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How to transition from the help desk to a sysadmin job

The help desk has long been a necessary component of IT shops, but if you're ready to transition roles, here's how.
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The help desk has long been a necessary component of IT shops, especially in larger organizations supporting thousands of users plus the devices and services they rely upon to do their jobs. As such, it’s also been a common starting point for an IT career.

Here’s a quick indicator of the help desk’s continued importance in IT: A recent search for “IT help desk” on jobs site Indeed.com produced more than 58,000 open positions. Certainly, some of these roles require prior experience. But the help desk – also referred to as the service desk – is also flush with entry-level positions. You don’t really need a decade in the field to handle issues such as forgotten passwords or desktop troubleshooting. So the help desk can be a good place for greenhorns to cut their teeth.

After gaining a solid footing in IT at the help desk, however, it’s time to think about the next step in your IT career. One logical path from the help desk leads to a system administrator role (or comparable roles like network administrator,) ideally one that tasks you with solving more complex problems or being responsible for applications and infrastructure.

However, just because that path makes sense doesn’t mean it’s lined with blinking lights for you; you’ll need to map out the best route. We asked several experts for their advice on key strategies for moving from a help desk position into your first sysadmin (or similar) job and here’s what they had to say:

1. Look to your current employer first.

“The best thing you can do to transition from service desk to sysadmin is to find a company that wants to help you with that transition,” says Sam Larson, director of service engineering at OneNeck IT Solutions.

This is an ideal strategy because it solves an old job seeker's dilemma: how to gain experience for the job you want when the job you want requires experience.

“The best way to build the skills to become a system administrator is to administer systems,” Larson says. “A company with a good program in place to help techs transition to admins will likely provide structured opportunities to gain that experience.” Do keep in mind that such a “program” can be informal if you can find the right person to champion your professional development.

Larson recommends that current help desk professionals find out if a program exists with their employer, and that candidates for help desk positions do the same during the interview process. Here are some potential ways to pose that question:

  • “Is there a program in place to develop service desk technicians’ skills to help move to higher-level technical positions?”

  • “What percent of entry-level systems or network admin jobs does the company hire internally from the service desk or internship programs?”

This can be a game-changer for early career IT pros thinking about the next step because you’ll ideally get the chance to prove yourself on the job, rather than in the traditional recruiting and hiring process.

“The transition becomes less about building a resume or interviewing and more about auditioning, which can make a much more compelling case,” Larson says.

2. Practice the sysadmin fundamentals.

Of course, the answers to the above questions might be “no” or “none” in some organizations, however, as Larson also notes, “If you don’t have the opportunity to work for such a company, all is not lost.”

You’ll simply have to direct your own learning and professional development – which you’ll want to do to some extent regardless. Larson points to the tips he shared with us recently on preparing for a sysadmin interview, noting that all of the advice he offered there directly applies to making the transition from the help desk to system administration, especially this part:

“Know your technical fundamentals. Be able to describe in plain language how all the parts of a server (hardware) and operating system (software) work together. Be able to do the same for the OSI model, LAMP, RAID, DNS, and basic virtualization concepts. Be prepared to discuss interesting examples of both configuring (setup) and fixing (incident response) all of those technologies. If you don’t have interesting examples, create some. Read about those technologies, set them up in the lab, break them and then fix them.”

Will this require you to invest some personal time researching and getting your hands dirty with other technologies? Probably, but it will be worth it if it helps you land the job you want. Plus, the vast trove of resources available online makes that education more accessible than ever. Also, stay alert for opportunities to volunteer for projects with your current employer that will expose you to new tools and topics.

3. Consider relevant certifications.

Larson also recommends relevant certifications for catalyzing the journey from the service desk to sysadmin. He points to two, in particular, that will help less-experienced IT pros learn the basic proficiencies necessary to advance.

“A good way to learn those fundamentals would be to get an MCSA or RHCSA certification,” Larson says. “Training for these certifications, and applying the concepts in [a] home lab, is a good way to prepare to actually be a systems administrator.”

IT certifications can be valuable resume fodder in general. Here, they might be especially useful if your transition from the help desk to a sysadmin job requires moving to a new employer.

“Passing the test and obtaining the certificate will give you a valuable resume credential – especially if your first sysadmin job is going to be at a new company,” Larson says. “There are lots of training options out there.”

A good reading list is also key; Larson says he recently sent Taz Brown’s Enable Sysadmin article, “Learn the technical ropes and become a sysadmin,” to someone who was looking to break into the systems administration field.

4. Develop depth with key technologies.

The help desk can be a good training ground for juggling multiple issues at once – a vital skill for sysadmins. But, as a sysadmin, you’ll also likely be called on to bring deeper expertise in particular systems and tools than you do as a help desk tech. These could include internal systems, “crossover” technologies, or growth-oriented technologies.

If you can become one of the go-to people in your organization for a particular system or technology, then you can build the case for a promotion to a sysadmin (or similar) position.

“You want to hone your expertise on a specific system and start to become the subject matter expert for your organization,” advises Jim Johnson, senior vice president at the recruiting firm Robert Half Technology.

To become truly vital to your organization, choose a system to specialize in that many people rely on but few seem to fully understand the inner workings of. Some of the tools you already use in your help desk role might also continue to be relevant or otherwise have “crossover” appeal for sysadmin positions, especially if you take it upon yourself to build expertise with them beyond what your current position requires. Johnson points to Active Directory as an example.

“This tool is typically used by help desk professionals for password resets and adding and deleting users to a system or network,” Johnson says. “It is one of the tools that has crossover use with help desk and systems administrators.”

Finally, knowledge of cloud platforms and tools are also increasingly called upon in sysadmin job descriptions. Johnson recommends building at least moderate proficiency in automation technologies such as Ansible or SCCM to help boost the odds of a successful transition from the help desk to sysadmin.

5. Learn a relevant programming language.

Speaking of automation, you’ll also serve your sysadmin aspirations well by learning a relevant programming language.

“Learn to program,” advises Rob Hernandez, CTO at Nebulaworks. “All great sysadmins are great programmers. They learn how to automate common tasks and how to reason about problem-solving past just getting the issue resolved that day.”

Our article on valuable programming languages for sysadmins in 2019 is a great resource for identifying which programming languages to start mastering.

Hernandez’s advice is based on his own career experience and trajectory; learning to program was a key part of it early on.

“Getting into specifics, what really helped elevate me past the help desk role was Unix/Linux. I started with CentOS,” Hernandez says. “I can still remember how much I enjoyed automating bare-metal deployments with things like Kickstart and ssh.”

In conclusion, the help desk may feel like paying dues, but it can also be an ideal springboard for a long and fruitful IT career if you take advantage of the opportunities available to enrich your skillset. These lessons learned and shared by IT veterans can help aspiring sysadmins make the jump from the help desk and set a foundation for ongoing education and advancement in IT.

Topics:   Career  
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Kevin Casey

Kevin Casey writes about technology and business for a variety of publications. He won an Azbee Award, given by the American Society of Business Publication Editors, for his InformationWeek.com story, "Are You Too Old For IT?"  More about me

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