Leading with Empathy

Empathy is a highly valued trait in the workplace.

This shouldn’t be a surprise – people want to work in an environment where they are understood, valued, and are allowed space to be themselves. Building a culture of empathy is core to achieving this.

However, something I discovered early in my career as a business leader - and something I see other new managers discover as well - is that leading with empathy is a lot harder than simply being empathetic.

This is because the job of a leader is often to deal with the murkiest problems in the organization. Leaders have to make decisions that are in the team's best interest, even if the individual members don’t agree or don’t like it. Leaders are the ones that have to hold people accountable for results and to deliver direct feedback. As a leader, you can’t abdicate these difficult aspects of the job.
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Outside of a business context, empathy is associated with being thoughtful, warm, considerate, and good at listening. These all apply to being a business leader; however, living out these traits while being a decisive leader can be challenging.

At Collage, we recently participated in the Great Places to Work survey and achieved stellar scores across every dimension of the survey. While we are certainly not perfect, we are doing something right when it comes to cultivating a performant culture while maintaining a high degree of empathy.

Here are a few concepts that I’ve found useful when it comes to leading with empathy. 

Share context often

Many people come into leadership positions with a pre-baked idea that leaders are the keeper of team secrets and that they should only share information that feels necessary. Many people in positions of hierarchical power feel like they don’t owe their reports an explanation for all of their decisions. Additionally, leaders often feel like they need to maintain the image of confidence and unwavering authority, always appearing to have the right answer.

While some things in business need to be kept confidential, the best way to build a culture of mutual empathy between leaders and reports is for leaders to share their world with the team consistently. This starts with sharing information like revenue metrics or plans with the team, but to be an empathetic leader, it can’t end there. 

The best way to build a culture of mutual empathy between leaders and reports is for leaders to share their world with the team consistently.

Leaders should also invite teams into their thought processes and share the challenges or trade-offs they are navigating. Another term for this is being vulnerable with your team – opening up to the truth that you don’t have all the answers but are methodically working through them so that you can achieve the best outcome for the team.

Sharing context with your team has a number of magical benefits:

• They feel respected as professional adults rather than infantilized 
• They feel valued as an important contributing member of the team
• They feel trusted to be brought into the leader’s thought process
• They are more likely to act in a way that aligns with the needs of the team
• They are more understanding when difficult decisions have to be made because they were brought along with the thought process
• They are more likely to extend trust and respect to everyone else on their team

If a leader is nervous about sharing their thought process or strategic challenges with the team, it could be a sign that the leader is hiding sloppy thinking and needs to improve their internal roadmap to the point that they are proud to share transparently with their team. If you find yourself in this situation, ask yourself why.

Leading with empathy isn’t just about extending empathy to others. It is about building a culture of mutual understanding and empathy that starts from the top of the organization. Sharing context with your team is a crucial first step.

Be Consistent

To flourish in an organization, people need to exist in a predictable environment.

Individuals need to know what to expect from their manager and their organization to know how to go about their role and life. It is hard for people to do their best work and be their happiest if they are given unclear or conflicting objectives, a rotating door of managers or varying expectations about work hours or vacation.

Leaders also need to be clear about the direction of the team or company and consistently ensure that everyone is working effectively toward the same larger objective.

Leaders also need to be clear about the direction of the team or company and consistently ensure that everyone is working effectively toward the same larger objective.

Being consistent might not be an obvious component of leading with empathy; however, it is a key part of helping people feel valued and respected in an organization. When leadership fails to create a consistent work environment, they are sending a message that the needs of the individuals on the team are taking a back seat to the chaos occupying the minds of leadership.

Now I want to be abundantly clear that predictable and consistent does not mean static. 

Many startups and high-growth companies’ defining characteristic is their ability to change direction, iterate and make fast decisions. However, to be an empathetic leader, you have to: 

1. Be transparent about this and set expectations for employees fairly, and
2. Don’t use iteration or speed as an excuse for bad management.

If you are a leader in a high-growth environment, the bar is actually higher for managers to create a framework of predictability for their team because the team exists in an organization whose default state is change. Even though objectives and projects might constantly be changing, a manager can still create a predictable environment by defining how the team works and being transparent about how the team contributes to the organization's overall goal.

To lead with empathy, leaders need to ensure their reports feel valued and supported, and for this, consistency is key.

Go overboard to support your team

Many people have an established notion that individuals in an organization exist to serve the leaders; that every person should work hard to deliver for their boss because the boss holds the keys to praise, raises, and promotions (or, on the flip side continued employment).

While none of this is technically wrong, I’ve found that a more effective framework is to flip this idea upside-down. Leaders should instead exist to serve their reports, and the measure of a leader is the output, success and well-being of their team. 

I’ve found that a more effective framework is to flip this idea upside-down. Leaders should instead exist to serve their reports, and the measure of a leader is the output, success and well-being of their team. 

When a leader adopts this framework and takes specific action to support it, the individuals on a team get an overwhelming sense of empathy coming from leadership because the leader is now focused on helping them achieve their goals rather than acting as an extractive gatekeeper to rewards and punishments.

Additionally, it is especially effective when leaders take personal initiative to support their team in times of need. For instance, when a team is short-staffed, a leader can take on a portion of the excess work even though it might seem ‘below’ their job description. 

Or, if a leader has to give constructive feedback to an individual, they could spend a bit of evening or weekend time creating customized training to help the individual on their way to improvement. 

When leaders spend their time like this, it shows they are fully committed to the success of each person on their team and aren’t asking anyone to do work that they aren’t willing to do themselves. 

The opposite of working to support the team is when leaders spend their time on self-interested activities like self-promotion within the company, loose-tie external networking or taking additional time off because ‘they are the boss.’ When individuals see these behaviours but feel under-supported in their daily challenges, it can lead to demotivation and resentment.

When leaders go overboard to support their team, they demonstrate with action that they value their reports. In return, they will more often than not get a huge reciprocation of effort and focus from their team. In this kind of environment, everybody wins.

Adapt your style to each individual

So far, I’ve talked about building systemic empathy into the organization and a leader’s management style. 

However, a lot of empathy does happen 1:1 between managers and individuals, so interpersonal communication naturally plays a role in being an empathetic leader. Empathetic leaders need to adapt their communication and management style to each individual to guide and motivate them to succeed. 

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We have to recognize the truth that people are wired differently. 

Many personality tests like Myers Briggs or OCEAN have been criticized as pseudo-science or sarcastically labelled ‘astrology for MBAs.’ However, at the core of these tests are a powerful insight that different people perceive the world differently and respond differently to work and social situations. 

For instance, I am a highly competitive person who responds well to harsh criticism and tends not to take work-related disagreements personally. I tend not to need praise very much to be motivated and lean toward distrust when I receive frequent or trivial praise. On the other hand, other highly effective people in every organization are the opposite: they would find direct criticism to be highly demotivating and require frequent praise to be at their best.

Again, people are different.

A leader needs to understand what motivates each person and what kind of feedback they respond to best, and then incorporate those learnings into their interactions with their reports. 

A leader needs to understand what motivates each person and what kind of feedback they respond to best, and then incorporate those learnings into their interactions with their reports. 

The best leaders know how to present the right feedback to the right person at the right time. This type of adaptive leadership style is critical to being an empathetic leader because tailored feedback means that:

• Individuals will absorb more of what their leader is telling them
• Individuals will find receiving feedback to be a motivating activity and seek more of it
• People will feel more understood and valued on their team
• People will feel like they can be themselves at work rather than fitting into their leader’s prescriptive style
• There will be fewer miscommunications owed to communication styles, leading to better alignment and less resentment

The challenge of adapting your communication style is to do so while 1) staying consistent, as I outlined above, and 2) not simply telling people what you think they want to hear. The path to being an empathetic leader is filled with nuance. However, by following these core principles, any person can become a better manager and build a culture of empathy throughout the organization.