Small Biz

Smart Scaling: 5 questions you should ask every prospective hire (and 5 questions you shouldn’t)


TriNetThis post is part of a series brought to you by TriNet. VentureBeat is collaborating with TriNet to discuss smart scaling for growing businesses and best practices for managing growth. As always, VentureBeat is adamant about maintaining editorial credibility.


In the fast-paced world of startups and small business, hiring good talent is as much of a skill as programming, marketing or anything else. It requires its own brand of finesse and insight to identify top performers and separate them from the hundreds of other candidates that apply for competitive positions.

For this article, we’ll focus on the interview process. Sifting through resumes requires its own sharp-eyed endurance, but will never be as revealing as sitting across from someone face-to-face.

Professional culture, much like romance, is a lot about chemistry. This is doubly true if you have an established team and you’re looking to scale up fast. Your goal in an interview, in addition to checking qualifications, is to look for that chemistry — or the absence of it.

Here are 5 questions you should ask (and 5 more you definitely shouldn’t) that will help you zero in on the most likely, most compatible candidates.

Must-ask interview questions

1) What the best thing you’ve ever done?
In preparing for an interview, most people curate a neat list of answers to questions about their strengths, weaknesses and past experience. Few people will have singled out that one thing that has made them most proud, and they won’t see this question coming. Keeping it open-ended, without qualifying that it must be the best thing they’ve done on the job, may also elicit some interesting personal victories and give you a sense into who they really are, and how they might fit into the broader company culture.

2) What did you think of [recent news item about your company or industry]?
You want a hard worker who will ask questions when they need to and figure the rest out themselves. Someone self-sufficient but hardworking. The best way to gauge these qualities is to see if they did their homework for the interview itself. The best candidates will have vacuumed up the info on your website, stalked their interviewers via LinkedIn, and done a thorough Google News search for your brand and competitors. All it requires is several hours of their time, and really shows how much they care about nabbing this position. If they didn’t do any of this, it’s pretty clear that they just want or need a job, or they think they can wing it. And neither would make the ideal employee. So test them a bit. See how much they know. And if they start to sweat, don’t shy away from pressing further. They should know this is what it takes.

3) How would you handle [insert crisis situation here]?
Have fun with this one — it’s an opportunity to get extreme and see how someone can handle it. Don’t be surprised if this question flusters the strongest of candidates. It’s hard to think on one’s feet so fast. Some might even give up, or say they don’t have enough information about the company to say. Here’s the thing though: you want someone who will try to answer this question, and talk you through it as they do. This gives you a chance to see a) how they manage stress, b) how their brain works through a problem, and c) what degree of confidence and humility they will probably bring to their work — ideally a balance of both.

4) Why’d you leave Company X, Y or Z?
Sure, people may have a narrative planned to explain their twisty-turny job history — especially if they’ve hopscotched around quite a bit. But this is also a sensitive topic that tends to bring people’s emotional responses and nervous tics to the forefront. If you’re looking to suss out what their real goal or long-term plan is, it’s usually contained somewhere in the answer to this question. Things to watch for: allusions to burnout, mismatches with company culture, a lack of upward mobility. If they’re going to work for you, make sure their dreams will complement your own.

5) If you were me, what’s the last question you would ask?
No one will see this question coming. It puts them in the driver’s seat right at the end of the interview. Some candidates may awkwardly fumble here, pass, or flatter you by saying you did the perfect job already. Not impressive. The best response will be the candidate who smiles, and then uses the opportunity to hit a homerun on an interesting question they ask themselves. It will also tip you off to what they truly think their strengths are, rather than what you simply want to hear.

Questions to ditch

If there are some must-ask questions, there are also a few you should stay away from.

1) What are your top strengths and weaknesses?

You might be asking for these as separate questions, or for people to name their #1 awesome trait or shortcoming. No matter what though, this is what every candidate is waiting for (and therefore, prepared to answer like a pro). Why ask a throwaway question that has nothing to do with the reality of what someone is capable of? It’s a waste of interview minutes. How else can you explain all the people who are apparently “too much of a perfectionist or “annoying prompt”?

2) What did you do at Company X, Y and Z?
Asking people to describe their previous roles or enumerate past accomplishes is another good way to walk into an overly-prepped response. Remember, these are people who just dusted off their resumes, and had to comb through their brains for impressive cover-letter nuggets. They know how to spin past experience to speak to you and your company. Plus there’s no way to know if they really did double sales year over year, or plan that whole conference solo.

3) What are three (or however many) adjectives that describe you?

A lot of people seem to like questions like this. Maybe because they seem fun or unserious. But in the end, all it will test is the person’s vocabulary. You’re likely to get words like fun, hard-working (technically two words), sweet, creative, kind, and all the synonyms thereof. No one is going to throw in a weakness or character flaw here, and there are better ways to see how fast they can think through something. Other, even more “fun” variations of this question include: “If you were a color, what would you be?” “What’s your spirit animal?” etc. At best, these questions give the candidate a breather. At worst, they make them doubt your professionalism.

4) Where do you see yourself in 5, 10, 20 years?
No matter how many years you ask someone to flash-forward to, they aren’t going to envision a future that doesn’t include your company. In fact, few people will dare to say they will use the role as a springboard to get closer to their ultimate dreams. This is yet another opportunity for them to give a pat answer that they think you want to hear. Even if they say their grandest hope would be to turn your 20-person startup into the standard bearer for photo sharing, big data, online retail, etc., that’s hard to believe. After all, what if they don’t get the job? Will their dreams be eternally crushed?

5) How do you handle pressure or stress?
No one is going to tell you that they buckle under an intense workload, or that their brain short circuits around tight deadlines. It’s just not going to happen. Even people who do in fact snap easily won’t admit to it — even as they’re sweating bullets just sitting across from you. The best way to get the answer to this is to actually ask truly smart, incisive questions that get at what candidates have actually accomplished and what they want to get out of working for you.

Photo Credit: Eleaf/Flickr

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