This is one of those things that HN may not be great at overall. Most answers here are brainy: “read this book” or “follow these principles” type suggestions, but this is really something that isn’t solved by reading about it. Don’t get me wrong it helps to have an intellectual basis, but in reality you just need to be embarrassed and rejected a lot to get good at sales.

Sales isn’t about your product, it’s about the person your speaking with and picking up on queues and verbiages that help you cater the conversation to them.

There isn’t a magic algorithm here. Get out among people and learn how to hold an artificial conversation for longer than 1 minute with a complete stranger without making it feel artificial. Once you can do that and walk away feeing good about it, you can start to figure out how to convert that artificial-ness into something that’s hard to distinguish from comfortable conversation with someone you’ve known for 10 years. That’s sales. It’s being able to interact with people at a comfort level that enables them to feel relaxed and safe.

I push a lot of CS students to get jobs as servers at local restaurants and bars. The pure experience of interacting with a group of new strangers every 5-10 minutes is hugely beneficial to sales development. It’s also easy to practice selling stuff (convince a bud light drinker to try a local microbrew, or up sell the nachos to the nachos grande because it’s the freakin weekend and what’s life without a little adventure). The bonus is that you can obtain a huge amount of experience with very little commitment as serving can be a 4-6 hour /week deal if you need it to be.

In the end it’s not about sales. It’s all about how comfortable you are in your own skin and how comfortable you make them. That takes a bit of time and discomfort to achieve and a book won’t give you that by itself.

Go get experience.

I'm inclined to disagree with you at first. But I think Pareto's Principle applies here - this is the 20% that has 80% of the impact.

I've worked with people who run the sales part of things, and even they try to avoid conversations with strangers when possible. It's easy to hide behind "social media marketing".

Just be careful not to practice selling "anything" like many people start out. A big part of sales is being able to explain why something is useful to someone else.

Sales is simply finding a stranger whose problem you can solve, and explaining to them how you can help.

> I push a lot of CS students to get jobs as servers at local restaurants and bars.

One summer holidays while at uni I got a job as a door to door salesman selling internet packages.

I'm not a small talk kind of guy. But after doing this job for a month or so I noticed I was having all these conversations everywhere I went. I'd order a drink and be having a chat with the barman etc. I seemed to connect with people everywhere I went.

I'm a small sample in the world, but at the time I decided if I was struggling to get a job I'd do door to door (or some kind of similar commissions sales job) again while I was looking, not for the money, but for the interpersonal skills it seemed to bring out.

Yep, if you wanted to learn to ride a bike, you wouldn't talk about riding bikes online or read a book by someone who has won the Tour de France. You'd go ride a bike.

I think the question is more like "I have ridden a bike before, but I'm not very good at it. How can I improve?" in which case you could definitely suggest reading a book or watching videos on proper form, training exercises, etc. because just riding a bike will not be good enough past a certain point, and even getting to that point takes a long time that can be shortened by targeted practice instead of just "riding".

If your business is already running, take the time to take a sales course (I did Dale Carnegie many years ago). When I did this years ago I was in a class with people who sold chip mfg equipment (ASP in the tens of millions, 2+ year sales cycle), someone who sold ADT security systems, a couple of guys who started a T-shirt shack, and learned from all of them.

Then a few years later I was 30 with a wife who couldn’t legally work, a mortgage, and two cats and sold on commission. I had to execute or I couldn’t make it.

This is how I learned.

I have a program like this that my dad passed on to me, which I often re-start when I feel I'm loosing it:

0. "How to win friends and influence others" by Carnergie

1. "Zig Ziglar on Selling"

2. "Unlimited Power" by Tony Robbins

3. "Secrets of closing the sale" by Zig Ziglar

4. "Influence psychology of persuasion" by Caldini

Really made the difference for me when feeding the kids became a challenge.

Zig Zigler's books helped me during college when I'd have to do cold sales, but the lessons were amazing outside of sales.

One of the most important aspects of sales is a great thing - connecting with people. If you want to build a company, work on a product, or anything in between your new job is: "Talk to everyone and anyone about everything and anything".

From there you will see points of commonalities with anyone and will one day a) enjoy speaking to strangers b) learn from others c) most likely get better at sales as a result because sales at the end of the day is people connecting to people.

Good luck Andrew!

"Influence -- The Psychology of Persuasion" by Robert Cialdini is excellent background reading. Any reasonable bookshop has 100s of books on sales. Best to browse and pick one that resonates with you.

The best way to start learning is to watch and listen to a good salesperson doing their bit. For example, visit a prestige car dealership after you have read "Influence" and see how they apply the various aspects. Ideally get a job as a junior salesperson working for a great salesperson. Your learning will go much better under expert guidance. You just can't learn enough just be reading books, watching videos.

From your question you appear to have conflated marketing, public relations, negotiating, etc as being sales. They are all distinct functional areas that support sales, but are not "selling" as such.

I absolutely agree on „The Psychology of Persuosion“. There are some really helpful principles in there.

Like most things, getting good at sales is about practicing, learning and practicing again.

Books and advice are great to get started but eventually there is no substitute to actually doing it yourself.

That being said, we are all actually “selling” in our day to day lives without formally defining it as sales. From convincing your parents to buy you a toy all the way to landing the first job involves similar techniques.

For a really simple sales weekend task, try buying a pack of bottled water and see how many you sell.

My actual sales experience is limited to the one summer job of direct sales experience I had a couple of years back, so I'm not an expert. It was a very interesting experience, however.

If you can, it'd probably be pretty effective to get some "actual sales" experience and treat it as a sandbox for experimenting. The alternative seems to be vacuuming a set of sales training materials and then start applying them directly to other scenarios. Anecdote: A friend started reading up on sales and applying to his dating life and expressed positive surprise - but he recently started work as a door-to-door salesman, and has been talking about new sales-related observations at a higher frequency.

AFAIK (haven't read yet) "How to win friends and influence people" is good for the non-actual sales. Supposedly early editions are better than later, as later ones are written by committee? I can - on the basis of my tiny experience - recommend Zig Ziglar's books.

Zig Ziglar's books on sales are really great and can have fast effect, it made the difference for me back in the days I was 22 or so and had to wardrive by foot to get work done for customers that would pay me very few or not at all - to the point i had to choose between paying for child food or the internet bill.

I highly recommend Zig Ziglar books on sales and Dale Carnergie's book "how to win friends" which should indeed probably be the first one to read for anybody - despite the phony title that will put most people off.

It's one thing to read material around sales and another to practice it. That being said, one book I'd recommend is Daniel Pink's "To Sell Is Human"

In general, sales is something you need to practice every day. Like Sam mentions, it's about being able to convince other people of what you believe and you have an opportunity to do this in your every day life, from convincing your kids to clean their rooms to convincing your reports to adopt a new process.

The first step is to look for opportunities in every interaction to practice sales. Sales starts by listening, so try to understand the other person's point of view and why it's different from yours. Really step into their shoes and see things from their lens.

Once you identify where the difference is, ask questions to learn more. Why do they think that way? Why do they prefer the current process? Why are they hesitant to change?

Again, they key here is to listen. Once they list the reasons why they believe differently, summarize what they said. Then start to work through each difference together.

This is important. You're not competing with them. You need to work together to arrive at a common solution. If they say adopting a new process is a waste of time, then calculate with them how much time it will take and then work to reduce that time by offering help in some area.

In the end, you should both walk away having achieved something together without one person browbeating the other into it.

Here is my list of advice:

1. Think from their point of view. What are the biggest pain points they can identify with? What are you solving for them?

2. Show as much as you can upfront. Bring an app with their logo and name on it. Maybe mockups if you don’t have app. Their “customizing and correcting” instict kicks in an the conversation becomes about what to change.

3. Don’t charge anything serious upfront, just take their credit card for a “retainer fee” and have them authorize charges as you go.

4. Use a website for them to choose from predefined choices, like JS libraries used to let you choose what you wanted. Then they leave their email to get a quote.

5. Use your website or app in order to set up a portal for them, including their choices and initial product, and invite others to manage this portal. Make it as easy as possible for them to invite MORE stakeholders in their organization. Build onboarding for the stakeholders where they get to see the work in progress, choices, video, until some stakeholde enters the credit card.

7. Break things down into milestones and deliverables. Put as much as you can on a website to create a feeling that you have lots of customers vying for your tome so they don’t feel they can haggle.

7. Finally, reward your existing customers for adding testimonials, sharing good results, and bringing more customers, with some internal credit system, that can be used to reduce the amount they pay. Make onboarding process for inbound sales, which includes the social proof from the customers.

8. Oh yeah, and consider doing PR and bringing people to your landing page from 7.

I am an software engineer and an introvert. Have been sitting at my desk coding all my career. Once I got a job at a technology company, but the office I was sitting in had very few engineers and most of it was filled with sales and marketing personnel. I was surrounded by all sales and marketing people. The sales and marketing department at that company ran a one month programme open for everyone at the company to sell company products on weekends at multiple brick and mortar retail stores prior to Christmas season. I thought, hell why not I should participate and give it a go; what could go wrong? So I enlisted in the programme. On the first day I was sent back home from the entrance of one of the retail stores because I was wearing jeans pant which was against the retail store's policy. So I went back home and dressed accordingly and returned back. For the next 4 weekends over the month I spent selling company products at 4 different retail stores directly to consumers. What I experienced was that people started coming to me with their requirements and asking what product they should buy! I am not even a native english speaker and I was selling in an english speaking country. I went on to win an award for selling most products in that programme in that year.

So what did an introvert, non-english speaker with no experience of selling do to sell successfully and what did I learn? Here is what I learned, and it is really very simple:

The first rule of selling is don't sell; rather learn, inform and help i.e. genuinely learn about the customer's requirements/problems, genuinely inform the customers about the solution you have or anyone else who could provide the solution and genuinely help the customer with the decision making process. That's it. And your customers then become your recommender and help you "sell" more!

Speak with the customer. Or in fact listen to your customer. If you can do that and your product is good, you will be fine.

Stay away from books/blogs that teach you into manipulating your customer to sell them something. That usually leads to them regretting the buy later and you not finding product market fit .

Sam Alterman's advice is bad, people want to buy not to be sold, you will never convince them otherwise.

If you want to be good at sales you need to turn the question on its head. It's not how to sell but how do people buy?

There is a pain point that creates a want. Research is done into how to satisfy this want. Evaluate the possible solutions. Purchase.

Now you know what your customers will do regardless of you, you just funnel them to you at every step of their buying process. The earlier in the process the more work is required to get to conversion but the easier it is to build reputation with them.

Targeting before the pain point is a waste of time no one will spend money on a backup system until their system fails and they realise they needed it all along.

The information gathering point is the easiest place to target, the customer knows little and will look industry experts like you, to inform them what they should believe.

Don't sell to them, give them all the detailed unbiased information they need to get to the evaluation stage. The more information they get from you the more they will favour you at the evaluation stage as all they know is what you taught them. If you can control what some one hears and sees it stands to reason that you can control what they think and say.

At the evaluation stage, if you are not in their short list at this point you missed your chance. They will have already decided who to go with and are looking for reasons remove the rest from the list. If all their reasoning comes from your advice and you follow your own advice you have won. At this point they are already convinced they just need some reassurance from you to take the leap to purchase.

Purchase This is called the close, its easy Smile, Nod ask a few questions they will answer yes to, then ask them "Are you happy with that?" they will respond with a smile nod and say yes and think to them selves, you know what I am happy, let's do it. If they answer no ask them specifically why not, whats holding them back? Satisfy this concern.

The actual good idea of learning anything / or achieving anything comes down to good amount of homework and experience with introspection and improvising. This seems like too repeated and conventional advise, but it works.

When I was at university every week my roommates and I would invent a new student organisation and spend a few hours pitching it to passersby on campus. The organizations were ridiculous, things like "Students for the exploration of space" or "The Student Potato Advocate". Sometimes we would solicit money but always we would have a mailing list where you could sign up for more information.

We just did it for silly fun but in retrospect it was a great experience. Learning how to promote something, having the self-confidence to talk to strangers and sell something is really useful.

Take improv acting. You learn two highly relevant things:

1. Loosening up creatively(which helps you develop the pitch)

2. Playing a character appropriate to the scene. e.g. during the job interview both parties can play characters that represent themselves/the company in their best light.

Playing a character isn't about lying - it's in the word: play. Every conversation involves some performative aspects, and these skills simply give you additional ways to conduct conversation in business and in life.

> You have to evangelize your plans to customers, prospective employees, the press, investors, etc...

Listening is the new prospecting.

On this subject, John Jantsch is masterful > https://www.goodreads.com/book/show/21847226-duct-tape-selli...

There are surely many resources for sales theory. You can use these to inform yourself.

To get good, you’d need to practice and train your mental and emotional intelligence to the task.

Sales is a very human process and carries a lot of discomfort which you need to learn to work with.

Sell 10 things and you’ll get better. Sell a thousand things and you’ll get good. No shortcut.

I’m finding this “How To Sell” Startup School lecture by Tyler Bosmeny helpful: https://itunes.apple.com/us/podcast/startup-school-by-y-comb...

Fog Creek published some good articles before, but it looks like it's been affected by link-rot:

http://blog.fogcreek.com/the-very-most-basic-things-your-com...

Here's a copy on Archive.org:

https://web.archive.org/web/20161202094244/http://blog.fogcr...

A snippet I liked:

"I used to work as a waiter, and we were supposed to up-sell various things like top-shelf margaritas and seasoned sour cream for the french fries. I sucked at it...

One day the manager wanted to know what was up, and I said something like, “Man, if they want top-shelf margaritas they’ll ask. I don’t need to push it on them.”

My manager said, “That’s true, they are likely to ask if they want something. But what if they don’t know we have it?”"

Thanks - that's the article I was thinking of.

Off Topic: I hope the whole Fog Creek blog hasn't gone away.

I think it has. Fog Creek renamed itself to Glitch [1], sold off FogBugz (which then rebranded as Manuscript, then rebranded back to FogBugz). The last Fog Creek blog post was Feb 14 2018 (about becoming Glitch), and it looks like the blog was turned off in November 2018.

It's a bit of a miracle that the Joel On Software forums [2] are still accessible.

[1] https://glitch.com/about/fog-creek-is-now-glitch/

[2] https://discuss.fogcreek.com/

We do still have the archives, and are thinking of how to bring back the pieces that are still relevant. A lot of the technical content rotted long before the links did, and the more human stuff was due for an update.

That's good to hear.

Depends on the type of selling. Face to face? Online? Direct? Narrow it down and go sell.

But how do you start? You just do. There is no tutorial. The one thing that helps is selling things you know about and can provide an educated opinion on the subject.

Plenty of people have suggested books, etc., and have given you advice. Get the books. Test the advice.

If you want to get good at sales, go back and read Altman's post again (http://blog.samaltman.com/how-to-be-successful). Start with the section you asked about:

4. Get good at "sales"

Notice Altman puts the word "sales" in quotation marks. That means there are other words and terms that you could put in there to increase your understanding. Here are some that he uses: Convincing others, evangelizing, communicating, and believing in what you're selling. Can you come up with some more?

Now ask yourself, for example, "How can I get better at convincing others of what I believe?" What way could you practice convincing someone of something you believed? What would it feel like to convince someone of something you believed? Can you picture what it would look like to be in that situation? What would you need to hear from someone to know they were convinced? Is there any time in your life that you have convinced someone of something that you believed? (Imagine a small child convincing an adult that they believed someone they knew was in danger and you'll realize that a child in this situation knows everything they need to know about "selling.")

Repeat this process with each term. "How can I get better at evangelizing?" "How can I get better at communicating?" (Here he provides some more tips: "Is my thinking clear?" "Am I using plain, concise language?") "How can I get better at believing in what I'm selling?" (Would you buy what you're selling? Have you? Take your reward out of the picture, and find someone who needs what you are selling, and give it to them.) Try with some other terms that you come up with, e.g. connecting with others, understanding the customer's needs, serving the customer, etc..

Brainstorm every answer. The most important thing is that you take Altman's advice and "Show up in person." Test each idea in person, face to face. Engineer situations where you can test your ideas, collect data, and determine what works.

Your problem is not a lack of information. Reading another book is another way to avoid taking action. What you need is imagination, commitment, and a willingness to try everything until you find something that works.

Be patient with yourself. This is a process. It could be a lifetime journey. Enjoy it.

Zig Zigler was one of the early sales gurus and he frames a lot of his sales training around being thoughtful, caring and kind. His books are worth reading for the non-salesman.

There's a book called "The Accidental Salesperson" by Chris Lytle that is a very good read.

I learned to code by coding. I guess I could learn to sell by selling.

My reply is probably too late, but I'll post anyway for people referencing this later.

My own journey over the last 20 years has been a slow migration from a technical contributor (About 10-12 years of systems engineering, infosec consultant, pentester) to a full blown quota-carrying, territory-running sales guy. Surprisingly, I enjoy the work. My personal view of sales started negative based on my interactions with the last generation of salespeople, but I've seen a generational shift in Enterprise Sales recently, and there are a lot more people like me than 10-20 years ago when I started in the industry.

It turns out, sales and running a territory is like engineering to me. Like any good engineer, I enjoy building things. I built out a customer base that can contribute to local chapter events to be where I can't. The job is also highly measureable. I can't think of another role where performance is so easily measured day-to-day and forecasted into the future. It's also a critically important function of the company. Bringing in revenue is a top priority and receives a lot of benefits. One driving force that got me to where I am is that I always took steps of becoming more important.

Back to the question.. how to get good at sales? Easy. Take a sales job. A good place to start would be Sales Engineering or Sales Overlay (SME with sales responsibilities). I'd look for a field that is highly technical and complex. Something hard where real technical chops are required and respected. Customers value your output because they genuinely don't have the expertise that you offer. Nothing commoditized.. look for smaller, fast growing segments.

As for specific skills to succeed in sales in these environments, it's mostly about understanding the customer's business problems and objectives. Once you have a firm understanding and agreement with the customer on the desired business outcomes, then dig deeper into making the individuals at the customer successful. Make your customer a hero. Help them overachieve on their goals. Financial reward comes quickly after you reach this point.

Also important: good communication, systems-thinking (ability to navigate complex organizational decision making processes), and understanding people/empathizing with your customers. Over time you'll develop good instincts to know when to push or when to say no. So much of sales can be subjective, so try to use repeatable processes where possible. Your pricing strategy should be defensible and systematic. Don't make shit up.

To get the above to work for you, you must have strong communication skills. Sales is still about talking to other humans. You get small windows of time with influencers, decision makers, and buyers. You have to have good presentation skills and be able to convey value to a customer with clarity. To distill complex ideas down to simple, meaningful value and tie that to the customer's desired outcomes. The customer needs to be able to answer the question of "why choose these guys instead of those guys?" with confidence and expertise. Most of the real selling happens without you in the room, so you need to build them up to be your champion. When you are in the room, you need them to be your coach.. every meeting should be an open book test. Your coach should tell you in advance who cares about what so you can craft your messaging around things that matter to these decision makers or influencers.

The idea that there is some magical persuasion element in sales seems dated to me. Enterprise sales campaigns are complex. 6-18 month sales cycles with dozens of influencers, decision makers, users, buyers, and so on. You don't take someone out to a steak dinner and close a deal. Does charisma and charm help? Sure.. in a few marginal ways. But you don't have to be a cliche salesperson to be successful. You have to understand how the organization makes a decision, and then work backwards to provide the right information to the right people. Explain the technical value to the people who care about technical aspects. Explain how the license model scales to the person running the budget. Explain how your added services will help the guy in charge of operations scale up the program and over achieve on his goals.

Also, the best sales people pick great products in growing markets. That's where the money is. Mediocre products in stable markets do not attract talented sales people.