people handled the situation fine. They stayed on management's good side, even though they were failing to deliver along with the rest of us. I will try to distill what I observed them do:
1) They did not fight on the estimates. If a manager forced them into a certain timeline, they registered their disagreement and just accepted the new timeline. I think they realized that fighting would just make the manager judge them less capable. (Pick your battles, eh?).
2) When the schedule slipped, they would communicate it in a way that made them seem more competent instead of less. The explanation usually had three parts: unforeseen events kept us from hitting the deadline, we accomplished some great things in the meantime, and here's why we're in great shape to hit the next deadline! For example: "When we made this schedule, we did not realize that AWS nodes were so unreliable! Despite this, our team has made incredible progress on implementing a fast method of storage and solid compression! We have reworked the schedule to reflect this new information, and we are already on track for the first milestone!"
It's possible that this trick just worked for the specific situation at $OldJob, but I really enjoyed learning it. They seemed to understand that certain explicit rules were not important, but that other unspoken rules needed to be followed. Are accurate estimates important? It depends on the situation! Sometimes wrong estimates can be more valuable than correct ones. Construction companies give wrong estimates all the time in order to win projects. Is staying on good terms with your boss important? Yes! Even if they are total shitbags, being adversarial won't help, only leaving will. These people demonstrated that there are often ways to fix a bad situation by breaking some explicit rules and carefully following implicit ones, and I wish I had the acuity to see these possibilities on my own.
> 2) When the schedule slipped, they would communicate it in a way that made them seem more competent instead of less.
In other words: Enable the bad estimates, then externalize accountability when they can't be achieved. In the past, I called these people "blameless go-getters" because they were always first to volunteer to take on work, but somehow it became everyone else's fault when they failed. If management is asleep at the wheel, it's a win-win situation for them.
You're exactly right that this method works in many companies. Like you said, it's all about understanding what the company actually values. When unrealistic schedules are forced on teams, the exact date might not be important. Instead, it might be leadership's dysfunctional way of emphasizing focus, urgency, and quick iteration. The savvy engineers and managers know how to put on a show that hits these key points while steadily delivering progress in the background.
Still, there's no escaping the fact that this is dysfunctional. More importantly, it doesn't have to be like this. It's eye-opening to move from a dysfunctional company like you described toward a company that values honest communication and understands engineering project management at the executive leadership level. When hiring someone out of a dysfunctional company like you described, it can take some time to break them of bad habits around schedule misdirection and estimation dishonesty.
If you look at the examples, they are clearly on the format "get the unavoidable problem -> understand the root cause of the problem -> fix the root cause -> tell your manager what you did".
Those people are basically doing their managers' jobs, and telling them that. If the managers aren't technical, they would be completely unable to do it, and are probably very afraid of somebody finding out, having somebody doing it will bring a lot of confidence.
> ... there's no escaping the fact that this is dysfunctional.
It may be "dysfunctional" but it is how things get done in many places.
Even in places where people pretend to follow a strict "Agile" methodology, there's often a level of management that is brokering deadlines and promises for the "completion" of the whole damn thing.
This strikes me as an understandable but pathological response to managerialism. Managerialism being our current dominant business philosophy.
To see it in contrast, think for a moment about a well-run hospital. At a hospital, the people who make the key decisions about cases are medical professionals, not managers. If a surgery was supposed to take 4 hours but takes 12, well, that's how long the surgery took. Everybody recognizes that the 4-hour number was an estimate, and estimates are not commitments. The most important thing is patient health, not manager feelings. Managers help organize the work, but they do not control the work.
I would love to see software development become a true profession, where stroking manager egos by making them always feel correct and in control is not the most important thing.
Yeah, this. At my current company, which I would consider large (20k+ employees) and bureaucratic, we've actually gotten this part right. Managers in no way control what the team is working on or deadlines for that work. They behave more like career coaches and therapists. They DO ultimately have control over your career, and I feel like that's a part here where having a good manager matters. But it's very rare for them to step in and shape the teams sprints etc. This is all in my own experience, so it probably depends to some extent on the department you're in and your manager in particular, but I can say this is all true for every team in my department.
The managers are held accountable by their bosses, but usually what this boils down to is teams not doing what they said they would. Which of course happens from time to time because as the article mentions we're all pretty terrible at estimating and shit happens sometimes. It makes me nervous to think about changing jobs because it sounds like this is NOT the way it is in most other places...
> Managers in no way control what the team is working on or deadlines for that work. They behave more like career coaches and therapists. They DO ultimately have control over your career,
I work in a place like this. It's a horrible idea. It's politics 100% of the time for managers, because there's no other way to climb for them. Welcome to half-brained initiatives and goalpost technologies being championed rather than ROI exploration and derivation, because the managers that do get stuck on projects that cost money don't want to talk about that.
Same in the arts, until you get a Heaven's Gate or other big artist-driven films that flopped at the box office and ate up UA's budget and then company. The studio model is savagely more effective at survival.
This works because no-one is demanding estimates because they want to know the answer, they are doing it to apply pressure to get it done. The project manager is being subject to the same thing, and if her minions are savvy enough to provide a story that she can take to her management, and if she's smart enough to realize that's the most she can realistically hope for, a sort of equilibrium is achieved.
Stakeholder management is an important but often forgotten art. Keep them up to date on what they can expect. Don't fight them, just inform them. If a deadline is unrealistic, don't fight it, just let them know you cannot commit to that deadline with any certainty. Once it's clear you're not going to meet that deadline, let them know in advance.
- CYA above all. The chances of a significant project succeeding in such an environment are pretty slim. Prepare your umbrella from the get go for when the inevitably will hit the fan. Some heads will have to roll, and you will not be easy pickings as you have been prepping for this since day 1.
- Greenshift like there is no tomorrow. Your manager is going to anyways until 80% of the budget is spent and the last thing she wants is someone pooping on her parade. Always be positive, but make sure not to get caught on factual lies. Remember, you don't want to be the one easily thrown under the bus when she needs to find a scapegoat.
I think your two points are really important soft skills or work politics skills that apply transferably to any job.
Your points illustrate:
- Communicating your concerns clearly and in a timely manner,
- while also committing to do the work as it has been agreed to the best of your ability,
- and also communicating your progress clearly and regularly.
> there are often ways to fix a bad situation by breaking some explicit rules and carefully following implicit ones, and I wish I had the acuity to see these possibilities on my own.
Now extrapolate that to working in BigCo, which has tens of thousands of employees worldwide, with each country having its own unique unspoken rules and hidden undercurrents. The greatest lesson I learnt is the importance of giving people the benefit of the doubt unless they've really proven they are a bad actor, because over and over again problems turn out to be cultural at base.
But I noticed that some people handled the situation fine. They stayed on management's good side, even though they were failing to deliver along with the rest of us. I will try to distill what I observed them do:
1) They did not fight on the estimates. If a manager forced them into a certain timeline, they registered their disagreement and just accepted the new timeline. I think they realized that fighting would just make the manager judge them less capable. (Pick your battles, eh?).
2) When the schedule slipped, they would communicate it in a way that made them seem more competent instead of less. The explanation usually had three parts: unforeseen events kept us from hitting the deadline, we accomplished some great things in the meantime, and here's why we're in great shape to hit the next deadline! For example: "When we made this schedule, we did not realize that AWS nodes were so unreliable! Despite this, our team has made incredible progress on implementing a fast method of storage and solid compression! We have reworked the schedule to reflect this new information, and we are already on track for the first milestone!"
It's possible that this trick just worked for the specific situation at $OldJob, but I really enjoyed learning it. They seemed to understand that certain explicit rules were not important, but that other unspoken rules needed to be followed. Are accurate estimates important? It depends on the situation! Sometimes wrong estimates can be more valuable than correct ones. Construction companies give wrong estimates all the time in order to win projects. Is staying on good terms with your boss important? Yes! Even if they are total shitbags, being adversarial won't help, only leaving will. These people demonstrated that there are often ways to fix a bad situation by breaking some explicit rules and carefully following implicit ones, and I wish I had the acuity to see these possibilities on my own.