How to craft thoughtful interview questions

The job interview is a two-way street. It’s an opportunity for the interviewer to learn about your qualifications and for you to get a feel for the company culture and specifics of the role. As an interviewee, it is crucial that you do your homework and come prepared to an interview with creative questions.

Great interview questions demonstrate to your potential employer that you’ve done thorough research, are able to think critically, and have the intellectual curiosity necessary to thrive in an innovative startup environment.

Having no questions for the interviewer is a huge red flag, and having boilerplate questions you got from Monster.com comes off as lazy and uninspired.

Let's outline a framework to create solid interview questions using Sidebench, an example company. Sidebench is an LA-based startup that offers management consulting, UX (user experience) design, and technical development services for businesses.

We suggest candidates focus on three areas when preparing interview questions: role, company culture, and company strategy or vision.

Here’s how a candidate applying to the Product Management internship at Sidebench might structure their interview questions around those themes.

1. Get into the nitty gritty of the role

You need to come away from an interview with a good idea of what your day-to-day responsibilities will look like.

Basic Question:

“What does the average day look like for a Product Management intern?”

This is an ok question, but it doesn’t demonstrate that you’ve done any research about Sidebench in particular, you could be asking this question to any employer.

Artisanal, hand-made Secret Sauce Question:

“I noticed that your internship program in Product Management doesn’t have any technical experience requirements where traditionally that role demands an engineering background. Do you feel Sidebench takes a unique approach to Product Management?”

Much better. This question gets at the role specifics and is tailored for Sidebench. You're also isolating the unique aspects of Sidebench's offering, showing that you understand the industry standard and what sets this company apart.

2. Company culture is more than Ping Pong and snacks

The people you work with will shape your career more than any technology or industry. Be discerning.

Basic Question:

“How would you describe the company culture?”

You’re probably going to get a canned response from a question like this. Your interviewer has heard this a thousand times before and is headed for autopilot.

Grass-fed, free range Secret Sauce Question:

“What about the company culture at Sidebench makes it a fit for you personally? And how do you feel it has helped you develop professionally?”

Similar idea, but now it’s more personal. When you ask an interviewer to use examples from their own experience, you’ll get a more honest answer -- not to mention you’re creating a better rapport!

Asking about the culture shows that you care about the dynamic of the team and understand that the people you work with have a massive impact on your career.

3. Find out where this company is headed

Good companies have clear strategies for the future. No exceptions.

Basic Question:

“Where do you see the company in 5 years?”

Not a bad question, it’s good to know about the longer-term strategy of your potential employer, but it is vague. Are we talking in terms of valuation? Market share? Head count? Be specific.

Wild Atlantic, mercury-free Secret Sauce Question:

“It looks like you recently invested resources in focusing on the Healthcare vertical with Sidebench Health. Do you see any more vertical specialization on the horizon?”

This question shows that you spent the time to dig through their blog to find that obscure press release and that you have the ability to think big about the company as a whole. This is exactly the kind of in-depth research and strategic thinking that employers like to see.