Books on Becoming More Socially Adept / Charismatic?

I avoided reading "How to win friends and influence people" for way too long based purely on my revulsion with the title - which just seemed nakedly manipulative.

However, when I finally brought myself to read it, I found it's a treatise on changing your attitude towards other people.

The core thought is that if you want to be interesting that you should be honestly interested in other people.

This really struck me as a humble and approachable way to do better with my communications and as you better understand people you'll just naturally be more persuasive.

The best succinct advice I have heard is to "know yourself, know your audience". And "trust/credibility is everything". The technical, financial, and logical arguments are best used as supporting devices (throw them in the appendix).

1. Know yourself. Create an elevator pitch of what you want. It needs to be one sentence maximum. Do not create a laundry list of unrelated items. What you want can be somewhat vague e.g., "Artificial Intelligence 3.0". But you need a phrase so that later searches can find all the emails, presentations, documents related to your proposal.

2. Know your audience. Your audience is busy, drowning in minutiae, tired of being cold-called/up-selled/bothered by salesmen. What's in it for them? Are you freeing up their time? Or are you asking for help, to free up your time?

3. Trust/credibility. People make mental short cuts. This also applies to people. If you have a reputation for being earnest and forthright, people are more likely to pay attention. If you don't have such a reputation, find someone who does.

I feel like being socially adept and charismatic are different from being able to communicate clearly and effectively.

The former comes from intrinsic self-belief and acceptance, as well as genuine curiosity about the people you interact with.

Clear communication is more of a skill that you could learn from a book or guide. It depends on if you want to write or speak convincingly - writing structured arguments is definitely one way to clarify your thoughts and organize them in a logical way. This guide from Animalz provides one great persuasive writing model: https://www.animalz.co/blog/bottom-line-up-front/ In terms of interacting with a team and leading different types of personalities, I like the business classic Five Dysfunctions of a Team: https://a.co/d/jc3UExI

I second How to win friends and Influence people by Dale Carnegie. You can pick and choose what to apply but the main advantage is that the advice is simple — communication is a real time activity and anything too complicated will be hard to remember and hard to deploy and is likely hard to improvise and adapt to the situation at hand. Simple rules are best. The Charisma Myth by Olivia Fox Cabane is also good but you have to be selective in adopting the advice she gives.

The one thing that really stepped up my communication skills was moving to Chicago. Chicago people are emotionally intelligent and are eager conversationalists — this creates feedback loops in which I just talked more and the more I talked and the more positive reinforcement I got, the more I did it and the better I got.

I think being immersed in a culture where communication is prized and people are good at it is a cheat code.

Join a Toastmasters International club - the single most useful thing you can do to improve your communication and leadership skills.

You probably already heard of it, but one of the all time classics on the topic is How to win Friends & Influence People by Dale Carnegie

Two recommendations

1. Stephen Covey, The 7 habits of highly effective people

2. Brinkman and Kirschner, Dealing with People You Can't Stand