Technology careers may have no set paths, but there are a few time-honored truisms that can help you get an edge. Here, seasoned IT pros lend their hard-earned advice on advancing.
By Paul Heltzel, CIO
October 3, 2022
Perhaps your tech career feels like you’re treading water, and you wonder why your peers are progressing more quickly than you are. Or maybe you’re looking to shake things up and take the next step in your career. Regardless, it’s helpful to regularly pause, reflect, take the long view to optimizing your path, and stay open to new opportunities.
Whether you’re just starting out or are a seasoned veteran, tech leaders say there are ways to keep moving forward that aren’t always obvious.
As with the technology industry, change is constant for IT pros. Here accomplished leaders offer their best tips on how to advance in your IT career so you don’t get left behind.
Jump in the deep end
For some, being in over their head — and fast — can help forge a leadership career in IT. Michiel Schipperus, CEO at Sana Commerce, found that out at just 20 years old.
“I was asked to lead a team,” Schipperus says. “The manager had just quit, and they needed a solution quick. I did not think I was ready, but my mentor did. And it worked out. I learned how to lead a team, foster a culture, and deliver results. It was the best experience I could ask for.”
Find a mentor
Many tech leaders say finding a good mentor may be the single best thing you can do to boost your tech career. Abhay Kulkarni, senior vice president and general manager for Webex at Cisco, says you should look for someone who can help guide you, and then when the time comes, pay it forward.
“Everything you do influences others, so think about the best mentor you’ve ever had — perhaps a manager, a colleague, a parent, friend, coach, or a grade school teacher,” Kulkarni says. “Remember their influence — you will at some point in your life have the chance to impart the same for someone else.”
Good feedback is a gift, says Schipperus.
“It helps you grow,” he says. “Reach out to your coach or mentor and ask for their perspective and insight. Another opinion will enable you to look at challenges in a different light. You will find both tangible solutions and new opportunities.”
Treat your career like a project
Kulkarni says that career trajectories are rarely linear. There will be ups and downs, setbacks, and you may even take a regressive role at some point. Keep going, he says, and you may find yourself catapulted into a greater role later on. He advises creating personal metrics to track progress, just as you would with a project.
“Create milestones that measure growth other than financial or corporate ladder progress,” he says. “For example, tracking learning new skills or techniques or certifications are great milestones to build on your career path.”
Kulkarni likes to cross-train and not just at work. He weaves in both tech learning and some unconventional methods to keep his brain sharp.
“One of the best pieces of advice that I received in my career is that learning is never finished,” he says. “I like reading diverse topics, listening to podcasts that stimulate thinking, and even making friends that bring diverse views to keep my brain satiated. Balance your work and your passion outside of work. Get out of your comfort zone — if you are comfortable the desire to learn goes away.”
Execute as well as you plan
Some IT pros hurt themselves by focusing too much on how something will get done rather than doing it, Kulkarni says.
“A brilliant strategy can be obliterated by poor execution,” he says. “Lots of people think about strategy too much but not enough about execution. Companies — and bosses — like people who can bring strategy and execution together.”
Get feedback from colleagues
Kulkarni says you should ask for feedback from your peers, who he believes will be your toughest critics.
“Solid feedback can open the door to realizing and growing ideas, self-evaluation, and developing new thinking that can influence your career in positive ways,” he says. “If you know your weaknesses, that knowledge can be your strength. Be honest with yourself — no one is perfect. It’s okay to have weaknesses, as long as you build on them and use that as an opportunity to grow.”
Take the road less traveled
Erin Fusaro, vice president of engineering at Chipper Cash, was an English major who picked up tech skills — including coding — by working what she calls tech-adjacent jobs, where she could learn from IT and engineering colleagues.
“Don’t hide or diminish your past, rather lean into your unique background,” Fusaro says. “Diverse teams are more equipped and more resilient to the variability of working in technology. Different lived experiences and backgrounds will help us solve problems we haven’t even come across yet. Use your past to boost your future.”
Be open to opportunity
Fusaro doesn’t begrudge those who’ve planned out their entire careers right out of college — it works for some. But she’s found that being ready to pivot to new opportunities as they have appeared has been the best approach for building her career.
“When you’re less fixated on the one road you started out on, you open up your field of vision to possibilities beyond it,” she says. “As people find a down market or recession has thrown them off their original plan, resilience and agility will help you keep momentum. Instead, be open to opportunities, take calculated risks when there is an option to learn or stretch.”
Make a call, then revisit
IT managers sometimes feel paralyzed by the lack of a clear solution in the face of uncertainty, says Fusaro, and navigating chaos is critical especially in startups and other high-stakes technology situations where things change quickly.
“Paralysis is your enemy, don’t be afraid to make a decision,” she says. “Sometimes you will have to pick from a variety of flawed solutions in the spirit of moving forward. You will not be spared criticism, as most leadership often comes without sympathy. This is why resilience, humility, and a strong sense of your own intrinsic value is key to getting and staying ahead while keeping your mental and physical health in check. Some decisions have a shelf-life, that’s okay, revisit them later. Every decision you make on the way was right at the time if it navigated you to a better place.”
Take a step back
Marcus Merrell, vice president of technology strategy at Sauce Labs, says IT pros sometimes feel stuck in their current position, in part, because they may lack perspective on how their work is positively affecting the organization.
“To realize your impact, take a step back and look at other teams and how you all rely on each other to really succeed with a great product,” Merrell says. “You will see how much the team and product needs you and that your contributions are needed for success. To make a greater impact, find out what the biggest risks are to your business, and find a way to focus your time on those risks. By understanding the most fundamental things that keep your CEO awake at night, you can start to help with those specific problems and your impact has grown.”
Keep it simple
Advancing your career is often about focusing on the simple things rather than chasing the more interesting ones, say Jake Vygnan, COO and co-founder at Taimi.
“For example, it’s essential to know how to build a user’s journey, which seems simple and grounded,” Vygnan says. “But the person who does it well on each product will be a more precious specialist and asset than the one who wants to build a white elephant.”
Keep thinking big
Dena Campbell, CIO at Vaco, recalls that when she was a young analyst, her own CIO at the time stopped by to see why she was working so late. She was developing a software project that was facing many last-minute changes leading to a lot of stress.
“She listened, pushed me to share, asked me questions, and challenged me to articulate what happened,” Campbell says. “The next day she pulled me into a conference room filled with leadership to share the issue we discussed the night before. And although I was nervous, I was prepared to articulate the facts of the scenario and think bigger than I did the night before.”
Allison Lasater, vice president of enterprise technology and operations at Lincoln Financial Group, agrees that you can grow by taking a moment to reframe the situation you’re in.
“Check your perception,” Lasater says. “Feeling stuck doesn’t make it a fact, but the stories we tell ourselves are powerful. Changing the way you look at something really can change your experience. So frame the situation in a way that puts you in the driver’s seat and empowers you to take action.”
Lasater advises looking for assignments that push your limits, teach new skills, or connect you with a leader you admire.
“Rather than thinking of this as temporarily stepping out of your comfort zone,” she says, “allow these new challenges to permanently expand it.”
Rather than how hard you work, or how difficult your situation is, it’s key to remember you get paid based on how much value you bring to an organization, says Prasad Ramakrishnan, CIO and CISO at Freshworks.
“A lot of IT work is counted as overhead cost, but it is not necessarily so,” he says. “If feasible, try to not be just overhead, but make your work provide actual, measurable benefit. In some industries this is easier, for example when technology is the revenue generator, like in SaaS or software development companies. In other cases, IT supposedly just supports the manufacturing and sales operations. To advance your career, try to make your work count as actually cost saving, or even better as a revenue generator.”
Ramakrishnan urges IT pros to lead with empathy, a trait that benefits the organization, shows off your soft skills, and recognizes that your colleagues are humans first.
“IT careers are meant for the service-oriented, and empathy is the key ingredient to keeping employees happy,” Ramakrishnan says. “When employees contact IT, it is most likely because something is not working as desired for them. If the IT engineer does not show empathy for the user’s problem, they are hurting their reputation with the user, which can hurt their own career. Empathy is also a necessary trait for IT leaders to demonstrate. Beginning this practice early in your career will set you up for future success.”
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