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5 Comments

Collaborator dating

I wanted to ask for anyone's thoughts.

I've been sending around a idea for simplifying the elderly care search process. During that process one ex-CEO type said he was very interested in that space - it was in his top 5 things he would want to see happen. He then proposed if I would be interested in collaborating on it.

I believe his strengths are leadership, sales, deep network, passion for the space. I'm more worried about compatibility - as I don't know if we're on the same page on many issues that could sink the collaboration.

My plan is to take 4-5 months to slowly see if there is compatibility.
If you have any thoughts on this please do share.

on May 10, 2022
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    If you are worried, how about:
    a) you both do a little test project that is not directly related to the actual project, but that results in you getting to know the other person really well? Set a deadline for a month and see what happens. Or,
    b) You both don't become business partners for now, but agree on an easy to dissolve contractual relationship, e.g. you hire him as a freelancer for a fixed timeframe and fixed fee. That way you are limiting your downside.

    In general, if you are already worried now, spend some extra time on figuring out if these feelings are imaginary ... or warranted.

    Note: the post title is a bit misleading ;)

    1. 1

      Great thanks - a test project that is not related is a great idea plus a deadline.

      If he doesn't agree to it then it's already a good filter.

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    So as an update to this I had a coffee chat.

    Here we shared personal backgrounds, what upsets us about people we worked with, lay the table clear on many items. I think what made it work so well was our common ground of having worked with folks before who weren't completely honest with us. So this gave common ground for how we would want to work with each other.

    So as a beginning, we're just going to pass back and forth more about this idea to see if it has any potential. And I will continue to discuss all other aspects I worry about open and honestly to see if any red flags come up.

    I'll continue posting about this xp if anyone finds it helpful...

  3. 1

    If you have the budget just hire him for a short period to test him.

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      Hmmm.... that's a good perspective to take would I hire him? I hadn't thought about it that way. The way it would split would be I'd focus on technical he can focus on biz side.

      I have a coffee chat with him today and will post my results here.