Hiring Employee #1

While I appreciate Carson's candidness in blogging how they do things, there's a couple of dangerous things in his recommendations.

"I’d recommend waiting until you’re overwhelmed with your work." This is a bad idea. Do not. Hire when you can afford to pay close attention to what you are doing. Your first hire is crucial to your company culture and direction, so you need to be on the spot here. Packed schedule and cognitive overload do not a good hiring setup make.

Additionally, that recommendation assumes that you are hiring someone to do the stuff that you don't have the time to do. While that's certainly true and helpful in many cases, it shouldn't be the whole truth. I like the maxim "hire people smarter than yourself". Because if you do, maybe you'll see that you weren't packing your schedule with the right things after all.

"Avoid hiring a friend as a first employee." Right, there is the fact that it potentially changes the dynamic. But not in all cases. If you, say, hire your closest friend since childhood, it's very possible that your friendship will survive anything the work life throws at you, and makes that in turn stronger. On the other hand, hiring a more 'distant' friend has the massive benefit that you not only know the person, but likely know their network, too, and there is no better filter or background check than sharing the same social circle. Carson does mention this in "ask friends for recommendations" of course.

"I’d recommend your first employee should be a designer with strong frontend dev skills." Um. What if that's exactly what we don't need? Ok, cheap shot, but it's a bit silly to say that everyone needs a designer-dev (then again, Treehouse training does prepare people for that...).

And while he says that you should start with freelancers, he doesn't mention that the first hire can also (in most legislations) start as a contractor or on trial period, which is a safety net for both the employee and the employer.

Because I suck at business, I've had had to hire employee #1 way too many times. Here's what I've learned:

1) Hire someone with skills that fill in deficiencies that you have. If you hate paperwork, find someone who is diligent. If you like meeting customers, find someone who will do the heavy lifting when you've sealed the deal.

2) Don't hire a jerk, and make sure you get non-competes and non-solicitation agreements in place. Take your prospect out to lunch and watch how they interact with the waitstaff. That's a good window into their behavior, unless they are very shy.

3) Be a good example - any character flaw your employee picks up on will be parroted by them if they can get away with it.

I'd have more, but like I said, I'm not too good at this :)

I respect Ryan and usually enjoy his advice, but I must say I disagree with most that's written here.

Having freelancers who have 0 emotional attachment to your vision build the first version of your product and then replace them with someone else is a really bad idea in my experience. Your #1 employee should be someone who is almost as excited about the product as you. Furthermore, they should ideally have substantial skills and experience and complement you and the rest of the founders well. Most important: they should be a culture fit. Competitive salary and benefits shouldn't be cruical for the first employee. Vision and stock options should. Trying to save money by hiring someone less experienced or indifferent to your vision does not pay in the long run.

Ryan's advice is more about economics, but I feel that, since we're talking about hiring the first person, it should have been about vision and personality.

Don't forget that when you get to the point of Hiring Employee #1, tell them that you may have to fire them or that they may be let go through not fault of their own if the revenue and expenses don't line up the right way.

I have had that conversation with each of my new hires (we're at 10 people). I want them to know up front that they're taking on some risk and that there's no free pass in a small company in the same way that there is in a big company.

That all may seem obvious to anyone reading here. It may seem to be an implied part of joining a small company (or any company). But that part of the conversation is important. It also reminds people that their work has actual value.

"Be generous with benefits" seems like a good policy in general, but should be optimized for employee #1 (and the next few).

I wouldn't feel a need to get excellent healthcare for my first few employees if they have existing good insurance on their own (I plan to keep my $100/mo HSA plan indefinitely), but I value a $10k equipment budget and basically unlimited Amazon book ordering more than they cost to provide, I'd value a place to receive packages during the day, including cases of ammo, far more than the cost to provide that. If you are a tiny startup, don't just do cookie cutter benefits, pick benefits your current and prospective employees would particularly value.

I'm not sure about spending a marginal dollar on benefits vs salary.

I had tweeted Ryan the suggestion of writing this post yesterday and am delighted that he's published it already. I was considering hiring employee #1 for WP App Store and this post has given me some extra confidence that the time is right. Thanks again Ryan. I'd love to hear experience and advice from HN'ers on this topic as well. Fred Wilson, perhaps a post of your own?

I haven't drafted the job posting yet, but if you're interested, sign up to the email newsletter at http://wpappstore.com and I'll send out an email in the next couple of days.

Would be interested in hearing stock option philosophy on first hire. (how much, vest schedule, etc)