Remote Work Expectations: How To Set Them And How To Manage Them

A lot of our remote work articles examine how to find remote work; however, some of them – like this one – are more concerned with managing remote workers. Many digital nomad entrepreneurs will, over time, need to hire teams of their own and when they do, they’ll mainly hire remote workers.

For many new employers, this leaves a big question. “Remote work expectations: how can you set them with your employee and how do you manage them?” Well, having been burned once or twice and having had a few successful attempts at hiring other people over the years – this is what we’ve learned.

Work Out What Matters To You


Firstly, it’s a good idea for you to have a written job description of some form and for you to understand that this should not be a shield that an employee can use to say; “not my job.”

If someone’s taking a salary and your instructions are reasonable and they are capable of doing the job, they ought to do the damn work. You ensure this by adding “and any other reasonable duties” to the job description. It’s a nice catch-all that spells out the reality of the situation from day one.

No, the reason for a job description is so that you can communicate the essence of the role:

  • What skills must they have to succeed? Be detailed – if you want to hire “a writer” what will they be writing? I consider myself to be a decent writer, but I can’t write fiction of any kind and my poetry is beyond awful. If they’re to code for you – what languages do they need? What technology stack?
  • What other qualities matter to you? Remote workers need to be held to a standard but what standards are important? If you need somebody to attend a weekly meeting, then it’s best to get this upfront. That way a potential hire that doesn’t do meetings won’t apply. Do they need to talk to customers? Will they interact with suppliers? Write it all down.

Then cut it back. An honest employer is going to end up with a very long list of tasks if they want to write a job description from scratch.

Once you’ve got your list you need to go through it twice. On the first pass, cut any unnecessary language – get sentences to be as short and simple as possible. This eliminates room for confusion and means you can get more in on the second pass.

The second pass is where you start to boil this down to the essential skills. If you have 8 pages of notes – you need to get them down to a maximum of 2. That’s because you cannot reasonably expect someone to read and understand 8 pages of notes before they even apply for a job.

If you can’t do this yourself, you can always outsource it to an HR consultant to do it for you but, truthfully, it’s not hard to write a job description – just a bit tedious.

Don’t forget to add “and any other reasonable duties” at the end. Yes, we had a lousy employee where a business partner forgot to put this in his contract. He would throw a tantrum every time he was asked to do something he saw as somehow “beneath him”. He was an idiot. So was I for letting that slip past me.

That’s A Start: The Future Is Communication

Telling someone their rough duties is an important step forward but it’s not enough by itself unless you’re very lucky.

You need to make time, at least once a week, to confirm your expectations to your remote worker in writing – for that week.

  • Clarify deadlines
  • Clarify deliverables
  • Get confirmation that your remote worker agrees to and understands what you’re asking
    • Call them and talk to them if you’re not certain after talking to them via e-mail or Slack or whatever you use

If you’re the kind of remote employer that likes to see when someone’s online – tell them that too. Make sure that they sign into Slack, Google Hangouts, Skype or whatever project management or communication tool you use.

When I work for clients, I tend to leave their chose tool open all the time. But they understand that I may not respond immediately but will come back to them when I’ve read and understood (which may be the next working day).

That’s because we set out expectations upfront. When someone works for me, I don’t much care about them being online – all I care about is deliverables. If they have issues, I need them to tell me as they arise. Otherwise, as long as the work gets done – it’s cool, I don’t want to manage their time for them.

There are advantages and disadvantages to both approaches. I find myself able to draw from a larger talent pool than I might if I used a fixed working day. However, I also sometimes find myself waiting on an answer for longer than I’d like and have to leave a client dangling for a response too.

That hasn’t cost me any work, to date, but it might.

You should also make sure that your remote worker reports at the end of the week.

  • What was done?
  • What wasn’t done?
  • What obstacles are they facing?
  • Do they need any help?
  • A general outline of how they are feeling?

It is a good idea to cover these points in regular face-to-face video calls too but everyone should be expected to communicate what’s going on each week. You can’t manage your remote work expectations or their remote work expectations without data.

When Things Start Going Off The Rails With A Remote Worker


It is hard to get communication exactly right when working as a remote team. It is best, in the first instance, to assume that when something goes wrong – it is a communication problem and not a problem with the individual.

It is important, however, to address issues as soon as they arise. You can talk via Slack (or whatever) if you need to but I find that a video call is often the best way to work something through.

The questions you need to answer are:

  • What went wrong?
  • Why did it go wrong?
  • What would have stopped it from going wrong?
  • How can you implement that in the future?
  • Do they need additional support?

In essence, focus on the problem and not the person. Hiring workers takes time and money, ideally – you want to make the relationship work and reap the fruits of your mutual labors rather than going off the rails and firing people.

Having Said That: What To Do When Things Don’t Get Better With Your Remote Worker


If I’ve learned one bitter lesson in these last few months – it’s this. Always trust your gut feeling when it comes to remote workers. If they don’t deliver once, start paying attention. If it happens twice, give them a final warning. The third time let them go.

Now, this doesn’t mean “come down on them like a ton of bricks for every little thing” but it does mean that if the big stuff – the reason that you employ them – isn’t getting accomplished, you need to move on.

Don’t be sentimental about this, either. Make sure you have a probationary period clause in your contracts and a disciplinary process too. Then use them.

I watched nearly $200,000 of a business partner’s money go down the tubes this year thanks to a bad hire. Sadly, the two other partners in the company (including me) had warned him that the guy was a waste of space, but he kept giving him another chance until he was out of funds.

Don’t be that guy.

No company can afford to carry dead weight for long. The trouble with remote work is that it attracts people who aren’t good enough and people who aren’t motivated enough to do the work. They then manage to get through an interview before they start to let you down.

You don’t have an office situation where you can micromanage them to get what you need (which happens everywhere in offices). So, you have to take evasive action early. Instead of working with them endlessly to get nowhere – if they can’t or won’t do what’s expected of them to a reasonable quality standard, let them go.

This is the ultimate moment of managing remote work expectations, it’s never nice to have to fire someone. But it’s even worse to lose a business because you didn’t. Trust me on this. We know.



The key to managing remote work expectations is communication. Outline the main skills and duties of the job in a job description. Communicate constantly even when things are going well. When they’re not going well – address it immediately. If they continue to go badly – cut your losses and move on.

Nicholas Barang

Nicholas Barang is a veteran digital nomad. In fact, he was probably "digital nomading" before it was called that. He believes that anyone can make a free and independent life if they want to. He wants to help those who commit to finding their own path. And to cut through the nonsense told about this "lifestyle" by those in search of a quick buck. If you want to reach him you can send him an e-mail to nick at You can learn more about him here - About Us

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