Take the Lead in Your Remote Work Relationships

At the beginning of a new project, it’s easy for the freelance remote worker to leave the decision-making about the project to the client. Often, I find myself thinking, “Well, they know what they want; I’ll let them explain it.”

But it can be extremely valuable to promote conversations about your remote working arrangements with clients yourself. By taking the lead in initiating discussions, you can:

  • Communicate your enthusiasm for their project.
  • Raise — and propose answers to — questions the client hadn’t even thought of.
  • Identify your preferred working arrangements, technologies, and so on, and have a good chance of having them adopted.
  • Set expectations early, and make sure everyone’s on the same page.

Recently, a client asked me to send me an outline of my rate for a project. Ordinarily, I’d have done just that — and only that. But this time, I decided to take a different approach: along with that information, I explained some of the thoughts I’d had about the way we might work together, and asked a few questions.

There was nothing unprecedented in my message — I included information on the standard hurdles remote web workers need to cross when they start a new gig — but raising these topics up-front, before the project’s terms had even been finalized, helped to set a certain expectation between myself and the client.

First, let’s look at the topics I raised, in addition to the rate question the client had asked.


The rate I provided was based on a certain number of hours’ work each week, so I explained my weekly availability and capacity to take on extra work as required.


The discussion of time lead me to consider workflow, and how we’d manage that in a remote, yet close working situation.

I outlined a few of the technologies we could take advantage of, and explained how I thought they could fit together to help the work progress smoothly. The brands weren’t important; the main thing was the capabilities they had and how I thought they might support the project.


In outlining a proposed invoicing schedule and payment terms, I explained that my time-tracking tool would allow me to provide an account of all the time I spent on the project.

This lead to a quick outline of my invoicing timeframes and terms, and allowed us to agree on a payment frequency and method that suited us both. This client is located in my country, and will be paying me in local currency; otherwise we’d have needed to decide that too.

This information prompted questions from my client about tax, benefits and other aspects that I hadn’t considered to be a part of the deal. The answers to these questions tend to vary with the freelancer’s, or client’s, locations, so it’s important to address them early on.

Other Questions

By putting my cards on the table so openly, I encouraged my client to do the same: he sent back a few questions about whether I could meet with him every few weeks, how might fit in with other team members’ schedules, and the kinds of additional tasks he might ask me to participate in.

Again, this expanded the scope of our discussions and the potential for our relationship up-front. By discussing these questions in advance, I’ve made clear my enthusiasm for the project, and helped speed up the decision-making process. Now the client’s in the process of working out where and how I might fit in with his plans.

Setting Strong Foundations

Clearly, being up-front is a good idea when it comes to establishing boundaries — and scoping out the possibilities — with remote clients. It achieves all the points I outlined above, but it also sets one other crucial expectation: that my time, and my contribution, are valuable.

This is something beginning freelancers often struggle with, especially if they’re remote, and the approach I’ve outlined here is a good way to imply a sense of partnership, and avoid winding up in the standard employer-freelancer (or tyrant-slave!) kind of arrangement. By showing respect for the client’s project, the client, and yourself, you can help to ensure you’re seen as a valued ally. And in the world of web freelancing, that’s exactly the kind of reputation you want to build.

What kinds of issues do you try to anticipate, and questions do you try to answer, to set the right tone with your clients at the beginning of a working relationship?

Image by stock.xchng user memoossa.

Related GigaOM Pro content (sub. req.): Enabling the Web Work Revolution