11 Offbeat and Revealing Interview Questions

Working for an early-stage startup can be hard. New companies need teams that are agile and active, resilient in the face of setbacks, and cool under pressure. Startup employees wear many hats and need to be dynamic enough to fit wherever they're needed. At the same time, they need to be fearless and opinionated, capable of working on a small team while willing to challenge the status quo.

Needless to say, it isn't easy to hire people who fit that bill. Not only are the right candidates hard to find, the standard interview questions aren't very effective at helping you find them. These 11 questions can help you dig deeper to see whether a candidate is the right fit for a fast-paced startup environment where culture is so crucial. Of course, they might not be as applicable everywhere, so adjust your questions or look for different answers depending on your own work culture.


I prefer to open with a question that forces the candidate to be thoughtful and opinionated. I’m not looking for them to slander their last or current employer, but I want to find out what the candidate values in a work culture. If the candidate complains about his or her supervisor’s micromanaging, for instance, that sends up a red flag for me. In my experience, micromanaging usually happens when employees require it. Startups are intimate environments, but that's all the more reason I need to trust my team's autonomy.


This question might seem like a a preemptive assault on a candidate's work ethic, but I’m less interested in whether they're a workaholic. I'm more curious about their passion for their job and desire to be prompt and responsive. Since startup hours can stretch long after normal quitting time, an employee whose passion keeps them on the ball is critical.

At a young startup, a team's needs can change on a dime.


You can learn a lot about a candidate from this one. Single-track minds tend to be more focused, but they can get bogged down in details. At a young startup, a team's needs can change on a dime, so I prefer employees who thrive on transitioning quickly between tasks—developing, communicating, innovating, doing—all while keeping up a standard of excellence.


This question measure how a person reacts to a sudden change in direction after putting in an enormous amount of effort. Do they see the new challenge as a fresh battle to wage or get frustrated and shut down? Or do they take a middle path, learn from what they’ve already done, and bring as much of it as they can to bear on the latest undertaking?


This is a tough question for candidates to answer, and that’s why it’s so important to ask. I’m worried less about the "yes" or "no" than the "why." A candidate who says they don’t do so isn't immediately disqualified as long as they offer a confident, convincing reason for it. By the same token, if someone says they do check work email on their own device, but then explain they only do that because they’re too disorganized to also manage a company phone during working hours, that could be a problem. The point is that I'm looking for an employee who's easy to reach, even if just to bounce an idea off of them now and then—and I care less about how they keep the channel of communication open.


Many startups don’t have a set vacation policy and tend to encourage staff to take the time they need. Still, I'm interested in learning how long candidates feel comfortable spending time away from the office. It can also be helpful to learn whether they tend to vacation for pleasure, for education, for personal growth, etc. Which leads to the next question...


People don't join startups because they just need a job—they join startups because they're excited to create something from the ground up. That, of course, means all hands on deck. Every opinion matters. So if an employee takes too much time off, there typically isn't someone else who can take over their workload or match their expertise. By all means, I want a candidate who feels comfortable stepping back and recharging. But even if it's just for an hour each morning during vacation, a willingness to check in and stay involved shows me an employee is committed to pulling their weight.


This is a more direct way of asking someone to describe their strengths and weaknesses. Do they emphasize hard or soft skills? And how long do they take to respond? A quick answer might indicate more confidence, someone who chooses a path and blazes it. Slower answers hint at someone who's thoughtful and deliberate, but also maybe a little deferential.


The answer to this question should always be longer than the previous one. Startups need employees who are confident of their strengths but equally aware of areas where they can grow and improve. The ideal candidate doesn't hesitate to let you know how eager they are to hone existing skills and build new ones.


A quick answer might indicate more confidence...Slower answers hint at someone who's thoughtful and deliberate.

No working environment is all rainbows and butterflies. Startup workplaces can be especially intense, and some employees might resent the pressure. I want to know what kinds of things a candidate doesn't deal well with. Do they hate being micromanaged? Can't stand loud colleagues or a strict dress code? No one gets eliminated based on this question, but it does help me get a fuller picture of a candidate’s preferences—and maybe even help improve our office environment.


This question presents the two ends of a very broad spectrum. I'm not looking for a candidate who operates at one extreme or the other but one who's malleable enough to succeed in either. Startup workplaces are fluid. Employees might work in complete isolation while designing an app, for instance, only to spend the next day breaking it apart during a marathon brainstorming session. Being able to adapt matters most.

Asking the right questions during the interview process can not only help you better understand potential candidates, it can also help your candidates understand you. However you adjust these questions to suit your own company's needs, keep in mind that a finding a culture fit is about striking that balance. Each question should say as much about you as the responses do about the candidates answering them.

Article originally appeared on Fast Company 

Business Development Representative at SignPost (NYC)

About Signpost

Backed by serious names (Twitter, Tumblr, Google Ventures and more), Signpost helps businesses get the most out of their marketing spend and their customer relationships. With a proprietary engine that captures consumer emails, calls and other crucial data, this thriving, well-funded company is called by Forbes one of America’s Most Promising Startups.

Office Life

Signpost offers all the energy, great perks and camaraderie-boosting events you’d expect from a fast-moving startup. What makes it stand out from the rest is a flexible, independent, self-motivated and no- micromanagement culture that led to Crain’s naming it one of the Best Companies to Work for in New York.


  • Contact prospects via telephone and e-mail daily

  • Manage and qualify inbound lead traffic

  • Complete due diligence on prospective clients

  • Research prospective clients and verticals

  • Be a brand champion and educate prospective clients on Signpost

Professional Requirements:

  • Undergraduate degree from a 4-year university

  • Excellent written and verbal communication skills

  • Experience conversing with C-Level executives

  • Knowledgeable about digital marketing

  • Experience selling SaaS products

  • Salesforce.com and Google Apps (preferred)

What We Expect from You:

  • Hungry and driven to make an impact

  • Very organized and detailed oriented

  • Have a track record of over-achieving goals

  • Possess 1+ years of trained inside sales experience

  • Want to win individually and as a team

  • Speak clearly and persuasively in positive or negative situations

  • Listen and get clarification, respond well to questions

  • Ability to thrive in an ever-changing, upbeat environment

Working at Signpost:

  • Ranked in Inc. 500 as one of the fastest growing private companies in the U.S.

  • We believe a healthy employee, is a happy employee! Signpost offers competitive health, dental, and vision benefits for both employees and their dependents

  • Pre-tax commuter and 401k contribution benefits

  • Unlimited PTO

  • Stock options

  • Monthly lunches, happy hours, and team building activities

  • Upbeat office space with bagel Tuesdays, a stocked kitchen, a kegerator, and ping pong table in the heart of downtown!

Sales Development Representative at Narvar (SF)

About Narvar

A rapidly growing early stage startup, Narvar offers a complete platform of shipping and delivery solutions for retailers. Narvar is passionate about dramatically improving the online shopping experience, creating loyal customers for top retail brands. Its team blends diverse backgrounds and a passion for exceptional customer experiences. Collaborative self-starters who love building important things will thrive at Narvar.

Office Life

Narvar’s San Francisco office reflects its innovative spirit and passionate mission -- a brand new, large and open space that drives collaboration and fresh ideas. Every week sees recognition for efforts above and beyond the usual. Weekly happy hours build and maintain a strong sense of teamwork and camaraderie.

Sales Development Representative at Narvar - San Francisco

Narvar is looking for their first sales hustlers who will be on the front line driving our growth. You will be working on qualifying inbound leads, closing warm leads and building our sales pipeline. This is an amazing opportunity for someone who is looking to grow with a truly unique Silicon Valley startup. Their ideal candidate is hard working and highly motivated to execute the sales plan. You are scrappy, a quick learner and comfortable selling a technical product. Above all, you are passionate about innovating in the retail space and delivering the best possible customer experience.

  • Conduct online product demos

  • Cold call leads and close deals

  • Review sales progress in weekly sales meetings 

Qualified Candidates

  • 1 to 2+ year of experience in executing sales plans

  • Relentless drive to meet or exceed goals  

  • Strong self-starter

  • Excellent attention to detail and follow through


Customer Success Manager at BetterCloud (NYC)

BetterCloud puts IT in control of the modern workplace through user lifecycle management, data discovery, and IT and security automation purpose-built for SaaS applications!

BetterCloud Customer Success Managers (CSMs) are a critical part of their customer-facing team. Starting with user onboarding to identify needs and set goals, CSMs manage all elements of the post-sale business relationship with customers (including renewals and customer growth), and drive customer usage within the BetterCloud software. Customer Success Managers are trusted advisers on how to use the product and map it to a customer's specific business needs. betterCloud's role is to serve as customer advocates by delivering product feedback and feature requests to the BetterCloud team. At the end of the day, the mission is to delight BetterCloud's customers and have them truly love their time with BetterCloud.

Who are you?

  • Deeply committed to customer satisfaction and happiness

  • Analytical both quantitatively and qualitatively

  • Expert at juggling competing demands and managing limited time

  • Team-oriented, but eager to act aggressively to get things done for customers

  • Passionate about building a great company and a great product

Key Responsibilities

  • Build deep, long-lasting relationships with our customers that help deliver BetterCloud’s world class customer experience

  • Consult regularly with clients to fully understand their needs and actively solve their pain points

  • Act as the liaison between the customer and other teams at BetterCloud to prioritize issues, elicit feedback, or present customers with new opportunities

  • Monitor customer health to be ahead of problems and continually drive product adoption

  • Negotiate and renew current customer subscriptions

  • Work across the company (Product, Support, Sales and Marketing) to identify how we can constantly improve our product and customer experience

Preferred Background

  • 3+ years of sales, account management, customer success or support experience

  • Experience in SaaS is a major plus

To learn more about getting a quick intro with the recruiter, email amic@switchapp.com

Sales Development Representative at BetterCloud (NYC)

BetterCloud puts IT in control of the modern workplace through user lifecycle management, data discovery, and IT and security automation purpose-built for SaaS applications!

BetterCloud, voted Crain's Best Place to Work 2015, is looking for a highly motivated Sales Development Representative to join thier rapidly growing team. They are looking for an individual who wants to roll-up their sleeves and make an immediate impact on the organization.

BetterCloud's Sales Development Representatives serve as the front-line in their customer engagements efforts, contacting IT professionals who have yet to install their product, with the goal of generating qualified opportunities for the sales team. This role actually reports into the marketing team, which helps to streamline our marketing automation efforts and ensure that Sales Development Representatives are contacting the right people, at the right time, with the right message, ultimately giving the sales team more qualified opportunities to win business.


  • Identify and generate leads for BetterCloud through various databases

  • Initial relationships with customers and represent BetterCloud professionally

  • Engage with organizations of varying size and type. From small business to large enterprises

  • Help to build the sales pipeline and architect the sales processes

Qualifications | Required

  • Familiar with Google Apps

  • Highly motivated, professional and hard working

  • Comfortable on the phone and ready to talk to customers every day

  • Past experience in cold calling: to IT professionals is a plus!

  • Attention to detail and highly organized

  • Creative thinker; comfortable with ambiguity

  • Excellent communication skills

  • Bachelor’s degree

Qualifications | Recommended

  • Foundational knowledge of Google Apps (Gmail, Drive & Calendars) and Cloud & SaaS Applications is a plus

  • Some sales experience and familiarity with Salesforce

  • Strong analytical skills

  • Proficiency in Spanish

Compensation | Benefits

  • Competitive base salary

  • Full benefits package

  • Stock options

  • Career growth with an industry innovator

To learn more about getting a quick intro with the recruiter, email amic@switchapp.com

Account Executive at BetterCloud (NYC)

BetterCloud is tier one venture backed, having raised $47 million to date, with more than 50,000 organizations and 20M users, looking to disrupt the modern IT workplace. BetterCloud can only achieve its lofty aspirations by finding and hiring amazing sales talent.  

If you are looking to be part of something profound and build something special, BetterCloud is for you.  They are looking for a highly motivated Mid-Market/Enterprise Account Executive to join its rapidly growing sales team.  They value hard work and positive attitude and are looking for an accomplished, quota carrying sales professional to share their skills, who can think creatively and make an immediate impact. They need talented people to generate leads and prospect for new customers and serve as the voice of our company as we convert leads into deals. You will find and engage with customers, own relationships and ultimately close business for BetterCloud.

In this role, you will report directly to the Chief Revenue Officer and the executive team to support your pursuit of your sales goals. You will receive hands-on coaching and mentoring to expand your skill set and will be encouraged to share your ideas and expertise to coach and mentor others!


  • Own relationships with key customers and represent BetterCloud professionally

  • Execute customized presentations/demonstrations via Google Hangout and in person when required

  • Employ BetterCloud’s sales process to drive prospects from initial install, qualification, build business value, proof of concept (evaluation), through to contract closure

  • Engage with Mid-Market/Enterprise organizations to close deals

  • Help to build our sales pipeline and improve our sales processes

  • Support resellers engaged in opportunities, coordinating with the Channel Managers to drive more revenue through our partners

Qualifications | Required

  • A strong track record of prospecting leads and closing deals

  • Familiarity with Google Apps

  • Highly motivated, professional and hard working

  • Attention to detail, highly organized, and efficient in managing multiple projects at once

  • Creative thinker; comfortable with ambiguity

  • Excellent communication skills

  • Bachelor’s degree

Qualifications | Recommended

  • 5+ years experience selling software products/solutions in B2B environment, preferably in the information technology space. Cloud and SaaS experience a plus.

  • Foundational knowledge of Google Enterprise

  • Familiarity with using Salesforce

  • Strong analytical skills

To learn more about getting a quick intro with the recruiter, email amic@switchapp.com