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I have a question that was probably never asked before here in the workplace StackExchange. Let me give you some background about me first:

  • I own a small software company which isn't going well (financially)
  • Over the years I have had only a few clients (and sadly almost all of them refused to pay in time, or at all)
  • A few months ago a business owner of a small, but sustainable company (has been in business for over 20 years and made tons of money) contacted me about some minor programming work and was very impressed with it.
  • Because of that, he reached to me about a big project that he wanted to develop for quite some time, but never found someone good enough for it.
  • Over the time, I started to think of this person as a friend more than a client.

Now after giving all that background information, let's get to the point. My business is going awfully at the moment; I do not have any paying customer besides that person, and I am seriously considering shutting down my business and going back to work for somebody else if the conditions do not improve within a month or two.

Once my business is closed, before trying to contact any other company, I would like to ask that person to hire me full-time. Although I am confident (about 60%) that he might say yes to it, I would like to do it without "hurting" any current friendship in case he decides not to.

What's the best approach to do that?

PS: Just to point that out, in case it was not obvious: I have never discussed any financial problem of my company with him, especially because after all he is a client.

I am sorry for the long text; I just felt like it was necessary to give you some background information first.

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  • almost all of them refused to pay in time, or at all was there not a contract in place?
    – rath
    Commented Aug 6, 2016 at 10:02
  • @rath sadly yes, I was the one that messed up with the ones that refused to pay. I trusted the client too much and didn't specify any paying time in the contract. While with the clients that didn't pay in time they just delayed it for a long time (sometimes, as much as 2 months)
    – Jack O'neill
    Commented Aug 6, 2016 at 10:05
  • Wow... you want to give up just when your business is turning a corner? Going from one job to another is one thing, going from entrepreneur to employee is quite another. You brand yourself as a failure in some ways and it's a big change to go into. It has it's pro's and cons but mostly cons the way I see it.
    – Kilisi
    Commented Aug 6, 2016 at 11:19
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    @Kilisi I get your point, but my business is at the point of failure. I am not making enough money to sustain all the business related costs. I made absolutely no profit this year (I had to spend almost every single cent I earned). I have more costs than I can sustain and don't think I can keep my business any longer. It does not mean that I will permanently give up being a business owner. It means that I temporarily work for someone, for a few years until I'm confident again I can start a new business.
    – Jack O'neill
    Commented Aug 6, 2016 at 11:38
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    Do you employ people? Do you rent space? What are some of your largest costs?
    – a25bedc5-3d09-41b8-82fb-ea6c353d75ae
    Commented Aug 6, 2016 at 11:55

1 Answer 1

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What's the best approach to do that?

Just keep it simple but direct.

Approach him and say something like "As you know, I've shut my software company down. I'm now out looking for a permanent job. I've enjoyed working with you recently, and I thought I'd reach out to you and see if you happen to have an opening for someone like me? And if not, perhaps you could put me in touch with someone who could help me?"

I find that people don't use their personal network very well, because they are afraid to ask for what they want.

Many years ago, I worked for a startup. I was brought in to (among other things) help automate their software testing. As part of my role, I chose the software we used for our test automation - which happened to be provided by another local startup company.

When my company went public, it unfortunately went downhill rapidly. I decided I needed to find a new job. The first company I talked to was the vendor of the software we used. I called them and asked if they knew of any companies looking for someone like me. I figured since their customer list included people with my job description, they would know some. And I had really enjoyed working with them as a vendor.

As it turned out, the vendor itself was looking to fill my role in their company. We talked, they hired me, and I ended up with the best job I ever held in my entire career.

It pays to ask people for what you want, particularly if you already have a good relationship with them. If you ask pleasantly, they won't be offended (they may even be flattered). And even if they can't help you directly, they often can put you in touch with someone who can.

Just ask.

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