12 Questions To Ask Your Future Employer

2.12.15 New Employer

Story provided by 99u – 

Job interview prep is often focused on nailing the questions your future employer will ask you, and delivering the best answer. Usually that means running through your answer to, “What’s your greatest weakness?” over and over in the mirror.

Less preparation, however, is given to the inverse (but just as important) scenario: asking your future employer the right questions to get to the heart of what you’ll do, and who you’ll support, at the job.

Finding the right culture fit and team match is even more crucial when the company you are applying to is in the early growth stage: these are the people you’re going to spend the next few years of your life with. You’ll need to be able to be honest, and strategic. Your success in navigating the job interview can affect how well you’ll fit in with your new colleagues.

So how do you take it upon yourself, as the candidate, to find out everything you need to know about the job you’re about to take—and the company you’re (hopefully) about to become an integral part of? This is your chance to get to know the people behind the mission, find out what’s working, and cover critical ideas about what next steps you’ll take with the company. Your task is to dig in and compare the “dream vision” behind the glossy pictures and mission statements with the real facts.

But people don’t always report their behaviors and ideas accurately. So how do you build a picture of what the company needs—and whether you’re a good fit for the role? And how do you make sure you don’t walk away thinking you’ll have a great job, only to hear silence for weeks later? Ask the right questions.

Know the Job and the Constraints:

Sometimes, especially with a startup, what the company is looking for isn’t too clear. Here are a few key questions to dig into what the company really needs—because your job description may be changing from day to day:

What’s the biggest thing you’re working on solving right now?

Not their mission or the larger company vision—what are the biggest blockers to the company reaching its goals? How are they going about solving this, and what is getting in the way? Ideally, they’re hiring you to solve a specific problem and/or take ownership over a process. How will you know that you’ve delivered? How can you get clarity around what the core functions of your job are? Another follow-up question:

How does this job currently get done?

Get to know what the company is doing to solve its specific problems that relate to your areas of expertise. You want to walk in the door ready to work and not be surprised that about how badly the company is organized.

What could I do immediately to make your job easier? What about my job will help alleviate your workload?

If you get a vague answer to “how does this job currently get done,” try the above follow-up questions. It gets at the same issue, but in a different way.

Know Your Future Peers:

In a study of casual social conversations amongst employees, Lynn Wu at the University of Pennsylvania’s Wharton School found that those who have greater connections with their team members were the least likely to get laid off during hard times.

Employees who used words like “lunch,” “baseball,” and “coffee” in email conversations and social communications was a greater predictor of longevity than purely objective performance measures. In other words, it pays to get to know your peers.

What’s your morning schedule, and what time do you wake up in the morning?

Getting to know someone’s morning routine will tell you a lot about how they prioritize, organize, and how you’ll work together during the day. Do they start early meetings and want to hit the ground running? How do they spend their free time?

If I could free up time for you to do anything, what would you do with that free time, personally OR professionally?

If you’re interested in accelerating your personal learning and career capital, the collection of skills that make you valuable (as Cal Newport suggests in So Good They Can’t Ignore You), you’ll want to find a company that energizes you and encourages learning, growth, and challenges. You could tire quickly of a job that keeps doing the same thing over and over again—instead, look for a company where people are engaged both in the office and off the job.

What else are you learning right now?

One sign of a healthy organization and team is when people have enough energy to have outside interests. “What are you learning about right now?” can yield answers from “I’m learning how to change my new kid’s diapers” to “I’m becoming a DJ on the side, mixing beats and sharing them on my Trello board.”

This also lets you connect with your team by learning about what motivates them. Get to know whether or not they are an open, supportive culture that encourages the growth of the whole team, or whether the culture is 100 percent company-focused, preferring not to let personal life get too involved.

Know the Organization’s Culture:

We’re not great at reporting our own behavior—so it’s better to ask questions that showcase behavior, rather than allowing your interviewer to paint a rosy picture of an imaginary work environment. Employers are going to want to tempt you with ideals of work-life balance, but asking “What time does everyone go home at night?” can seem like you’re uninterested in working hard.

“What would your last five hires say about the company?”

One of my favorite questions to ask a new employee is “What would your last five bosses say about you?” I got asked this by Mattan Griffel, CEO of One Month before I joined his team, and he explained to me that you can tell a lot about a candidate by whether or not they look uncomfortable about this question. Sometimes jobs end poorly; sometimes there’s miscommunication. In the best world, however, an employee leaves their previous organizations loved by their colleagues, and the boss has nothing but kind things to say—and the company wishes they could have kept them longer. As the interviewee, you can ask a similar question about the organization.

Who are your most recent hires, and have any hires not worked out? Why not?

What you’re looking for is whether they hire and fire quickly, and a deeper understanding of how well the company knows their hires. If things haven’t worked out, learn why—so that you’re more prepared to start the gig and you have more information about what didn’t work before.

How would you feel about me taking risks and experimenting with new processes, if the work results showed up and improved over time?

Instead of asking if people show up late, stay late, or work from home—you can ask how it would be welcomed if you decided to try to mix things up. I spoke with a potential employer about how to balance my time, and I told him, “I work extremely hard, and sometimes I overwork myself and burn out. As a result, I’ve implemented yoga and meditation sessions, and I take a day to work from home each week. I’ve noticed that my output, performance, and happiness is at an all-time high, so I’d like to implement this at your company.”

By focusing on results and experimentation, you can find common ground to agree on: you’re both interested in trying to get results that haven’t been achieved before, so why not present experiments in how you work to maximize performance along the way? For sure, these things don’t happen the moment you start working, but explore if they’re even possible.

Know the Pain Points of the Hiring Process:

Sometimes a job interview is going great and it seems promising. Yet something still isn’t being said. If you’ve ever walked out of what felt like a great conversation and then been the recipient of silence, what gives? It doesn’t work to just show up with a pretty face and a good-looking suit and smile through the interview.

Your future company wants to know how you’re going to work, and whether or not you’re going to be a good fit. “I’m trying to find out whether they have self-awareness; whether they are able to be critical; and most importantly, whether they’re able to tell the truth—when it’s difficult,” explains David Reese in a Harvard Business Review article. And if he can’t get a handle on what makes you tick, “I leave the interview wondering: Who are you?”

Don’t let this happen to you. As the interviewee, dig in:

What’s the biggest obstacle you’re facing in fulfilling this position?

Begin to ask your interviewers about how they’ve approached fulfilling the position. The answers may surprise you. When you’re direct, they may respond with clarifying information about when or if you’ll be hired. If the company is waiting for funding—say, from the next round of investment or from improved sales—they might not be able to hire you for another six months, at best. Get a good picture of what they really mean when they say they want to hire someone “soon.”

If you’re being honest, what’s the biggest hesitancy about adding me to your team, and what could I do to alleviate this?

If the interview is going extremely well, this question can begin to take possibilities into realities. I learned this key interviewing tip from Willo O’Brien, a multiple startup co-founder and business owner. The key phrase “If I’m being honest,” can trigger people to peel back layers and reveal more of their inner workings. (It works great as a survey question for product reviews, too).

Know How To Walk Away With a Win:

At the end of conversations, I like to ask people about what would make them happy. I’m not joining a team just to tuck in and perform like a rat on a wheel—I’m here to help affect company culture, create a great work environment, and deliver amazing results. Along the way, I want to encourage people to grow and learn, to challenge themselves, and learn from failure.

My favorite final interview question is:

What could I do to delight or surprise you?

Rather than make it all about “me,” however, I want to ask the company leaders and team members how I can make their life easier, how I can integrate into their team, and how I can take the work and make it even better. So ask them what would be delightful for them. I’ve asked it over and over again—whether as a consultant or as a corporate employee—and the results are always good.

As a consultant trying to win a gig or a get the upper hand on a proposal, this is a great strategy as well—you can ask your future clients not just what they think they need, but how working together could be surprising, delightful, and a joy for the months to come.


Ask lively, different, and interesting questions to get into the heart of the organization, and to connect with each person on a deeper level. If you can dig into meaty subjects during the interview, the chances are higher that you’ll keep the conversation going—when you join the company.

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