Karl Hughes

Karl Hughes

Empathetic Leadership: Finding the Problem Under the Problem

Empathetic Leadership: Finding the Problem Under the Problem

Empathy tends to be one of the most underrated qualities in a professional environment. As a recent survey by Ernst & Young reveals, its capacity to improve office dynamics, employee satisfaction, and organizational productivity is immense.

You’d be surprised at how many workplace disagreements boil down to avoiding open conversations.

A while ago, I found that a part of our editorial process at Draft.dev wasn’t working from a quality control perspective. The editorial team knew we needed a fix, and my Director, a very pragmatic, action-oriented person, came up with a solution and put it in place.

It was a good solution that some of the editors agreed with. Many of them, however, weren’t comfortable as it added some new responsibilities to their plate, and a couple had trouble following through with it.

When we analyzed the situation, we realized it wasn’t so much that the editors didn’t want to fix the problem; it was that they had no say in _how _we fixed the problem.

This often happens when leaders try to solve company-wide issues with directives sent from above — however apt and well-meaning those directives may be.

This was an important learning for me and the rest of the company. We’ve had to rethink our decision-making process, our change management process, and our communication practices to better serve our team.

In this piece, I’d like to explore more about how empathy can be a driving force for productivity and positive work experiences within an organization. I’ll also delve into how leaders can become more empathetic managers and empower their employees to level up.

Empathetic vs. Other Leadership Styles

“To me, what I have sort of come to realize, what is the most innate in all of us is that ability to be able to put ourselves in other people’s shoes and see the world the way they see it. That’s empathy.” - Satya Nadella, CEO, Microsoft

Empathy is the ability to understand what the other person needs and being conscious of their thoughts and feelings.

The opposite of an empathetic leader would be an autocratic one — a dictator who makes all the decisions without feedback from their team. While caricature-ish leaders of this sort do exist, in my experience, most managers fall somewhere in between the two.

Some in this middle ground will try to be “empathetic” by expressing concern for their colleagues or offering pleasantries without really asking after what the problem is. That’s not empathy as much as sympathy. It’s not enough to know that someone is dealing with a problem. Showing empathy is trying to understand how you can make a difference. It has to _matter _to you that the person resolves their problem.

Why Should It Matter?

There’s an idea that a team should be like a second family and colleagues should aim for that level of rapport.

I don’t like this idea. And a lot of people who like clear boundaries between their work and private lives will question the merits of being too involved in team members’ personal problems.

So why should you do it?

The short answer is that it’ll help improve team performance. The long answer is that productivity is directly linked to mental wellbeing, which can be affected by a range of underlying factors.

As people juggle everything from ambition to workplace conflict, family problems, and financial struggles, they can find it a challenge to be happy at work. Empathy can be a powerful antidote to this by creating a positive experience in their lives.

In a recent survey of U.S. employees by Catalyst, 76% of people reported feeling more engaged at work and 86% as having a better work-life balance when their leaders were empathetic.

More tangibly for an enterprise, it also affects employee retention and innovation. 61% of employees with highly empathetic leaders reported always or often being innovative at work compared to 13% without.

There’s a great story about how Steve Jobs had to become a more empathetic leader before he achieved his biggest successes. His Co-Founder at Pixar, Ed Catmull, once described him as a “boorish, brilliant, but emotionally tone-deaf guy” who became a changed man after getting fired by Apple in 1985. To paraphrase Catmull, after this all-time low, Jobs went from being “dismissive and brusque” to treating people with empathy and respect. Over the next 20 years of his life, he founded NeXt and Pixar and returned to lead Apple — arguably some of the most innovative and successful companies in American history.

In his famous commencement address at Stanford, Jobs said “I’m convinced that the only thing that kept me going was that I loved what I did…Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do.”

I’ve personally experienced the benefits of having an empathetic boss as well. In 2018, I was CTO at the Graide Network. My job was to lead the engineering team, but I noticed we had some issues with the operational processes, and I wanted to help. I remember being nervous to ask my boss about it because I was asking her to let me take on responsibilities completely outside of my usual role.

But instead of being cagey or protective of her turf, she was receptive and empathetic. I spent six months on that project and the company used the systems I put in place to scale from grading a few hundred articles a month to tens of thousands a month.

If you’re in a workplace where you don’t feel heard and can’t contribute your best, you’re not going to love the experience. This is why some of our editors pushed back on the changes we made without consulting them, and it’s why we made changes to involve them more directly in the future.

How to Be a More Empathetic Leader

Empathy is in part a genetic trait, which means it comes more naturally to some than others. However, that doesn’t mean you can’t practice and get better at it.

Here are a few techniques I’ve found helpful to train myself to be more empathetic:

1. Listen and Observe

Active listening is one of the most useful skills you could ever pick up — even more so than communication. You can navigate any conversation when you understand where someone is really coming from.

What’s more, people feel respected when you make an effort to listen to them. Managers should make it a point to look for the meaning behind people’s words by paying attention to not only what’s being said, but also how it’s being said, the feelings being shown, facial expressions, gestures, and body language.

This is an excellent way to empathize with someone even when they’re not being straightforward with you. In fact, doing this and addressing their real feelings will help cultivate trust to the point where they do feel comfortable telling you what’s actually bothering them.

2. Go Out of Your Way to Help

Sometimes, just listening isn’t enough if you don’t often touch base with your team members.

At Draft.dev, I frequently have one-on-ones with my employees which is a chance to ask them how they’re feeling at work. If they’ve consistently missed a KPI for a while or I sense that there’s something wrong, it feels good to discuss it and help them through the problem.

This is also a good way to deal with stress and burnout. As a manager, if you see a team member putting in more hours than they should, it’s a good idea to encourage them to take a break while reassuring them that it won’t negatively impact their career.

Other ways you can go the extra mile is by understanding the unique needs and ambitions of each team member. This can mean assigning specific work projects or catering to their life goals. A few years ago, at the Graide Network, one of my team members came to me with what was an unusual request at the time — to work remotely while she traveled the world. While it wasn’t something the company had offered before, I said I’d be happy to put together a proposal and speak to the CEO about it. It worked out and the fact that I was willing to go to bat for her not only helped keep her around for longer, but also led to her being more engaged at work.

3. Empower Others to Find the Solution

Sometimes, your employees will come to you with a persistent problem that they can’t seem to solve. It’s tempting to try to solve the problem for the person, but a better approach is to involve them more in the problem: show them the constraints you’re facing and ask them to help guide you to a solution.

In other cases, the “problem under the problem” is fear or a lack of confidence. Teammates that don’t feel empowered to solve their own problems may only feel capable of complaining about things, and too fearful to step out on a ledge and propose solutions. In this case, you have to build them up and help them develop the confidence to solve problems independently.

Other times, the person is actually facing other stressors in their life that are completely out of your control. For example, an employee may be having financial issues, family issues, or health problems. While as their boss you can’t fix those issues, you can try to be empathetic and understanding of the situation. Give them more time and flexibility to handle their external issues and try not to make work another stressor.

How Can the Organization Be More Empathetic?

As a founder or business leader, there are steps you can take to instill a culture of empathy throughout your organization.

Make empathy a key part of your company values. Let it permeate organizational thinking and encourage your employees to make decisions from a place of compassion.

Empathy has helped us improved collaboration within the company, but also helped us improve relationships with our clients. Our account managers make it a point to try and understand what’s really behind client feedback and objections. Over time, this has helped create a positive environment where our clients trust us enough to tell us what’s really on their minds so that we can brainstorm a solution together.


For me, empathy means treating people the way I’d like to be treated, and this is important, because empathy is all about choice.

Are you willing to give trust without expecting it in return? To be patient and look at a behavior beyond its face value? And to give people the space to be wrong or less than transparent?

You have to be vulnerable to make these choices, but you will be happy you made them.

Like what you see? Find me on Twitter to continue the conversation.

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