If the IT department is the engine room of the modern business, then system administrators and their colleagues play indispensable roles in keeping the department afloat. Depending on the organization, these roles could be tasked with anything from employee on- and offboarding to network and server maintenance and end-user technical support.

In a startup with less to spend on IT staff, an administrator may be tasked with an even wider variety of jobs. For those just starting out, it can seem like a daunting position. That’s why AccessOwl sat down with some of the industry’s most experienced IT admins, engineers, and managers to hear their insights into what success looks like — and about the challenges they had to overcome to get there.

This is what they said.

1) Don’t be afraid to nag

According to a fintech IT administrator AccessOwl spoke to, it’s vital that employees follow security policies and procedures — everything from watching training videos and activating hard drive encryption to setting up lock screen settings. These are the foundations of effective cyber risk management, he says. And, given that many employees either forget or ignore such requests, IT administrators can’t be shy about reminding them.

“It’s important not to be afraid to nag people to do their tasks or to follow emails,” says the IT expert. “It's okay to keep on sending people messages: ‘You need to watch the video. You need to watch the video’.”

Part of this mindset is about predicting a worst-case scenario — then taking action to make sure it never materializes, adds Picus Security IT Engineer Emre Kurt.

“Being proactive as an IT admin is the most important thing — making sure that you see problems before they happen,” he argues. “You make necessary adjustments and take necessary precautions. Because, if there’s a problem, people will look at you first.”

2) Get your documentation in order

For Connexin IT Infrastructure and Security Manager Patryk Przepiórkowski, IT administrators can sometimes be their own worst enemy.

“There's a propensity in technical people to over-complicate solutions, because it's a puzzle — and our people like mental puzzles,” he explains. “But I've been in situations where people have done that, and then they left the business and nobody knew how things worked.”

For this reason, documentation of IT infrastructure, systems, software, and processes is a vital way of sharing knowledge and ensuring consistency and standardization. It’s also useful for rapidly onboarding large numbers of users, if the business is growing quickly, he adds.

“The biggest project that I would do now is carve out time to actually document what you have,” Przepiórkowski says. “So if somebody new joins, you have that ability to onboard them more efficiently — without having to spend as much time shadowing them.”

3) Focus on communication

Documentation may be important, but — in the early days of a new role — so too is listening, says Gearset IT Manager Nathan Goodfellow. When joining his current employer, he understood there was a specific way of doing things.

“What I didn't want to do is copy and paste what I'd done throughout the rest of my career, and just put it in there — because Gearset was a different kind of company with a different approach,” he explains.

“So I interviewed the heads of all the departments to try to understand where they were coming from, the things they were struggling with, and any areas that could be improved. It was about getting to know the specific culture and ethos of the company, rather than just trying to import the default.”

These same communication skills are just as important when building out an IT team, Nathan says.

“Having good communications skills — especially In the beginning — can make or break the future of a team,” he adds.

4) Don’t just say ‘no’

Maxio Senior IT Manager Shane Fritts learned the importance of an open, collaborative approach in a previous role at Rackspace. It’s about finding ways to meet end users in the middle, rather than simply adopt the usual “department of no” stance.

“Their whole ‘fanatical support’ concept was amazing. And I continue that in my everyday work,” he says. “Especially when dealing with customers, if you always start an email with, ‘no, we can't do that,’ it instantly triggers them. Instead, start with, ‘here's what we can do’.”

If, for example, an end user wants a $5,000 Dell notebook — but the organization is an all-MacBook shop, the IT admin could offer a Mac with a Windows VM installed, he says.

“Giving people options tends to go over a lot easier. They don't always get exactly what they want, but we're at least showing an effort to try and address their concerns and find a solution,” Shane says. “And a customer will be much more willing to work with you down that route.”

This could also have a beneficial impact on reducing shadow IT, where users often try to circumvent an overly restrictive IT department — ultimately increasing business risk.

5) Make “user empowerment” your North Star

This chimes with the philosophy of Erik Ours, former IT Manager at Drivemode, who years ago came to the conclusion that there’s nothing to be gained from putting excessive rules and restrictions in the way of users.

“They're going to try to use these systems, no matter how. So why don't we work with them to make it work?” he says.

Feeling supported, mentored, and reassured in this way will ultimately encourage users to be more productive in their day-to-day roles, he believes.

“IT's ultimate purpose is to ensure the confidentiality, integrity, and appropriate availability of the company’s proprietary information. That's it. That's the only reason we exist,” says Ours. “To make sure that people are using it correctly, and appropriately, and responsibly — and that they’re being productive for the company as a whole. That's why IT exists. And empowerment is a central part of that.”

It’s clear there are many facets to an IT administrator’s role. But as this insight shows, technical skills are usually a given. It’s the harder-to-define-and-learn softer skills that often differentiate success from failure.