The First Step in Making Your Startup’s First Hire

Estimated reading time: 4 minute(s)

One of the most rewarding parts of my job as a startup founder has been meeting the nearly one hundred St. Louisans that I’ve talked to while hiring for my company, Curate.

When you’re hiring your first employee, it’s a little bit like a seventh-grade dance. It’s going to be awkward but everyone will enjoy it more if they know it’s a 70s theme ahead of time.

The key to helping those conversations go well has been ensuring that both people are on the same page. At Curate, we’ve laid this foundation through the job description. Here are three insights we’ve discovered about building your first job descriptions.

1. Build Around What You Need

It’s tempting to say, “We need someone to handle all things development.” In your mind, a developer should be excited about that freedom.

But that will scare great candidates off because you’re less than crystal clear about what you need. Define what you feel that you need as a company then build your description and interview questions around those qualities.

Reid Hoffman, in his book, The Alliance, presents the idea of hiring employees for a “tour of duty.” This a viewpoint where employees are hired for a specific function.

Do this from even your first hire. You should have a very tangible, measurable, and time-connected goal for what you’re wanting someone to help you do. This approach helps prepare them for what they’re committing to, but it also helps you if they fail to keep their end of the bargain.

For example, if you need someone to handle all marketing efforts, it’s fine to write that one of the tasks will be managing social media. However, before that, you need to define very clearly that they’re responsible for driving 200 leads in the next year.

This can cause a problem if you have no idea exactly what you’re needing. You can find out by creating some basic projections.

In the example above you could look at how many leads you had over the last few months and then take the average and grow that by 10 percent each month. If you’ve yet to have any leads and you’ve never exited a company before, you need to do the legwork yourself first to get the cadence and then bring in someone else better.

When preparing to interview prospective employees, write questions specifically around their experiences in doing what you need done. Avoid asking for opinions by starting questions with phrases like, “What do you think about.”

There is so much more insight that comes from asking questions that start with, “Tell me about a time when.” It’s OK if they’re unable to answer everything.

If you found the perfect candidate as a startup, you’d be unable to afford them anyway. This interview strategy helps ensure you’re both on the same page about specifically what their experience and capabilities are.

2. Choose the Right Job Title for the Position You’re Offering

Yes, you might offer a creative title like, “Chief Happiness Officer”, but keep in mind that people will have their own interpretation of what that really means. We once put up a position for a “Director of Customer Success” and we started getting some incredible applicants of amazing pedigree.

Just to be honest, I had absolutely zero context for what a “director” position even was. I learned pretty quick.

We ended up offering one of the candidates a salary of $50k. He turned it down because he was currently making $140k. Oops.

We never even asked him his salary goals. We just assumed he read through all of the job description.

When you give your first employee a title like Chief Technology Officer, you’re setting them up for failure. If you scale like you’re hoping you will, your first employee will be tremendous for covering all the development you’re doing now, yet in most instances there is just too little time for them to scale their knowledge and abilities to be over all development two years later.

Even more than the work, there’s an entire mind-shift in the approach to things that happens when you’re the “CTO” of a five-person company versus when you’re the CTO of a 50-person company. The other scary thing about throwing around titles now, is that you’re going to have to take that title away from them at some point when you are right-sizing positions.

Yes, it’s tempting to think that a title will sway someone, but let’s be real; if it’s the title that is convincing someone to leave their job for your company, you’ve got the wrong person. For the most part, people are totally OK with a position like “Developer.”

3. Be Transparent About Current Challenges

We’ve found, consistently, that transparency makes the right candidate more excited rather than less. We were looking for a digital marketer about a year ago and here’s how the description went:

“We’re trying to find someone who can help us build out our marketing arm. We have some leads coming in through free download resources but we really have no idea what paid efforts are being effective. Just to be transparent, one of the biggest challenges you’ll have is figuring out how to measure and drive leads with little in place. You’ll be expected to do this even though we have no idea how. Are you up for that challenge?”

It turns out this question excited people. People are used to hearing companies talk themselves up.

So, it’s refreshing for them to hear about your struggles. The key though, is stating the struggles then moving on.

Many times, we over-stated the issue. In retrospect, this was just to make me feel better and I was failing to give people credit for being able to hear me the first time.

In conjunction with the challenges, emphasize in the job description how big of an impact they’ll make. This is what makes the right people feel drawn to your opportunity. We attracted so many people who felt like a cog in a wheel at their current company.

It’s incredibly appealing to candidates to be able to walk into an organization with a transparent picture of what job they’re applying for and what will be expected of them. In the end, those team members who are up for the challenge of making a big impact are exactly who you need.

Especially if you’re going to get that seventh-grade dance event management app up and going.

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Ryan O’Neil bootstrapped his company into a multi-million dollar startup from scratch by hacking a Wordpress theme into a web-app. He saw his wife slaving away at very complex wedding bids and manually creating 17 different files for every event that her wedding floral company did. Using $600 he won from a hackathon, he built the first version of Curate, the industry-leading application for event florists and caterers. After having miserably failed at a previous startup, he learned lessons of building lean and iterating based on users feedback. He’s now focused on building the best team in St. Louis and creating a scalable organization guided by core principles.