When you dive into the world of a startup business, one of the toughest things to replicate is your passion for the world you’re trying to create.

Like P.T. Barnum in “The Greatest Showman,” often you’re the only one who can look at an empty warehouse or a grown-over plot of land and see your vision of future success: customers, lights, products, that fantastic buzz of business.

But if your startup is going to be a success, at some point, you’re going to have to branch out and hire employees to help you shoulder the load. And that’s where things can become difficult as you try to find the right blend of passion, drive, experience, skills, and economic motivation to round out your burgeoning business.

When you go from entrepreneur to interviewer, you might find the evolution a rough one. Big companies spend millions of dollars a year on human resources and recruiters solely because their existing staff is seldom the best fit for finding and connecting with new employees.

The worst thing you can do when you start interviewing for startup employees is looking for versions of yourself among the candidates. You don’t want another version of you running around the property like the Energizer bunny on a caffeine rush. What you’re most often looking for is someone who is not you; either in the skills they possess or the knowledge that they’ve accumulated by way of experience.

If you’re an ideas person, you’ll need someone practical to ensure the day-to-day processes get done. If you are the world’s best salesman, you will search for a person who can take the revenue and grow the company with it.

Interviewing at any level can be immensely time-consuming, and that’s a resource that is continually in short supply for startup owners. With the additional complication of just how easy it is to post a job ad online and start getting resumes, you might yourself deluged in candidates ranging from The Perfect Fit to the What the Heck?

Youth Movement

Most startups aren’t the best place to go if you’re a mid-career worker seeking an upgrade in pay and benefits. Almost by definition, most startups are staffed by younger workers who are themselves ‘starting up’ a career.

Going young at your startup has plenty of advantages, the most significant two that young people generally are willing to work for less and that they are independently motivated to work at a company that drives them through the passion for the project involved. A smart startup CEO will seek to harness those two factors to glean the best and brightest out of the interviewing process.

Once you’ve sliced your way through the form letters and fake resumes, you might still have a substantial amount of candidates to get through before you can start extending offers.

The interview process is where you’ll separate the real contenders from the pretenders. As much as candidates are coached to prepare for interviews, the people doing hiring must do likewise to make it a worthwhile experience.

Here are five must-ask questions when you begin interviewing candidates for your startup.

1. What’s Your Dream Job?

In the opening salvo of the interview, you’re going to gauge whether the person across the desk is a butt kisser or a confident individual. The butt kisser will invariably answer “this one,” which smacks of schmoozing, particularly if you haven’t described what the job is yet.

This question is a great way to feel out what the candidate believe their strengths are – whether it’s writing code, building communities, teaching, selling, creating, or anything else.

It can also give you a sense of how long they might stick around if hired. If the candidate’s dream job is working for an international billion-dollar firm, expect them gone in less than a year. But if they stress words like ‘change’ and ‘passion’ you might have a diamond in the rough that you can start shaping to be a big part of your company’s future.

2. What do you enjoy doing outside of the office?

We call this the double curveball because you’re two questions into the interview and still haven’t mentioned the actual job here. The real answer here is irrelevant, whether it’s hiking or baking cupcakes or constructing a Death Star out of Legos in your basement.  What you want to hear is passion and focus.

You want people who take their hobbies and pastimes to a level beyond the “watch Netflix” stock answer. Ask specifics about their response to get more of an insight into how they achieve success as well as the emotions that come with it.

3. What direction do you see this industry taking?

A great query to separate the cream of the crop from the rest. Although startups have a lot of variety, a lot of the positions have the same ring to them such as marketing director, SEO specialist, social media manager, etc.  People in these positions usually take one of two approaches to an interview if they don’t already know the industry. Either they’ll:

  1. Research it before the meeting so they can have at least a working knowledge of the subject matter.
  2. Do no research and figure they can wing their answer in the context of the discussion.


By asking this question before going into detail on the job or the industry, you’re going to see who did their homework for the interview and who didn’t.  You’re not asking any candidate to be an expert in your industry, but reading a few news articles and looking up some trends online can go a long way to having a quality conversation. For those who can’t answer, an excellent follow-up can be: “Why didn’t you prepare more for this interview?”

4. Would You Rather Be Good At Many Things Or an Expert at One Thing?

There isn’t a wrong answer here, but again the insight gained is from how the answer is crafted. In general, startups tend to thrive when you have a lot of flexible people on board to lend a hand to little problems while concentrating on the ones they are best suited to fix.

But that’s not always the case. If your site needs a fantastic web designer, you’d rather have the best on the market rather than a guy who knows a little Java, a little HTML, a little WordPress, etc.

5. Where do you see the company in five years and what can help us get there?

This question is a good capper because you’ve given the candidate a working knowledge of the job, the company, and the industry by now.  In this question, you’ll likely get a sense of the candidate’s business acumen.

Five years can either go by the blink of an eye if you’re successful or like an Ice Age if you aren’t. Don’t judge them on their overall vision, but consider their role in it. Are they only interested in the next paycheck or do they see a real future here?


About the Author

James is an avid investor in real estate and the stock market. He has found an edge in his real estate investing with digital marketing.