Unique Challenges Of That Very First Experienced Hire

You're about four or six years into this thing. So far, your success has come in part from hiring inexpensive eager young people who wanted to build something with you. They didn't hesitate to jump in and do things which were new to them; they positively loved living on the edge and figuring things out, building the plane while it flew, just above the trees. Or, as I like to say, "diving into an empty concrete pool and hoping to invent water on the way down."

Your firm literally thrived on everyone wearing lots of hats. You look back on those heady days, though, and you tend to forget the terror and suboptimal results and remember the glory of jumping off a ski slope, way ahead of your skies, while another staff member kept looking to make sure that they had hit RECORD on the old GoPro.

But now it's a bit different, and you're being judged by more senior clients who know competence when they see it. It's time to fold what you paid two less experienced people into that single person...with experience. This new person isn't a tabula rasa that you can fill with your own way of doing things, but someone whose experience you can trumpet—versus someone whose inexperience you try to hide—and who can think on their feet and handle a slightly adversarial client meeting without you there. Maybe even better than you would have handled it.

But moving from "everybody does everything" to "highly experienced practitioners" isn't easy, either, and that first really qualified person you hire is often sacrificial. Think of the new guy assigned to lead the assault team into the breach, and the odds are just about the same.

What happens with that first highly qualified person you hire? It could be a Creative Director, VP of Engineering, Senior Account Director, Director of Business Development, Chief Strategist, or anything like that. Here's what happens, and why that first hire is usually sacrificial:

• They are not as entrepreneurial as your team. They are used to having policies and procedures, multiple meetings before decisions are made, and fail-safe research before signing off on things.
• They are used to delegating rather than rolling their sleeves up. They accepted their management role by giving up the dirty work, and now they are above that. "All hands on deck" means "all the other hands on deck."
• Your expectations are too high. You've stretched financially to hire this person, and they might even be making more money than you! You've made this leap, finally, but you feel like they had better deliver, and quick. Time slips by and you don't see the progress you expected and your patience gets even thinner.
• They bring in their posse of like-minded contractors and suppliers and software tools and ways of doing things. You welcome large swaths of this, too, as you worship at the altar of emulating the big firm that grew like you've always wanted to grow.

So, what's the solution? I always think of this story when I think about that question. A patron walks into a cafe and says, "How much for a cup of coffee?" The reply is "It's $2". Then comes the second question, "How much are refills?" The waiter says, "Oh, they are free." The smart customer says, "Okay, just give me a refill." What he's done is skip the first cup, but you can't really do that when hiring in a new style.

I guess one option is to make sure you never hire a friend for that first big hire! Or, maybe just inch up to more experienced hires and keep your expectations realistic. If you run a dev shop of 25 people, it's very unlikely that someone who has spent their entire software engineering life at Google or Twitter is going to make a great employee for you.

Hire in smaller steps and don't think that first huge hire is going to always work out.