Contributing writer

Empathy: A CIO’s force multiplier

Apr 29, 2022
IT Leadership Staff Management

The traits that define transformational leadership are evolving to include soft skills centered on connection and relationships, resulting in improved cultures, talent retention, and business outcomes.

Hands clasped in a heart shape against a background of abstract data / collaboration / empathy
Credit: Ilyast / Violka08 / Getty Images

There was a time, probably in your career, when you could say, “I’m not that empathetic,” or “people aren’t my thing,” and advance to a management position in IT. More recently, emotional quotient (EQ) became something that — combined with IQ and technical skills — made an IT leader a unicorn capable of being both an inspiring leader as well as an effective technology producer. In the past couple of years, however, the ability to demonstrate empathy has shifted from “nice to have” to a CIO’s force multiplier — the skill that elevates a team’s productivity, keeps hard-to acquire technical people from leaving, and is the sinew and tendon that connects your company’s culture.

If you are feeling this is a difficult ask, you have every reason.

“For a long time, empathy was farmed out to the HR department,” says Dessalen Wood, chief people officer at Syntax. “And suddenly leaders are expected to have the interest, time, and capacity for discussions we would previously have told them never to have around their staff’s personal life, mental health, and issues of social justice.”

Why empathy is suddenly a key leadership trait

“Empathy has always mattered,” says Heidi Brooks, senior lecturer in organizational behavior at Yale School of Management. “Employees want to feel seen. They don’t want to be cogs in a wheel. It matters more now, though, because work has become focused on questions around what work is and why we do it.”

All of this is happening because people have options. Your team — and everyone working in IT for that matter — is being recruited for jobs elsewhere, given the massive employment opportunities and the fact that, with the rise in remote work, they don’t have to uproot their lives to make a change.

“It’s a hot market,” says Wood. “Whenever there is unemployment, employers have to raise the bar. We’re in a bar-raising moment. And empathy is at the forefront of that raised bar, as is social justice and purpose.”

Eric Sigurdson, leader of the CIO practice at leadership consultancy Russell Reynolds Associates, sees firsthand how important an empathetic leader is when his team tries to recruit people. There are some people who aren’t interested. “They won’t call us back,” he says. And when his team asks why, in surveys, the reasons they give are telling. “They say things like they feel valued, their boss shows appreciation both monetarily and emotionally, or ‘the company moves me to different jobs so I can round out my skill base.’ They are all things that show the leader is empathetic,” Sigurdson says.

Empathy has benefits beyond recruitment and retention as well. As Wood puts it, “Leaders who connect with their people have a deeper relationship in terms of loyalty and the discretionary effort they get from their team.”

One of the first benefits you, the leader, will experience is knowledge. People will tell you things. “If you have trust and feel like your leader understands you, you are more likely to open up to that person when you’re blocked, when you don’t have clarity on work streams, or when you have ideas about how to innovate or change processes,” says Elizabeth Burstein, CEO and co-founder of Neura Health. “Empathy opens communication.”

According to Brooks, the reasons are even bigger than that. Your ability to lead with empathy can change the culture of your company and, through that, the world.

“Leaders embody organizational culture,” she says. “And since technology is changing the face of the world and of work, it is important — at a meta level — for tech companies to think about empathy. This is an exciting invitation for people to realize that the way they are doing this is not just for their team or company. These norms may guide how the world thinks about work.”

So, not to put too much pressure on you, but you need to embrace empathy in your leadership practices.

What is empathy?

You don’t have to get a psychology degree to become an empathetic leader. There are manageable ways to build this skill. The first step? Understand what empathy is — and isn’t.

According to Brooks, there are two kinds of empathy. “Cognitive empathy is about understanding where the other person is coming from,” she says. “Emotional empathy is actually feeling what they’re feeling.” Your job as a leader requires cognitive empathy.”

Cognitive empathy, Brooks explains, involves two key elements: “First, that you can see the situation the way the other person sees it, which involves imagining yourself in their shoes and asking questions so you can get more textural data on what they are experiencing. And then — and this is very important — you have to express that understanding,” she says.

This does not mean that you have to agree with the person’s worldview. You only have to understand it and demonstrate that you do.

“People get stuck because sometimes they feel that if they say they get where another person is coming from, then it’s like condoning or agreeing with their perspective,” Brooks says. “Sometimes you don’t agree. But you are just taking it in and letting people know that you see them and where they’re coming from.”

It sounds simple enough, but expressing cognitive empathy is a complex process that is easy in some instances and difficult in others. And, as a leader, you are being asked to show empathy equally in every situation. That’s the challenge.

“There’s what I call judgmental empathy,” says Wood, “That’s where, if I can identify with you, I have a never-ending pool of empathy for you. But if I can’t — and this has a lot to do with bias and inclusion — I think of you as a complainer, high maintenance, or full of drama.”

If, for example, you are a leader with small children at home, you might easily feel empathy for someone in the same situation. But you might be annoyed by someone struggling with loneliness, mental health issues, or anxiety.

Bring your beginner’s mind

IT leaders are accustomed to being subject matter experts. But empathy can be more difficult to define and master, putting it outside the comfort zone even of those who are good at learning complex — but predictable — subjects. “We don’t love to step out of our expertise, where we’re comfortable, feel elevated, and have earned the role of expert,” says Brooks. “You may have to come to this with a beginner’s mind. But think of it this way: You’ve earned yourself into a new level of problem to navigate.”

Rasheed Behrooznia, vice president of campus ID solutions at Transact Campus, agrees. “Leading with empathy was something I had to learn. Early in my career, I lead a small team. I had always worked hard and drove things to completion quickly. My expectation as a new team leader was that I would tell them what needed to be done and they would make it happen. I cringe thinking about that now. A leader must listen, take time to understand the individuals, what they need, how they learn, what’s their why, and then provide them with an environment to thrive in.”

What if no one will talk to you?

Chances are good that if you are leading a team, you have some history with your staff. Deciding to become a more empathetic leader might mean you have baggage to overcome first.

“You can’t just walk into a meeting with somebody you’ve been harshing on and ignoring and think they are going to disclose to you,” says Brooks. “You have to start by creating psychological safety.” If people won’t talk to you, they have reasons — either institutional ones or ones you have created.

“I have a rule,” says Volodymyr Semenyshyn, president of EMEA at SoftServe. “A leader always speaks last.” Because when the leader expresses an idea, it’s a decision in the mind of the team and no one is likely to contradict it. “When a general in the army says something, it’s an imperative; it’s a directive. It’s no longer an idea,” he says. “So, the general needs to listen to every idea about strategy or tactics and then decide what to do. It’s the same with leaders. It’s tough because we already know the answer. But speaking first kills autonomy and creativity and shows you are not an empathetic leader.”

Fake it until you get there

It turns out that you don’t have to start this process by feeling empathy, at all. You just have to practice a couple of very simple steps to start your journey. You will discover empathy as you go.

“Start by asking deeper questions,” says Wood. “When you’re asking people — as we were all told during COVID — how they are doing, be ready to ask some follow-up questions.” What you are doing is acknowledging what the person said and curiously digging a little deeper. “From those three to seven minutes of curiosity, you will gain a greater understanding of that person and that person will feel seen. Both of those things lead to deeper connections and a stronger bond.”

Wood tells a story of trying to teach empathy to a difficult tech leader who was reluctant to learn. After a workshop in which she suggested he start by asking questions and follow-up questions, he sent her an email asking a question. She answered. He asked three follow-up questions. Even though she knew he was irritably following a script she’d just given him, it worked. “We ended up becoming collegial colleagues, as a result of that.” He also saw the value of the strategy — and of empathy — and worked on it with his team.

Be careful of the words you choose

Language can be tricky, especially in hybrid environments. Words, outside the context of facial expressions and body language, can have unexpected results, as May Habib, co-founder and CEO of, points out.

“We did a survey that found that when people communicate asynchronously, the level of perceived toxicity and bullying goes up,” Habib says. “I think this has a lot to do with the fact that text-only communication is so two-dimensional.”

Watching the language you choose to use over these methods of communication — eliminating terms that seem passive aggressive, condescending, or riddled with cultural bias — can go a long way to improving how you are perceived by your team.

“So much of our language gets to undercurrents of culture,” says Habib. “When we change the words we use, we can change our thoughts. People may have good intentions but might habitually deliver feedback or communicate a certain way. Checking your language — and having awareness of the problem — is the first step. It also creates an opportunity to connect in a more positive way, which can lead to better performance and outcomes.”

This is one area where training, even group training, can help. Though there are also tools, Habib’s Writer being one of them, that can watch and make suggestions as you write.

Get coaching

Everyone I spoke to for this article suggested that leaders should get coaching on empathy.

“This is a skill that you can develop and learn, if you put in enough time,” says Semenyshyn. “But you need to work with a coach. Within our organization, all managers have training on empathy. We explain what it is, what to do, and which questions to ask. It is like a certificate from a university, though,” he laughs. “It doesn’t guarantee that you have knowledge, only that you had the chance to get it.”

Wood suggests that you do a mix of one-on-one coaching and conceptual training.

“When it comes to trust, empathy, or empowerment, it’s wonderful to attend something with your peers,” she says. “Then you should have two to four hours of coaching with an HR business partner or external person who can help you see how this impacts your relationships.”

She references her relationship with the leader who was reluctant to embrace empathy as a management tool. “Conceptually, we’re smart people,” she says. “But the action of sending me a message and having a connection with me was like cognitive behavioral therapy. It showed him how these actions do show empathy and improve outcomes.”