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IT Experts on How to Take Your Time Back at Work

Gamifying your intentions and honest communication top the list

Time. In IT operations, there’s never enough. And while it’s perfectly okay to "waste" a little bit of your time every day, it can often be challenging to keep time from wasting you.

Never fear, though. There are simple – even fun – ways to corral your time and make it work to your benefit.

Today, we’re talking with Automox Senior Customer Success Engineer Dean Goss and Senior Systems Engineer Ben Rillie (both system administrators in their previous lives) to find out how to take your time back at work.

But before we get into the time-saving nitty-gritty, let’s meet your hosts for this discussion.

Dean Goss: An entrepreneur at heart, Dean was an administrator for 15 years. His passion (and priority) has always been automating the impossible and helping business units with their most significant challenges, especially recurring problems.

Before coming to Automox, Dean worked as the escalation point to the project managers, director level administrators, and level 3 developers. He was constantly interacting with IT directors and the C-suite. Dean helped solve problems for entire company units. In those roles, he was a customer of Automox. Whenever he hopped off a call with Automoxers, he thought, “There’s no way a company could be that happy.” So, he made the leap.

Ben Rillie: Ben was always interested in computers, development, and help desk work. He cut his teeth on the Mac team at Pixar. From there, he moved on to endpoint management.

At Automox, Ben started out on the Worklet Factory team writing macOS Worklets but has since moved to the Factory Tools team. There, he works on the Core Worklets and is also developing a command line tool that will enable customers to easily interact with the Automox API.

As you can see, these guys have a wealth of experience. So as you might imagine, they’ve run up against some urgent matters and time-stealing dilemmas. They’re here to share their experiences and some hard-earned words of wisdom.

Here’s what Dean and Ben have to say about taming time.

How do you prioritize IT tasks?

Dean: When prioritizing tasks, I gauge the scope of the job and the urgency and importance of the request. Importance and urgency may sound like the same thing, but they’re not. Calculating them as different elements of the equation is essential. It allows for a dynamically scaling, self-reprioritizing task list, enabling the ability to focus on what will benefit the company and clients the most.

Ben: For me, it’s relatively easy these days. I use Jira. Before, it was tough. Daily standups and directives from management about changing priorities or customer issues were tricky to track. In Jira, prioritization is easier and transparent across departments. At Automox, we work in two-week sprints. I try to get all my cards done within the current sprint. Luckily, there aren’t many people with their hair on fire here.

How do you limit distractions?

Dean: I limit distractions by partitioning my attention in a gamified manner.

Gamification of a process is fully defining everything out, including the order of operations. Without a defined structure, you can’t create a framework to accomplish issues as quickly as possible.

For example, I have four monitors on my desk – two on top and two on the bottom. Each monitor has its own purpose.

Top left: Email, calendar, KB articles, and web research
Top right: Slack and file browsing
Bottom left: Data analytics, virtual machines, Zoom calls, and scripting
Bottom right: Notes and postponed items I need to address later

In video games, I’m a “completionist.” Translating experience across platforms (i.e. video games to work or rock climbing to work) helps me use the same skills in multiple areas. Boiling things down and converting your working knowledge to that process is crucial. It allowed me to go from acting as an administrator for a single org to being the go-to guy in a disaster situation.

Ben: Limiting distractions can be challenging, especially when working from home. You’ve got your favorite TV shows to roll through, your music library to organize, and the kitchen calling your name. But I have a unique work habit: I work in short spurts. Then I take a break. Then, I’m back at it.

Naturally, I’m a little bit scattered. The thing is, I’ve figured out how to work that into my flow. Previously, when I was managing an IT department, I couldn’t limit distractions. I could only prioritize them. So, you look at what’s truly needed.

In the end, limiting distractions isn’t really the way to look at it. You’ve got to remain mindful of everything. But if you filter out what you don’t need and focus on what you do, eventually, it’ll become second nature. It’s a game of reevaluating priorities down to the day (sometimes even the hour).

How does "found" time at work help you balance your work/personal life?

Dean: Found time allows me to maintain all of the “hygiene” work, such as transposing my notes from Grammarly to Confluence. These items are essential. However, they don’t need to be maintained every day.

Found time also allows me to reach out to other internal teams that may require my assistance or guidance on who to contact, allowing for their issue to reach the fastest resolution. Clearing those “hygiene” items off my list allows more free time to not think about work when I’m not working.

Ben: Agreed. Honestly, work-life balance has become incredibly important to me. Found time at work helps you balance your personal life. But, unfortunately, I’ve worked for companies where there’s just no such thing as work-life balance. Some organizations expect you to give your entire self to the job. It’s dangerous to operate that way – that lifestyle can cause mental health concerns.

Now, I work hard to maintain a healthy work-life balance. My wife is a site reliability engineer for Etsy. Luckily, they share a similar work-life philosophy to what we’ve adopted here. Together, we’ve come to view our work lives like a bank account. Here’s how we see it:

Every day, you attack your tasks. That’s like making deposits into your bank account, filling it up with savings. But some days, you don’t feel great, or you’ve got something personal you need to do. On those days, you make a withdrawal. Of course, you have to keep a positive balance. Most days, you make regular deposits, but you need to make a withdrawal now and then.

If I find free time, I can knock another thing off my list – a quick deposit. Or, I can duck out a little early – a mini-withdrawal. And found time isn’t always about getting more time to work. Sometimes it’s about running out to grab a coffee from my favorite spot. Or maybe I’ll go zone outside for a beat so I can shut my brain off to recharge. Then you come back in and get your brain back on the clock.

What time-management lessons have you learned from situations that required you to pivot at the last minute?

Dean: At a previous job, I tracked down a virus on our network and finally pinpointed the infected computer. At the same time, an employee was on the phone with support. While listening to the call, I noted some red flags indicating an attacker – that employee wasn’t actually interacting with a support team.

Rather than fixing the computer with the virus, I confiscated the infected laptop to concentrate on the call with the possible attacker. Unfortunately, it turned out I was right. The person on the phone was an active attacker attempting to gain access to the company’s systems.

I physically took the phone from the employee and ended the call. Immediately, I contacted the CISO. I could only prevent one disaster at a time. I made the split-second decision to end the call. Once I blocked the attack, I could bring everything back to operations.

I learned that it’s okay to act with urgency during critical moments, even if the person you’re speaking with doesn’t understand that urgency. Demanding the phone and hanging it up seemed rude at the moment, but acting on instinct allowed us to protect our organization.

Ben: I was working for a pretty big alcohol conglomerate. The higher-ups were pretty disconnected. For instance, once they assigned a long-term project, like rolling out Cisco WebX for 10,000 people, and asked us to complete the task in 48 days. Under natural conditions, a task that size takes about 18 months. So I thought, “Um, what? You’re crazy!”

Of course, I have no problem speaking up, so I went up the chain to question the initiative. I was informed that the new CIO wanted some shiny way to show immediate progress to our CEO. Like, “You hired me, and look what I did!” But the project was unrealistic.

Sometimes, you just have to grit your teeth and go with it. But at the same time, you have to stand up and fight against the lack of concern for your well-being. So how do you do both?

Sometimes you can't. In those events, I write down why an idea is terrible and send it to management. At times, it helps; often, it doesn't get attention.

Unhealthy companies push their employees to meet nasty timelines. But in a healthy company, when you’re chipping away at your systems engineer job and something breaks, it can be fun, especially if you’re a member of a good team.

Pivoting doesn’t need to mean disaster. If you ask, “Who’s dying?” and the answer is, “No one,” then it’s much better to prioritize realistically so people don’t get burned out and start hating their jobs.

Right now, what’s your biggest time-management challenge? If you could wave your magic wand, how would you fix it?

Dean: I’d say a significant hurdle has to do with duplicated efforts due to having too many software packages that perform the same function or require the same information. For example, we shouldn’t have to go to the Salesforce platform when we already have Jira. I typically automate such tasks.

Ben: My team is good at judging how long tasks will take. Again, we work in two-week sprint cycles. That helps. But more importantly, my managers’ styles are flexible. Planning for those cycles is always a two-way street. Discussions of what we can truly get done are open, honest. We’re not just working toward what someone outside the department wants to hear.

What IT productivity tools do you use? How have they added to your success or given you back time for higher priorities?

Dean: I’ve used every type of software under the sun. I use Powershell for process automation, like translating my notes to Confluence pages. Powershell can interface with both web and server applications. So I’m able to do things once and translate them everywhere. I use toolsets like Mode Analytics to perform routine discovery processes, focusing on the issue and not the symptoms. The discovery process is handled for me. Also, I get pretty graphs.

Ben: My wife and I use Trello and have our own Confluence site for at-home and personal tasks.

When you have an emergent issue, how do you reprioritize recurring tasks?

Dean: Well, I gauge the scope of the task and the urgency of the request. If I have multiple client requests pending, the importance of that client applies weights to the task list. It allows for a dynamically scaling, self-reprioritizing task list, which lets me focus on what will most benefit the company and clients.

Ben: I simply ask, “What’s on fire?” Find out who’s yelling the loudest, and then talk to them. Evaluate tasks case by case. If the urgency is directive, like it’s coming from a higher-up who’s interrupting your work, you just have to try and communicate what it is they’re pulling you away from. If their fire’s bigger, it gets your attention.

What hacks can you share to help other ITOps professionals look like superheroes to their supervisors?

Dean: Make lists. For instance, I make a list of people with whom I’ve worked on specific issues. First, I find out where escalation paths are broken. Then, to facilitate the fastest route to remediation, I create communication pipelines for those groups or teams. Following the same escalation paths creates solidified processes. So, not only have you gamified it, but you’ve also taught others how to play the game.

Once everyone’s playing the same game, the world is on your plate because everyone’s rallied behind a unified experience. This also helps fight against the “not my job, not my department” mentality. Instead, you’ve helped create a team that works together to identify and remediate issues.

Ben: Constantly look at what’s needed. Asking, “What do we need?” allows you to try your hand at solutions. You’re actively trying to improve the experience; then, you can better serve your clients (internally and externally). It’s basic customer service – how can we make you (and keep you) happy?

Also, script repetitive tasks. Or, if there’s a process that takes many steps, script it, so you don’t have to remember each step next time.

Finally, I’d say to have a beer with your workmates. Check in with your manager on non-work-related topics. In a distributed environment, these things become even more important.

There’s no water cooler around which to gather and just chat about life, but simply asking your coworkers how their lives are going fosters empathy. It’s more important than you may think because as we grow, siloing is natural. But if you have compassion for what others are doing, you can eliminate animosity between teams. That allows a community in which togetherness is a shared value. And groups that work together work faster.  

So, what are Dean and Ben’s key takeaways when it comes to taking back your time in ITOps?

  • Gamify your process

  • Communicate directly about bandwidth

  • Write scripts for repetitive or step-heavy issues

  • Automate tasks

Often, loss of time is inevitable. You may have the best intentions, but some mornings you just can’t make it to your computer on time. The day gets away from you. Meetings beget meetings. Tasks pile up.

With some of these time management skills under your belt, you’ll find you’re able to pivot more readily and meet the demands of your day. You might even find a little time to duck out early and take care of the to-dos that matter most to you – a workout, a good read, a home-cooked meal, or time with family and friends.

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