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The Beginner’s Guide to Startup Hiring

A new hire can make or break the culture and have a lasting impact on the trajectory of the business. Just last week I made the fifth hiring decision of my young entrepreneurial life. I know, five hires may not seem like a lot, but I’ve learned plenty of valuable lessons along the way. And while I may not be an expert, I do have some insights that may be able to save you some time, money, and heartache the next time you face an important hiring decision. Without further ado, here are 14 ways you can get a little closer to mastering the art of startup hiring:

1. Clearly Define the Role

A well defined job description doesn’t just benefit applicants. It will help you attract more qualified candidates, and force you to think about what it is you’re really looking for in a new hire. When your company is small, growing, and getting busy, it’s easy to assume that hiring more people is the answer. Sometimes it is, but oftentimes there are tasks that can be automated, outsourced, or skipped over completely.

Once you’ve determined that hiring is indeed the path to take, spend some time crafting a well thought out job description with clear responsibilities. You should be able to articulate exactly what that person will be doing on a daily basis and where they fit in within the company.

2. Don’t Sell Yourself Short

Don’t be afraid to sell the perks of the position. There are plenty of larger companies out there offering more money and better benefits, but fortunately that’s not the end game for most people (the right people at least). Hopefully you think your company is a great place to work, and assuming you’re paying a liveable wage, there’s no reason you shouldn’t be able to compete for the best talent out there.

What is it that makes your company unique? Is it your culture, your office space, your flexible hours, work from home policy, Friday lunches, Sega Genesis, or the people who work there? Maybe it’s all of the above. Either way, don’t sell yourself short. Be proud of what you’ve created and don’t settle for second best.

3. Post Strategically

Most people know that blasting out resumes to as many companies as possible is not the way to land a job. The same is true when posting an open position. By posting your opening on every Craigslist and out there, you’re opening yourself up to a potential deluge of applicants, and bad ones at that. Not only is it time consuming to sift through hundreds of resumes, it’s stressful (what if I miss the needle in the haystack?).

Instead, be strategic about where you post the position. Start with local, targeted websites. I use startup-friendly job boards like Built in ChicagoStartupers, and StartUpHire. Make sure to tap into your existing team and network for referrals.

4. Require More than a Resume

Try to make it as difficult to apply as possible, without turning off truly qualified candidates. If all you require is a resume and cover letter, you’re going to be slammed with resume-spam from anyone who remotely matches the qualifications you’re looking for. And while it may be a win to get plenty of applicants, sorting through hundreds of unqualified resumes and generic cover letters is far from a win, in fact it’s probably a loss of hours or even days of your time.

Lately, I’ve been requiring applicants to answer 5-10 custom questions about them and why they think they’re a good fit. Occasionally, I’ll even require a video interview before I’m willing to pick up the phone or schedule an in person meeting. The idea here is to ensure that you’re getting applicants who care enough to work a little for it. If someone isn’t willing to take an hour or two to complete a few extra steps during the application process, they’re probably not interested enough in the job.

According to Jason Fried at Basecamp, effort during the hiring process is rare and “it’s the one thing a candidate can offer to really stand out”.

5. Stay Organized

When I made my first couple of hires, I was receiving applications and trying to track everything through email. Bad decision. It seems manageable when you only have a few applicants, but as the resumes start to pile up and the back-and-forth communication starts, things can quickly get out of hand.

Fortunately, I eventually stumbled across a couple of tools that help organize the hiring process, RIVS (a Demo Duck customer) and Workable. Both of these services keep your inbox clean and provide nifty features that allow you to track and rate candidates, schedule meetings, administer video interviews and questionnaires, and more.

6. Have a Schedule

Hiring is a big decision, and if you’re anything like me, what should be a 1-2 month process can quickly turn into 4, 5, or 6 months. Trust me, I know from experience. Not only is this a distraction to you and your team, you may lose interested and well qualified candidates along the way.

My best advice here is to have a schedule and stick to it. Set specific dates for accepting applications, phone interviews, in person interviews, second interviews, and an offer. Sure, things may go a little faster or slower, and getting the right person on board is more important than following a self imposed schedule, but ultimately this will keep you on track and set some expectations up-front.

7. Assign a Mini Project

This is probably my favorite one out of the group, and I’m surprised more companies don’t do it. It depends on what type of role you’re hiring for, but in most cases you can assign some type of mini project to see how people actually perform. A resume and sample work can only tell you so much. Having candidates complete a mini project just for you shows you what they can really do (not just cherry pick) and give you further indication that they’re willing to put in some extra effort.

For example, when hiring for a marketing position, I had top candidates write a sample blog post and develop a video concept and script for a company of their choice. For a project management role, I had applicants role play and answer angry emails from clients to see how they would handle themselves. It’s very insightful and I put a lot of weight on the results when making a final decision.

8. Personality Testing

A personality test, while sounding like something your high school guidance counselor might administer, should be a no brainer for any potential new hire. Fortunately, companies like Criteria Corp make pre-employment testing easy. They usually take only 30 minutes to complete and they can provide some very accurate insights about your top candidates. Anyone can say they’re hardworking and motivated, but this is just one more tool to help you verify it.

9. Check References

It sounds pretty basic, but plenty of people skip over reference checks because they take time or they don’t feel they’ll receive an honest summary of the applicant’s strengths and weaknesses. I’ve found that most references are more than happy to talk, and whether they’re sugar-coating things or not, you can still glean some valuable insights.

Make sure to prepare some specific questions to discuss with the reference, and if you have a concern or two about the candidate, don’t be afraid to bring them up. Most people are going to be honest with you and don’t want to tarnish their reputation by recommending someone who may not be the right fit.

10. Avoid Criminals

Hopefully it goes without saying, but typically you want to avoid hiring criminals. In most cases, by now you know the candidate well enough and running a background check is more of a formality. But, if you watch enough TV, you know that it’s always the people you least expect. GoodHire makes it fast and affordably ($29.99 for a basic report) to run a background check. Better safe than sorry, right?

11. Don’t Forget the Fine Print

When it comes time to make a formal offer, you want to have the right legal documents in place. It may not seem important when you’re a small startup, but having the proper agreements in place can become critical in the years to come. In most cases there is the offer letter, which outlines the terms of the offer (position, salary, requirements, etc.) and the employee agreement, which covers topics like confidentiality, non-compete, vacation, sick leave, holidays, termination, and so on.

If you can afford a lawyer, great, otherwise DIY legal tools like RocketLawyer and LegalZoom offer “template” offer letters and employee agreements that should be sufficient. Make sure to thoroughly review any offer you send out with a fine tooth comb.

12. Take the Plunge

Eventually there comes a time when you just have to make a decision. Many times towards the end of the hiring process you’ll end up with 2 or 3 candidates that could all be a great fit at your company. Over time I’ve come to believe that there is no single perfect person, and that so long as you do your homework up-front, at some point you need to trust your gut and take the plunge. So try not to drag things out for too long (see #6) and once you make a decision, move full steam ahead with your new hire, no looking back, no regrets.

13. Have a Training Plan

Once the offer letter and agreement are signed, hopefully you and the candidate are excited to get started and hit the ground running. In order to kick things off and maximize your first few weeks together, have a training plan ready on their first day. Nothing fancy, just a quick document that outlines the topics you’ll be covering, when, and by with whom.

Below is a simplified 4-week training plan for recent Marketing Manager hire we made:

Week 1: Take It All In

  • Meet the team, understand their roles, and ask plenty of questions
  • Get setup and familiar with all of the relevant tools and logins (e.g. Gmail, Sprout, etc)
  • Read over our mission and values
  • Get very familiar with our website
  • Review tasks and marketing dashboard
  • Peruse the existing content on our blogs and social media accounts for tone and content

Week 2-3: Develop a Plan

  • Create a weekly task list and schedule based on the Marketing Dashboard
  • Discuss and prioritize future initiatives with Andrew
  • Work with Andrew to formulate a marketing plan and high level goals for the remainder of 2014

Week 4+: Execute!

14. Schedule a 90-day Checkup

Whether you have a probationary period in place or not, schedule a 90-day checkup. It’s a chance for you and your new hire to have an open and honest conversation about the last 3 months. By setting that expectation from the very beginning, it’s easier to be up-front about what you think is going well, and where there needs to be improvement. And while no one wants to have to let a new hire go, the popular wisdom is hire slow, fire fast.

I think it’s safe to say that hiring and retaining great talent is one of the biggest challenges that leaders face at companies small and large. It’s also one of the most important decisions you’ll ever make and a process that needs to be treated with the respect and diligence it deserves. Over the years I’ve had success following these 14 steps for hiring at my startup, and hopefully you will too. If you have any suggestions from your own hiring experiences, please share them with us!

Written by Andrew Follett
Andrew is the Founder of Demo Duck, a video production agency. He lives in Chicago, loves startups, and enjoys traveling. You can follow him on Google+, Facebook, and Twitter.