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.)
workplace.stackexchange.com/users/16983/David K
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.
workplace.stackexchange.com/users/80678/LaughU
"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.
workplace.stackexchange.com/users/83963/Twyxz
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...
workplace.stackexchange.com/users/75821/Solar Mike
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.
workplace.stackexchange.com/users/28773/Host Color
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?
How to tell my freelance designer to deliver on time
workplace.stackexchange.com
<communication><colleagues><freelancing>
workplace.stackexchange.com/questions/128953
workplace.stackexchange.com/users/99642/nshunz
Be honest about your reasoning. Tell the designer that you can only work together if deadlines are met. The best choice in this situation is probably just be honest and explain that they will need to meet deadlines in the future if you are going to continue working with them. You could add an ultimatum if you think it is necessary.
The best policy in this situation is probably to be honest and simply explain that you can only continue to work with them if they meet their deadlines. If you think it's necessary, you could consider adding an ultimatum if you can follow through on it.