Hackers, how do you control freelancers?

I think there are a lot of different things going on here that you might want to look at. Managing people is really hard.

As a direct answer to this specific problem, I think a first step would be to be proactive in explaining how you expect communication to work.

So for example you might want to explain when and how you expect updates from the freelancer (eg an update on when they expect a task to be finished, and then an extra update if they're not going to manage that deadline...)

That won't solve everything, not by a long way. But it's a start.

tl;dr My suggestion is start with micromanaging and once you get better with setting expectations and communication, release the reigns.

Hey Sergey:
I will share you my two experiences.

I can't design. I use contractors for designers.

The first designer I used was a friend. I love her designs. She's also a great full stack developer. Well, I asked for design and let her have it, no management. She returned a month later having rewritten the app in Redux and React. I call this "Resume Driven Development." I DO have a great design, but a big learning curve if I want to change anything in the app. This is problematic. Okay so I learned.

The second designer I used, I repeated had to say: "do not using anything other than generic Bootstrap." I had to say this at least 5 times. "Do not use anything other than Bootstrap." "It must be Bootstrap." "Yes, I am serious."
A week later, I have a nice website designed in nothing but Bootstrap....and a 1000 line custom css file :/

Do I like the work? Yes. Did the designer follow directions? No.

Managing is hard. Communication is difficult. Contractors do not read minds and it's my fault when I expect them to. I really need to work on managing and then saying: "What did you just hear me say? So what are you going to do?" Defiant, creative types. I get it. I am too. But like my tl;dr, the next time I work with a contractor I will further micromanage until I learn to effectively communicate with surgical specificity exactly what I am looking for. And get it.

I hope this helps.

I make sure everyone has specific tasks to be working on (I use Trello). I also make sure they have "ongoing" tasks which are repeatable so that they are always able to work on something if they don't have specific instructions. I spend a few hours each week making sure their trello column is as full as possible.

I also have a slack group and I insist that everyone says good morning and has it open while they are working. This helps me know when they're around and gives them the chance to banter with the other folks who are working on my stuff.

I've been working with freelancers around the world for many years. It's normally hard to monitor the progress of tasks that freelancers are working on.

Basically, two things are essential:

1. Use one of the time tracking tools - UpWork or RescueTime or similar tools. This cannot provide everything we need, but it's an important tool to add accountability in between.

2. Discuss the goal and time line for each task and make sure everyone is on the same page, understands the complexity and agrees the time line. Have a daily stand up meeting to update on progress. It's risky if there is no regular talks/meetings in between.

I've been thinking about this issue as well, some new ideas are to make the tasks as games and allow multiple freelancers to compete. The better performance they achieve, the bigger reward they get. But I haven't experimented the new ideas yet.

I beat them with a big stick ;-)