Hire someone who annoys you.

I’m lucky to have great people around me helping me run my business, and I’ve made some decisions lately to have people around me who annoy the shit out of me all the time. They are really good people and I actually like them a lot, but their jobs frustrate and annoy me, and that is a great thing. Owning a business gives you a huge sense of freedom, but not everyone is built for it. I personally never planned to become a business owner, or an employer, or someone who other people, you know, pay to do things for them. I’m just not really built for the responsibility of it, so to combat that I surround myself with people who help keep me accountable, keep my thoughts in check, and help me succeed at what I’m trying to do.

I hired Crystal recently to help me stay on track with a huge pile of deliverables that is always growing around me. This includes things like writing blog posts, Tweeting interesting shit, and helping to promote CoSupport and UserConf to our followers and friends. Yes, I have an entire human being on my payroll who exists to help me do these simple things because I am so, so bad at it. CoSupport is in the very lucky position of never having to need social media or marketing, so it’s just not something I invest in. But that makes me a hypocrite because I always tell our own customers: Master something before you ever need it.

So, Crystal’s job is to help me complete tasks I have been putting off or haven’t prioritized correctly. This means a lot of reminders from her, sometimes 3-4 emails in an hour about the same thing. Her job is literally to annoy me into work so it gets done on time and without error. Crystal is way annoying.

Here’s an example of what the kind of  emails I get for the to-do lists she creates for me:

Here’s the kinds of texts I get from her minutes after she has sent me an email:

THEN LOOK AT THE IM I GET ABOUT IT:

Here is me being annoyed at these reminders all the time:

But here’s the deal: I hired Crystal to do this. I sat her down and said, “I need you to get me to do this stuff, even if I am traveling and even if I am busy with customers or meetings. I have to get this stuff done.” And guess what? You’re looking at this post because I’ve gotten shit done, finally! Most likely, I did whatever it was I had to do because I was so annoyed by the reminders I requested.

Next, there’s Evan, who’s part of the amazing UserVoice team and co-produces UserConf with us. Evan is so fantastic and smart and funny, and he is annoying in a different kind of way. He prevents me from being rash, too spontaneous, and making bad, complicated decisions. Ten times a day, Evan and I have conversations that go like this:

Me: I HAVE A GREAT IDEA LET’S DO IT!!!!!!
Evan: That is not a great idea yet, let’s think about it.

Or:

Me: Can we do X for UserConf because I like X.
Evan: Let’s ask the attendees if they want X, then decide.

And here is me reacting to Evan:

OH MY GOD SO FRUSTRATING I AM A BRILLIANT CREATIVE. But really, if I didn’t have an Evan around to reign me in, chances are UserConf would be held on a cruise ship to Mexico without any insurance, and I would have surely set something on fire by now, and everyone would die. I know I’m a visionary and all, but I could really make people die.

You get the idea. These people are really, really good at what they do, even if it’s annoying to my precious snowflake entrepreneurship.

Ambition and drive are amazing things, but there has to be a balance of what you pursue. Every good idea is a path that can derail other ideas, so thoughtful consideration is a must, no matter how great of an idea you have. On top of that, if you don’t have people keeping you accountable to your work, that drive can veer way, way off course.

Surround yourself with people who can challenge you lovingly, correct you kindly, and push back against your big ideas with just as much gusto. You’ll find you’ll do better work, you’ll make better decisions that have greater impact, and maybe actually get shit done.