Read any interview tips article, and it’ll tell you that preparation is key to nailing a job interview. I couldn’t agree more. Most people focus on being able to effectively answer questions in an interview, but crafting smart questions to ask is essential. When someone asks me an easily google-able question like, “How many Fellows are there,” I can’t help but think: “Next, please!” A thoughtful, pointed question, however– one that reveals background knowledge and critical thinking– now that’s what I’m talking about! Ask me question I haven’t been asked a dozen times before, and I will remember. Guaranteed.
So, what kinds of questions will impress an interviewer at a startup? Let’s take a moment to contrast the following questions, from the perspective of an employer.
1. To show that you’re thinking about the broader industry…
What you would ask:
Which competitors are you most worried about and why?
What you should ask:
I know a lot of people are saying that [something insightful about the future of the industry]. I just read Fred Wilson’s post related to that, too. Do you think that [this company] fits into that vision? What do we need to get there?
Why the “should” is better:
Let’s be real: anyone who has accidentally stumbled into any business 101 course could ask the first question. You might as well say, “I didn’t take the time to research it, so why don’t you tell me…” What you’re trying to communicate here is that you’re aware of the industry landscape, right? So do that! It’s okay to have your entree into the question include a quick assertion of your knowledge. Mention a blog or article you read, propose a pithy hypothesis, or state an informed opinion and ask your interviewer to respond.
The benefit is twofold: first, savvy interviewers (like me!) know that past behavior is predictive of future success, so seeing that you are the kind of person who prepares and has a demonstrated interest in their space will do wonders to shape my positive impression of you. Second, a question like this opens up a dialogue. Startups draw a lot of passionate people, so chances are that your interviewer is really, truly excited about what’s happening in his/her corner of the entrepreneurial universe. By tapping into this passion, you enthrall your interviewer. Turn the stiff game of Q&A ping-pong into a genuine conversation and you’ve transformed from “potential employee” to “desired coworker” just like that.
2. To indicate that you’re forward-thinking…
What you would ask:
What are some of the biggest changes you see on the horizon?
What you should ask:
What’s the team’s next big milestone or goal, and how would you see that affecting my role as [job function]?
Why the “should” is better:
While broad, open-ended questions may get your philosophy professor fired up or inspire lively conversations around the dinner table, they’re really not ideal in an interview setting. The specificity of the ‘should’ version of this question paints you as being more thoughtful. Your interviewer will think of you as practical and thoughtful because you’re already anticipating how the climate of the company will shape your experience and performance. Further, by phrasing your question in terms of a ‘milestone’ or ‘goal’ instead of the more neutral ‘change,’ you’re suggesting that you care about the company’s progress and success– and that you want to be a part of it.
3. To indicate that you’re attuned to team culture…
What you would ask:
How would you describe work/life balance here?
What you should ask:
From reading everyone’s bios on the site, it looks like you all have pretty awesome senses of humor. What are some other things about the team that make [Company X] a great place to work?
Why the “should” is better:
The first question is fairly cookie cutter and self-centered. At worst, your interviewer will assume you’re not a particularly hard worker and that you’re trying to figure out if you’re still going to have time to devote to weekday Netflix binging. At best, you’ve just asked a bland question that’s not much fun for your interviewer to answer (“Oh, you know… We work hard. We love what we do though, so it’s not bad…” [Shifts in seat]).
Ask me about my funny, awesome coworkers instead? Yes, please! You’re no longer the egocentric slacker. Now, you’ve brightened my day, reminding me of all sorts of workplace shenanigans and making me feel all warm inside (“I’m so glad you asked! Yes, they’re a riot. There was this one time…”). Let me ramble about our ridiculous Secret Santa exchange or how brilliant my colleague is, and we’re sharing a moment instead of blundering through an interview.
4. To demonstrate an interest in your interviewer…
What you would ask:
What are the biggest challenges you are facing in your job right now?
What you should ask:
If I were to take on this role and do a really great job, what would that free you up to do?
Why the “should” is better:
If you ask me the first question, I’m automatically inundated with thoughts about what’s not going great. This is not the sort of tangent you want your interviewer going on. I’ll end up all disgruntled and red-faced, eager to get back to my desk and the million things I have to do– thanks for reminding me. Instead, the ‘should’ version of the question flips it from negative to positive. This revised question is brilliant in its simplicity. In just one sentence, you’ve got me simultaneously picturing you crushing it in the position you want and imagining myself with more bandwidth to pursue my career goals. You’ve communicated your desire to contribute to the team without making yourself the focus of the question, and you’ve asked me to talk about my favorite topic: me. Bravo!
So…
Given these points, it’s clear: if you’re asking a question just because you’re curious about the answer, you’re missing a chance to be strategic and to impress. Remember that the best questions are specific. Superior interview questions demonstrate passion, interest, critical thought, and background knowledge. You can’t google the answers to them. They build rapport with your interviewer; they help him or her to imagine you as a colleague in that role. Pose the right questions, and you’ll walk out of the interview with only one thing left to ask: “When is my offer going to come through?”