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> ANGSTING INSTEAD OF ASKING

This is a great way of describing one of my biggest peeves in the office: So many unnecessary conflicts/dramas can be avoided by simple and honest communication.

There’s a related dysfunction where managers are (wrongly) convinced that they must answer every question in the most positive and upbeat way possible. I had to leave a company once because my manager was frustrated with many people, including me, but he was too nice to actually explain what he thought we were doing wrong. He thought it was best to try to gently encourage us with hints and rhetorical questions and vague allusions to what he was actually thinking, but when you’d ask him for a direct answer he’d switch to “everything’s great” mode. The faux positivity turned into toxic positivity and destroyed morale across the team.



I had to work hard to avoid being the "angsting" type of manager. I care deeply about the people around me and it can feel (to me) like I'm attacking them when saying things that might be challenging.

The first time I fired someone, I was completely crushed. But I was lucky to have that go particularly well in the long run. It was clear to me why this person wasn't going to succeed with us. I offered to give advice during their ensuing job search and they took me up on it. They had two offers at two very different companies. It was clear to me that they would have the same trouble at one but would fit the other. They had the same sense and they immediately found more success than they'd ever had before. A year later they reached out to tell me that firing them showed more care than any manager / mentor / teacher had ever shown them and it helped them take the next big step in their career.

It's still not easy for me to say things that I think might make people uncomfortable. But the experience of firing that person is a constant reminder that speaking hard truths is the deepest kind of caring a manager can show.


"Radical Candor" is a great book that is 80% summarized by the following 2x2:

              Care
            Personally
               ^
    Ruinous    |   Radical
    Empathy    |   Candor
  --------------------------> Challenge Directly
  Manipulative |  Obnoxious
  Insincerity  |  Agression

Managers don't want to end up in the bottom right, because no one wants to be an asshole. Everyone remembers the negative impact of assholes, and it's very hard to challenge directly without being a dick. A common management failure (and definitely a personal challenge for me) is avoiding directness instead of building empathy. But I've seen a lot more aggregate damage done by large numbers of managers being stuck in the two left quadrants (ESPECIALLY ruinous empathy) and causing a lack of progress from excess entropy.


> So many unnecessary conflicts/dramas can be avoided by simple and honest communication.

It's really not that simple in my opinion. The flow of information is "upper management wants this a certain way/at a certain time, I'm just the enforcer, if you don't work to accommodate/comply at a high priority, it's a problem" more often than not.


There are worlds of problems in teams and organizations that have nothing to do with what upper management wants, especially as a company grows.

Disputes between two developers on a team, disputes between two teams, disputes between a developer and a team, a bunch of teams dogpiling on another team, etc...

The above ones aren't always the same as the "what do you think of me" example for "angsting over asking" but are generally still problems of communication - the other team isn't doing what you would want them to do because they don't know what makes things easier/harder for you, vice versa, etc.

Angsting instead of giving negative feedback is an extremely common one too, and leads to people being pissed off and blindsided at performance review time.


> Disputes between two developers on a team,

The way I've seen it: you should aim to be the developer avoiding disputes at all cost. If you are responsible for a dispute whatsoever, you're the problem child and will be dealt with (by management)

> disputes between two teams,

At my last job, managers were proxies to teams. Engineers were basically encouraged not to talk to other engineers because it would "distract them from whatever they were working on" and any ask you had for them needed to get approved by their manager/other management anyway.

> disputes between a developer and a team,

Again, teams didn't talk to each other. You tell your manager, they go talk to that team's manager. And that team's manager's main job is to say "no, we have no capacity for that", shielding the team at all costs, unless upper management says something/asks something. All initiatives had to come from above, not below.

> a bunch of teams dogpiling on another team, etc...

You get the idea. Team manager -> team manager


The problem I described was the opposite, actually: We often couldn’t tell what upper management wanted or was upset about because the manager was too “nice” to communicate it. We had multiple situations where something we built was unsatisfying to upper management for some reason, but couldn’t address it because the manager was avoiding negative communication or anything resembling confrontation.

Getting it out in the open so we could at least do something about it would have been better.


Yeah I like to call these types of management "smile f**ers". My last org was like this. All smiles, everything great, everyones doing a great job.

Except that behind the scenes senior management was very unhappy about certain things, and our entire org got its clock cleaned over the following 18 months. Senior managers moved aside, others downgraded to IC roles, pushed a few people out, new leads hired from outside, etc etc.


In some worlds there are experienced managers that know processes and systems inside and out. they clearly stand out as leaders. But in areas where there is a lot of ambiguity, change and innovation, sometimes NOBODY knows whether something is a good idea or not. What else are you supposed to do other than say "it's sounds reasonable let's go for it". Only later to get the results back and find out it was a flop. Now changes have to be made to make it look like effort is being made to reduce flops. Could it also be something like that?


If these are the only sorts of problems you identify in your workplace, you are certainly running the risk of being on the wrong side of the other ones.


So many unnecessary conflicts/dramas can be avoided by simple and honest communication.

Communication isn't enough. If neither side is willing to compromise then knowing what everyone is thinking doesn't help, and often makes things worse. There has to be a culture of openness and willingness to change in order to avoid drama.




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