I've interviewed a lot of people in my time as a lead tech in desktop support, as a domain support admin, as an independent business owner, and system administrator. A lot of my colleagues loved to "grill" interviewees with impossible to answer questions and enjoy making them sweat on the "hot" seat. Now the ball is in your court—you get to ask some tough questions of your panel of inquisitors. It's your turn to make them sweat a little and hopefully gain some useful information about your potential new job.
I used to love going to job interviews. It was almost a hobby for me to scour classified ads and job postings to get an interview and go in just to have a little fun. Sometimes I was interested in the job, and sometimes I was just curious. I stopped doing this about five or so years ago and focused more on only going to job interviews that were really interesting to me and only when I was serious about changing jobs. Going to so many interviews helped me overcome my shyness and developed my confidence. I wouldn't recommend spending your time doing what I did, but I did learn which questions to ask in an interview that help you land the job you want. Here they are in no particular order.
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How is the company doing financially?
No interviewer has ever expected this question. Every time I ask it, I know I've struck a nerve and have required the interviewer or panel to think on their feet. I've raised more than a few eyebrows with the question, and it is rather challenging for all but the most seasoned interviewer to handle.
The answers I've received would surprise you. I've heard everything from, "We're doing very well," to "Our numbers for the previous year are...", to "We're a privately held company that is very financially stable," to "That would be a question for our CFO (or another company executive who's never available to answer it)."
This is the question you ask if you either are not interested in the company or you feel as if something might be wrong with the company. In either case, if you ask this question, be prepared for a quick interview wrap up. It's not a question any interviewer likes to answer.
What is the company's biggest challenge?
This question makes everyone at the table smile. Why? Because this question says that you want to take on challenges and that you have more in mind than the tiny bubble of your position. All companies face challenges, but the answers to this question will also tell you how the employees interviewing you feel about the company as a whole. Their answers are also a guide for you as a potential employee.
If a company's biggest challenge is generating more revenue, this is a yellow flag, and you should proceed with caution. Sure, every company wants to generate more revenue. Profit is how companies stay alive and how they afford new office chairs, new computers, and benefits. If there is a cash flow problem, you might rethink your desire to work there unless you can significantly contribute to the bottom line.
As sysadmins, we are typically identified as "overhead." This means that your salary and benefits directly affect profits. Yours is not a profit-generating position, and that can be a stressful position to be in. It's typical, so don't worry about it too much. There are some exciting challenges such as, "We need to scale this business but are struggling to meet demand." This is where you come in with ideas on how to scale the business without burning a ton of revenue in the process. One of those ideas might be to implement an "open source first" policy on new software. Think about your responses to the answers you'll get on this one, and you could get hired on the spot.
Where will I fit into the company?
This question might also raise a few eyebrows. You might be asked to elaborate. At that point, you have their interest because this is the type of question that opens dialogue and makes everyone want to listen to you as a contributor to that company.
When asked to elaborate, you can respond in any way that you want, but my favorite retort is to say, "What I'm really asking is how the executive staff views this position? Is this position considered to be part of a decision-making team or simply as an individual contributor?" This expansion on your original question lets the interviewer(s) know that you're someone who considers their role as integral to the company. Responses can vary widely here but listen to the tone rather than to the content of the answer. The tone will tell you whether you'll be taken seriously at this company or if you'll be tossed into a sink or swim environment.
Are there opportunities for advancement?
You can ask, but don't be surprised if the answer comes with an abundance of "umms" and "wells." The fact is that IT careers generally have a narrow band of advancement. For example, I worked in an environment where there were five levels of technical specialists that were meant to reflect your level of technical expertise and experience, from one being entry-level to five that was meant to be more advisory or architect-level. Unfortunately, each level had a specific salary band associated with it. Once your salary grew beyond the halfway point of a salary band, the company moved you up to the next band because it looked better "on the books" if everyone in a particular business unit were at or below the halfway point in a salary band. Needless to say, this was anti-motivational and just plain wrong.
Most advancement within IT careers is salary and benefits packages. And, once you're into a job, raises generally don't keep pace with your growing expertise and your increasing unhappiness with the job. There are exceptions, of course. I worked in one company that was very rewards-based, and they gave decent raises and very nice production bonuses. I can't complain. It was a good job with good people. Most often, advancement in the IT world is attrition-based rather than rewards, skills, or experience-based. In other words, if your team lead, tech lead, or manager leaves, you could be promoted to that position. I've seen it many times throughout my career. It's not a great method for finding or retaining good people, but somehow many companies seem to slog through the process, contradicting my opinion on the topic.
Have you ever had any layoffs?
After having lived through 16 years of quarterly, monthly, weekly, and randomly-spaced layoff "events," this question is one that I always ask. I don't care if it's perceived as offensive or brazen; I need an answer to it. If the answer is no, you can skip to another question, but if the answer is yes, buckle up because it's going to be a rough ride.
Layoffs are sometimes necessary to maintain a company's business continuity. But more often than not, they're to lower costs temporarily to manipulate stock prices or to satisfy a Board of Directors that wants to see more profit, regardless of how it's found. My experience was the latter. We had periodic layoffs to offset wrong decisions, bad purchases, and to implement more offshore outsourcing. Many great people were let go during that time. Many bad people were also let go.
Hopefully, your answer will include the reason why such a layoff event or events occurred. Good answers are the pandemic, economic downturn, a merger, and a new company direction—such as the dissolution of a line of business, a new CEO vision, or diminished market share. There are too many bad answers to list here, but you can fill in the blank for yourself. My advice is that if the company has experienced multiple layoff events, you should continue your job search elsewhere.
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These five questions will certainly set you apart from your competition in the job market. Do a little research on the company's behavior in the news, in forums, and on social media. The company certainly will scan information about you, so you need to do the same. Find out if you're a good fit before making a commitment or leaving a job that you already have. Risking your financial stability on a company that isn't a good fit for you isn't something you want to do. Ask the right questions in your interview and really think about the answers before accepting a new position.