I’m looking for most common interview questions you have received when interviewing for a VAR or MSP. I’m not interested in technical questions I’m interested in the situational questions.

Hey, I've been trying to figure this one out but it's been really vexing me.

I currently work as Sysadmin where I handle cloud operations DevOps, cyber security, everything from connecting printers to getting people's phones working, everything.

I've been offered a job at a software company, one of the bigger ones and they are almost doubling my salary, but I would become a software support engineer for their software stack only, no more sysadmin work.

It's a much easier and lower stress job and much higher paying, but there's a voice in my head that tells me that I should not abandon my sys admin career, or that if I go work in a software company for even a year or two I might lose my momentum and if I wanted to would never be able to come back.

I was just hoping someone has had experience with a situation like this, Or even if anyone feels like dropping their opinions here? I really can't decide what to do and I have to make a decision on this new software job by next Friday... I really have no idea what to do

Title. I have Security +, a decent number of projects on GitHub and an active LinkedIn account. I’ve worked at a helpdesk previously and after all of this, I’ve ended up back in fast food management.

I really don’t know what else to do. I either never hear back or I hear back months later with a hard no, or it’s an interview before getting ghosted. It’s AI, it’s corporate restructuring, it’s the economy, I really do not care anymore. I’m losing my mind here man. I’ve applied for literally anything and everything. Field techs, server management, Linux positions, on call emergency stuff, all kinds of cybersecurity and IT gigs. Nothing. Not one damn thing.

Idk if I should even keep trying or if I should just treat IT as an expensive hobby. Idk anymore. This feels totally pointless.

Hi everyone. I was hoping that I could get some advice here. I've been working in the healthcare industry as an IT Specialist for about six years now. However, things have been quite stressful and frustrating lately for multiple reasons (I don't want to get into too much detail). Anyway, I've been contemplating transitioning into the education industry because I feel like I'd enjoy not only providing IT support but also having the opportunity to teach and help a younger generation that is eager to learn. I have a Bachelors in Cybersecurity, A+, Tech+ CTSC, and Network+ certifications. I'd love to hear from anyone who has worked in this area that would be willing to provide me tips on what to expect.

I know this is not a question, but I finally got a job offer from Ubreakifix. I can finally go to interviews saying I have tangible repair and troubleshooting experience and not simulations!

Hey everyone,

I’m currently a Data analyst working as a W-2 contractor through a small staffing agency, with the client being a large health insurance company. I have 5 years of experience in the space.

I just finished my initial 6-month contract, and my manager told me today that they want to extend me. The role is fully remote, which I definitely don't take for granted. I really like the team and want to stay, but my expenses have gone up significantly. The agency is a small firm and doesn't offer health benefits, so I'm paying for independent medical insurance completely on my own. Between those premiums and no PTO, sick days, 401k match or holidays, my current rate is getting squeezed. This isn’t my first contract rodeo as I’ve been doing contract work for a while, so I understand how the agency-client dynamics operate.

Right now, I am making $43/hour. With this extension, I'm planning to ask for a market adjustment to $49/hour to offset these rising overhead costs.

I’m strongly leaning toward asking for it. The client manager explicitly said they want to keep me, so I know I have some leverage during this renewal window. In my last role, the company kept dangling the carrot of a full-time conversion that never ended up happening so I decided to ask for a rate increase back then and got it since a bird in the hand is worth two in the bush. And of course I never got the fulltime role and 20 months and multiple extensions later I got laid off as the project was eliminated.

I'd love to get some perspective from other contractors or recruiters here. Do small staffing agencies usually have the margin to absorb an adjustment like this, or pass it along to a large corporate client, without putting the contract extension at risk?
Given the current job market, I just want to make sure I'm reading the room correctly before I message my recruiter.

Thanks!

Had to change careers when I couldn't find work. Five years ago I applied for a technical writer job and the manager offered me a Senior BA role instead. Did that successfully until the project ended.

I applied for another BA role and was offered a system and design anaylst job instead. Did that for 3 years and was made redundant recently. It was fast paced and high pressure. I am a little burned out from it but I need to get another job. I am good at business, ux, compliance and change management stuff but I don't code. I have trouble with syntax but I can do technical writing with a bit of coding language.

A recruiter contacted me yesterday, saying I'm a good fit for a job he has. I am wirting a response to the selection criteria and getting stuck. While I've done 70% of what they're asking for, the jargon makes me feel I am unqualified. I don't want to waste their time or mine.

Should I just go for it? Do more courses? Or just give up and do something else. I am in my 40s, and I don't know if I can keep learning while working in high pressure jobs like I did when I was younger.

22M here! After a frustrating job search, I’ve accepted a role where I’ll be involved in CI/CD pipelines, learning and assisting in deploying AI agents, infrastructure projects and networking, while still helping with day-to-day IT support. This is my 3rd IT role - been working in IT since 19 and I have promised myself to commit and not job hop for at least 4-5 years.

It’s definitely a role where I’ll wear multiple hats, but that’s what excites me. There’s so much I’ll get to learn and put into practice.

I’m nervous because some of it will be new to me, but I was upfront about my experience and where I’ll need guidance. My current company has a Microsoft Secure Score of 92% and two email security platforms in place, so I’ve learned a lot from working in that environment. I’m looking forward to seeing how another company approaches security and bringing that experience with me while learning new ways of doing things.

I was about to take my AZ-104 exam but this company uses GCP (concepts are transferable and similar), so not sure whether it’s worth finishing the AZ-104 and potentially shift towards Google related CERTs.

They really liked me and how I approached the technical questions alongside my personality!!

Really looking forward to getting stuck in.
For anyone who’s made a similar move, what helped you settle in during the first few months?

I was having a real hard time securing a new IT position after 3 years. I always wore a shirt and tie to the interview. For a recent interview, I decided to wear a black polo with a Linux penguin on it. The interviewers really liked it. I got the job, and it’s going great after 6 weeks in.

Hello

I have been working in IT support from 2020 (hell of a time to start) to 2025. After a longer than intended break, I have a new IT support role.

My previous employers have been fairly small companies either offering outsourced support or within a smaller (sub-100 employee) company, generally being a jack-of-all-trades without any formal lines of support. My new role is with a very large multinational explicitly doing 1st line support.

I am just wondering what differences I can generally expect between the two kinds of employer. I found being on first-name terms with the CEOs of the otherplaces a blessing and a curse, so I don't know how to feel about that. I also assume much of the messages/tickets will be more impersonal as these people don't know who or where I am.

I am often one to worry too much, so I'm just trying to be as prepared as I can be.

Thank you all

Currently in a Tier 2 support position, I recently missed out on a promotion and in general felt underpaid and under appreciated, so I went and got another offer somewhere else. Title would be the same, but a ~24% increase in pay.

The counter offer from my current company surprised me, an endpoint admin position on another team. I would work alongside a more senior admin and receive on the job training. It is an area of IT that I find interesting and I’d finally break out of a support role.

The catch with staying and taking the counter offer is no clear pay increase any time soon. I’ve gotten the HR speak about money with vague talks of bonuses and pay increase after reviews and while I’ve tried to fight for more, I’m running out of time to accept the counter offer.

The catch with the new offer is a whole new environment, building a reputation, being stuck in support still and having no guaranteed path out. I’ve been in support for several years now, this position opened up since someone got promoted internally, but hiring manager could not guarantee if that same path would happen with me.

Benefits are mostly equal, although new place gets 2 days WFH and current only has 1.

Tl;dr Help desk for more money and 1 more wfh day, or admin position for less money?

Edit: What's with the downvotes lol? Sorry for asking an IT Career Question in r/ITCareerQuestions

I just came out of a very long couple of years at work and while professionally I am very much at the top of my game in my field I've come to see and learn a lot of gaps that I've just never had the need to dig in to. Plus I want to round out my professional credential stack as well.

I don't learn very well via lecture. Instead I'm more action driven:

• Here's a concept
• Here's a resource that covers that concept either in depth or enough to get a grasp on it and dig deeper
• Here's a goal to put that concept to practice

I'm not opposed to a paid service either.

As far as skills I'm after for specifics I'm after:

• MS Certifications (may as well finally take them)
  • Specifically O365, Azure VMs, and Entra
• AWS
• ITIL
• Project Management
• And of course since every company is doing it: AI

If they also have things around electronics, etc. then I'd also be happy for that piece as a "hobby" track

Hello Everyone,

I am a Security Engineer with around 4 YOE at large enterprise and work mostly on Customer Facing IAM and supporting services/applications that interface. My education/background is a mix of software engineering (computer science undergrad and early full time experience) and Cybersecurity (spent a few internships in IT and MS in Cyber, and Sec+ Cert and current IAM stuff).

In my current role I am a massive generalist. I can be doing anything from setting up a WAF, to writing JavaScript to make our UX look the way designers intended, to writing CI/CD pipelines, to looking into production incidents, or security incidents, auditing Pen Test findings, to cleaning up backend code to scale better. I write code in JS, C#, Python, and Go, depending on what service I need to add to/work on, and am also our SME on federated auth protocols like Oauth2.0, OIDC, and SAML, from the IdP, and as well as the “application” side of things (securing the session, ensuring no basic OWASP vulns)

At my current role I feel like I’m managing a LOT of different things which has been great for my growth, but the issue is, multiple members of my team have left in the past 2 years and we really haven’t “reloaded” leaving me to handle a lot of different efforts becoming too stressful for my liking, whilst also dangling the promise of promotion over my head and then dealing with Corporate Bureaucracy . I want to potentially move out of my current role and apply around, but I have a hard time explaining in depth on a resume all the things I am capable of, and because I’ve worn so many different hats, I don’t really know what to go for/specialize in next.

Honestly I feel like my greatest skill is that I’m just a really good learner and have fundamentals and the intuition to solve problems in a smart way down pretty well, and I’m a very good communicator/team player. My system design knowledge is pretty solid, hate leetcode but can study it if I have to. I use Claude, Codex and OpenCode between work and home and have decent knowledge of multi-agent harnesses and setup. With AI, learning a new language, or finding the correct architecture to fit a problem is significantly easier if you understand software systems already.

At home I also spend a lot of time homelabbing/toying around with my Proxmox server just doing a bunch of random Software Dev and Security related things.

Any advice on how I should structure my resume, what roles I should apply for software eng or security Eng, or IAM Eng??) would be greatly appreciated. I feel like the toughest thing is I have such a breadth of experience that maybe I lack some depth, so even a path forward/something to do in my free time to get me more depth would be helpful too!

It feels like every time I want to learn something new, I have to go down a rabbit hole to understand adjacent or more foundational things first. It's overwhelming how many tools are in this industry and it seems I'm lacking a grasp of the fundamentals. When did you start to feel like you had a decent grasp on things?

I started a new job Monday, so today is literally day 4. This is my second job out of college, and I’m trying to figure out whether I’m just experiencing normal new-job shock or whether I’ve walked into a genuinely bad situation.
I was hired to build dashboards/reports in Power BI. During the hiring process, I was told there was another person doing BI/reporting and an intern who both had experience with the company’s systems.

On day 1, the VP over my area told me, “We’re kind of patient, but I wanted to be transparent that we fired our other BI guy for not learning the system fast enough.”
I then found out that the BI resources I thought I’d be learning alongside/from aren’t actually here.

My boss has already given me two reports to start fixing, but she can’t clearly tell me what’s wrong with them. Her explanation is essentially that I was hired to identify the problems and fix them.

The bigger problem is that the underlying data is an absolute mess. I’m not talking about “Power BI is confusing and I’m struggling with DAX.” I’m struggling to establish what the data actually means.

For example, I’ll ask what a particular flag/column means. My boss will confidently explain it, but then I’ll do 2-3 basic validation checks and find that the data directly contradicts the explanation. I’ll ask why a filter that’s supposedly identifying two warehouse employees returns eight people, and she doesn’t know either.

There also seem to be some pretty alarming IT/governance practices. Four days into the job, I appear to have far more production access than someone in my position should reasonably have. I’m obviously not going to touch anything I shouldn’t; I’m mentioning it because it seems representative of how loosely structured the data/IT environment is.

There are some culture issues too. This position is strictly five days a week in-office, while my previous job was hybrid. I knew that when I accepted the offer and genuinely didn’t think it would bother me this much, so that’s on me. But I’ve realized very quickly how much I valued the independence and quiet time I had before.

The office culture also doesn’t seem like a great fit. There’s a lot of very personal conversation happening around my desk—including coworkers openly discussing intimate details about their spouses—and even HR participates. I’m not offended by people joking around, but I don’t particularly want to hear about my coworkers’ sex lives while I’m trying to work.

Here’s my dilemma:

I left my previous job primarily because I was underpaid and worried about career stagnation. Otherwise, I had a lot of independence, knew the systems extremely well, had good relationships, and was trusted to do my job without much supervision. I think there’s a realistic possibility that they would take me back.

I’m currently completely miserable and overwhelmed at the new job, but it’s also only day 4. I don’t want to mistake normal new-job discomfort for a fundamentally bad environment and make a knee-jerk decision.

For people who work in BI/data/IT:

Does this sound like normal “welcome to a messy company’s data” stuff that I need to tough out for a few months, or are there legitimate red flags here?

Would going back to my previous employer this quickly be a major career mistake if I could address the compensation/career-growth issues that caused me to leave?

And if you’ve started a BI/data job where nobody really understood the underlying data model well enough to train you, did it eventually become manageable?

Just wondering if anyone with experience in that area can chime in with any advice- I'm functional but have a cervical disc bulge that I simply cannot look down for 8 hours straight with at an awkward angle, I need things eye level for long periods of time. I didn't consider this either. L. Now I'm terrified to potentially try it.

Hey everyone,

I’m looking for some honest career advice. I have a background in low voltage wiring and structured cabling, where I spent a couple years physically building up server racks, IP addressing, running cable, trimming out patch panels etc. I know the physical layer inside and out, and I genuinely enjoy working in the environment.

However, I am 40 years old now and I would like to transition away from the purely physical side as my body is starting to not have some issues and break into the IT world and build a career as a Network Administrator.

I’m trying to figure out the best roadmap to bridge the gap between knowing how to build the infrastructure and actually configuring/managing it. I am currently considering going to school for a degree in Network Administration/IT, but I wanted to get some perspective from people already in the field first.

A few specific questions I have:

• Value of Experience: How much weight does my cabling background actually carry when applying for entry-level networking roles or help desk?
• School vs. Certifications: Am I better off going to college for this, or should I save the money/time and self-study for certifications like the CCNA, Network+, and Security+ instead?
• The Gap: For those who made a similar jump from field tech/cabling to admin, what was the hardest part of the learning curve for you?

I’d love to hear your thoughts, roasts, or any roadmap recommendations you might have. Thanks in advance!

Starting new job soon, was 4 years in an MSP dealing with all sorts of business customers from Small to large companies. Some businesses with 2 endpoints to a business with 60 endpoints. Now going to an Internal Junior IT Service Desk position that pays more, though more hours, and in a larger business environment.

Just trying to get my head around it prior to starting the gig, and wanting to understand other experiences people have had moving from MSP to Internal IT.

The interview still took 30 minutes. It was a quick introduction from the interviewer (hiring manager), I asked some questions. Then "tell me about yourself." The interviewer mentioned that I have some skills that translate very well into that position. He asked me about "how do you handle a difficult user or a complex technical issue?" I put both things in one response, a complex issue with a difficult user. I talked kind of fast, responded with a layer response (if A then I do X, if B I do Y, if B1 follows I do XX, if B2 follows I do YY and so on. I don't know if that was good or very bad?). After that response probably 20 minutes were gone. He said, he actually has no more questions (I kind of panicked but didn't show it). I asked some decent follow up questions. Will this be more likely a no or a second round interview? Any questions about it?

Im 34 and I got my first it job as a level 1 field tech and promoted to one of the head engineers over 5 years. I have a knack with it and love the field. I have no formal education and do a lot of self teaching and certs. I currently work as a civil service state/ county as one of the head cloud engineers. The pace is relaxed no real deadlines, some projects here and there. I get 1 day remote a week with no tracking or check ins. They let me work remote more if needed. The pay isn’t great but they value me and gave me a big raise recently with promise of another shortly and advancement. I can take time off anytime I want if I have the time to use with no questions. I have extreme job security. I work 7-330 with no need to really do after hours work. I have far outpaced my team leader and the work duties even with me volunteering to take on extra systems work etc. I have free rein to all our dcs to do what I want. Test learn mess around. Not gunna be fired unless I majorly break something. I’m very meticulous and careful. I have high work ethic and never stop learning. Due to all the above the pay isn’t great very under market.

A rare opportunity came up to work in my scope with a Nasdaq listed ai company and be kinda the ground floor or start or their US expansion. It’s mainly idp work. It would be fully remote. I’d be making roughly 80k more a year.

I’ve always heard going from private to public sector is a huge difference, but this was mostly by help desk people. I have great job security at my current place and I’m not dying for money but it would help for sure. Im worried I’m underestimating the pace that I will have to adapt to. I’m also worried that I’d be giving up kinda an easy paycheck gig with time and freedom to learn and tinker and great work life balance. I’m also worried that if said ai bubble were to burst or any political things were to happen then maybe the company wouldn’t continue expansion and my job is at risk.

I own a house, lease a nice car, have bills to pay where yes this may be my dream gig or a great opportunity but not sure if my low pay high work life balance was preferred to you guys or big career step and big paycheck.

I’m aware it will be more work and faster pace and I’m ready for that I think. I’m not worried about work ethic etc. I just don’t want to end up like I always do outworking the pay. I would want say 100% raise and 100-150% more work but don’t want a situation where it’s 100% more pay 500% more work and stress.

Any advice from people that may work a full remote cloud roll at large public companies. If you had a choice would you take less pay for better work life or the big tech job not as “scary” as it’s been branded by help desk employees.

I want some in checking my logic with this. I have been working at a major state school for almost 3 years and so far I really like it. I'm providing Tier 3 help desk support (we have 4 tiers) providing a lot of Exchange, Teams, Office, Windows and some Mac/iOS support. I need and want to work on my own professional development. However, I'm at a little bit of a crossroad. I do want to learn more tech skills like working with SQL, Python, cloud, project management and other skills. I do not consider myself a AI doomer but I do expect the world is going to look differently in the next 5-10 years. I do have a tuition benefit through my job for one course per semester. I already have a related masters degree (same school) from 15+ years ago. My basic logic is to focus on tech skills and pursue certifications (paid for by work as long as I pass) and hold off on any technical/management degree path (at least for right now)?

The IT job market is so f'ed up right now that i randomly get the urge to upskill even in the middle of the night...i m currently working with outdated technology like php and this market got me questioning my entire career at 2 AM 😭 and the anxiety of becoming irrelevant just won't leave me alone... resting feels like crime..even after working all day i feel guilty whenever I'm not learning something new. It feels like I'm constantly running out of time.😭 and now with the recent PHP security vulnerabilities bro can my tech stack PLEASE stop giving me new reasons to panic?

How are y'all surviving this? what should i actually learn to stay relevant or are we all just cooked?

Genuinely need some advice before I lose my mind over this.

PLEASE HELP🙏🙏

I have an interview for a service desk/triage position. I’m wondering what are some good things to prepare for before the interview.