Books with Impact: How to Win Friends and Influence People

The “Books with Impact” series takes a deeper look at specific books that have had a profound impact on my financial, professional, and personal growth by extracting specific points of advice from those books and looking at how I’ve applied them in my life with successful results.

In the past on The Simple Dollar, I wrote some “book club” series where I walked through several of my favorite personal finance, career, and personal growth books in great detail over a series of posts. You should check them out; here are links to each of those “book club” series:

Your Money or Your Life
The Total Money Makeover
Getting Things Done
Making It All Work

Born to Buy

These series were pretty popular, but I always felt like they could be a bit better, so I spent some time looking at what worked and what didn’t in those series. The biggest value, I felt, was the depth along with how the book really related to my life; the weakest points were how it was broken up across a bunch of posts and some of those individual articles weren’t as good as the others because that particular piece of the book didn’t click with me.

Today, I’m starting a different approach. Once every few weeks, I’m going to take a personal finance, career, or personal growth book that had a real positive impact on my life and take it apart by looking at the pieces that really impacted me. Hopefully, those pieces will impact you as well.

Why How to Win Friends and Influence People?

how-to-win-friendsIt isn’t much of a secret to tell you that I’m an introvert. I find it really challenging to interact well in social situations, particularly with people I don’t know very well. I tend to clam up and I don’t know what to say, so I’ll just choose to say nothing.

This does get better when I’m around people I’m familiar with or people with which I have a clear and obvious shared interest in something, but in most social situations, I’m not exactly smooth.

How to Win Friends and Influence People is a toolkit for those situations. It’s basically written for me as an introvert – it gives very concrete ideas and steps to take when you find yourself in those situations.

It has helped me immensely in terms of taking those initial steps toward building relationships with my neighbors, making friends in the community, and getting involved in civic organizations. I’m fine once I’m on familiar ground, but without the advice in this book, I would simply talk myself out of trying.

I listen to How to Win Friends and Influence People as an audiobook at least once a year and each time I pull something valuable from it while also sharpening some of my old familiar social tools. During this listen, I’ve been jotting down some of the key points that have really impacted me and I want to share them with you.

How to Handle People

We’re all faced with interactions with others on a daily basis, whether at work or on the street or when we’re a customer. Quite often, it’s not the substance of our interaction but how we go about it that makes all the difference in the world. If you walk up to a customer service person with an angry attitude, for example, they’re probably not going to want to help you out as much as they would if you came up with a friendlier attitude.

I put these three principles to practice most days. I usually try to start a conversation with someone I don’t know well at least once or twice a day, and these are the principles I use to do it.

Don’t Criticize, Condemn, or Complain

If you can avoid a negative comment in such situations, do so. There’s no reason to dole out negativity in the vast majority of situations we find ourselves in. If you’re feeling like you should criticize or complain in some way, just keep it to yourself.

I often try to have “negative-free” days where I keep this concept front and center in my mind. I focus on not making critical comments or condemnations to others. When I do that, I find that, overall, people react much better to me. Plus, over time, being positive in those situations just comes more naturally.

Give Honest and Sincere Appreciation

I’ve found that putting myself in the other person’s shoes helps a lot. How would I like a customer to act? Would I like it if they told me I was doing a good job and seemed to mean it? Of course I would – anyone would.

Whenever you’re interacting with someone, try to look for things about the situation that are positive and appreciative. What’s good about this person? Is this person doing his or her job well? Is this person doing a good deed? Is this person wearing an interesting shirt? Is this person being a good parent? Those kinds of positive things make for great conversation openers because you immediately put the other person in a positive frame of mind.

Arouse in the Other Person an Eager Want

If you want to start a great conversation with someone, try to look at that person and figure out something that they really care about. What are they passionate about?

You can set a great conversation in motion with just two steps. First, compliment the person on something, ideally regarding that thing you figured out that they care about. Second, ask them about that thing they care about in a way that will encourage them to tell you all about it.

A few days ago, I was riding on a bus when I saw someone reading a book. When they closed the cover, I said, “You’re a pretty avid reader, huh?” The other person said “Yeah.” Then I said, “I heard about that book… is it good so far? What is it like?” This caused the other person to start talking at length about the book.

People love to talk about the things they care about and if you open the door to that, they’ll almost always walk right on through.

How to Make People Like You

It’s often hard to turn a casual interaction into a conversation, but it’s also really hard to turn that conversation into the beginnings of a good relationship. It’s a transition that I find just as difficult as that initial conversation. These nine steps really address that difficulty.

Become Genuinely Interested in Other People

As I discussed before, the best way to get someone talking is to find something that the person is passionate about and get that person talking about it. The way to keep that conversation going is to make yourself genuinely interested in what they’re saying.

It’s not fake and it’s not as hard as it sounds. All you have to do is watch them and listen to what they’re saying. If they’re engaged, even a little bit, just let yourself get pulled along for the ride. If I’m having difficulty with this, I try to look for any aspect of what the other person is talking about that interests me and then steer it toward that area with a question or two.

More than that, it’s vital that you become genuinely interested in the other person. You want to know who that person is, what makes him or her tick, and what he or she cares about. Your goal in the first conversations with someone else is to really get to know who they are as much as you can.


I try really hard to associate things I learn about that person with things I know I already like and care about. This makes a smile come naturally to my face.

For example, if I notice that someone cares deeply for their children and I get them to start talking about their kids, I mentally relate what they’re saying to my own children. This triggers a smile almost every time.

I usually don’t turn that thought into a conversation topic, though. I let the conversation remain centered on their children unless they ask me about my own.

Remember People’s Names

I’m terrible about remembering people’s names – or, at least, connecting those names to faces. I can associate lots of details to a face and lots of details to a name in my head, but I somehow often fail to be able to connect the name to the face.

People do like it when you remember their name. Think about your own experience – it feels good when someone you don’t know really well remembers your name and greets you positively using your name.

My solution is to write down details about a person in my pocket notebook as soon as I can. I write down their name along with any visual details I need to recall their face, plus a fact or two about them to recall later.

Be a Good Listener and Encourage People to Talk About Themselves

If you can hold onto a detail or two about that person from previous interactions, you have a starting point for conversation that encourages that other person to talk about themselves.

For example, let’s say that I remember that a guy I met at a soccer game a few months ago like making his own beer. I can then stroll up to him and ask him if he’s made any good home brews lately – and then he’s got a perfect opportunity to talk.

When people are talking about themselves, don’t spend that time just thinking about the next thing you want to say about yourself. Turn that off. Instead, listen to what they’re saying and try to maintain interest. You’ll often learn a thing or two along the way, both regarding the person and the thing they’re talking about, and the conversation will naturally give you new things to talk about.

Talk in Terms of the Other Person’s Interests

If you can keep the conversation on topics that the other person is interested in or passionate about, you’ll give the other person an avenue to keep on talking and feeling comfortable in the conversation. When in doubt, stick to things you know that the other person cares about. When there’s a lull, bring up a subject related to one of their interests, preferably in the form of a question.

The more you know about a person, the easier this gets, as you’ll be aware of a lot of interests that they have. During the first few conversations, though, don’t be afraid to listen carefully and try to make a list of their interests in your head.

I have a friend that, when I first met him four years ago, I could only really observe one interest that he had (a particular game that he seemed almost obsessed with). So, each time I saw him, I’d ask about that same topic. Gradually, I began to notice other things he was interested in – he enjoyed long fantasy novels, for example. I didn’t learn that until after several conversations with him, though, but now I have lots of things to talk about with him.

Make the Other Person Sincerely Feel Important

If a person mentions an achievement to you, compliment them on it. Even better, compare that achievement to your own in a positive light.

A few sections back, I mentioned a friend of mine who enjoys homebrewing. Whenever they tell me about a good brew they made, I’ll tell them that the brew sounds pretty good and that I really want to try making that kind of beer sometime (which is actually true).

If you can find ways to make the other person feel really good about what they’ve achieved or what they have in comparison to you, they’ll feel really good about the situation and be much more open to continuing conversation with you.

How to Handle Disagreements

Eventually, you’re going to disagree with people. You won’t like how the customer service rep handles your problem, or maybe your new friend will make a political statement that you don’t like. A disagreement can quickly sour a relationship if handled poorly, but it can go by with barely a blip if you handle it well. Here are some tactics for handling disagreement.

Avoid Arguing

Whenever a discussion steers into a stage where people are raising their voices and emotions are coursing, then you’re steering into an area where negative emotions are ruling the day. This isn’t a good state to be in. It’s not conducive to building a good relationship with the other people involved.

If you find yourself headed toward argument, just simply stop and say, “This isn’t worth it. I don’t want to argue with you over such a silly thing.” I usually promise to read more or think more about the issue and then I move on from there.

Respect the Other Person’s Thoughts; Avoid Saying “You’re Wrong”

If at all possible, you should never tell someone else that they’re wrong, even when they are wrong. Does it really matter to you if someone else states an incorrect fact? There’s nothing really to gain by correcting the other person; just let it slide and move on from there.

At best, you’ll look good at their expense, causing the other person to like you less. At worst, you’ll look bad in front of a group, causing everyone to like you less. Correcting someone else in a public situation rarely does either party any good. Just avoid it.

This can be really hard for some people to do, particularly people who put a high value on facts and correct information. I certainly feel that way, but I’ve also learned that speaking up at those moments usually causes more problems than it’s worth. If you feel you must correct an error, save that correction until you’re alone with the other person.

If You’re Wrong, Admit It

Sometimes you’ll be wrong and further conversation will show it. When that happens, just be polite about it. Simply state that you were wrong, do it very clearly and quickly, offer a compliment to the person who had the correct information, and move on from there.

A simple statement of “You know what? You’re right. I was wrong. Good work in figuring that one out.” can go a very long way when conversing with someone, particularly in a group setting. It’s not only the humble way to go, it also makes the other person feel really good, too.

Start Off in a Friendly Way

Anatol Rapaport once offered up these four rules of engagement. They’re good ones to follow every time you find yourself headed down a road of disagreement:

1. Re-express your opponent’s position so clearly, vividly, and fairly that your opponent says, “Thanks, I wish I’d put it so elegantly.”
2. List any points of agreement – especially if they are not matters of general or widespread agreement.
3. Specifically mention anything you learned from your opponent.
4. Only then are you allowed to say as much as a single word of rebuttal or criticism.

There is no better way to start off a disagreement than to try to re-state your opponent’s position in a fair and clear way. It shows respect for your opponent and his or her thoughts and puts them in a positive state of mind right off the bat, one in which they’re willing to listen to you and hear your thoughts.

I would give almost anything for every politician in the world to adopt these four principles whenever they disagree with another politician, publicly or privately. Wouldn’t you?

Get the Other Person To Agree on Shared Points at the Start

The second of Rapaport’s rules requires you to list points of agreement that you have with the other person. When you do that, you’re not only continuing the positive mindset of the discussion, you’re also establishing that, for the most part, you’re actually in agreement with the other person.

If you can show that both you and the other person are in agreement on an awful lot of things, it becomes much easier to work through those areas where you happen to disagree. It establishes how much the two of you actually have in common and makes the disagreement look small in comparison.

Let the Other Person Do Most of the Talking

When you let the other person talk during a disagreement, you often allow them to take the wind out of their sails and get rid of the negative feelings that caused the conflict. Plus, if you listen, you’ll often get a good sense as to what the other person really thinks.

I’ve found that it’s easy to do this while still practicing Rapaport’s four rules. I’ll go through restating what I think their position is and I’ll end each sentence as if it were a question. If that’s unclear, I’ll go, “Is that right?”

This prompts the other person to speak and they’ll usually either just say “Yes” (which is a good thing, as it puts them in an agreeable mindset) or they’ll elaborate on the specifics of their position (which is also a good thing). In either case, you’ve maintained the positive air of the conversation, keeping things from becoming emotional or negative.

Let the Other Person Feel the Idea Is His or Hers

I’ve found, quite often, that in the process of laying out ideas, the other person puts pieces together and comes to a different conclusion. Sometimes, it’s my own conclusion.

Although I might be tempted to view that as a big “win” (and I might want to laud it as such), I just keep my mouth shut. I’d far rather have the other person have a good idea in their head and feel really good about it than anything else.

Results always matter far more than credit. If you can sway someone else to your way of thinking, there’s no reason to take credit for it. Let the propagation of your ideas be the reward.

Try Honestly To See Their Perspective

As you’re laying out all of the points of the other person’s argument, try really hard to see things from their perspective. How are they drawing their conclusion? What’s taking them from these points to the conclusion that they’re holding? What other elements are present that is causing them to take that road?

In a political discussion, for example, a person’s life experience often has a lot to do with what they consider to be the right political path for the nation to take. They may call upon historical evidence or grand philosophies in making their case, but it’s often their own life that is pushing them one way or another. That’s part of their perspective and it’s not something you should dismiss.

For example, I’m a mixed bag of political perspectives, but I tend to be in favor of policy stances that give people opportunities to improve themselves and make the most of their situation. Why? I grew up poor and without a few great opportunities given to me by various government programs and wonderful people, I would never have been able to achieve the things I have in life. My own personal experience pushes me to support certain policy stances.

Because I realize that, I can look through the eyes of other people and think about their experiences in life and see how those experiences shape their viewpoints. While I might not think their viewpoints are the right ones to hold, it becomes a lot easier to have a healthy discussion when I understand how they came to those viewpoints.

It’s pretty hard to get angry with someone when you see how their life experience is deeply connected to the ideas they hold.

Be Sympathetic

The more you understand about a person’s viewpoint, the easier it is to put yourself in that person’s shoes when you’re disagreeing with them. That makes it easy to be sympathetic.

You don’t have to give into their ideas, but expressing respect for their viewpoints is never a bad thing. When they make a good point, agree that it is a good point; don’t just shout it down. When they veer into the realm of personal perspective, acknowledge their perspective positively; don’t ridicule it.

When you take the lead in showing sympathy for other perspectives, others are likely to do the same for you. When you actually consider other viewpoints, others are likely to follow your lead and do the same.

Appeal to Nobler Motives

If I sense that someone is disagreeing with me on a specific point, I’ll usually back off and look at the broader motive behind that point. What is the greater reason behind that point?

If you can tie your point clearly to a nobler motive – friendship, advancement of human knowledge, personal freedom, and so on – you not only make clear why you believe in this point, you also give an easy path to agreement between you and your opponent.

The discussion changes from whether your point is “right” or “wrong” – something that can cause conflict – to whether your point actually connects to that higher value – something that is much less likely to cause conflict while also increasing understanding.

Dramatize Your Ideas

This is a tactic that politicians often use when sharing their ideas, but it works really well to make any sort of disagreement a lot more friendly.

Rather than just arguing on behalf of your point, tell a story that shows your ideas in action. Connect your ideas to the life of someone you know or even a person that you fictionalize a bit. The purpose is to give a living, breathing life to what you’re talking about.

For example, if I’m arguing about a political point, I’ll look for someone I know whose life is affected by that point and use them as an example. I’ll talk about my friend rather than about the issue specifically. That way, the abstract idea becomes something real.

Throw Down a Challenge (In a Friendly Way)

The best way to put aside an argument in a friendly way is to simply ask the other person for more information. Ask them to send you the information that they’re talking about so that you can look through it yourself.

When they send that information to you, actually take the time to read it. I usually try to make a list of questions that I came up with from reading whatever it is that they sent me. That not only shows that I respect what they sent me enough to give it a serious reading, but that I’m interested in their ideas as well. It’s pretty hard to be angry with someone who treats you with that kind of respect.

Be a Leader

If you have a lot of good relationships with a lot of people, it’s inevitable that you’ll eventually be called into a leadership position of some kind. Leadership can have its own set of challenges, of course, and the rest of the book focuses on those challenges.

Begin with Praise and Appreciation

If you notice someone not doing what they should, the first thing you should do is praise them on what they are doing.

For example, I serve on a community committee where one of the members wasn’t attending meetings. That person would respond to email discussions quite well, however. The president of this committee eventually had to deal with this person who wasn’t attending meetings (and I happened to be around when this happened).

The very first thing the president did was compliment that person about their participation in email discussions. This immediately shaped the conversation in a much different way. Rather than making it seem like he was being taken to task for not attending the face-to-face meetings, he instead was being asked to attend because his input was valued so much. By starting with a compliment, the tenor completely changed.

Call Attention to Mistakes Indirectly

No one likes to be told the specific things that they’re doing wrong. It brings about some pretty negative feelings toward oneself and toward the person making the comments.

A much better approach is to simply ask them what they think they can improve. Often, people have a sense of what they’re doing wrong and if you let them say it, it doesn’t feel like criticism.

My first boss would give us a performance review every few months. One at a time, we’d go into his office for our review. He never, ever criticized us. Instead, he’d list several things he noticed that we did well, then ask us what we thought we could improve. Later on, he told me that the vast majority of people would suggest the very thing he thought that person needed to work on. There was no need to criticize.

Admit Your Own Mistakes

If you’re in a leadership position and you make a bad call, it can be tempting to just throw dirt over the mistake and pretend it didn’t happen. Don’t. If you mess up, admit it openly and state what you’re going to do to fix it.

No one expects perfection from you. However, attempts to hide your mistakes and not take charge of them tends to reduce what others think of you. The best solution is to always admit to them and talk about how you’re going to solve them.

Ask Questions

There is never a bad time to ask a question. Questions serve lots of purposes. Questions give you information that you might need to make a better decision. Questions give others the chance to shine and show off what they know and what they’ve done. Questions can lead others to coming up with good solutions to problems.

If you’re unsure about how to solve a particular leadership difficulty, try asking some questions. Don’t make them pointed, either; ask questions that give people room to talk about what they’ve achieved rather than where they’ve fallen short. Ask questions that cause people to craft their own solutions rather than just taking orders.

Let the Other Person Save Face

People don’t like to admit mistakes. As a leader, you’re going to see people constantly making mistakes and then make an effort to cover them up. Unless it’s damaging in some way, let that person save face.

Always, always keep in mind that everyone is human. Everyone makes mistakes. Few people like to admit them.

Praise Improvement

Whenever someone takes a positive step, even if it’s not a big one, praise that positive movement. You don’t have to gush over it, but a single statement that says that you noticed their effort and that you think it’s good means a lot – both from the noticing and from the praise.

Someone who is very close to me is struggling with quitting a smoking habit. Whenever I notice that person taking a hard step with it – even a little one – I try to compliment that move. For example, if that person doesn’t light up after a meal, I’ll wait a few minutes and then give that person a big vote of confidence.

Give the Other Person a Good Reputation to Live Up To

When you’re introducing someone, give them a great introduction. Describe the person in glowing positive terms that makes his or her positive traits seem wonderful. This is true whether or not the person is present.

I still fondly remember how I was introduced to the person that gave me my biggest professional break. The person introducing me made it sound like I was an absolute wizard at solving certain types of problems. I certainly didn’t think I was all that good, but after that introduction, I certainly wanted to show that I lived up to those words.

Make the Problem Seem Easy to Fix

If you’re pointing out a problem, make sure to talk about things in such a way that the solution seems incredibly easy. Don’t make it seem difficult or impossible.

The best way to do that is to be encouraging. If someone is facing a difficult challenge, offer to help them with it. Turn it into something that you can work on together. Set up milestones that are pretty easy to achieve – if you make it to the first one, the second one is pretty easy to reach and so on.

Working with someone to break a big project down into little bits while encouraging them that they can do it can convince them that something really hard isn’t actually that big of a deal at all. They’ll step up to the plate, primed to make a big impact.

Give the Other Person Reasons to Be Happy About Your Request

Whenever you’re asking someone else to do something, think of it from their perspective. What do they get out of it? What will they earn by taking on this task?

If you’re making a professional request, talk about how it will benefit their larger career. If you’re making a civic request, look at how the community will benefit and how it might bolster their standing.

With any request – personal, professional, or otherwise – make it clear that you personally appreciate their efforts in taking care of this. Simply saying that you really appreciate it makes a big difference; showing that appreciation later with simple steps like a public thanks is a simple gesture for you but can be huge for the person being thanked.

Final Thoughts

I usually listen to this book once a year or so – and each time I do so, I find new things that I should be working on.

For me, the best approach to take with the material in this book is to find one specific point and focus on mastering it in my life. For example, I might focus on describing the other person’s viewpoint at the start of any disagreement before I ever say anything else. I don’t worry about other aspects of it – I just concentrate on that one part. I try to keep it in my mind at all times and I keep thinking about it until I find that behavior coming naturally, at which point I’ll move on to another one.

This book is simply a gold mine of positive ways to interact with people. Almost every page contains a good idea for building better personal and professional relationships, all of which pay off over time.

There are times when the book can seem “mechanical,” almost to the point of seeming false. That’s the point. It’s intended to be useful for introverted people like myself for whom the finer points of good social interaction don’t come as easily as they do to others. Breaking it down “mechanically” makes it easier to understand.

If you’ve ever found it difficult to dig into a social situation, there’s probably something valuable in this book for you.

Trent Hamm
Trent Hamm
Founder of The Simple Dollar

Trent Hamm founded The Simple Dollar in 2006 after developing innovative financial strategies to get out of debt. Since then, he’s written three books (published by Simon & Schuster and Financial Times Press), contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.

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