[ChrisDutrow]

He was set up to fail in this scenario. Lack of oversight and prompt feedback when he started slipping caused this situation to snowball.

Some personality types can handle this amount of autonomy, but most people cannot. Most people need more structure than what existed here. I also think highly creative people are even more likely to slip.

This is a reason why startups are so hard, it's really hard to put together an organization where people can be productive together.

I have three remote workers and I check in daily. When someone inevitably starts slipping, I try to let them know immediately. Otherwise it's my fault when I have to fire them and destroy value that I worked to create. It's throwing money down down the drain in the form of training, familiarity with the organization and acquired skills.

[ArkyBeagle]

IMO, you have to be a bit... "spiky" ( as Eddie Izzard might say ) to work independently. It's worth being a bit paranoid about expectations. This means you have to manage expectations, design deliverables very carefully and perpetually review them.

And if you don't hand in progress reports, do them anyway and keep them for audit - you'll need them eventually whether there's any conflict or not.

It's nearly impossible to describe just how ambiguously most people communicate. I've been places where I was in-house and it got to the point where I simply made it a point to be as irritating and lawyerly as possible, not long before I left. It at least communicates "I'm not the one giving up here..."

[ChrisDutrow]

This is a really good point. When I think of the people who I've worked with who are successful without structure are usually a little bit paranoid/neurotic. Even if no one has checked on them for months, in the back of their head, they are still concerned about the repercussions of slacking off.

I should note that people without this personality trait can be successful too. But in their case, the repercussions for slacking off must be real and immediate (usually just being verbally called out). As a business you must have systems in place to know when this is happening.

There is another type of person who cannot be successful at all in this scenario. They will do everything in their power and intellect to get away with slacking off. ...Oftentimes because they cannot stop themselves from slacking off so their options are either: quit, get fired, or try to get away with it. Most people don't quit.

[thelynchmob1]

You're totally right. You pretty much nailed it. I'm not one of those paranoid/neurotic people at all.

Funnily enough, this is why I've been a lot better at freelancing: I get instant feedback from the client if they're not happy, and I get instant rewards (payment) when I finish a job to a good standard.

[ArkyBeagle]

I think it can be developed as habits. Really, it comes down to just another checklist, but it may be a checklist you have to sort of muse about now and again - "is that really done?"

[thelynchmob1]

Author of the article here -- I think you're right to some extent, but if you can't handle that amount of autonomy, you shouldn't be working in a remote role at a startup. Also, I did a pretty good job of performing just at the level where I wouldn't get fired (in the short-term), but that I wouldn't have to work that hard either.