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Relationship Management

If you want to go fast, go alone, if you want to go far, go together - African proverb

Relationship management is the ability to cultivate beneficial and meaningful relationships in your life. The amount of stuff you can accomplish by yourself is extremely limited, and no one can live in isolation in this society. Relationship management is the productivity pillar with the highest skill ceiling because approaching building relational skills can be so confusing and nuanced. Maybe because of this, most people looking to improve their productivity vastly underestimate the benefits of having good people in their lives.

Many people highly undervalue how having good people in their lives can improve the quality of their lives. Here are some ways having good people can help you:

  • Help & Support: They can do work that you otherwise would have to do yourself. Many projects can't be done by a single person. Getting multiple people to row in the same direction will help you get what you and everyone else wants.
  • Knowledge & Skills: Relationships can provide knowledge that you would have a hard time acquiring. Want to learn about a specific topic? Instead of spending 4 years getting an undergraduate degree in economics, you could ask an economics friend to answers your specific questions given your context. They can identify opportunities and unknown-unknown.
  • Access to Other People & Other Resources: People can acquire and build up resources like capital and connections that they will only share with certain people. It's the phrase "good people know good people".
  • Inspiration & Accountability: Being close to good people can be a source of inspiration and provide some kind of accountability. There is a lot of truth behind the phrase "you are the average of the 5 people you spend the most time with".
  • Emotional needs: Having social support is important for fulfilling your social needs. Lonely people are prone to be less happy and therefore less productive.

Your relationship with other people matter just as much as your productivity habits, especially when you can't accomplish your goals by yourself.

Relationships are so complicated because they involve interactions with people whom you are equally as complex as you with wildly different values, beliefs, and backgrounds. How do you navigate these relationships and move in a meaningful direction towards developing positive relationships? Unfortunately it takes a lot of reading and even more ground-level practice.

We'll lay out the map to cover some foundational skills that are important for any kind of relationships. Then we'll dive into the skills that are useful for different types of relationships. I've roughly grouped the types of relationships into positive relationships (e.g. friends, communities, acquaintances), neutral relationships (e.g working relationships), and adversarial relationships. This allows me to highlight important skills that would pertain each type of relationship.

Foundational Skills

Knowing What You Want

Having more relationships isn't strictly a better thing. Relationships take time and energy to maintain, so if you invest a lot of time developing the wrong relationships, then you're not only wasting your resources, you might develop relationships that sometimes can harm you. Maintaining a consistent sense of what you're looking for can prevent you from chasing whatever's shiny or popular. If what you really need is emotional support from other people, then chasing after physically attractive or traditionally successful people might not be rewarded.

Take some time to answer these questions for yourself:

  • What are the types of people you want to be around?
  • What kind of relationships do you want?
  • What are you hoping to get out of a new relationship?

It's okay to not know the answers to these questions and spend some time exploring different relationships. A lot of our preferences and relationship needs are only revealed from lived experiences. As long as you aim to gain more clarity in this domain, you're in a good spot.

Reading People

The ability to read people will help give you more clarity on your relationship with people so know what type of relationship you want with them and what kind of skills you'll employ. A kind, friendly person you meet at a party can be very beneficial and you'll exercise social skills to build positive rapport. A neutral colleague may not think much about you but you may still need to work together so you'll need communication and negotiation skills here. A toxic person may be deceptive and hinder or sabotage you, so applications of adversarial skills will be helpful here.

A lot of qualities are fairly easy to read. Are they supportive? Are they active listeners? Do they share similar interests as me? There are also relational qualities. Are they genuine, authenthic, and consistent? Assessing these qualities will give you a feel of how you'll want to treat these folks.

Social Exposure

Increasing your exposure to people who add value to your life while decreasing exposure to people who don't would ultimately increase the serendipity in your life. Spending time at night clubs is probably not going to help you find members to join your board game group.

Besides developing the social skills that would help you approach and interact with potential people, I would take an inventory of what social environments you tend to be in and what types of people you're exposing yourself to. Is it conducive to meeting the types of people who you want in your life? Are there other opportunities to meet the types of folks you're looking for?

Social skills

Social skills are the skills required in an interaction to generate positive sentiment towards you. It is extremely broad of a set of skills and I don't think enumerating all the subskills and describing them would be a productive use of time. The reason is that most social skills are acquire via practice. The theory-to-practice ratio can be roughly 1:10. Therefore, I'll list a set of interventions I've tried and come across that I think are work trying to improve your social skills.

Improv class: By far the best way I've been able to improve my social skills. Getting practice interacting with human beings and being on your social toes does a lot to improv your intuitive understanding of how human relationships work. You can read my improv journey and some of the lessons I've learned here. Reasonable substitutes that are worth considering are standup, storytelling, and public speaking classes.
Social exposure: Consistently being in social situations both serve as an opportunity to practice your social skills and an opportunity to benchmark your progress with other social skills interventions. There are a lot of social-gains you can get from simply setting the intentions to improve your social skills and going out to practice them. Meetups, hobbies, even online dating can be good and consistent way to get social exposure.
Copying a charismatic friend: The second highest source of self-efficacy is vicarious experiences 1. If you are know someone who you consider socially adept, consider hanging around them more and observe what they do. Aim to copy what they do and ask questions if you have them. This strategy does suffer a bit of a bootstrapping problem and also requires that your charismatic friend have enough introspection and intentionality to give you good advice. I would consider this both opportunistic and high-risk/high reward.
Social skills classes: I haven't really explore these interventions but I hear good things about these (with caveats). Social skills classes can create a safe learning environment. These classes run the gamut from basic professional social skills to dating bootcamps. If you're interested in going down this road, I would have these caveats:

  • Classes should include real-life practice, not just classroom theory.
  • Don't pay too much money for the courses. Paying more money increases the student's expectations for what they'll get out of the class and adds pressure to the instructor to give students the impression that they are delivering results, which may result in learning gimmicky or toxic material. Wanting to pay a lot of money for social skills is a sign of desperation and unrealistic expectations. If you find yourself in this position, I would caution against any interventions that prey on those feelings.
  • Hold the tools you learn lightly. Any social skills you learn are ultimately a simplification of human relationships. Anything you learn will also ultimately be a small part of your social skills journey. Don't treat the things you learn as the sole ultimate truth.


Empathy is the ability to understand and share the feelings of other people. Empathy helps you understand people's motivations and predict behavior and it helps you build trust with other people which is the foundation to cooperation.

Most people believe empathy is an inherent trait and that you either have it or you don't, but it's not true. Empathy can be cultivated, and it's broken down into three separate types of empathy.

  • Cognitive Empathy is the act of “thinking in someone's shoes”. It's understanding where their motivations and personality comes from. It's imagining how someone with a set of beliefs and experience will behave in a certain situation.

  • Emotional Empathy is the ability to feel someone's emotions. When I can't emotionally relate to someone, I call that an empathetic gap. Bridging empathetic gaps builds the “intuition” around people's emotions by feeling the “weight” of how someone's emotions motivates them.

  • Compassionate Empathy is emotional response to want to help the other person. Some people are so drowned out in feeling another person's feeling that they become ineffective in helping other people. Compassionate empathy helps complete the full empathy response by wanting to help people. Their problems become your problems.

If you want to cultivate empathy, I've found this article a good summary of how I cultivated my sense of empathy.

Positive Relationships

Staying in Touch

Staying in touch is the ability to remain friends against time. Friends who have grown apart have a hard. So how do you stay in touch with people?

Some people resort to CRM's to be intentional with how they stay in touch with people. I've found a lot of leverage with the following tips:

  • Assume you've never been out of touch: This is the easiest and yet most difficult tip for myself. No two people have the same boundary of what's considered in or out of touch, and you may feel like you've lost a relationship with someone by not spending some amount of time with this person, but you won't know until you ask the person. If you're socially anxious, it's easy to get caught up in thinking that being out of touch means people don't want to hang out with you. This is not true! People are busy, have other priorities, or just like you are bad at staying in touch. If you don't assume that you've lost a friend, you can actually keep your network larger than you think.
  • Maintain live context: If there's something that reminds you of a person, let them know. It's easy to let these opportunities pass by even though they come up so often. Maybe you saw a painting that referenced your friend's passions, or saw something funny on the internet that was part of an inside joke you two had.
  • Open invites: Part of staying in touch is leaving the door open for people to participate in your life. Having open invites to those opportunities is what makes it feel like people are welcome in your life anytime. Personally, it's easy for me to invite people to large parties, events, or gatherings if I think it's something they'll be interested. These are low-pressure invites and just a signal that "hey I still want you to be part of my life".

Relationship Wisdom

We all inherited our conception of relationships from our parents and our culture. We all have implicit assumptions about how relationships work and shoehorn our relationships into our own worldviews.

But we don't have to treat our implicit understanding of relationships the same way we might treat laws of physics. Relationships are ultimately no more than the sum of its parts - what expectations, rules of engagement, and communication we have with each other. Treating it as a solid, monolithic, and permanent thing will only cause problems down the line, especially if you live in a culturally diverse society where people have different conceptions of how relationships work. Recognizing the flexibility of relationships and being able to reason about it through its individual components is extremely helpful for navigating relationships.

To help me understand this I recommend reading a polyamory relationship book. I write about my book review of More Than Two here. Polyamory relationship is unique in that managing polyamorous relationships involves multiple people, yet the polyamorous community doesn't have a unifying concept of how poly works, so they must provide guidance to people without any cultural assumptions. The way these authors approach navigating these poly relationships apply very well to everyday, platonic relationships as well, and thinking about relationships this way was a huge level-up for me.

Communication and Conflict management

Having conflicts and disagreements with other people is unavoidable. Whether having those conflicts is a productive endeavor depends a lot on how you handle it. I find three books very useful for navigating conflict.

  • Crucial Conversations introduces a framework for having high stakes conversations. It helps bring conversations to be less combative and more collaborative.

  • Crucial Accountability builds on Crucial Conversations to dive deeper into conversations where expectations are violated.

  • Nonviolent Communication introduces a framework for having emotional conversations. Crucial Conversations lean more towards high stakes conversations, but Nonviolent Communication leans more into the emotional aspects of communication. It teaches you how to express feelings in a healthy way.

Bringing People Together

If you want to take more control in who you hang out with, be prepared to do more of the legwork of bringing people together. This can largely include reaching out and staying in touch with people, handling logistical stuff like planning and hosting events, and being the social glue of diverse groups of people.

There aren't many books I've found that cover this topic. I generally find someone who's adept at this and mimic their behavior.

Neutral Relationships

Alignment & Negotiation

Alignment is figuring out what everyone wants and ensuring how what everyone wants moves everyone in the same direction. Alignment conversations in the context of work is actually really easy to achieve. The top-level executives set company goals, then the directors set organizational wide directives, and then the managers set team-level initiatives. At work, all you really need to is point to one of thoes layers and say "aren't we all trying to ___?". No one should disagree with you2 and it centers the conversation around how people's behaviors are in line with those objectives.

But still, people are motivated by different things, and stated motivations may be different from what they really want. Finding alignment in the art of exploring the search space amongst multiple parties, multiple motivations, and finding a solution that people are willing to cooperate in.

Negotiation is the communication aspect of both finding alignment and communicating alignment. It is not twisting someone's arm into getting what you want, it's figuring out what people want and working together to make sure everyone's happy 3. It is also possible to generate new motivations by being a likeable person. Want to make someone happy is a potential motivation that is useful for aligning with folks and one that you have a direct control in, hence highlighting social skills in the foundational skills section.

To develop the intuition to spot and identify alignment here are some material that I've found useful in developing my own sense of alignment:

  • Influence: The Psychology of Persuasion: Understanding the universal things that make people tick. The list is not complete but has good coverage of things 99% look for.
  • Systems Thinking: A Primer: Understanding how individual components contribute to a system phenomenon is critical for simulating how you expect people to behave in a system. This book is a good starting point for how to think in this manner.

Materials useful for negotiation:

  • Never Split The Difference: Teaches negotiation strategies that revolve around framing away from an adversarial relationship and toward a common ground where people are willing to cooperate. Lots of pearls of wisdom here.
  • Getting to Yes: Teaches basic negotiating strategies that talks about alignment as well. Might be a bit outdated but good place to read into as well.

As with most skills listed, the real development of this skill comes with practice rather than book learning. There are negotiation class you can take or you can practice with a friend.

Adversarial Relationships

Adversarial relationships does not imply that people are out to get or hinder you. It simply means that people don't and won't have your interests in mind. Maybe it's because they don't like you or it could be that they simply don't know you or have the desire change their relationship with you. If you unwillingly end up with a relationship like such, it's time to employ these skills. I find it rare to need these skills in my day-to-day life (because there's usually a good amount of goodwill to go around to smooth conversations) but maybe you work in business or politics.


If negotiation is reaching a point an agreed upon outcome, then strategy is the art of reaching a desired outside of a cooperative agreement.

I haven't found any strategy books that teach strategy in a straightforward way. Some people will point to game theory but game theory tends to be self-contained toy-examples that demonstrate certain mathematical concepts and only augment the strategies and decision-making people make in real life.

Most people agree strategy tends to be more of an art than a science.

The best strategy books often come from business, politics, and war:

  • The Art of War: Highlights the use of deception and strategy in combat. There are a lot of small sound bites and quotes that makes them easy to carry with you.
  • Thirty-Six Stratagems: Similar to The Art of War, a list of strategies employed in war that can be transferred to other aspects of life.
  • Business Case Studies: There's a reason why a lot of MBA students read case studies in class as a way to learn strategies that don't have a neat form factor as the previous books. Getting deep into these case studies will help you generalize and identify similar patterns in your life.
  • The Power Broker: Robert Moses and the Fall of New York: A really long book and a narrative about an individual but if you read it in the mind of thinking about power, it'll help you get a much better idea of what power is and how people manipulate it.


I honestly don't know how people learn this outside of acting and board/card games but it's worth noting how important it is to conceal your intentions in adversarial relationhsips.


That's roughly I currently know about relationships! It's a 10,000 ft view and perhaps not the most comprehensive, but it's more than enough to get people started.

  1. The first is mastery experiences. 

  2. If they do, that's what's called an "escalation", and it's actually a good thing. 

  3. If not happy, at least placated. There's a funny saying in legal arbitration that goes "A good outcome of arbitration is that everyone comes out a little unhappy". y. 

Last update: 2023-03-12