How can I repair an awkward freelance relationship before applying for full-time work?

Question

Once upon a time, I did some freelance work for a local company. They were a big name in the sector, and I'd wanted to work with them for a long time. I never met the person who commissioned the work, but he seemed happy enough with what I'd done to keep on giving me regular commissions.

He eventually left, and his successor stopped offering me regular work. I kept pitching for it, but polite refusals. Eventually, after some months of persistence, he did commission something from me but he wasn't happy with the result. I re-worked it at no extra charge until he was satisfied, but I got the impression he was only barely satisfied with my effort.

We then had a couple of idiotic misunderstandings via Twitter. On the first instance I used it to ask him if he could reply to my latest pitch. He took offence at being asked that in public, and unfollowed me. On the second occasion I asked a question about his professional opinion on something which I did in the spirit of learning, and he took it as my challenging his point of view.

I have carried on pitching regularly, but not getting any work. He does continue to reply, however, so I presume he can't have been that offended.

We've never met in person, but it seems likely that we're simply two different types of people who are going to struggle to communicate well together.

A full-time position has just arisen at his company, and I would very much like to apply for it. However, as things stand I presume I'm just wasting my time.

Is there anything I can do to try and repair this relationship? Or ought I just to let this opportunity pass me by?

Answer 1

I doubt he's holding any particular animosity toward you: politely turning down freelance pitches sounds like part of his job, and unless the Twitter incidents got heated I doubt they've done much major damage (especially if you apologised at the time)

Not being happy with your previous work... well, that may influence his decision, but there's little you can do about that: it's one of the risks of being a freelancer, that after someone being unhappy with your work, you have little opportunity to repair that opinion. It's unfortunate, but it happened.

His opinion will be his opinion now, based on that project and your application. Attempting to discuss that project now will likely just bring it to the forefront of his mind and if anything may jeopardise your chances.

Answer 2

Just apply for the position if you want it and you think you are a good match for it.

If he is in a position to influence the hiring process (you don't mention this) and he feels negatively towards you, you won't get an interview. Then take the hint!

If he is not involved in the hiring process, or he feels positive or ambivalent towards you, you may get an interview if the recruiter feels you are a good match.

Either way you'll know the answer without expending (and therefore possibly wasting) much effort.