Last year, I wrote up a document of social skills resources I'd prepared for sharing with others and possibly making a post. I haven't yet made that post, so I'll dump what I've got here. Sorry for not including links and better presentation generally, I'm short on time just at the moment.

Dump of a Google Doc from June 2018.

Introductory Notes

Although this document lists the books which have helped me interact better with others, I’d attribute the bulk of any gains I’ve made in social skills to simply observing others carefully. More than any theory or recommendations, I’ve found that paying careful attention to how people say things, their body language, their responses, etc., has helped my social skill and understanding. My best guess is that if you throw enough data at your mind (at least of this sort), it will learn what do it with. So read the books in doc, but I as much advise others to pay more attention to others if want to improve. 

Also, a major component of social skills is having your own shit together. Or at least, my own ability to interact well with others has increased alongside mastery of myself. Emotions, fears, insecurities, desires, agendas, prejudices, etc., all interfere with one’s ability to interact well with others. 

Books

Start With No by Jim Camp

This is a book on negotiation (mostly enterprise and corporate) but it drove home some crucial general lessons for me that hadn’t fully sunk-in from elsewhere: 1) the utmost importance of inhabiting the world of your “adversary” (or conversation partner), 2) the skills of listening well and asking good questions, 3) investing the effort to think about what your “adversary” really wants, 4) focusing on what you can control (actions) rather than outcomes, 5) investing the time to understand what your adversary wants, even when they themselves don’t know.

Personality Types: Using the Enneagram for Self-Discovery

Personality Type systems aren’t always the most rigorous or predictive models, but those responsible for the Enneagram have paid a lot of attention to humans and what drives them. I’ve found Enneagram materials to be very useful for recognizing underlying patterns of motivation and behavior in myself and others; and in particular, it helped me appreciate how what’s driving other people is quite different from what’s driving me most of the time.

The Charisma Myth

It’s been a few years and I’m due for a re-read, but I liked this book. Links charisma to learnable traits/states of mind and actions which can be learned.

Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity

This book is aimed at bosses and managers and does a fantastic job at describing how to set-up a two-way, feedback-rich relationship notwithstanding professional context and power asymmetries. Worth reading for most people.

How to Talk So Kids Will Listen & Listen So Kids Will Talk

Related to non-violent communication, this book is really good for getting you to think about the emotional state and desires of your interlocutor as well as your own. It generalizes well to adults.

Non-Violent Communication

Makes for good relationships when generally adopted. The skill of learning to say things without making others defensive is definitely worth learning.

Circling & Authentic Relating [not a book, but start attending groups and sessions on these.]

Elephant in the Brain

The Gervais Principle & Be Slightly Evil: A Playbook for Sociopaths

These two books by Venkatesh Rao’s are great resources on status. While Elephant in the Brain explains why status is such fundamental motivation and shows how it explains broad macro features of society, Rao’s books analyze status in individual interactions.

While I encourage people to become more aware of status if you don’t think about it much, I strongly caution them not to obsess about it.

Books I Have Only Read Small Parts Of

• Impro
• Games People Play
• I’m OK-You’re OK
• Influence: The Psychology of Persuasion by Caldini
  • Definitely the Dark Arts. I read a few chapters and it’s interesting to see the subtle tricks people can employ to get us to say yes to things. If you say yes more often than you like, worth reading.

Books I Have Collected by Not Yet Read

(Appears,  I have a habit of buying books on social skills whenever I see them and then forgetting about them.)

• How to Speak How to Listen by Mortimer Adler
• The Charisma Code
• It’s Not All About “Me”
• Superhuman Social Skills
• The Social Skills Guidebook
• Emotional Intelligence 2.0
• The Definitive Book of Body Language

Books on Relationships

A General Theory of Love

You might expect a book about romantic love,  but it instead spends a lot of time focusing on Infant attachment. Still, very interesting for modeling human attachment in general.

Avoidant: How to Love (or Leave) A Dismissive Avoidant Partner

Generally helpful book on the topic of Attachment Styles. Useful for understanding that different people have learnt (or deeply ingrained) different patterns of behavior in relationship and that the interaction of these patterns matters.

The Mastery of Love: A Practical Guide to the Art of Relationship

This is a crazy book. But has some great stuff on letting your partner be who they are recognizing that you’re not responsible for solving all your partner’s problems. 

Here's the thing though. When someone asks a vague question like "how do I learn music", to me that means they're not trying. Otherwise they'd have specific questions, like what's that chord in a given song, or how to pick across strings, or how to improve timing on the kick drum. If you have no such questions, just a vague "how to get better at social", you need to start trying and getting more specific questions, not reading ahead.

The 3 areas in which you'll experience rapid gains to your charisma are:

1. Presence

2. Emotional Expressiveness

3. Confidence.

After that is 4:

Language expressiveness

For 1, depending on your learning style, I would look at "Practicing the Power of Now" by Eckhart Tolle.

For 2, again depending on your learning style, there's a great out of print book Ronald Riggio called the "Charisma Quotient" that has a number of exercises for improving emotional expressiveness. Impro by Keith Johnstone is also a great resource.

For 3, I mostly recommend internal work (check out my sequence on here on Memory Reconsolidation), going to a Toastmasters regularly will also help with this.

For 4, Look into the work of John Antonokis et al. specifically their list of "Charismatic Leadership Tactics" and accompanying exercises to practice them.

Note that none of these are about listening/social calibration/etc, that's another skill set that's important for social skills but not as much for straight up charisma.

I want to write up a more detailed post eventually, but the gist is that understanding Polyvagal Theory is an exceptional multiplier on all the charisma and social skill books you could read. It is the underlying *why* the tips and tricks work, what you should be aiming for, etc. It's the building block to make your own social skill tips and tricks from first principles. So,

First, watch this: https://www.youtube.com/watch?v=br8-qebjIgs.

To really grok it, I recommend following with listening to the Polyvagal Podcast - start from the beginning.

For the rare written resource on the topic, here's a transcribed interview with Stephen Porges, the researcher who originally described polyvagal theory: https://www.pesi.com/blog/details/967/wearing-your-heart-on-your-face-the-polyvagal-circuit

If you get this + attachment theory* you've got a good sense of how people work socially.

*I pointedly do not recommend Avoidant: How to Love (or Leave) and Avoidant Partner, as it's focused on just one attachment style, the dismissive-avoidant style. My favorite explanation might be from Stan Tatkin, in his audiobook Your Brain on Love. He has another book on attachment styles specifically, if you want to read with your eyes, called Wired for Love, though I haven't read it.

Books are useful for many things, but this area is best learn by doing. Find a master and become her apprentice for a time. You will not become a natural, but can get passable. And also meet many more people you otherwise wouldn't. And yes, learn active listening. It's pretty formulaic (listen, imagine how they feel, recap what they said in your own words, express anything positive you feel, ask an open-ended question, repeat), yet rare enough to get quick results.

Patrick King has published a lot of short, accessible books that are available on Kindle. They might seem a bit lightweight but they're generally well-written and I've taken quite a bit from the books I've written.

(One tip that has stayed with me: avoid asking people what their "favorite" book/band/movie/whatever is... instead, ask them about a good book/band/movie/whatever they've read/listened to/watched/whatever recently, or a favorite - it gives people more wiggle room and doesn't push them to make a definitive statement. Little things like this are valuable to know.)