/r/Sysadmin Frequently Asked Questions – Interviews & Job Searching

In the “this is common” section of the Internet, I’m going to cover my thoughts on interviews & interview threads that crop up often on /r/sysadmin & /r/ITCareerQuestions. Relevant search links: /r/sysadmin , /r/ITCareerQuestions

Moral Support Provided by Pinkie Pie!
Moral Support Provided by Pinkie Pie!

There are typically three or four scenarios in  life which someone will be
interviewing for a job:

1) Employed, Looking for a new job …
Because you want more pay. Because you aren’t respected. Because you’re bored. Because another company looks appealing for XYZ reason.

If this is you, interviews are easy mode because you probably don’t care if you get hired or not because you aren’t necessarily hurting. This is a good thing & can be used to your advantage in the interview. You can exude confidence in the sense that, there’s no penalty for wrong answers — you’re here looking to see if the company is a better organization in terms of compensation, world view, your professional skill growth or other reasons.

2) Currently Unemployed …
You need a job. It may not matter what you’re doing or what the company is about.

If you’re in this boat: learn to give double-speak as to your current situation. Many System Administrators have blogs that they admin — they keep this as one of their current ‘jobs’ at all times on their resume. This is the reasoning why. If someone asks you what you’ve been doing if you’re really unemployed, you can say that you are always re-tooling or improving your skills.

I’m of the opinion that, you shouldn’t necessarily lie about why you were previously let go, but use some logical (see the PDF linked later) on explaining your situation. Never talk down of your previous employer, boss or peers.

3) Returning from Hiatus/Burn Out …
You used to work as a Sysadmin. You took a break for a year or two for health reasons & now need to get back into things.

With technology professionals, it is common for us to burn out. This is generally accepted in the right organizations & work cultures. As such, honesty is probably the best policy here: your mental health is of vital importance. Depending on the length of your absences — they may become harder & harder to explain. This isn’t so if you traveled to a different country for a number of years, given what I’ve seen in threads.

4) First Job/Career Transition …
You currently work as a line cook but your passion is malware analysis. You do construction but you are sick of going home in pain everyday. You don’t want to work at McDonalds for the rest of your life. This is going to be hard for you to prove in an interview, but passion is key. Things will vary greatly for you if you have a degree or not, certifications or not and existing experience you can pass off.

Being nervous & stressed when looking for a job is normal.

Each of these situations is unique when it comes to the interview process, but getting to that point is usually the same. I will give a shout out to an amazing book, Women in Tech — you should read Tarah’s chapters on Resumes, Interviewing & Communication. This covers a lot more detail & in a concise matter than I ever could. Some bullet points to consider that I used to share with others:

-> Try to list only month/year on your resume. Maybe just the year depending on the gaps.

-> When listing what was done at each job, try to show value — “Increased capacity of our server farm by 300% utilizing Docker” sounds much better compared to “Implemented Docker, Ansible & Puppet to create an automated deployment platform” … this will vary from company to company.

-> Add a skill matrix

-> Check out potential co-workers on LinkedIn – what do their profiles, resumes & sites look like? Copy the good parts. You’ll know what they are when you see them. This helps especially after you get a first job because you can quickly update your resume & profiles accordingly.

-> Purge social media – you should know full well that recruiters, potential interview staff & future bosses will comb through your social media looking for potential signs of weakness: this could be disagreements with viewpoints of the company, signs that you are not an ethical individual, partying/drug influences, or other issues. You should be wary of what you post on forums as well, but it’s harder & harder to do this if you want to be involved in any sort of community.  If you want to know why this may be a bad idea (or, why you may want to alternate usernames between forums), check out a company/software suite called RecordedFuture.

-> As far as websites, social media & branding: consistency is key – my friend _r00k_ has an awesome logo that he uses everywhere (and it isn’t a creepy face like mine!) – it’s consistent, high quality & awesome looking. (@_r00k_)

-> To take the cohesive image, your brand further: make sure it is the same on all social networks, business cards & how you carry yourself interacting with other individuals. If & when you finally do get the jobs that you want, other opportunities may lend themselves to you if you show that you produce consistent results. My LinkedIn Profile is a good example, which led to me receiving free training from a company for a year.

-> Any jobs where the previous company is no longer in business, or something happened to the previous owner (e.g. jail or something shady?) may want to list the company name as redacted, blank, omit it entirely depending on when the position was, or give generic names “no such agency”, “a generic software company”

-> Military person? You’ll probably want to highlight condensed skills that you gained in the Armed Services. Unfortunately, this stuff does not translate well into civilian life, is my understanding. You may want to ask someone who you served or who has experience in this sort of thing for more targeted advice. Key things you will want to mention later in an interview or otherwise: discipline, dedication to the company’s goals & mission, tendency for strong OPSEC in all decision making processes, following rules & guidelines when given a task.

-> What do you do if you are here & have none of these things? If you’re one of the few that is unemployed or looking for work & experience is critical, you will want to go through as much gratis material in every waking moment you have. There’s a fascinating list of machines & information that went around on Twitter over here.  In addition, if you’re one of the group that is transition careers or is looking for a new job making a lateral move, I really adore hacks4pancakes megamix set of posts here.

So, now you have a resume. It looks decent. If you don’t have one still & are part of the unemployed crowd, I highly recommend your local Department of Workforce & Labor Office (Unemployment Insurance) – they generally offer gratis workshops on these sorts of things, which can double as a networking opportunity. Further, they have job boards where you can register & provide your e-mail — they’ll e-mail you job listings each time it matches your profile or a predefined set of variables!

If you aren’t able to get to such a workshop, I highly recommend checking out /r/sysadminresumes – we’re a helpful bunch & we don’t bite! You will want to be very clear about what you’re looking for. When when looking at jobs, you’ll want to apply, even if you don’t meet the requirements.

At this point, you need to start looking for a job. Your resume may need to change slightly depending on the roles that you are looking for. I’m of the opinion that, if you have time for whatever reason & getting a job isn’t critical (e.g. rent isn’t due or you aren’t out on the street) you can be picky with the jobs you apply to. Perhaps one company has values in line with your own than another. Perhaps you’ve always wanted to work at (insert cool electric car company here). Apply to the things that fascinate you & let your passion shine that you want to work there.

Always include a cover letter. In the cover letter, use words, language & bullet points from the job posting that you are applying to. In addition, in any job application (see: iCIMS) portal software, be sure to use keywords from the job description into the actual job application — these keywords will put you higher to the top on the pool of applicants.

With determination & some LOUDER cheers – we can all succeed!

If you’re all the way down here, you’re probably at the interview stage! HOORAY!
Before I delve too far, I highly recommend the following before any job interview: Illegal or Inappropriate Interview Questions

You’re now at the important part, the interview!

If you’re freaking out or don’t do well in social situations I highly recommend a public speaking class. Most community colleges offer them & they are cheap & can be taken in the summer. If you have the patience, you can attend a Toastmasters, but the quality of clubs can vary greatly & you might feel overwhelmed by rules & commitment.

One takeaway I can give you from taking a class is to record yourself in a mock interview with another peer who gives you unscripted questions. Play back the video, several times: once at normal speed. Another time, at half (or as slow as you can), speed. Watch for any verbal cues from your own body. Nervous tics. twitches, utterances, body language & so on. These are things you’ll need to iron out or be aware of when you are interviewing.

Interviewing is super stressful. Read up, practice & gain as much knowledge & insight into the process as possible. Twilight Sparkle is constantly researching stuff!


The biggest part of interviewing to me, is YOU interviewing the company & finding out if you’ll be a fit & if the company can provide for YOUR goals professional. Do you like what you hear from your boss? Is there upward mobility? What are the perks? Different people have different opinions on all of these things. Frankly, it is important to have just as many, if not more questions for the person interviewing you. Generally, the vibe of the interview should feel like a conversation: if things feel hamfisted or one-sided, something is wrong & you need more practice.

Also, if you find you don’t care about the company mission overall or don’t feel like you can find yourself being passionate about the products & services you are improving (I may be an oddball here) you may want to re-consider applying. When applying or working somewhere, I try to learn a small amount of every facet of the company. At a previous company, I learned about our 3D printer & the basics of Solidworks — this is what helped me with the research behind the 3D printed TSA keys produced alongside J0hnnyXm4s & nite0wl_2600.

(Oh, Yes: research & speaking engagements are encouraged on a resume, however, most jobs will probably not care unless it is related to you working in the industry!)

Some additional books/references (not all these books have had posts written for them yet, this is just a helpful list)
* You, Inc
* Getting More
* What to Say & How to Say It
* FISKE Word Power
* What color is your parachute?
* Body Language
* The Book of Five Rings

These aren’t necessary, but they will help you get into an appropriate (albeit strong) mindset for interviewing. You should be prepared & confident. You should be well read. You should be familiar with what it is like to treat yourself as a company or brand that you are selling to others, companies & businesses. You should be familiar with all the little things that go on in an interview & how to gain a quick rapport with who you are interviewing with. I recommend peeking at these books & looking at all the links prior to going crazy thinking about getting a newer, better job.

After all this hard work, you should have a job in the field that you want. Get out there & be awesome! If you find that you have an existing job & are struggling to advance or make sense of the job, I highly recommend reading some posts by /u/crankysysadmin on /r/sysadmin over here – he is very good at dishing out truth from a management/senior perspective & pulls no punches with what he sees. He’s also willing to debate with people on their perspective if he gets called out. Lastly, if you’re looking for a dose of truth as mentor, just ask him for his perspective. He’s always willing to help people out.

If, after all this hard work, you need more words of encouragement or advice, I suggest giving this post a glance by my friend Matt Simmons (@Standalone Sysadmin)

Note: this post might be updated over time. I generally don’t post ”new” blog posts on the same subject – I just update existing blog posts with changes in my thoughts, perspectives or narrative structure of the post.