What dating & delegating have in common

Let’s imagine you have a friend. (Hopefully, this isn’t too hard to imagine because you already have one or more of these for reals.) A single friend lookin’ for love. She’s mostly had good experiences, but goes on this one wildly horrific date. We’re talking sitcom levels of bad. And after that, she swears off dating entirely. She’s going to be a nun if that’s what it takes – no. more. dating. for this lady.

Seems a little extreme, right?

It does, doesn’t it? But – I see a lot of people doing something similar when it comes to delegating in their business. I’ve talked to people running very successful businesses who are still refusing to bring on any help because they had a bad experience once. Quite frankly, it’s seriously holding them back in their business.

Am I denying that bad experiences suck? No. 

Heartbreak – whether it comes from a bad date, an awful relationship, or totally getting screwed over by a service provider you thought you could trust – is no fun. It feels shitty. And you’re often left feeling like an idiot, too, for trusting someone and then having them later proven untrustworthy. I get it, I do. But you’ve got to pick yourself up & dust yourself off, and move on. (After you’ve soothed your hurt feelings with chocolate, of course.)

Once you’re past the chocolate and moping stage, ask yourself: what comes next? (And you’re in luck, because I have an answer for you!)

Here’s what comes next:

Analyze why it didn’t work & figure out what to do differently next time

  • Did a friend hook you up without firsthand knowledge? “I know a guy” can be a great thing to hear, but if you’ve been burned before and want to make sure you aren’t burned again, make sure that you get referrals from people who have actually used this person, and who are okay answering any questions you have. If you get a referral from someone who doesn’t have firsthand knowledge, email the service provider & ask for references and to set up a time to talk. Anyone who’s worth their salt will be absolutely fine with that.
  • Were there obvious personality incompatibilities? Did they expect you to do things that seemed absolutely off-the-wall to you? Did certain quirks of theirs grate on you like nails on a chalkboard? If so, try to figure out specifically what those things were, so that you can either look for them in the future or avoid them in the future. For example, some people want day-by-day updates – which is fine,if they’re paired with someone willing to do that and who understands that the client wants/needs that. However, another service provider might not roll that way – they’d rather check in only when a milestone has been passed. And if you’re laid-back and already have a full inbox, daily updates might sound like a nightmare.  If you’re incredibly clear on what you need and what you reallydon’t want, you’ll prevent future mishaps.
  • Did y’all have different visions for the future? You wanted a permanent team member. They wanted to work on one project and leave. Or vice versa. These problems are pretty easily avoided by having a “getting to know you” chat (which is something that you should be doing anyways). During that chat, clearly state what you want out of the arrangement and what you envision it looking like. Then ask them what they envision working together looking like, and what they want out of the arrangement.
  • Were there communication issues? In relationships of any kind, communication issues are the number one disaster-causing factor. Start asking yourself – am I assuming anything here? Am I hearing ‘tude when there’s no ‘tude? When all else fails, assume that people are being polite and trying their best until proven otherwise. (Which is a good rule of thumb in general, actually. Until they do something like telling you to go die in a fire. Then it’s probably safe to assume they’re just an asshole.)

Here’s the thing: even if you’ve had a bad experience, you’ve gotta get back on the horse if you want to find true love (and/or grow your business). Fun? Not necessarily – at least, not at first. You’ll probably be nervous for a little while. You might have some trust issues to work on. But eventually, you’ll get over it and be able to see the joys that come with having someone else do work that you don’t need or want to do (just like, even after the worst date ever, eventually you’ll have fun on a date again – if you allow yourself to do so!).

PS: Here’s some comfort for you – no matter how bad of a date you’ve been on, this date was worse. (If you have a worse date story than that, I have to hear it.)

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