Why is Listening with Empathy an Important Skill for Every Leader?

Many leaders have problems with empathy, especially managers with software engineering backgrounds. Before transitioning into people management, they were usually senior engineers: the knowledgeable ones who got used to providing opinions. But now, they hold a different position—one that requires them to understand people.

The fundamental change during the transition happens in perspective. People encourage software engineers to give input, which trains them to talk more and share more thoughts. In leadership, instead of being encouraged to input, you start encouraging others to share opinions. You have to listen and understand more; you have to silence your inner software engineer, keep it on hold and understand what people are saying.

Leaders who cannot silence their inner engineers lead the team members into difficult situations and conversations. They forget that they were once in the same position, annoyed by the hands-on micromanager who always talked and gave directions. Now, they are in the same place and unintentionally repeating the same mistakes.

The leader has holistic knowledge; others don't

Leaders often see things others can't. They have a more holistic view and knowledge of projects, people, and goals. Although they can use this perspective to bring clarity to the problem, many leaders unintentionally force people to follow their solutions. They fail to become great leaders; instead, they succeed as mediocre micromanagers.

As the leader holds authority, their view has more weight and impacts the discussion. That's why leaders are discouraged from sharing opinions all the time. The leader has to let other people learn. Instead of assuming the engineers have similar knowledge and perspective, the managers have to listen, stay silent and develop understanding through people's growth and problems.

Genuinely understanding an engineer, or anyone, results from listening with empathy and requires a lot of work. Sometimes, it becomes difficult because the person is unaware of what they really need. They want something, but they actually need something else. The need often differs from the want. This mismatch is the difficulty of developing empathy.

For example, imagine an engineer who wants to work on a specific project. If the skill set matches with requirements, the non-empathetic leader assigns the person to the project. After a while, the engineer begins to have significant problems with the project. The manager starts to think that the engineer is the problem. As a manager, they did what the engineer asked for: assigned them to the project. However, the problem is not on the engineer but on the manager. Yes, the engineer said they wanted to work on a project and the manager assumed this was what they needed, but, instead, they either needed recognition, or a new challenge, or less stress, or to prove themselves. It's rare that what a person asks for is the same as what they really need.

Assuming rarely works; assuming without empathy never works

The first thing the leader has to do is active listening: silencing the noise both in the mind and in the mouth and focusing on the other person, seeing through and beyond them.

Humans naturally form assumptions to find a common understanding between each other. However, many leaders unintentionally stick to these premature thoughts. Leaders have to constantly abandon assumptions until they find the correct route to the truth. Many discussions lose track because one side sticks to a premature idea and drives the conversation with it while the other side is talking about something else. These switch-track conversations are easy to fall into and lead to many conflicts.

Assumption and empathy are mutually inclusive: without one, we can't have the other. Building empathy requires forming a lot of assumptions and premature thoughts and constantly abandoning them. If the wrong assumptions drive the conversations instead of a sudden dispersion, empathy will be hindered. For empathy to surface, assumptions have to repeatedly disappear until they are replaced by genuine understanding.

Approaching with empathy

Leaders confuse empathy with being nice. Empathy indeed provides the source of power for kindness and care. It's also true that empathetic leaders are nice. But empathy is more than that.

Empathy is listening and seeing another person; preventing all personal judgment, fitting another lens on life, wearing another jacket, and putting on someone else's shoes. Empathy is becoming a different person each and every time.

While these definitions are nice, empathy is easier said than done. Approaching another soul with empathy is difficult. There are only a handful of known techniques which also don't guarantee great success. Actively listening encompasses these few techniques including increasing transparency, asking clarifying questions, and repeating the other side's message.

While many leaders try to do one or two of these, they still fail to understand the person in front of them. The real value emerges when these three techniques are done in the correct order. Many leaders begin by asking clarifying questions after listening to another person. This technique is the first recommendation attached to empathy in leadership literature, but it actually should come after bringing transparency to why you're asking clarifying questions.

It should be a universally accepted understanding that when someone asks a question, they also give the reason why they are asking. Giving the reasoning behind a question brings transparency and, therefore, builds trust. Yet many leaders fail to form a simple sentence before asking a question: "I would like to ask a few questions because I want to understand the core of your message, feelings, and thoughts." One sentence is often more than enough.

Without transparency and clarification, there won't be trust. Without trust, all questions are meaningless, and all answers fall short. That's why before asking any question, the leader has to be transparent. Once the engineer understands the person behind the questions, getting the proper answers for clarifying questions becomes easier.

Asking the right question at the right time is an art that many leaders work hard to become experts at. However, many of them also stop right after they get answers to their questions. There is one last thing to do, one of the most overlooked actions to understand another soul: simply repeating the message as heard.

The power of the technique is in its simplicity, and that's why many people underestimate its value, yet, it solves almost all implicit misunderstandings. Both clarifying questions and repeating the message give the engineer a chance to, and the confidence to, elaborate on their message and correct any misunderstandings without the fear of judgment.

If we put all the actions in order, the correct guide for becoming a leader who listens with empathy emerges as follows:

  1. Explain your intention about why you'll ask questions to bring transparency and build trust.
  2. Ask clarifying questions with curiosity. Let the engineer feel your curiosity.
  3. Repeat the other person's message as you understand it to seek alignment.

Truly listening and seeing another person is a long journey. Learning these simple techniques takes time.

"To see takes time, like to have a friend takes time."
— Georgia O'Keeffe on the art of seeing.

Aside from taking the time to learn and practice empathy with this technique, there is another element of empathetic listening that has to spread through the whole conversation—staying silent.

Making peace with silence

Saying nothing always scares people. A moment of silence is one of the most vulnerable moments of our social lives. It creates heavy stress and an urge to speak up. Silence causes stress because it actually starts the busiest conversations; conversations between feelings. Instead of a mouth, it uses the heart. This vulnerability scares leaders because the tough business leader image that society has drawn for decades cannot handle being open with another person.

However, when the leader effectively uses silence, the message, "I hear you, let's think and digest the words together," shouts to the engineer. It becomes clear that the leader takes time to comprehend the message. In conversations, there is usually no place to think things through. That's why during the small pause, the leader publicly and silently announces that they heard and are currently thinking. Practicing this kind of silence is difficult because the software engineering leaders got used to giving opinions so much that staying silent always feels intense and miserable.

It's the urge of not only every software engineer but also every human to fill a silence after four seconds. During this time, many leaders fall into the flow because they want to take action on projects, while deadlines are putting pressure on them, and they interpret the silence of others as uncertainty on what action to take.

Leaders don't have time as they rush through from a 1:1 meeting to a weekly update meeting, from discussions to a decision, from action to feedback. Within this busy life, taking a ten-second silence is terrifying. The always-on, urgent life tricks leaders into destroying the beauty of silence and breaks the first opportunity to build true empathy. In empathetic listening, there is no place for urgency. Taking the time is mandatory to understand the other person (and ourselves) and to let the feelings have a great conversation.

"If we were not so single-minded
about keeping our lives moving,
and for once could do nothing,
perhaps a huge silence
might interrupt this sadness
of never understanding ourselves."
Pablo Neruda

Getting comfortable with silence is difficult. But it gets easier with practice. Without practice, trial and error, it's impossible to build empathy.

While assumptions hurt relationships, silence and active listening strengthen them. With every empathetic action, the leader makes a deposit into the trust bank and opens another line of connection with the engineer. Once the leader begins understanding the engineer and their actions, the sky becomes clear, and coaching and guiding the engineer becomes easier.

Before offering advice or reassurance, leaders have to offer empathy. Many leaders fall into the trap of giving advice because they believe they have to "fix" the situation. By approaching analytically and intellectually and sticking to wrong assumptions, empathy is blocked. The only way for the leader to hear what the engineer is saying is by starting with active listening and empathy. When the leader sees that the engineer releases their tension and their flow of words come to a natural halt, the leader becomes successful with their empathetic approach.

Long Form Last Updated: Sep 24, 2022