By Jon Xavier

Picture this: You’ve just accepted an offer to be the first IT manager at a rapidly growing startup. It’s your first time calling the shots on technology at a growing company, and you couldn’t be more pumped! You come into work on your first day and you have an email from your boss waiting for you entitled “projects for this month”. Excited to see what big things you’ll be working on, you open it up.

and...

Oh no. Oh no.

If that scenario seems familiar, congratulations! The test came back positive, you definitely work or have worked in IT. Virtually every IT manager has had the experience of feeling like they’ve bitten off way more than they could chew. It’s normal.

What makes this job manageable rather than a never-ending deluge of impossible tasks is three things: Process, mindset, and culture. The good news is that you’ll never have a better chance at perfection than you will as an IT manager at a company that has not had them in the past. You’ll be coming in fresh, not beholden to another manager and the processes they created, the relationships they’ve built (or neglected), and the culture that’s developed. It’s a chance to do things right—and this first 90 days is a critical period.

The bad news: this is still going to be a lot of work.

At Fleetsmith, much of our team has been in this exact situation, some of us on multiple occasions. So we feel your pain, and we want to help out.

This is the first in a series of posts aimed at helping new IT managers navigate their first three months on the job. We’ll outline the general approach you should be taking to set yourself up for success, as well as give some advice about mindset and how you should tackle this work. In subsequent posts, we’ll go into each of these topics in more detail, to give you a better understanding of what you should be trying to do and why it will make you more successful in the future.

Your goals in your first 90 days

Situation audit

Your first job, before you do anything else, is to do a full situation audit. You need to know everything about the environment you’ll be working in, the devices you’ll be dealing with, the people you’ll serve, their needs, the needs of the business, and the ways those needs are and aren’t currently being met.

Obviously, performing a full device and network audit is one of the first things you’ll do as an IT manager. You need to know systems you’ll be responsible for and their current state before you can make intelligent decisions about security and compliance. But your initial audit can’t stop at technology. The secret to being an effective IT manager is that it’s often as much about people and processes as it is about machines.

As you’re a new person stepping into a new role, the people and processes you’ll deal with are probably not well-defined. That does not, however, mean that the processes don’t exist. Chances are the things you’ll be doing will replace or augment work that’s already being done by other people. You need to know who these people are and how they work, because anything you decide to implement here will have a direct impact on them and their productivity.

One question it’s especially important to answer is “what do people think I’m responsible for, and does that line up with what I think I’m responsible for?” It’s very common for people to assume something is the purview of IT, without actually telling IT about it. This can lead to either critical functions not getting done, or a big mess of work landing in your lap without warning.

If you know about a problem, you can fix it. It’s the things you don’t know about that are killers. So job one is to learn as much as you can.

Triage and problem solving

While it would be great if you could spend your first three months learning and planning the best possible technology stack to tackle the needs of your company, chances are you won’t have that luxury.

The unfortunate truth is that most companies wait too long to hire an IT manager. This is because it’s a role that is most visible when things are going wrong. Chances are good if your new bosses thought to hire you, they did so because things are already seriously messed up. Your first 90 days won’t just be about dealing with emergencies—it’ll be about deciding which emergency you’ll work on out of the wealth of disasters you’re presented with moment to moment.

You’ll probably notice that the tasks you need to tackle fall into three groups:

  • Something is currently on fire.
  • Something will catch fire pretty soon if you do nothing.
  • Fireproofing.

In the very beginning, it’s likely that you’ll be dealing mostly with the first two groups. There’s probably a lot of small things that are currently snarling productivity, and there’s probably one or two larger projects that are just on the cusp of causing real headaches for the team.

This is fine, but you should plan your work with the understanding you probably won’t get to everything. It’s easy to solve lots of small, urgent problems while ignoring larger issues that aren’t urgent… until suddenly they are. Your triage process has to be rooted in a holistic understanding of what each problem means in material terms for the company and for other teams. This is why discovering this context as a part of your situation audit is so critical.

Develop process

Of course, if you only ever put out fires, you’ll only ever be a firefighter. One of the most important things you can do is to develop processes whereby you learn about issues more quickly, address them efficiently and consistently, and then revisit the process itself in light of results so that things can continually improve.

In the beginning, every problem will feel unique, and it can be tempting to simply address it and move on. Over time, you’ll notice a few “one-offs” that recur on a regular basis (employees getting locked out of things and needing to reset their credentials) as well as things that are regular workflows that are never really “done” (onboarding). These are the obvious targets for developing a well-defined process.

But even things that truly are one-offs could usually benefit from better processes. Whenever something occurs and is resolved, it’s a good idea to take a step back and answer these questions for yourself.

  • Could this have been prevented?
  • If not, what could be done to find out about it earlier?
  • When resolving this, what were the steps I took? Which of them took to long?
  • Who needed to hear about this, and how was it communicated? Was that enough?

These questions will probably unearth parts of your process that are less-than-great and suggest clear areas for improvement. This exercise will also suggest other projects you could undertake to improve functioning, make things more reliable, or automate busy work (what we earlier called “fireproofing”).

When you’re fighting your way out from under a mountain of more urgent tasks, fireproofing projects can seem like a “nice to do someday.” That’s not the right way to think about it, however. Each of these projects will actually prevent work once they’re fully implemented. That means they take on an exponential importance—the work you do on these projects now will multiply the effect of all of the work you do afterward, and the sooner you do it, the more benefit you’ll get. You actually can’t afford not to do these things ASAP.

Document everything

Documentation tops the list when it comes to critically important tasks that everyone ignores because they don’t feel urgent. After all, as long as you know what you’re supposed to do, what need is there to write it down?

Here’s the thing, though. One of the main things you’ll be doing as a new IT admin is centralization—you’re taking tasks that were being handled in an ad-hoc way or not at all by people across the org and bringing them under your jurisdiction. As long as you’re centralizing these in a process, this is great.

If you’re centralizing them in a person—i.e., you—you’re going to have a bad time. Centralizing everything in a person means you’re creating a single point of failure. It means either you do the thing, or it doesn’t get done. It means you never get to take a day of vacation ever again, in other words.

What’s the difference between centralizing things in a person and centralizing them in a process? It’s documentation. It’s having the knowledge on how to do the thing down somewhere in human-readable format rather than existing solely in your head. It’s the first step in taking things only you can do and making them delegatable, or even automatable.

Documentation is also easy, so long as you make it an ongoing practice. If you block out as little as 30 minutes to an hour each week to document the things you worked on, you’ll be surprised at how quickly all your processes will be documented, and you’ll naturally keep things updated. But if you keep putting this off, you’ll gradually accumulate “documentation debt,” which will quickly turn into a project so large that you’ll never do it.

Raise your profile

“Be more visible,” is going to seem like counterintuitive advice to most people getting started as IT managers. After all, being invisible is often a sign that an IT department is really on its game—if things “just work,” then there’s no reason for people to think about you at all.

Certainly nobody is going to tell you that you should try to raise the profile of your IT department. IT is uniquely solitary as far as corporate jobs go—if you want to stay locked in the equipment closet the entire time you’re at work, only dealing with people via email, and only when there’s a major problem, you can.

There’s a couple reasons why this is a bad idea, however. The first is that even if you want to keep a low profile, you probably also want to get raises, be promoted, be allocated adequate resources to do your job, and maybe even get permission to take on interesting and important projects that are outside of your day-to-day responsibilities. Unfortunately, invisibility is at odds with all of these goals. They’re all examples of what’s possible when a company understands the value that a person is bringing to the organization. Yet people can’t value what they don’t see. So even if your goal is for IT to be as unobtrusive as possible, it’s absolutely critical that your bosses and your coworkers see all the hard work you’re doing to get it there.

The other reason it’s important for IT to be visible is that it will actually make it easier for you to do your job. We’ve previously mentioned this in our article on security culture, but it also holds true here: this is a team sport. Even the most isolated IT department isn’t an island unto itself. You still have work-streams that you share with other departments (HR and People Ops especially), and there are going to be times when your success is highly dependent on other people. If the rest of your company only sees you when something has already gone horribly wrong or when you pop up to ask them to do something, you’ll be associated with problems, not solutions. People will be less likely to talk to you before something breaks, creating more headaches in the long run. They’ll also be less motivated to help when you need something from them.

So how do you raise your profile? Basically, get out of the equipment closet as much as you can. Ask to give updates on IT at company meetings. Hold office hours. Show up to social events at your company and actually talk to folks instead of posting up near the snack table. When you fix something, particularly if you know it’s something people have been annoyed by, drop an email or a slack message to the rest of the org to let people know it happened.

Conclusion

Starting at a new company is always hard, but IT is uniquely challenging because you’re being asked to take on a lot of important functions all at once, and if you mess something up, everyone will know. It can feel a bit like swinging on a trapeze, blindfolded and without a net.

That’s the bad news. The good news is that if you do IT well, you’ll become one of the most indispensable people in the entire company, while doing some of the most intellectually stimulating and rewarding work of your life.

These first 90 days set the tone and the tempo for the work you’ll be doing for the rest of your career with a company. We hope this advice, and the subsequent posts in this series, make them as smooth and successful as possible.

Good luck!