Interviews are a Two-way Street

I was recently chatting with a friend who was seeking advice about difficulties in their job. This was a job which, a year ago, she described as her dream job. It quickly became evident to her that it was actually a nightmare job. The company, her coworkers, and her boss were all dysfunctional in one or more ways and it was making her life miserable. One of her big questions was “What sort of questions could I have asked during the interview that would’ve helped me foresee what it’d actually be like to work there?”

It’s Not Only About Pleasing the Interviewer

Many times, we intuitively know that you won’t get the job offer if you can’t establish a bit of rapport with the interviewer, prove your value to the organization and remove reservations about employing you. Many candidates also know that they’re basically in a competition of sorts with other candidates. So even when you demonstrate ample enthusiasm for the work and interest in the employer, you know you might get knocked out of the competition because you have a few errors on your resume or a few less qualifications than the other candidates.

What a lot of candidates seem to forget in the face of interview jitters is that this is also your best opportunity to discover if the employer is a good fit for you. In a sense, not only are they interviewing you, you are also interviewing them.

Interviewing the Interviewer

When you’re in an interview, you want to impress the interviewer and the organization. You want to demonstrate competence, professionalism, and credibility. We all want that. But what sort of questions should you ask to get a sense of character of this potential employer?

Let’s frame your counter-interview questions in terms of goals. The main things I want to figure out during the counter-interview revolve around corporate culture. I want to discern how employees are treated by their managers and executives. Is it high-pressure or laid back? Is it process-driven or informal? I want to know about team dynamics and peer-to-peer employee relations. Are there prima donnas and drones? Is it highly-competitive within or across teams? Is it highly-cooperative? Or maybe it’s highly bureaucratic with lots of institutional inertia? Finally, I try to perceive the values and the overall operating environment of the organization. What is the financial health of the organization? Is the organization a family-owned affair in a highly-competitive, low-margin business? (Then you can probably forget good raises). Is it an agile start-up in a crowded market? (Then you can probably expect merciless working hours).

Here are some sample questions to help you get more insight into the organization:

  1. What’s the history of this position since it was created and the people who held this position before me? You want to determine if this is a dead-end or a launching point for better things in this company. Has the position grown over time or is it static? You also want to know what happened to previous people who held this position. Were they supported and encouraged? Or were they ignored and allowed to flounder? You also want to know whether the position was vacated more than once in the past. That’s a big red flag. On the other hand, take it as a good sign when people formerly in the position were promoted and are still happily employed by the organization. In fact, try to determine overall employee turnover for the manager and for the position. Good organizations tend to keep people, while bad ones shed employees frequently.
  2. What’s the top priorities of this position for the short-term and the longer-term? How does the candidate succeed when in this position? You want to know as much as you can about the expectations for this job and whether you have the skills to succeed. Are expectations clear and achievable? Have your predecessors been successful? Was their successful behavior something you’d feel comfortable emulating?
  3. What qualities do successful managers possess in this organization? Who would you point out as a successful manager here? In many organizations, managers need both technical skills and soft skills. The answer to this question gives you a lot of insight into the pressures and needs of the organization at present. If they answer “multitasking, prioritizing, and time management”, then you know there is way more work to get done than time in the day. If they answer “good problem solvers who think independently”, then you can guess that there is some autonomy in the job with an emphasis on getting things done. Don’t forget that the interview is also trying to sell their organization to you.
  4. What are some examples of how teams and teammates collaborate here? How do teams sort out technical differences of opinion? You want to know if teams, especially your team, works well together. Is there any bullying? Is there a clear pecking order or is it rather egalitarian? Is there a comfortable way to talk about disagreements? Is there a structured way to resolve problems? Is there a set of proven IT processes already in place or is the team making it up as they go or trying to implement something entirely new (presumably because the old process wasn’t working)? Does the manager understand the technology or does s/he have a favorite technologist who makes all of the decisions?
  5. What do you like about your job and this organization? This question is especially helpful if you can observe the person’s body language when they respond. Do they appear genuinely positive and give you real-world examples? Or do the slouch in their seat and stare out the window when they answer? Do they take a long time to think of a response? Or do they have a ready reply with a list of things that they like? If you feel like you’ve built up some rapport with the interviewer, you could even be so bold as to ask the inversion of this question – What are some challenges about working for this organization / in this job?
  6. What’s your feedback on my qualifications? Two of the key things I look for in an employee are attitude and aptitude, more so than a laundry list of specific technical skills. And a major element of both of those is coachability. This attribute is very attractive in a candidate. By asking this question, you express confidence in your skills and in your person. But you also open yourself up to discuss your vulnerabilities. And if you honestly address those gaps without glossing over them, you’ve just scored a dozen points with me. And even in the worst case scenario of not getting the job offer, you now have some advice for how to ensure that you get the job on the next interview.

There are millions of ways to ask these questions. But make sure that you spend some time figuring out how managers relate to their employees, how teammates relate to each other, and how the overall organization works, what it values, and how well it is doing financially.

Interview Questions NOT to Ask

Lastly, there are a few questions that you should not ask, since they don’t present you in a positive light:

  • What does this company do? (Heard of the Internet, have you? Do the research thoroughly ahead of time!)
  • When can I take time off for vacation, assuming I get the job? (Wait until you get the offer to mention prior commitments).
  • How do I get into management / another team? (Don’t indicate dissatisfaction with the job before you’ve even hired).
  • Can I change my schedule if I get the job? (Try not to indicate you need special treatment compared to other candidates. You want to be memorable for good reasons, not for negative reasons).

Again, the goal in asking questions is to make sure the organization knows that you’re someone they want. You want them to know that you are perceptive, intelligent, and worth pursuing. You also don’t want them to think that you’re hard to please, self-centered, or require a lot of pampering.


Have you employed questions and techniques like these in an interview? Did they help or hurt? What insight would you share with your colleagues who are doing a lot of interviewing?

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