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How to Lead with Empathy in a Remote Environment

by Gábor Zöld
/ January 19, 2022
Leading with EMpathy - Jossie Haines cover

How to Lead with Empathy in a Remote Environment - Interview with Jossie Haines (VP of Engineering, Tile)

Leading with empathy should be table stakes in any workplace.

However,most people are sure they’re every bit as empathetic as they need to be. This is why so few leaders make the effort to include empathy into their day-to-day leadership practices.

So we bring you stories, exercises and examples from Jossie Haines, VP of Engineering and Head of Diversity, Equity and Inclusion at Tile. Her thoughts will help you figure out whether you have room to grow in practicing empathetic leadership, and show the way if you do. This post is based on episode 55 of the Level-up Engineering podcast hosted by Karolina Toth.

This post covers:

How do you define empathy in the workplace?

Empathy is the ability to put yourself into someone else’s shoes and to understand how they feel. It’s especially important for leaders to have compassion for their team members. It’s crucial to take all the different perspectives into account when you’re leading a team.

Empathy is a vague term, and you need to try to make it concrete for your team members. When it comes to software engineers, I start by talking to them about empathy in code reviews because it’s tangible and they do it on a daily basis. This makes empathy actionable.

Example: Empathy in code reviews

Empathy for creators

When it comes to code review time, you may just want to push the code out and move on to the next project. You may be in a rush, but remember that the people reviewing your code haven’t been beside you during the development process, and others will have to work on it later. Have some empathy towards your present and future colleagues, and create documentation that explains why you pulled crazy stunts in your code.

I advise my teams to treat code reviews as an archaeological dig. Present the facts to the others. Write clean code and give it context.

This is the purpose of code reviews.

Empathy for reviewers

On the other side, the code reviewers need to practice empathy as well. You can often look at a piece of code and think, “Why would anyone do that?” But starting your comment with questions with, “Why did you” or “Why didn’t you” makes it look like an attack and puts the other person into defensive mode.

Assume that you all aim to build the best possible product, and trust that your colleagues work with the best intent. They may have a good reason to write code like that. Or maybe they had an off day and made a mistake.

It may be better to phrase your questions like: “I noticed there’s an extra variable, and I don’t see it here. Did you mean to use it here?” Asking the same question this way shows more compassion.

How do you define leading with empathy?

I consider Brene Brown’s definition of empathy spot on. She defines empathy with four attributes and these explain how empathetic leadership works.

1. Take others’ perspective

As a leader, you need to be willing to put yourselves in other people’s shoes, and process what they’re going through. Leaders, especially former engineers, often get into the habit of trying to fix everything.

When I switched from engineer to manager, I thought my job was to fix things, but I was wrong. I had to learn that my colleagues don’t need me to fix everything. They need me to help them fix their own problems.

The first step towards leading with empathy is listening, reflecting and acknowledging how the other person is feeling.

2. Hold your judgement

Keep an open mind to the fact that others face challenges that you don’t. Never say something like: “I don’t know why you’re upset.” Take the time to listen to what the other person has to say to fully understand it.

3. Acknowledge emotions

Recognize what the other person is feeling, and acknowledge it.

When somebody comes into your office frustrated, it’s better to say: “It sounds like you’re really frustrated,” before you start focusing on the solution. Failing to acknowledge that emotion stops it from dissolving, and it’ll cloud the entire conversation.

4. Communicate deliberately

Be deliberate about phrasing your thoughts. Show the other person that you understand their experience by saying something like, “I’m sorry you’re feeling like this. I know it sucks.” Or, “It sounds like you’re in a hard place; tell me more about what you’re going through.”

How do you infuse leadership with empathy?

Master emotional intelligence

The challenge is showing up as a leader during difficult conversations. It’s especially important in remote work, because you don’t get as many interactions to show who you are as a person.

You need to work on your leadership soft skills to realize what emotions drive you at each moment. It’s key to realizing that you need to pause and reflect before you respond. Leaders need to understand the emotions others are conveying as well.


In an executive leadership position, you can’t afford to lose control and snap at anyone, especially not in a large meeting. This may only happen once, but if you do it in front of 30 people, you give them all the impression that they should never disagree with you because you’re likely to react poorly. As a leader, you need to stay cognizant of your behavior and your communication.

You don’t have to be perfect, but if you snap at somebody, apologize. The sooner you do it, the better, and if you snapped in front of others, it’s a good idea to apologize in front of others as well. You can say, “I’m sorry. I didn’t mean to react that way. Please, can we have this conversation again? I would like to hear your point of view.”

If your employees or peers start thinking that they can’t bring up something that you might disagree with, you’ve failed as a leader. Encouraging disagreement is an essential part of leadership.

Coach emotional intelligence

Work on your own emotional intelligence, and coach your direct reports, especially if they’re leaders themselves, to improve their emotional intelligence as well.

You can’t build great products with everyone agreeing with you. You need diversity of thought and constructive disagreements to come up with the best possible solutions. This requires a safe environment, where everyone can speak up.

Psychological safety starts with the leader not shutting people down. You also have to make sure that no one else shuts them down either. You can’t tolerate this behavior consistently in your team; a leader allowing bad behavior without calling it out is the same as encouraging it.

What are the challenges of leading with empathy in a remote environment?

Lack of personal interactions

The biggest challenge is missing the verbal and physical cues you get when you’re in a room with somebody. This plays a big part in why it’s difficult to engage remote employees.

In a remote meeting with a large group, there are times when you may want to turn your camera off. It’s normal, I do this occasionally as well. However in a one-on-one conversation, I recommend you use the camera, so you can see the other person’s facial expressions.

In a remote environment, you need to be more intentional about building relationships. You can’t rely on running into people in the coffee room or at lunchtime.

Empathizing with external challenges

Humans don’t like change in general. Currently, we’re going through a worldwide crisis, which forces everyone to deal with changes. Everyone has been impacted in some way.

Show empathy for the external changes the people around you are going through. This goes beyond the pandemic and beyond work; you can apply this to your personal life as well.

How do you lead with empathy in a remote environment?

Currently, we aren’t just in a remote environment, but in a remote environment with a global pandemic. It adds an extra layer of stress for everyone. It makes it more important to practice leadership with empathy.

It’s easier when your team is working from an office. You have casual conversations, and you can build trust and relaationships organically.

You lose these in a remote environment, so it’s important to take leading with empathy to the next level. People have a lot going on in their personal lives that you may not know about because you only talk to them in remote meetings.

Add chit chat to one-on-ones

I advise every leader to spend the first 5-10 minutes of their one-on-one meetings with casual chat about how their reports are doing, and get them to open up. This may sound like a big part of a 30-minute meeting, but it’s not just chit chat. This is relationship building.

A tip for this is to take notes about the topics that come up in these casual conversations. We’re all humans, and we can’t keep in mind everything we’ve ever discussed. But taking a note that someone mentioned their daughter is starting dance lessons can help you kickstart the conversation the next time by asking a follow-up question.

People appreciate this kind of empathy. This will help you engage remote employees.

Some say that taking notes is cheating and it doesn’t count as empathy, but I disagree. I spend most of my time in meetings, so I can’t keep in mind what I’ve talked about with everyone. Given this situation, making an effort to create and use reminders counts as empathy.

Most people with a large network I know have their black books of everyone they’ve networked with. They take notes of what they talked about. It’s a great method to learn about people and practice empathy.

How did you learn the importance of leading with empathy?

Moving into management

When I left Apple, I was dealing with impostor syndrome. I thought I was a bad manager and that I didn’t have it in me to turn it around. In reality, I just needed to learn how to be a good manager.

In engineering, we promote great individual contributors into engineering leadership. In a management role, they need an entirely different skill set to be successful, and generally no one prepares them for that. The tech knowledge comes in handy, but there’s a lot more they need to learn.

This is a struggle for engineers transitioning into management. They’re used to being a star employee, but they’re mediocre when they start out in a management role.

Practicing vulnerability

I had struggled for a while. The solution for me was developing the willingness to be vulnerable.

Every day I looked for the most difficult, uncomfortable thing I needed to do, and I started with that. People tend to avoid these, but these are often the most pressing issues. Repeatedly putting myself in this position was one of my methods to practice vulnerability.

Continuous learning and practice

There’s a difference between academic and practical knowledge. Learning about empathy in theory isn’t enough, you need to turn it into action and practice on a daily basis. To master leading with empathy, you need to do it, make mistakes, and learn from them.

Leaders should never stop learning. The best leaders I know realize that leadership is an endless learning journey. If you stop learning, you’re doing a disservice to your employees because you can always get better at practicing empathy, holding people accountable, and refine your leadership style.

Story of a failure in empathy at Apple

Here’s an example about how the developers’ opinions can end up in a product, which in turn can influence the rest of the world.

If you ask Siri about sports, it defaults to men’s sports. At one time, a female developer asked the male devs about this, and they told her: “It’s because the public doesn’t think women’s sports are as important as men’s sports.”

This conversation actually happened.

This is why you need to apply empathy in every aspect of the business on every level.

How do you coach leaders who don’t consider empathy an important leadership skill?

Understand their reason

Have an open mind and learn about the reasons why they don’t think learning about empathetic leadership wouldn’t be valuable to them. You need to be genuinely curious, listen to what they think and feel, and take the time to understand it.

Present your perspective

Once you understand where they’re coming from, you can share your own perspective on why it’s important and how it makes the world a better place. Additionally, you can reflect on where applying more empathy could help them in their job.

Research shows that inclusive and diverse teams improve profitability. It may seem counterproductive, but it makes you money. It doesn’t work as a side project; it has to be holistic across the company from diversity in recruiting to designing your product for inclusion.

What are the common mistakes of people trying to lead with empathy?

Focusing on solutions

Move yourself out of the headspace of trying to fix everything.

A subtle sign that you need to improve in this may be starting to answer others while they’re still talking to you. Most people don't realize that they do this. You may think that you know what someone is going to ask you when they’re only halfway through, and start to formulate your response, but this means that you don’t actually listen to them.

Fear of silence

People often feel like silence is uncomfortable. A short pause in a conversation can make you feel like you have to fill that void.

Sometimes, when you ask a difficult question or you ask for an opinion, you start thinking after two seconds, “Nobody answered, I must have asked a stupid question. Let’s move on.” When you start talking at that moment, you don’t give anybody a chance to answer because you’re stuck in your head.

It’s better to let others finish what they have to say and let the silence be there before responding or moving on to make sure that you’ve listened to them properly. It’s going to feel uncomfortable. If it doesn’t, you’re likely doing it wrong.

Being too hard on yourself

I advise every leader to reflect on the day’s events at the end of each day. Consider what went well and what you may improve on.

Remember, the point isn’t to beat yourself up. You may feel like you did something wrong and you’re a horrible person, but if you go down that path, you can’t go back to figure out how to do better.

When you feel this happen, you need to remind yourself that you aren’t a horrible person. After making a mistake, figure out what you can do next, and do it. This may be as simple as scheduling a calendar appointment to have a difficult conversation rather than keep avoiding it.

Bonus advice to leading with empathy

Listening exercise

Here’s a listening exercise that you may use to practice. All you need is another person and a timer.

The first person shares a story for two minutes, while the second person isn’t allowed to say anything. Then the second person has two minutes to reflect back what they think they heard, and the first person isn’t allowed to interject. Finally, the first person has to share what the other person got right, what they got wrong, and what they forgot.

It’s an interesting exercise that helps you get better at active listening. It points out that you can miss a lot of things both when listening or when explaining your thoughts.

Empathy is for life

We’ve been focusing on empathy in leadership and the workplace, but the same skills help you build your personal relationships as well. Listening exercises are a common practice in marriage counseling. This is how empathy can help us make the entire world better.

About Jossie Haines

Jossie is currently VP of Software Engineering and Head of Diversity, Equity and Inclusion at Tile. She’s been in the tech industry for over 20 years, and she’s been holding engineering leadership positions for over 10 years. She’d worked on Siri Music Media and Sports at Apple, where her team and she won a technical Emmy for integrating Siri to Apple TV.

After leaving Apple, she considered leaving the tech industry. She chose to stay to be able to impact the future, and came to realize that the industry needs more diversity. Tile provided her the opportunity to work on getting underrepresented minorities into tech and create an environment where they’re happy to stay.

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