I have a really talented designer working for me remotely. No complains with his work but he always delivers them late. I couldn't handle it anymore so I stopped sending him work.

Just a while ago I received his message asking if his services are required. I want to send him work but also want to let him know that I will only do so on the condition that he delivers them on time.

How do I do this in a gentle way?

  • 1
    Hello and welcome, have you tried talking to him about this? Feb 13 '19 at 13:21
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    I have in the past but this needs to be in an email.
    – nshunz
    Feb 13 '19 at 13:25
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    Does he have any definitive deadlines, or penalties if they overrun?
    – user34587
    Feb 13 '19 at 13:31
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    How do you define "late"? Were there mutually agreed upon deadlines before?
    – nvoigt
    Feb 13 '19 at 14:26
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    @DavidK But sometimes the full realization of what you are committed to is not understood until you are knee deep in it and sinking fast.
    – Peter M
    Feb 13 '19 at 14:37

First thing is to be honest with him about the situation.

Jack, we have always been happy with the product you deliver and would love to work with you more. Our biggest problem is that things are never delivered on time. We can only agree to work with you if you can assure that you will be able to meet the deadline.

You also need to make sure that any deadline you are setting is reasonable to him and not just dictated by you. The problem in the past may have been that you set deadlines that he is simply unable to meet. (I don't know if this was actually the case for you, but it's still good practice in general.)

If we ask for a deadline that you think is unreasonable, then please let us know! We would much rather know a realistic estimate upfront than have you just agree to what we ask and then be late.

You can even add an ultimatum if you want, assuming you can follow through with it.

If we get a late delivery from you again, we will not be requiring your services anymore.

If you give the ultimatum, he's late, and then you hire him again, then he'll know that he can be late with no consequence. I also assume that you aren't paying him in full until you get the final delivery, otherwise there's no incentive for him to be on time at all.

Lastly, you can do a little preemptive damage control on your end by giving him a deadline that's earlier than when you actually need it. If he's usually about a week late, then tell him you need it a week early. If he successfully delivers to you on time, you can slowly move the bar back to normal, if you want. Or just leave the bar early for when he inevitably relapses (and he will. It's just a question of how much you can put up with it.)


I assume that the OP is in more or less good terms with the designer and therefore there should be a mutual understanding that work needs to be done.

In this light make him aware of the problem by sending him a mail detailing what needs to be done in order for him to get another gig.

In addition, if possible make a contract in the form of:

Deadline : X $

Deadline + 5 working days: 75% of X

Deadline + 10 working days: 50% of x

Deadline + 15 working days: no payment and no further gigs.

  • It might be safer to write the contract at 50% of what you are willing to pay, and include bonuses for earlier completion rather than penalties for later. However, beware the interaction of money on the human mind, it may not work out the way you hope. Feb 13 '19 at 15:58
  • @ChrisStratton that's what I put in my answer below...
    – Solar Mike
    Feb 13 '19 at 16:15
  • These type of reward structures are often well intended but ill conceived. Fines are counterproductive to creativity quality and cause price inflation. Under such a contract, the designer needs to increase his base rate in order to offset the risk of being fined due to circumstances outside his control.
    – MvZ
    Feb 14 '19 at 12:15

"One condition, do it on time or you get paid half".

If he has a track record for being late with work. A "gentle" reminder isn't going to change the fact that he won't be rushing.

Simple as that.

  • 1
    +1, but personally I found 5% or 10% / day more encouraging - With one day delay freelancer still has motivation to finish ASAP.
    – Mołot
    Feb 13 '19 at 13:57

One model that seems to work is not to decrease the pay for late BUT to offer a "bonus" for delivery by date X... If it arrives on time then pay the bonus...

A garage did similar, if you paid within 10 days you got a 10% discount - that quickly reduced the number of late payers...

  • I believe this is referred to as something like "30 days net, 10 days 90%" (or "10 days 10% off").
    – user
    Feb 13 '19 at 14:29

As I see it, the person probably has some issue with organizing oneself and this would be the reason to deliver late.

I don;t think you need to search for a gentle way to explain that. Just be open and say that if you have a deadline, you must deliver in time. As you like the designer's work, tell one that you appreciate his/her work and lot, but you can work together only if any deadlines set are met.


Pretty simple, delay payment.

Since you have already tried the direct approach you can either resort to threats or just save the grief and take action.

A lot of freelancers muck around while they don't need money, then quickly submit when they do and expect immediate payment. Delay the payment by ignoring requests for a little bit and they wake up their ideas.

When you do pay just apologise saying you'd missed it since you were expecting that project to be handed in on XYX date not YXY.

It's not a misunderstanding or honest mistake if it happens all the time. They know they're handing it in late, they just don't care because there are no repercussions.

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    The tit for tat response is pretty passive-aggressive and just avoids addressing the issue directly. It's not very professional either.
    – David K
    Feb 13 '19 at 13:45
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    Note: this answer may be plainly illegal in some jurisdiction, and may trigger penalty interest on such payments (for example, in Poland there is a law that makes such interest on delayed payment mandatory, wouldn't be surprised if it appears in other law systems).
    – Mołot
    Feb 13 '19 at 13:54
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    @Kilisi this wouldn't fly in any court, and you would risk paying late payment interest plus court costs (around $1000 in Poland).
    – Mołot
    Feb 13 '19 at 13:58
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    Maybe that's the case where you live. Where I live, if you delay payment, case in electronic court is fast, easy, and court bailiff simply takes money from your account and gives it to person you owe, and all you can do is to beg him he takes it in one part, because you are paying him for every action he takes. Oh, and he can lock all your accounts preventing any spending until your debt is paid, so in the end you may need to beg him to take your money finally, and release your bank account.
    – Mołot
    Feb 13 '19 at 14:05
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    @Fattie in such case, one could simply not accept the work at all. But if purchaser accepts the work, he has to pay, it is really that simple. And explanations like "dog ate my receipt" does not work.
    – Mołot
    Feb 13 '19 at 14:08

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