Should you Hire a CEO?

To all the solo-preneurs out there: I’m talking to you.

A lot of folks who I’m friends with, and probably you too, fall under that category. You either have your own business or you’re looking to make one and you’re probably doing it solo like solo-preneur.

Most of the time we try to be our own CEO, our own web guy, our own tech guy, our own video guy. One man show, right? That’s fine. Most folks who start in business start on their own in shoe-string budget. You want to test the hypothesis of your business and start generating some revenue before you double down on it. Although in hindsight that’s exactly when I wish I would of taken steps to do this and hire someone for that CEO position. 

Really what a CEO is, is a chief execution officer: the person who’s in charge of execution in the business.

I’m a big fan of the personality test stuff (like Myers-Briggs, Strengths Finder), and I’ve realized knowing a bit about what my tendencies are has been a big help to making the right decisions. These tests aren’t a set in stone type of thing, but I’m an INTP which describes me well and means that I’m very focused on my own kind of world, and craft, and I can get into a place where I overthink things a lot of times. I am poor executioner, it’s just not a big strength of mine. I’m great at coming up with ideas, laying the pathwork, creating strategies, and the R&D side of the business… but execution is very difficult for me because I get so caught up in detail.

I was looking for someone like the ESTJ in Myer-Briggs, which I’m pretty sure is actually called the executive in most descriptions of it. When I went out to look for somebody, I put a post on Craigslist and did a couple of things differently. First off, I didn’t stick to the traditional format of a job listing. I really wrote out specifically what I was looking for in the person, and the responsibilities weren’t just these cookie-cutter “in charge of this, in charge of that”, it was more “are you willing to help solve very interesting problems that we haven’t even defined yet? Part of your job is to help me find those problems” type of thing. It was more of an abstract description of the type of person I was looking for.

I put out a job listing on Craigslist and I got a bunch of great applicants. Interviewed a bunch of people and I actually put the pay at a little lower than my final number was going to be because I wanted someone to apply not just for the money, but I wanted them to be interested in the job. I also asked them to take a personality test and send me the results. I got a lot of interesting people and I ended up hiring a perfect fit (I’ll have to do a whole post on that whole process too). The main point is, I found somebody whose strengths complemented my weaknesses. They’re very organized, great at identifying time lines and asking the “Hey, have you done this yet?” It was framed as almost an assistant position but in reality it’s assisting me in the business while I focus on strategy and developing the business. I need someone to help do a lot of the footwork of building a company.

My suggestion to you is, if you’re in a place in your business where you’re seeing some results but if you’re feeling stagnant and overwhelmed, it might be time to hire a CEO. To a lot of people the barrier to this next step is the fear that “it’s too expensive”, but in all honesty the value it brought to my business right away was 5x the revenue. It may have been partly placebo effect in the sense that I just took it more seriously because I had bigger responsibilities now that I had someone else working with me. This person works directly with me every single day in the office. When we’re working, we’re working. It’s amazing that mindset shift that happens when you start going from, “This is kind of a fun thing I’m working on my business, and it’s pretty cool” to “Wow, I have a business. I have responsibilities” and execution is the most important thing at this point because I’ve got a lot of the strategies proven. It’s time to execute.

This whole process was a big shift for me. I’m a very …perfectionistic when it comes to my work. I don’t like letting go of things so this was a very big jump for me. But it’s paid off really well and I’m excited to see how far it leads.

Something you can do right now if you’re on the “should I hire a CEO, or should I not?” fence:

Just start the process of interviewing people. You don’t have to accept them, and if you do then maybe make the pay incentive-based to start. You could also do a base pay plus incentives or incentives based on the profit of your business so you don’t have to go off the deep end and take a hefty business loan to make it happen. You can just work with the person to make sure their needs are met and that the projected goals for both of you pay what you both need. I would say right now, go out, start interviewing people at the very least to start seeing what possibilities are out there for you.

Another thing, I love It’s a free test for a ‘Myers-Briggs’ style personality test (the one I used for the applicants, and myself). Go take it to find out what your tendencies are, and then my suggestion to you is to find your opposite, or the personality tendencies and strengths that will complement you best.

If you’re on the edge of this decision, let me know in the comments. I’d love to hear where you’re at and what hurdles you’re currently facing.

Until next time!



1 Comment
  1. Jeff McDermott

    This is me, exactly me! I suck at execution, I know how to do it but I just do not enjoy it.

    I have some great businesses that I have built but I just don’t run them.

    Any help would be appreciated

Leave a Comment

Your email address will not be published. Required fields are marked *