columnist Alison Green answers questions about workplace and management issues--everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

A reader asks:

I manage 15 to 20 part-time, remote freelancers. Let's say our end client sells access to a recipe database; my job is to find great recipe writers, teach them how to develop recipes according to our house standards, and then get them to create recipes for us on a regular basis. Once a recipe is submitted, I assign someone to test it, and then it is published to the database.

There's no real timeline to our need for new recipes, since we're just building up a back catalog of content. In order to keep things moving and to plan the schedule, I ask my freelancers to produce one new recipe per month. But consistently, after their first couple of assignments, the work comes in later and later. It's not that developing these recipes takes more than a month. It's that this is a side gig for everyone, and there are no real consequences to submitting late work other than inconvenience for me and the recipe tester.

How can I get my freelancers to complete their work on schedule, or at least on a schedule? If I stopped giving work to those whose work is late, I'd have to hire an entirely new team. I try guilting them by highlighting how much it inconveniences the recipe tester when their work is late, but it has little effect other than my getting lots of emails apologizing.

Green responds:

It sounds like you either need consequences for late work or incentives for on-time work, or a combination of both.

On the incentive side, can you offer a monetary incentive for on-time work? Paying a bonus for work received by, say, the 20th of each month gives people more motivation than they currently have to get things in on time.

On the consequences side, I hear you that you don't want to just stop giving work to late writers, since that would leave you having to hire a whole new team. But you're losing much of the value of your freelancers if you can't rely on them to keep commitments and get you work on time, so it's worth being open to the idea that maybe you do need to hire different people (and perhaps set up expectations with them differently from the start -- more on that in a minute). If you really don't want to do that, though, you still need to build in accountability somehow. One option would be to hire some extra writers so that you have more than you need -- and then let people know that you'll prioritize assignments for the people whose work is on time (and those who are late will go to the back of the line, assignment-wise, and may not get work as frequently).

The other thing I'd look at is what signals you're sending to freelancers, particularly when you first hire them. For example, make sure that you're talking about their work schedule as firm -- not leaving anything loosey-goosey. It's the difference between saying something like "we'd like to get these from you once a month" versus "we require one recipe a month, delivered no later than the 20th of each month." And when someone is late, that's a prime opportunity to reset expectations -- meaning that you'd call them and say, "This was late. What happened?" and "Going forward, I need to get these no later than the 20th of each month. Can you commit to that?"

Note that none of this language is saying "if you don't do this, we'll stop working with you" -- but most freelancers will assume that's the implication, and they should. If you don't actually want them to assume that, you can still reinforce the idea of accountability by instead saying something like, "If you think you'll be late one month, I need to know about it at least a week before your due date" or "If you don't think you can commit to that, let's talk about whether there's another schedule that would work for both of us."

I think, too, that in your head you have to be willing to let them go at some point, because if you're not, it's likely to come across in the language and framing you use with them. If you aren't mentally willing to consider cutting them loose if they don't meet commitments, then you're more likely to rely on trying to guilt them into action (as you've been doing). But if you know in your head that you will impose consequences after a certain point, it's likely to lead you to use firmer language, and that's likely to make people take you more seriously.

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