How to choose the right IT career path: Advice from IT leaders

Learn more about an IT career path

IT Kit Presents: Career Growth in IT

Starting a career in IT can be fairly straightforward. You pick an area of focus, learn it, and eventually find someone to hire you to do that type of work. As you grow, though, the path forward can become much less clear.

Eventually, you have to ask yourself: “Should I continue working as an individual contributor and perfecting my technical skills, or is it time to move into IT management? It’s a tough question to answer. Being great with technology doesn’t guarantee that you’ll be great at managing people—or even enjoy doing it.

To help you make an informed decision when you come to a fork in the road of your IT career path, Spoke and IT Kit brought together four IT leaders for a panel discussion:

Our panelists advising on how to pick the right IT career path.

IT Kit Presents: Career Growth in IT

Here’s the advice our panelists provided on topics like knowing which IT career path—technical or managerial—is right for you, what success looks like in each role, and how to build the relationships you need to succeed regardless of which path you choose for your career.

Which IT career path should you take: technical or managerial?

For IT pros with a few years of experience under their belt, the next “logical” step in their career means management. But for many people, moving into a managerial role could be a misstep.

You might think to yourself:

Those are merely assumptions, not necessarily truths. Being great at your job doesn’t guarantee that you’ll be a good leader; in fact, studies show that only one in ten people have a natural talent required to become a great manager. Titles also don’t guarantee you an audience with decision-makers. As Manuel says:

“A manager or director title alone doesn’t make you a leader. It sounds super cliche, but it’s true: everybody is a leader. The best managers I’ve worked for really encouraged us all to be leaders, regardless of our titles.”

Manuel from Greylock

Let’s abandon assumptions about what the next step should be, and instead, ask the right questions.

What do you really want to do?

Answering this question is the first step. And it’s a hard question to answer directly because what you really want sometimes gets warped by aspirations and visions of prestige—things you want because you think you’re supposed to.

To get past those ideas of what you’re supposed to want and get to the heart of what you really want, Erin recommends asking a different question:

“When you dream about what you’d no longer have to do, what does that look like? That’s where you start to see where your path is trying to take you. If you could give something up, what would you desire to give up, and what would you lament giving up?”

Erin from Pixar

“I’ve heard from so many people who went in and were like ‘I have to know Python,’” she says. “But you don’t see them get excited when they’re talking about it. They just know that it’s a fundamental, basic necessity for the job.”

“Ask yourself: is that really what you want to do? Is that what gets you up in the morning? Or do you want to be the manager—the person who’s representing those other departments—and let somebody else do the technical work?”

Are you willing to delegate your work to others?

Manuel recommends taking the last question a step further and asking yourself: “Am I willing to give up control of this stuff? If the answer is no, you probably need to stay on the technical side.”

Handing off ownership is an issue that Lauren has struggled with over the course of her career:

“I’ve been a one-person team a couple of times, and I’ve managed people a couple of times. You’re never completely giving up the technical part; that’s always a part of the job. But it’s not always about you getting to play with the fun new thing. You have to be willing to shift your enthusiasm, to look forward to watching your team play with the fun new thing instead.”

It was terrifying at first, Lauren says, to give up control of different systems she owned, but she realized she wasn’t looking at it the right way:

“It didn’t take long for me to let that early anxiety go, and now I get really excited about things for my team. I actually enjoy that more now—watching my team do well.”

Lauren from Blend

Think about handing off the set of work you enjoy the most—or a system you’ve built from scratch and managed exclusively. When you imagine it, can you see yourself feeling happy to teach someone else to do that work?

How will you handle difficult conversations?

Manuel says that another factor to consider is how you would handle dealing with an employee who’s not performing to your standards:

“When you take on managerial responsibilities, the hardest part is the people—not the technology. For example, if you have an employee who’s not performing well, you’ll find out quickly if you have the chops or not to have that performance conversation.”

Manuel from Greylock

Lauren believes that it’s important in this scenario not to fall into the trap of thinking “‘He’s the only one I’ve got. I can’t be alone.’ But you can. You might suffer for a while until you find somebody, and it feels hopeless. But at the same time, if they’re not happy—and they’re not getting the career growth they need for where they are—you’re doing them a disservice.”

While it’s a difficult conversation, Lauren says it’s necessary to be completely frank with employees in this position. “Say ‘this is what I need from you,’ and ask ‘is this what you want to do?’ If they say no, you obviously need to try to find a fit someplace else in the company. But if you can’t, you have to go your separate ways, and that’s important for both you and them.”

If it’s in your nature to avoid confrontation, the managerial track may not be right for you. Having hard and frank discussions is part of the job, and few leaders—if any—get through their careers without having to have them.

Are you willing to work with other departments?

Being an IT manager or director is about more than just managing technology and technical professionals. That’s the easy part. The harder part is realizing the larger role that IT plays in modern organizations, and figuring out where you fit in and how you can help with broader concerns.

“Being able to articulate what you’re trying to do to other departments is definitely a huge aspect of being a manager in the IT field,” Lauren says. “Sure, you might get along great with teams like engineering and ops; you speak the same language and just talk about the tech. But you also have to communicate with other teams and find out what they need and are trying to do.”

Manuel says: “It’s important to ask yourself, ‘Do I have the ability to go to other business units and involve myself in what they’re doing?’ Sometimes people are just uncomfortable communicating with other people. But as a manager, you have to do it, even if you don’t like it.”

Luckily, this question is a pretty easy one to answer, even before you’re in a management role. As Steven says:

“If you work in desktop support, you’re the perfect person to be going around and talking to people because you’re out there fixing things in the field. It’s a good way to start communicating with people in other departments before advancing in your career.”

Steven from Pantheon

Manuel agrees. “That really shows you should be thinking about the managerial career path. But if you’re more like ‘if I have to help that person one more time’—if you just want to fix the issue and get out of there—the managerial path may not be right for you.”

Success in IT—technical or managerial—starts with relationships

Regardless of where you currently are in your career, there are a few things you can start doing to improve your chances of a successful future IT career path. Getting to know your company on a broader level is a big one. As Erin says:

“Having a fundamental understanding of your organization will lead you down the path that’s right for you. It’s also something that someone looking from the top down will probably be really excited about. With that understanding, you can start to pitch the things that you’re most interested in and get buy-in for them. It builds that trust and autonomy that someone is probably looking for as a decision-maker.”

Gaining that understanding and driving your own success—all participants agree—is about relationships. But how can you start building them?

Getting to know people

Lauren says that one of the things that’s unique to IT is that sometimes you’re the group that has to “throw a cold bucket of water on the fun plan. Someone has a great idea but didn’t tell anyone about it, and then they bring it up in an all-hands meeting. And you have to be the person that says, ‘Well that violates SOC2 and all of our certifications and policies.’”

Manuel says that you can be proactive in those situations by building relationships before you have to have those tough talks:

“If you’re just getting coffee in the morning and see that one person you never talk to, make eye contact. Ask ‘How was your weekend?’ Work-related conversations are easier when you’ve already built a pre-existing personal relationship.”

Manuel from Greylock

Getting to know people also opens the door for offering to help them. “If you communicate with people,” Lauren says, “you can say, ‘There are a lot of complaints about X, Y, and Z and it looks like this tool will really help you.’ Being able to communicate that, asking people what they want instead of telling them, is really helpful.”

Join other teams’ meetings

Another way to start getting a feel for what other teams do and building personal relationships is to join one of their weekly team meetings.

Lauren says: “This is just as important at the technical level as it is on the manager level. You can’t advise teams at the technical level if you don’t know what they do, and you can’t help them at the manager level either. Go be a fly on the wall at their weekly meeting. It may be over your head, but if there’s something you can fix on the technical side, you won’t know if you don’t ask.”

Conduct a survey

Another thing Lauren recommends is conducting a regular survey: “I take a survey and ask how we’re doing. And all the feedback—brutal and non-brutal—is good. You’re probably doing a lot of stuff wrong, but you can never fix those things if you don’t know about them. Once you start having a survey, do it regularly. Do it a few times a year.”

But surveys aren’t just good for managers. Steven, a one-man IT team, agrees that surveys are key:

“At Pantheon we have 150 people. Of those, 70 or so are in physical offices, and the others are remote. How can I know if I’m doing a good job if I don’t see those other employees? The survey is really important coming from my position.”

Steven from Pantheon

Surveys also help limit surprises as an IT manager when you release your roadmap, according to Manuel. “The last thing anybody wants is to be surprised. So when the roadmap comes out, it hopefully has things on there that people have mentioned recently as issues in the survey.”

Admit your mistakes

Everyone makes mistakes. As Lauren says: “You’re going to make mistakes. You’re going to screw up. That’s okay. The important thing isn’t the mistakes, it’s acknowledging those mistakes and trying to fix them. That matters more than even getting it right the first time.”

Erin agrees, and argues that you have sometimes have to get comfortable with being a contrarian. “Sometimes when you own things you have a dissenting opinion. Expressing that opinion means you’re representing your team, giving them a voice in the room. Confidence in your ownership of things, especially when it’s not going to make people happy, is crucial.”

Know your allies

Being a contrarian or tossing the bucket of cold water on an idea isn’t always fun, but you don’t have to do it alone, either. Lauren advocates bringing in people from other impacted teams when you have to be the bearer of bad news:

“You have to call in reinforcements from security, engineering, finance, and maybe legal. If it’s illegal, the legal team won’t hesitate to say so. And finance will say, ‘We don’t have three million dollars for that.’ Let other teams help you.”

Lauren from Blend

Manuel agrees: “Sometimes you don’t even need to know that other person. You just have to know who the right person is and say ‘Let’s bring in the CFO. Let’s bring in legal. It’s not necessarily up to my team.’”

“But don’t not say something,” Lauren says. “We sometimes feel like we can’t say no because we’re trying to help everybody, and sometimes you don’t feel authorized because you’re just the IT person. But you have to say something—or at least get someone more appropriate to say it for you.”

Final tips for transitioning from a technical role into management

If you decide that moving into a leadership role is right for you, our panelists also shared some tips and lessons from their transitions that could help you along your path:

Again, communication is key. “I’d say over-communicate,” says Manuel. “When you go into a company and they really don’t like IT, the root cause boils down to a lack of communication.”

Additional resources

Looking for more tips and advice on choosing the right IT career path and succeeding in your career? Here are a few resources to check out:

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