Logical Empathy

We often hear about empathy as a singular concept—a soft skill, an essential quality of being human that connects us to others. But empathy comes in two flavors. It has shades, and understanding them might make us better humans.

We often hear about empathy as a singular concept—a soft skill, an essential quality of being human that connects us to others. But empathy comes in two flavors. It has shades, and understanding them might make us better humans.

Two Sides of the Same Coin: Logical and Emotional Empathy

Emotional Empathy: This is the classic definition of empathy that most of us are familiar with. It’s feeling what another person feels. If your friend is sad, you feel sad. If they’re excited, you feel their joy. Emotional empathy happens almost instinctively. It’s raw and visceral.

Logical Empathy: This form is more calculated. It’s understanding what another person feels without necessarily feeling it yourself. It’s more about perception, awareness, and insight. It’s about seeing things from their perspective, even if you don’t feel their viewpoint.

Emotional empathy might be more natural for some people. You know the type, those who can feel a room’s mood as tangibly as a physical touch. I’ve always admired that, but it wasn’t me.

And then there are others for whom logical empathy might be more innate. These individuals are perceptive, analytical, and capable of seeing a situation from various angles without becoming emotionally entangled. Many of us who make our careers in technology are attracted to the industry because we have these skills.

Learning the wrong lessons early

Most of my first jobs were at large companies with very competitive and hierarchical cultures: IBM, Silicon Graphics, and Microsoft. Microsoft in the 1990s was legendary for its’ hyper-competitive culture. I worked there for eight years. Microsoft taught me that I had to expect that other teams were constantly looking for how to undermine mine and that every outstretched hand was likely masking a knife held in the other hand behind the back. I eventually realized that the environment was a bad fit for me, but sadly, I didn’t get out until I had internalized those lessons.

After Microsoft, I sought out more collaborative environments, but I struggled. I constantly expected ill intent behind every action from a peer. I knew that this was hurting me and that I needed to move to a mindset of expecting positive intent from others, but I didn’t know how to rewire my brain.

A Splash of Insight: David Foster Wallace’s “This is Water”

My epiphany came when someone recommended that I read David Foster Wallace’s commencement address to Kenyon College, “This is Water.” If you haven’t read or listened to it, it’s enlightening. Wallace talks about default settings, the unconscious, automatic ways we interpret everything around us. He speaks about learning to think more compassionately and understanding that everyone around you has a unique inner life full of dreams, fears, and struggles. And it’s not always about feeling their pain; sometimes, it’s about understanding their pain.

Wallace’s speech was a masterclass in logical empathy. And it gave me a better way to try and understand others’ intents, especially when you don’t know someone well.

Developing Logical Empathy When Emotional Empathy Feels Unnatural

So how can you foster logical empathy if emotional empathy doesn’t come naturally to you? Here’s a roadmap:

  1. Listen More, Talk Less: You don’t have to feel what someone else feels to understand them. Listen actively, engage with their words, and seek to understand their perspective.
  2. Ask Questions: If you don’t understand something, ask. Asking not only clarifies but demonstrates that you are engaged and interested in the other person’s perspective.
  3. Seek to Understand Their Context: What could be the pressures on them that they may not be vocalizing? If you are talking to a salesperson near the end of the quota, could they be pressured to make their quota? Is the Product Manager being held to unrealistic expectations by their boss? Leverage what you know about the business or organization to understand what subtexts may be unsaid.
  4. Reflect: Spend time thinking about the perspectives of others. Consider why they feel the way they do. Analyze their thoughts without judgment.
  5. Use Imagination: Try to visualize the scenario from their perspective. This mental exercise helps in understanding without feeling.
  6. Practice Compassion: Logical empathy may not be instinctive, but it’s still a form of compassion. Approach situations and people with an open heart, even if it’s an analytical one.

Embracing Both Forms

The truth is logical and emotional empathy are not mutually exclusive. You can be someone who mainly engages with logical empathy while still having the capacity for emotional empathy and vice versa.

The real beauty lies in embracing both and recognizing that there’s no right or wrong way to connect with others. It’s a journey, and it’s one worth taking, regardless of where you naturally fall on the empathy spectrum.

In our complex and diverse world, empathy in all its shades is more than a desirable trait; it’s a necessity. Understanding how you relate to others and working on enhancing that connection, be it through emotional or logical empathy, makes you not only a better colleague, friend, or partner but a more complete human being.

This exploration of empathy, fostered by wise words from thinkers like David Foster Wallace, has been a personal awakening. It’s water, and now I see it.

The p-word

I have never heard the word “politics” used in a positive light when describing a work situation. On the contrary, the words “corporate politics” evoke memories of cynical executives in ’90s movies quoting The Art of War to their reports while figuring out how to undermine their peers. One of the Merriam-Webster dictionary’s definitions of the word is “political activities characterized by artful and often dishonest practices.”

I propose that we reconsider the word “politics,” especially when used in a work context. The word, and the techniques ascribed to it, are inherently neither good nor bad. You can use politics for ill intent or good. Good intention aims for a win-win solution, whereas bad intent aims for a win-lose solution. Instead, let’s use this Merriam-Webster definition for the word “politics”: “the total complex of relations between people living in society.” For our purposes, let’s call the company we work in our society. A company is a society in that it can have a panoply of personal relationships, group dynamics, shared goals, and systems of governance.

If we can get over our initial reaction to being political, how can we use some of these techniques for win-win solutions to problems?

Thinking politically means thinking ahead (being strategic), understanding the motivations of the people you need to convince (having empathy), and understanding the interactions of the systems you are trying to influence (systems thinking). You are working to make something happen-something you cannot do on your own. You may be working to overcome resistance to a new idea in a conservative institution. You could be trying to persuade another group to help your team with a project that will be good for the company but might make that group miss their quarterly goals.

Thinking politically will help you gain support for your ideas, soften resistance to change, and focus people on the bigger picture. If you improve everyone’s situation, your peers will appreciate you, and you will find the way forward easier in the future. Conversely, done poorly, where you or your team move ahead at the expense of others, you will find it increasingly hard to gather support in the future.

Playing politics so everybody wins: A personal example

In the early days of the public cloud, I worked in a company that already had established data centers worldwide. Getting a new server racked meant requisitioning a server from the central IT organization, following all their guidelines around the machine’s configuration and which technologies could be used on it, and giving them access to maintain and manage it. The process to get a single server going with a public-facing interface could take months.

I was leading a new team trying to incubate a new product. We had adopted a Lean Startup approach, moving to get to market in under six months. As this was a brand-new area for the company, we couldn’t be sure how quickly the public would adopt the product, and we wanted the ability to add capacity quickly if needed or shut the project down if it wasn’t getting traction. The company’s lead time for servers was not going to work for us. So, we decided to leverage Amazon’s young AWS offering. I knew that this would be a controversial decision and might incur opposition from other teams, especially IT. I could have chosen to “ask forgiveness, not permission” and hope that my small team could fly under the radar long enough to launch, but that was very risky. Our actions could be interpreted as a deliberate avoidance of company security and budget policies, which could prevent us from launching if we were found out.

I spoke to my peers in other teams to understand their prior experience working with the centralized IT team. I learned that if I approached the IT team directly for permission to use the public cloud, I would get an immediate “no.” That would put me in a position of having to get their decision overruled, which would take a lot of time and energy. I decided to go a different route.

I put together a presentation on our plan for our product. I included our quick path to market to mitigate risk for the company, our plan to leverage the public cloud (to scale quickly and manage cost-effectively), and how we would address any corporate security concerns. The goal of the presentation was to build trust that my team was thinking about the business and not just playing with new technology, and to show that we had answers to the issues I expected other groups to raise. I portrayed our product plan as an innovative experiment in new product development; a low-risk approach to moving faster as a company. I wanted to get some protection for my team at a level that would short-circuit other teams worried about this new way of doing things.

After working with my boss to ensure I had their unequivocal support, we got time on my SVP’s calendar to discuss the plan. I prepared for any argument against the plan, but I also left room for input from the SVP to help them feel invested so they would help protect the project. We left the meeting with approval for our approach and moved forward quickly enough to launch the product within our six-month window.

The product was more successful and grew more quickly than we had planned. Our public cloud adoption made it far easier for us to scale as the number of our customers did. Our success also increased our visibility within the company, however. The teams invested in managing and growing our worldwide data center infrastructure now started to see us as a threat. I began to have many increasingly tense meetings with them to discuss moving into the corporate infrastructure. I could have used my product’s success to force the other team to back off, but that would have created even more enmity, setting up our teams for friction forever.

Instead of using my team’s success as a wedge to ignore the IT team’s demands, I worked with them to understand why we had to make the decision we had. I also identified what they could do to make switching to the internal infrastructure an easy decision for us and for other teams

considering following in our footsteps. I committed my team to switching to the company’s infrastructure as soon as it could support us.

Reading through that experience, you can see several political maneuvers I used to get my team the space we needed to ship our product.

  • Talking to my peers to understand what their experiences and anticipate challenges. Consulting my peers on the problem got them enlisted as allies. If I were successful, they would have a better chance of success themselves in the future. (systems thinking/having empathy)
  • Building a strategy to prevent the central IT organization from stopping my team’s plan. (being strategic)
  • Enlisting my manager meant I had an ally in my effort to convince other senior managers, someone who understood the SVP’s motivations and concerns. (having empathy)
  • Preparing my argument to the SVP not just to convince but also to engage. Making the executive not just an approver of the plan but a participant with a stake in its success. (being strategic/systems thinking/having empathy)

If I had stopped at this point or pressed my new advantage over the IT team, that would have been the type of corporate politics that people despise. I would have created a win-lose situation (and some very angry co-workers who would have justifiably felt I’d wronged them).

Instead, I took the following steps to help the group I felt I had to work around and improve the situation for everyone at the company:

  • I used the lessons we learned from AWS to help the centralized IT team understand groups like ours with less predictable or forecastable needs. (having empathy/systems thinking)
  • I committed to them that if they could support our needs (with our help), we would switch to the “official” infrastructure. (having empathy/being strategic)

Making sure we helped the IT team was more work for my team, but it was better for them and the company at large. It made the solution a win-win.

An outside observer, especially a jaded one, could look at each of my actions in a very different light. That observer would say that I schemed to isolate the IT team, skirted appropriate behavior, and cheated by going over their heads. If I hadn’t then gone back to help lift the IT team, I might agree.

One might say that the best thing to do would have been to work with the centralized IT team to convince them that they should allow and support my plan. I would agree with that sentiment if it were possible to gain the IT team’s support and ship my product on schedule. However, the experience of my peers told me otherwise. Those who have worked at large corporations with siloed functions working against different goals understand how intractable those other groups can be.

Don’t be a player of the p-word

When faced with a challenge at work, try to understand the motivations of the people you work with and the systems they operate within. From there, build a strategy to achieve your goal. If you can achieve your goal while helping others move towards theirs in the long term, you will be an innovator and a team player within the society that is your company. On the other hand, if you achieve your goal at the expense of others, you will be nothing more than a player of the unspeakable p-word.


Thanks to Laura Blackwell, Hannah Davis, and Mandy Mowers for editing help.