Best Sales Books to Read in 2021

Learning is part of the journey to becoming good at sales. In this article, we’ll be covering the best sales books to help you get better at selling.

Reading books lets you experience sales through the eyes of others that have tried and tested a specific approach and improved it to perfection.

To help you pick the best sales book from this list, we have highlighted the summary for each one, its key takeaways, and explained who is this book best suited for.

Let’s start.

New Sales. Simplified. by Mike Weinberg

8.2
New Sales. Simplified.: The Essential Handbook for Prospecting and New Business Development

New Sales. Simplified.: The Essential Handbook for Prospecting and New Business Development

Packed with examples and anecdotes, New Sales. Simplified. offers a proven formula for prospecting, developing, and …
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Summary

Only 10% to 15% of salespeople work on generating leads. The rest spend most of their time on trivial tasks, like providing customer support and managing finances. Reps should ditch meaningless work and focus on chasing new business instead.

Key Takeaways

Weinberg breaks down the sales process into three stages:

  • Target the right accounts.
  • Sharpen your sales weapons.
  • Attack your targets.
  • You want to target customers with characteristics similar to your best customers. If you’re selling enterprise software, don’t waste your time contacting SMBs. Record your ideal prospects in a list and keep it with you at all times.
  • A captivating story hooks clients, and good stories revolve around the buyer’s needs. Excellent stories do this – and they link your solution to the buyer’s pain points. You should also include differentiators that separate you from competitors in your conversation. In other words, what makes your solution better?
  • Keep your stories short (less than three minutes is best) and personal to keep prospects engaged. This rule applies regardless of whether you’re cold calling or selling in person.

Who Should Read This

Salespeople preoccupied with tasks unrelated to sales.

How to Win Friends and Influence People by Dale Carnegie

8.2
How to Win Friends and Influence People

How to Win Friends and Influence People

You can go after the job you want…and get it! You can take the job you have…and improve it! You can take any …
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Summary

Carnegie’s best-selling title is a scripture in sales and deservedly so. This book is not about selling per se. But, its lessons can be used to great effect when dealing with prospects.

Key Takeaways

You need to practice six habits to make yourself likable:

  • Show genuine interest in the person you’re talking to.
  • Smile more.
  • Mention the person’s name more.
  • Listen more.
  • Talk about the person’s interests.
  • Make the person feel important in a sincere way.
  • People are emotional. They enjoy working with people they like. Prospects buy from reps they trust even if the product itself is subpar. 
  • Avoid confrontations. There’s no use criticizing or arguing even if you’re right—you’re only making people dislike you. 
  • Look at the situation from the other person’s perspective. Great sales reps have a deep understanding of their prospect’s point of view, which helps them craft compelling pitches.
  • The best way to influence people is by talking about their needs and showing them how to achieve it. The same logic applies to sales. If you can’t identify their needs, your prospects will never be interested in whatever you’re saying, even if you have the right solution.
best sales books - How to Win Friends and Influence People by Dale Carnegie
The core principles of How to Win Friends and Influence People (Image Source)

Who Should Read This

Everyone. The knowledge from this book will serve you well in all facets of life.

SPIN Selling by Neil Rackham

8.2
SPIN Selling

SPIN Selling

Written by Neil Rackham, former president and founder of Huthwaite corporation, SPIN Selling is essential reading for …
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Summary

SPIN Selling is all about asking prospects the right questions. The book advocates a consultant-like approach in the sales process. You ask prospects what’s bothering them, how it’s affecting their business, and what they stand to gain from solving their challenges.

Key Takeaways

The SPIN framework revolves around four types of questions:

  • Situation
  • Problem
  • Implication
  • Need-Payoff
  • Situation questions provide preliminary insights into your prospect’s background. The facts gathered here serve as the foundation for the rest of the sales process.
  • Problem questions identify the prospect’s pain points. Interestingly, Rackham concluded that open-ended questions did not influence sales success in his analysis. You can use any type of question as long as it gets customers talking about their challenges.
spin selling book
The four pillars of SPIN Selling
  • Implication questions highlight the business impacts of their pain points. How much time and money are prospects losing by not addressing their challenges? You want prospects to realize the seriousness of the problems on their own, hence the use of implication questions.
  • Need-payoff questions get prospects to talk about how your solution benefits them. If the buyer mentions poor productivity as a challenge, ask them what they can do with the extra hours gained from your product. 
  • Your need-payoff questions should reference the problems uncovered from the implication stage. Don’t talk about benefits your product cannot accomplish, or you risk disappointing your prospect and losing the sale.

Who Should Read This

SPIN Selling works fabulously well for high-value enterprise deals.

The Challenger Sale by Matthew Dixon and Brent Adamson

8.2
The Challenger Sale: Taking Control of the Customer Conversation

The Challenger Sale: Taking Control of the Customer Conversation

What’s the secret to sales success? If you’re like most business leaders, you’d say it’s fundamentally about …
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Summary

There are five different types of seller profiles, according to the authors’ research. The Challenger profile is the best at consistently closing complex and high-value deals.

best sales books - The success rates of different seller profiles according to the Challenger Sale
The success rates of different seller profiles according to the Challenger Sale

Key Takeaways

  • Challenger reps excel at taking control of the sales process. They’re not afraid to steer conversations and extend the prospect’s view beyond price. They’re also comfortable with challenging customer assumptions to get them out of their shell and discover their pressing problems.
  • Challenger reps thrive at solution selling. They are experts at linking their products to buyer needs as they understand their customers on a deep level. They do their homework and ask smart, inquisitive questions to gather critical facts. Challengers tailor their solutions around their prospect’s pain points, which helps with closing deals.
  • Challenger reps provide value by showing prospects how to run their businesses better. Prospects are already aware of your solution. What they need is a trusted advisor to educate them throughout the buying journey. Demonstrate expertise by sharing valuable insights and addressing their concerns with confidence.

Who Should Read This

Salespeople who want to become more persuasive and authoritative in conversations.

Solution Selling by Mike Bosworth

8.2
Solution Selling: Creating Buyers in Difficult Selling Markets

Solution Selling: Creating Buyers in Difficult Selling Markets

Solution Selling is the most comprehensive sales and sales management process available today.
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Summary

Solution selling was introduced at a time when aggressive, closing-oriented approaches were the norm. Bosworth was not a fan of this. He believed that sales reps should tackle their prospects’ challenges and build the sales process around a solution. It was a strategy based on Bosworth’s observations on Xerox’s top sellers.

Key Takeaways

  • Solution selling involves two key components: understanding your product and your customer’s pain points. 
  • You need to know your product like the back of your hand to sell effectively. The features and advantages of your product must be second nature to help you react better when dealing with customers.
  • You must understand the problems your prospect is facing. Ask probing questions to help you grasp their situation. Be specific when asking to gather valuable insights. You don’t want to hear basic information anyone can find online. Your prospects are busy and won’t appreciate you firing off questions you can Google in a second.
  • Educate the prospect about your solution once you have identified their problems. Talk about how their problems will disappear with your solution. Encourage prospects to vocalize the benefits they gain from addressing their pain points. Saying it increases your chances of closing the sale since you’re making the buyer themselves realize the value of your solution.

Who Should Read This

Solution selling is an excellent primer for sales. Read this if you’re new to selling.

Little Red Book of Selling by Jeffrey Gitomer

Summary

This book is a collection of the lessons Gitomer learned on sales throughout his career. It’s not as thorough as the other books on this list. But, it serves as a great pickup book to keep your sales approach in check.

Key Takeaways

There are thirteen principles every sales rep must adopt to get better at selling. These are:

  • Work hard, and don’t blame others for your failures.
  • Do your homework on prospects before attending meetings.
  • Build a name for yourself.
  • Provide value and make friends.
  • Spend 75% of your time networking at places where your prospects go.
  • Make sure you talk to the real decision-maker.
  • Ask smart questions that make your prospects think, “No one has asked me that before.”
  • Learn to be funny. If you can make prospects laugh, you can make them buy.
  • Be creative when selling to differentiate you from competitors.
  • Reduce your prospect’s risk of buying by evaluating the pros and cons.
  • Use social proof (testimonials, referrals, case studies, and others) to convince prospects.
  • Be aware of what’s happening around you to identify golden opportunities.
  • Stay out of other people’s drama.

Gitomer advocates investing your time on self-improvement and tasks that drive you closer to success. You should also embrace a can-do attitude for all things you do in life. Positivity is contagious, and it will help you become a better salesperson in the long run.

Who Should Read This

Salespeople who want to brush up their knowledge before meeting clients.

The Ultimate Sales Machine by Chet Holmes

Summary

The Ultimate Sales Machine explores the strategies Holmes used to double the sales of the nine Charlie Munger divisions he worked at. This book looks at selling from a broad perspective—including marketing and hiring—to elevate sales performance.

Key Takeaways

Sales is not just about making money. It has to deliver value. Education-based marketing that Holmes advocates helps prospects perceive that value and not feel they are being sold to. The success of your customers matters just as much as your own.

Going above and beyond for your customers not only helps with sales, but it also builds strong relationships, which is never bad for business.

Focus on your most valuable customers that generate the majority of your revenue (read the 80/20 principle). Enterprise clients are not easy to land, but the rewards are immense. 

The Ultimate Sales Machine sales book - An illustration of the 80/20 rule
An illustration of the 80/20 rule

Never apologize for the time spent with high-value prospects. They should feel lucky if you can provide valuable solutions for their challenges.

Companies can skyrocket their sales performance by training employees consistently. Training is not a one-off. Sales reps should be sent to workshops regularly to hone their skills. The depth of training must increase over time for reps to become high-performers. Combine this with value targeting, and your organization will be well on its way to sales success.

Who Should Read This

CEOs, heads of sales, or other business leaders looking to improve their organization’s sales performance.

Additional Reading: The Ultimate Sales Machine Summary

Secrets of Closing the Sale by Zig Ziglar 

Summary

Zig Ziglar is a unanimous choice in any “best of” list. In this book, Ziglar analyzes the role of persuasion in making people buy. It also explores the types of closing techniques salespeople can use in various sales scenarios.

Key Takeaways

Persuasion is your best weapon. You can only effectively persuade customers if you have enough information about them, which means understanding their situation, objectives, and problems. Bear in mind that most prospects do not know what they want. Sales reps need to steer conversations around discovery questions to gather key information on prospects.

One of Ziglar’s favorite closing techniques is to break down prices into smaller chunks. Instead of pricing a product at $10,000, express it in terms of the daily, weekly, or monthly cost. Doing so helps prospects see the true value of your solution. Your prospects will almost always sign the check if the perceived value is greater than the product’s cost.

You will come across objections when selling. Don’t assume prospects don’t need your solution just because they say no. They may need more convincing. Invest in yourself (dress better, speak confidently, show product knowledge) to become a more persuasive sales rep.

You must have confidence in your product. Understand the value your solution brings to the table and have faith that it will address your prospect’s challenges. If you don’t trust your product, no one will.

Who Should Read This

If you find it hard to go for the close, this book is for you.

Additional Reading: Secrets of Closing the Sale Summary

Predictable Revenue by Aaron Ross & Marylou Tyler

Summary

Predictable Revenue was written on the back of Salesforce’s journey from a tiny company to the juggernauts they are today. The book touches heavily on modernizing sales teams to make selling more systematic and predictable.

Key Takeaways

Every business wants to have a steady stream of incoming leads, which is achievable by running cold outreach campaigns every few days (also known as Cold Calling 2.0).

How Cold Calling 2.0 works in the sales process - takeaway from a sales book
How Cold Calling 2.0 works in the sales process

First, identify your ideal customer profile. You want to spend time only on prospects who need your solution and have similar profiles to your current clients. Record your targets in a list for easy access—leverage technology to automate your prospecting and reduce manual work.

Send outbound emails to your targets every few days. Be careful not to spam your prospects. You don’t want them to be annoyed. The authors suggest sending no more than 250 emails a week to avoid the spam list.

Having consistent leads is terrific, but it’s unreasonable to expect sales reps to keep up with the increased workload. Instead, businesses should split sales teams into three parts:

  • Sales Development: Focuses primarily on prospecting to generate leads.
  • Market Response: Analyzes incoming leads to ensure only qualified buyers enter the funnel.
  • Account Executives: Responsible for closing qualified leads passed to them. They do not work on prospecting or any other tasks not related to closing sales.

Having a well-planned sales system and specialized roles makes selling much more efficient—and successful—compared to traditional sales methodologies. 

Who Should Read This

Businesses with large teams should consider using the Cold Calling 2.0 model to streamline the sales process.

Gap Selling by Keenan

8.2
Gap Selling: Getting the Customer to Yes: How Problem-Centric Selling Increases Sales by Changing Everything You Know About Relationships, Overcoming Objections, Closing and Price

Gap Selling: Getting the Customer to Yes: How Problem-Centric Selling Increases Sales by Changing Everything You Know About Relationships, Overcoming Objections, Closing and Price

The first ever playbook for B2B salespeople on how to win clients and customers who are already being serviced by your …
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Summary

The premise of Gap Selling is simple. If there’s no problem, there’s no sale. A sale only happens if there is a gap in what prospects have now and what they want in the future. Successful reps are experts at identifying this gap and alerting it to buyers.

Key Takeaways

Diagnosing your customer’s gaps is the essence of sales. Your prospects are not always aware of it, however. Your job is to challenge their assumptions and identify what’s stopping them from achieving their goals.

The value of your solution depends on how big the gap is between your prospect’s current situation and their future state. Where does the prospect want to be in the future? What’s in the way of their journey? 

The bigger the gap, the more attractive your solution is to the buyer. There can also be many gaps affecting the prospect—don’t limit yourself to one.

How Gap Selling works, visualized
How Gap Selling works, visualized

Uncovering gaps comes down to asking the right questions and discovering hyper-specific information. For example:

What is your prospect doing at the moment? 

Are they happy with their existing solution? 

How does the solution work?

What happens if the person working on this is unavailable?

You want your prospect to think twice about their current provider. Often, they’ll express their concerns without you explicitly asking them to do so. 

Tie in your solution to the gap. Does it reduce or, better yet, remove the gap completely? If yes, you’re one step away from closing the sale. Ask for commitment, and you’ve got yourself a new client.

Who Should Read This

Read Gap Selling if you want to get better at locating customer pain points and creating urgency.

Never Split the Difference by Chris Voss

8.2
Never Split the Difference: Negotiating as if Your Life Depended on It

Never Split the Difference: Negotiating as if Your Life Depended on It

A former international hostage negotiator for the FBI offers a new field-tested approach to high-stakes negotiations – …
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Summary

Never Split the Difference is perhaps the best book to learn about negotiations. You’ll get better at convincing prospects by understanding the link between empathy and emotions in conversations.

Key Takeaways

Good negotiators understand the importance of showing empathy. The best and easiest way to do this is by listening more than you talk. You build trust when you actively listen to prospects, as it shows that you care about them.

Good negotiators also mirror the other party in subtle ways. Reply to prospects with the last three words they used. If the prospect says, “This is too expensive.”, you should say something like, “Yes, it is too expensive. What’s holding up your budget?” 

Imitation is the best form of flattery, and it will do wonders in building the prospect’s affinity towards you.

Active listening is one part of the equation. Understanding how your prospect feels is just as important. Express your understanding of the person’s point of view in third-person. For example:

“It looks like you need more time to fix this problem.”

“It seems like you don’t have the capital to pay for this solution.”

“It sounds like you’re losing productivity to this challenge.”

You want to hear the prospect say, “That’s right.” By doing this, you’re building a strong emotional connection with the other person, which makes communicating your points a lot easier.

Who Should Read This

Everyone. Never Split the Difference will help you become a better communicator regardless of your goal.

Eat Their Lunch by Anthony Iannarino 

8.2
Eat Their Lunch: Winning Customers Away from Your Competition

Eat Their Lunch: Winning Customers Away from Your Competition

The first ever playbook for B2B salespeople on how to win clients and customers who are already being serviced by your …
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Summary

This book talks about how salespeople can land their dream clients even if they already have a solution. It emphasizes on differentiating your company from others by positioning yourself as part of the unique value proposition.

Key Takeaways

Most companies operate in ‘red oceans,’ mainly markets with fierce competition. It’s hard to generate new business in red oceans. Most of your clients will come from your rivals. The opposite is also true. Customers will jump ship to your competitors if you don’t keep them happy.

Iannarino talks about the four levels of value creation in sales. The best companies position themselves at the top of the chain as level four providers. They provide incredible value and act almost like an extension of their clients’ businesses by cementing themselves as trusted advisors.

At this point, your solution is no longer the selling point—you are the investment. Whatever decisions they’re making, they’ll go to you first for advice. Look at the situation from your customer’s point of view and provide relevant guidance. Remember, your success depends heavily on the customer’s success.

This applies to the sales process as well. You can attract clients away from competitors if they feel you’re a better person to work with. Don’t condemn your rivals. Instead, differentiate yourself by proving your expertise as a consultant in addition to solving their business challenges.

Who Should Read This

Sales reps operating in fierce markets. It’s also a great read if you work in high churn industries.

The Only Sales Guide You’ll Ever Need by Anthony Iannarino

8.2
The Only Sales Guide You’ll Ever Need

The Only Sales Guide You’ll Ever Need

“Contrary to what most underperformers claim, sales success is not situational. It’s not about the market, the product, …
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Summary

Iannarino reappears on this list with another excellent book. “The Only Sales Guide You’ll Ever Need” highlights the importance of personal development, with the author sharing actionable tips on how salespeople can rework their habits to succeed at sales.

Key Takeaways

Stay true to your principles and beliefs when selling. Don’t change yourself just to meet someone else’s needs. This shows that you’re genuine, which is a strong trust signal for prospects. 

Be optimistic. Pessimism kills success not only in sales but in life as well. You want to embrace positivity even if the outcome is not what you expected.

Businesses lose customers not because their products suck, but because they don’t care. Look after your clients during and after the sales process. Be empathetic by attentively listening to what your prospects are saying. Ask “why?” more to understand your prospect’s struggles. It also helps to look at the situation from the buyer’s perspective. 

Doing these nets you the ten commitments needed to close a sale.

The ten commitments needed before a sale can be made - sales books takeaways
The ten commitments needed before a sale can be made

You can go for the close without meeting every requirement. But, you’re likely to fail even if the solution matches the prospect’s problems to a tee.

Who Should Read This

This book is an excellent read for salespeople looking to improve their soft skills.

The Sales Development Playbook by Trish Bertuzzi

8.2
The Sales Development Playbook: Build Repeatable Pipeline and Accelerate Growth with Inside Sales

The Sales Development Playbook: Build Repeatable Pipeline and Accelerate Growth with Inside Sales

Raise your hand if your company needs more new customers.I suspect your hand is (figuratively) up. This book is about …
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Summary

Like Predictable Revenue, Trish Bertuzzi’s groundbreaking book advocates specialized sales roles in businesses, each with their specific responsibilities to increase sales efficiency.

Key Takeaways

The four core roles in high-performing sales teams are:

Sales development reps (SDR): Responsible for securing new sales leads and setting meetings for account executives.

Business development reps (BDR): Responsible for qualifying outbound leads

Account development reps (ADR): Responsible for performing outbound sales (e.g., cold calling, door-to-door sales, attending events).

Account executives (AE): Responsible for converting qualified leads into paying customers.

Businesses need to excel in all aspects of the sales process to succeed. However, it’s unreasonable to expect sales reps to be perfect at everything. Finding the ideal sales rep is almost impossible, let alone managing one—which is why businesses need role specialization.

The typical slick-talking approach no longer works. Instead, the modern sales rep should focus on helping prospects achieve better business results. Your solution must solve your prospect’s challenges while also being a business advantage.

Bertuzzi recommends using the ABCD framework to segment your leads, so you don’t waste precious company resources when selling.

The ABCD framework for defining ideal prospects - sales book by Trish Bertuzzi
The ABCD framework for defining ideal prospects

Companies should treat sales as a well-oiled system. This means looking at sales from a scientific point of view, whether using analytics to improve operations or streamlining processes to remove unnecessary tasks. This allows businesses to scale their sales effectively as they grow.

Who Should Read This

The Sales Development Playbook is a must-read for CEOs and sales leaders. The strategies listed in this book are essential to building successful sales systems in the modern age.

The Sales Acceleration Formula by Mark Roberge

8.2
The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million

The Sales Acceleration Formula: Using Data, Technology, and Inbound Selling to Go from $0 to $100 Million

Use data, technology, and inbound selling to build a remarkable team and accelerate sales. The Sales Acceleration …
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Summary

Growing a company involves more than just adopting a sales methodology. You need to hire the right people, train them to be top-performers, and reward them for their achievements. That was what Roberge did to grow HubSpot from a one-person sales team to $100 million in revenue in less than seven years.

Key Takeaways

Hire salespeople with qualities that complement your business. If you already have a high-performer among your ranks, analyze the individual’s characteristics, and incorporate them in the vetting stage.

Prioritize coachability and work ethic. You want to work with people who are willing to learn and are humble enough to be trained.

Great salespeople are not job seekers—you need to find them.

Roberge suggests using LinkedIn to find the right people. Use employment histories and past achievements to identify potential candidates. Reach out to your candidates, and don’t hesitate to express how much you’re willing to bring them on board. Ask for referrals if LinkedIn doesn’t work out for you.

Sales training is crucial to success.

Business climates change on a whim. Even top sellers fall behind if they don’t keep up with change. Invest in courses and workshops to maintain your team’s performance. Make sure your training is related to your clients’ industries. It will be easier for sales reps to spot new opportunities and challenges when dealing with prospects.

Who Should Read This

Founders or hiring managers on the hunt for talented sales reps.

Fanatical Prospecting by Jeb Blount

8.2
Fanatical Prospecting: The Ultimate Guide for Starting Sales Conversations and Filling the Pipeline by Leveraging Social Selling, Telephone, E-Mail, and Cold Calling

Fanatical Prospecting: The Ultimate Guide for Starting Sales Conversations and Filling the Pipeline by Leveraging Social Selling, Telephone, E-Mail, and Cold Calling

There are too many distractions today that impact sales productivity. Sales reps need to work smarter to get more done …
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Summary

If you can only read one book on prospecting, it’s this one. Jeb Blount’s best-seller dives deep into the whys and hows of prospecting, which he deems as ‘the most important factor in sales.’

Key Takeaways

Superstars spend time on prospecting more than any other task. They do this because they know an empty pipeline is disastrous—and that only happens if you fail to prospect.

You create your luck when you prospect regularly. The more you seek new business, the likelier it is for you to close deals. Never stop prospecting even if you’re busy. The prospecting you do in the next thirty days will fill up your schedule three months later. Not doing so will lead you to a sales slump when you run out of clients to pursue.

While fanatical prospectors are always looking for business, they’re not delusional. Great salespeople understand their prospects better than anyone else. They don’t force customers if the solution is not right for them. Paralysis analysis does not bother them because good sales reps know failure is inevitable when they’re pursuing so many clients.

Who Should Read This

Individuals looking to take their prospecting skills up a notch. Fanatical Prospecting is also a good sales book in general as it contains valuable advice for the entire sales cycle.

More Sales, Less Time by Jill Konrath

8.2
More Sales, Less Time: Surprisingly Simple Strategies for Today’s Crazy-Busy Sellers

More Sales, Less Time: Surprisingly Simple Strategies for Today’s Crazy-Busy Sellers

There are too many distractions today that impact sales productivity. Sales reps need to work smarter to get more done …
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Summary

There are too many distractions today that impact sales productivity. Sales reps need to work smarter to get more done in less time.

Key Takeaways

You need to tackle the productivity problem head-on. There’s no magic solution other than doing whatever it takes to stop you from lazing around. Identify your productivity challenges and eliminate them one by one, starting from the smallest obstacle. 

Aim to reduce one hour of unproductive work every day. Seemingly innocent tasks like checking emails can take up too much time with you realizing it. Remove these distractions or accomplish the tasks as quickly as possible if they’re must-dos.

Allocate time saved on more productive tasks. Read a book, learn a new sales methodology, or make cold calls. Regardless of what you do, make sure you’re spending time on tasks that help you develop as an individual. You can sharpen skills outside of sales too.

Motivation is the key to adopting new habits. Celebrate your achievements even if it’s a small one. Do this, and you’ll find yourself raring to check the next point off your productivity to-do list.

Who Should Read This

Busy reps struggling to balance between sales and non-sales tasks.

Conclusion 

This concludes our list of must-read sales books in 2021.

Read a few, and you can polish your sales process and improve on the areas that need refinement. Read them all and your sales knowledge will be immensely enriched by others’ experiences and successes.

Which book are you looking forward to reading soon?

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Daniel

Daniel

Contributor @samcx.com. Passionate about everything Sales, Marketing and Account Management.

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