The secret to a successful IT career development strategy

When Leon Kallikkadan learned that someone on another team had her sights on a role in his technology department, he sat down with her and mapped out a plan to help her get there.

“She’d been a recruiter, so she understood our business,” explains Kallikkadan, EVP of technology at Atrium, a global workforce management and talent solutions provider. “Then she moved to a business applications support role, so she knew our tools. I suggested she get PMP and Scrum certified so I could move her to a leadership role.”

Kallikkadan’s own career path had been defined by a similar conversation with a manager who helped him plot a route to leadership. So, this response, for him and others in his company, was reflexive.

The power of listening

With talent markets tight and high-potential employee retention on the line, building a successful career development strategy can be a difference maker for IT organizations. And it starts with one simple act: Ask where your people see themselves in three or five years and listen to the answer. If you use what you learn to build a roadmap for each person, that effort will have a profound impact on your organization, improving retention, bolstering the bottom line, and building careers.

According to a LinkedIn study, 94% of employees stay longer in companies that invest in professional development. Another survey from Pew Research found that a lack of career development is the most common reason for quitting a job. A study from agentic intelligence company Draup found that internal candidates are 50% more likely than external hires to stay beyond 18 months in a new role — and that companies that don’t reskill pay a 25-30% premium to replace midcareer engineers.

It is a simple act. But like many strategic moves, it is more complicated than it appears on the surface. I spoke to experts, career coaches, and leaders for advice on how to do it well.

Think like a coach

You may already be having conversations like this with your team. If you are like many managers, though, you then use a career ladder or organizational chart as a prebuilt map to the destination your team member has in mind.

“Most career development programs fail because they optimize for org charts and skills inventories, not for how people grow,” explains Brian Pulliam, CEO at Refactor Coaching. “If you come to this with the mindset of an athletics coach, the first thing you will want to know is what are this team member’s stats.”

Everyone has innate abilities, skills, and a destination in mind. Unfortunately, people are often the worse judge of those things. Humans are often blind to their abilities, underestimate their skills, and pick a goal based on other people’s expectations.

“It’s hard to read the label from inside the bottle,” says Pulliam. “So don’t trust the individual to rattle off what they’re good at.” He acquires stats via a skills assessment. (He uses CliftonStrengths.) Once you have objective stats, it’s time to think like a head coach. What skills does this person have? What are their innate strengths?

“If Betty is good at kicking a football 30 yards through a field goal, which is impossibly hard to do, it would be idiotic of me to make her the quarterback. It doesn’t take advantage of what she’s good at right now,” Pulliam says.

Give her work that plays to her strengths, and she will enjoy the work more, have lots of success, and become more engaged.

“Then talk about where this person wants to go,” Pulliam says. But keep in mind that you might have to create trust before you get a true answer. “Somebody might be afraid to say, ‘I’m a PM, but I want to go back to being a developer,’ because they’re afraid they’re going to get laid off.”

Switch things up to match strengths — and bolster engagement

Even if you don’t get that true answer, having each person’s stats will immediately improve everyone’s game and start building trust.

“Business outputs go up when there’s a match between the work an individual is good at and the work they do,” says Pulliam. Acting like a coach, finding each person’s strength, and throwing tasks at them that match is a small effort that pays huge dividends.

“If I shuffle tasks around for the next couple of sprints, I often see an engineering velocity spike,” says Pulliam. “And in my one-on-ones, I’ll start to see questions that suggest people are more engaged.”

The next thing that happens is that people stay. They like their job and stop looking for another.

Recognize that everyone’s path is different

The career ladders that many organizations rely on give the impression that every path is identical and linear. But no two paths are the same.

Pulliam explains it with an analogy. “You and I both want to get to a mountain on the other side of a lake,” he says. “I’m a terrible swimmer, but an accomplished hiker. So I walk. You went to college on a swimming scholarship. It would be stupid for you not to swim.”

You know where you are, where you want to go, and what skills you have. Every career path has to be charted by placing these data points on a map that includes the entire company and skills that can be acquired outside the company.

The course Atrium’s Kallikkadan plotted for the recruiter who wanted to move to tech was designed specifically for her. “It happened in baby steps, but also in a structured manner,” he says.

This isn’t necessarily hard to do. Yet many leaders don’t do it. MIT Sloan categorizes the type of manager who doesn’t as The Bystander. They don’t think it is their job; likely because no one did it for them.

Small efforts can change cultures

“We need to change this behavior because leaders are role models,” says Priyanka Dave, PhD, workforce upskilling leader at Oregon State University.

Turning bystanders into the kind of leader MIT Sloan calls Captains — leaders with a strategic, organization-wide perspective — happens before they become leaders. It starts when you sit down with a team member, listen to their goals, and help them get there. This makes them more likely to stay and get promoted to a senior role. Having experienced the power of that simple act, they then do it for their own team.

“It becomes a generational thing,” says Pulliam. “They do this because they have a role model that demonstrated something very effective. But it starts with a grassroots effort.”

That’s not to say that you have to do this alone. Your HR department can’t change the culture for you, but they can be a resource as you do it.

“HR can coach managers to lead this type of conversation,” says Dave. “Managers often fail to initiate these conversations because they are not sure how. The workforce development team from HR can offer support, guidance, tools, and techniques.”

When someone chooses the wrong path

It has been shown that people are often very bad at assessing their own skills, so you might find yourself in a conversation with someone who wants to plot a path toward a goal that, according to the skills assessment you have in front of you, might prove disastrous.

Pulliam sees this as an opportunity to have a deeper conversation about career development.

“Ask, ‘Do you want this because of reputation or salary? What if that work is not fulfilling for you?’” says Pulliam. “I’m not here to tell them one path is right or one is wrong. But I might explain that this hill will be steeper and it will take longer to get there.”

Meanwhile, put tasks in front of them that match their skills and abilities to give them some quick successes. “Focus on their current skills, current strength, current constraints and have a continuous conversation around where they want to go,” says Dave.

At the same time, find some actionable ways they can acquire the skills they need to progress on the path they have in mind.

Chances are that the experience of trying work that they are good at — and work they aren’t — will show them the right way. When they no longer dread Mondays and feel successful, this mismatch of goals to skills often resolves itself.

When facing a situation like this in the past, Kallikkadan let the team member briefly live both options.

“I let them spend 50% of their time with Team A and 50% with Team B,” he says. “We ended up very quickly learning that this person was a better fit for Team A.”

Build a chess board

Part of any career development strategy must also be self-serving. As a leader, you are building a business, a product, a solution. Creating happy people isn’t really the goal, though it does more to serve your business objectives than most people realize. Still, don’t stop there.

Once you’ve set the foundation by assessing everyone’s career development interests, strengths, and performance indicators, you can use that knowledge to build a powerful team. That might include trading team members with other teams to improve the skills and overall fit of your group — and theirs. For example, if you have a team of brilliant problem solvers, you might need someone with other skills, such as the ability to sell ideas or explain technical projects in simple terms to the C-suite.

“Consider a chess board,” says Pulliam. “You want pieces that will attack at a distance and some that’ll attack in short range.”

When Kallikkadan traded team members to help someone on another team achieve her goals, he got more than he expected.

“In my core, I’m an IT guy,” he explains. “I know technology. But selling things doesn’t come naturally to me. For her, it was easy. I thought I was getting someone who understood the business, but I got someone who could speak that lingo, too. She’s doing phenomenally well, performing at the highest level.”

She strengthened his team with her diverse skills. And she is the kind of leader who knows the power of that simple act of listening because, like Kallikkadan, she experienced it firsthand.