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A good friend of mine, James, is an unemployed graphic designer with a significant amount of time on his hands.

I really like his work and would like to commission him at his desired rate. However, I've asked him casually (although I did specifically mention that I would pay him his going rate, no more, no less) before if he would be interested and he said "No" in a very casual way.

I understand that he has no obligation to do this work and that I should respect his decision not to do work for me, but this seems to be a win-win for the both of us and I'd really like to convince him of this.

I also understand that situations like this can lead to awkward interactions. Dealing with significant sums of money, having to put time aside between us to work "professionally", and the risk that I don't like the work he's done could be reasons behind him denying the casual request.

The main drivers that make me want to specifically work with him are:

  • His style is something I desire
  • He has done free/work as a student for me before which the work I am commissioning would be based off of
  • I would expect we could have a good working relationship since we talk to each other often, potentially making the process more "fun" for the both of us
  • I want to support him in his career, especially since he is currently unemployed

How can I ask/convince him to do this work for me? Or at the very least, how can I ask him in such a way that he might give me a very specific answer as to why he wouldn't want to do this?

  • 7
    Have you asked him why not, and have you asked him if he can then recommend someone else who does equally good work since you really do need the work done and you respect his opinion? – Tab Alleman Mar 1 '18 at 21:01
  • So you asked him, he told you No, you ignored his answer and now you want to talk him into it. Do you see how this could be exactly the reason why working together as friends is complicated, in the first place? No offense, but the title of the question is misleading, it's not about asking a friend to do professional work (you already did that), but how to convince them to do something they don't want to do... – AnoE Mar 2 '18 at 12:50
  • @TabAlleman I did not ask him why not, because the question was asked in a very casual setting in a casual way and I didn't feel like it was a good time to pry/ask more. – Arthas Mar 2 '18 at 14:08
  • @Steve that's confusing to me. What specifically is asking in a casual way? That would help the answer writers I think, since this is a direct extension of that casual question. – user3316 Mar 2 '18 at 16:06
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    @AytAyt It was a conversation we were having while playing games together. I said something like "Hey, could I hire you to do some branding work for my website?" He brushed it off with a "No" which I attribute mostly to the fact that he didn't want to think about it while playing games. – Arthas Mar 2 '18 at 16:08
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he simply said, "No."

I don't know his reasons, but the elephant in the room is that working for/with friends has a tendency to result in drama and ultimately no longer being friends. Usually, it goes like the following algorithm:

  • Your requirements are not clear enough, because you treated this as a friendly meeting and not a business deal.
  • He does some work according to your unclear requirements, and shows it.
  • You change your mind (because your requirements were not clear enough). Perhaps you're a bit miffed your friend could not mind-read your expectations. You come up with new ideas.
  • Repeat, until he gets fed up.

Being friends means he will be more likely to do too much work for you, you will be more likely to take it as granted, and then you will both resent it when your mismatched expectations collide. Also, discussing money can get awkward.

This is like the "friend price". Will you pay him above market price because you're his friend, or will he do it below market price because he's your friend? Who gets screwed? This is an interesting question.

It is easy to fire an annoying client, or stop working with an unsatisfactory contractor, but this easy way out is not available if you're friends. This increases the stakes and the cost of failure, and therefore increases the likelihood he will have to do too much work to keep you happy, and he can see it coming.

If you want to hire a friend for work you should:

1) Make it clear you're aware of the above

2) Don't hire him to do the work, start with hiring him to clarify your requirements and brainstorm, and come up with a job description that you could use to hire someone. If you both come up with a plan that he likes, then you can discuss hiring him to implement it.

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    As someone who does freelance work, I really like point 2.) If the requirements become clear, you have something to give to the person you finally contract, and if your friend can imaging doing work to those requirements, he can do so with far less risk then in any other case. – Polygnome Mar 1 '18 at 23:15
  • "Your requirements are not clear enough" Having done plenty of work with professional clients, THEIR requirements aren't clear enough either. Just saying... – corsiKa Mar 2 '18 at 16:35
  • @corsiKa sure! It's unusual to have a client who knows exactly what they want... – peufeu Mar 2 '18 at 16:54
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First things first, he's already told you no, so whatever your approach don't get your hopes too high.

When you do approach it, offer up all of the reasons you think it'd be a good idea like you did above. It's also a good idea to acknowledge you heard him the last time you asked.

"Hey, I know you initially said no, but I wanted to ask you one more time if you'd reconsider allowing me to pay you for some design work I need. I'm looking for a style like yours and I believe we could have a great working relationship."

If he says no again, he'll probably elaborate a bit more on why he feels the need to decline your offer to help you understand why his answer is final. However, if he only says no, you could just say:

"Alright, I'll respect your decision and won't ask again. For future reference though, could I ask why?"

This approach is a safe bet because you're telling him that you're not looking for ways to convince him otherwise (by saying you'll respect his decision, and will not ask again). Additionally, by saying "for future reference" you're essentially asking him "Should I not come to you with future work inquiries either?" which is something you should make clear between the both of you anyway, if he's wanting to keep his friendships separate from his professional work.

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    I would tend to agree with this answer, although I might consider saying "allow me to hire you" instead of "allow me to pay you". It's not a big change, but the connotations are more businessy (to my ear). course, this depends a little on the reason for his objection. – Roland Heath Mar 1 '18 at 23:07
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There are so many great graphic designers looking for jobs that it really doesn't make sense to hire someone just because you are friends and happen to like his work. I'm sure there is someone else with great work and similar rates you could hire.

It's also incredibly unfair of you to continue to pursue this course of action when he already declined. You're not respecting his boundaries of friendship and before you ever actually work together you could lose him as a friend simply because he's tired of you asking.

Speaking from experience, you should shelve this idea unless and until he comes to you on his own. You already asked, he said no, ball is in his court.

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I have a friend who did some design work for me. Though he didn't necessarily get paid for it but that was due to me not having any money at all at the time.

Anyway, if you really want him to make something for you it should go a bit like this:

I will pay you X amount of money for this kind of design on this project and what I want is exactly this. We should put it on a paper and sign a work contract so that the details can't change too much later on. Also, I agree to leave the design to you and not try to tweak it, at all.

If he still doesn't want to do the job, then you can assume that he has a principle on this matter and won't work with friends professionally. You should consider the matter settled and move on.

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I suggest next course of action: ask him to suggest someone to do the job. He will request addition details. You should provide it for him. Also you explain how much you willing to pay. After all detail is clear he may suggest you to talk to someone (or maybe not). Then you casually ask him "how about you? Do you want that job?". You end up with better understanding what you need anyway. PS: try to not to waste a lot of his time, but show him that you really want his help, not excuse to ask him again.

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