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How to Get Better at Sales (Essential Guide and 4-Step Checklist)

get better at sales
Sales Process

If you’ve struggled to succeed at sales, you have 3 options for responding. You can quit and move on… give it your all and try to get better at sales… or transition out of sales and accept a different role with your employer.

There’s no shame in leaving a sales job or changing roles. 

But I want to assure you that most people CAN get better at sales — if they’re willing to do the work. 

If you’re good at engaging with people, it’s worth investing in your own skills to see if you can level up and start hitting (or crushing) your quota.

Here’s what you need to do to quickly improve your sales skills:

 


Want to Get Better at Sales?

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Step 1: Develop The Habits Of Successful Salespeople

When I’m working with salespeople who aren’t achieving their quotas, they are often looking for a “cheat code” to getting better at their job. 

What’s the trick? What’s the secret? 

The truth: There isn’t one. There is no “great line” for closing more deals or handling objections perfectly. 

You might be disappointed to find out that it’s going to take some seriously hard work, but don’t be! The work you put into developing the correct sales habits will actually have long-term benefits throughout your entire career. 

Now, let’s dig into 4 sales habits you need to get better at sales.

Positivity

Let’s start with the habit that’s most crucial to your success as a salesperson, which is having a positive mindset. If you can’t get this right, then you’re likely not a great fit for sales. 

Sales has its ups and downs and is filled with a tremendous amount of pressure. Working through the month with a smile on your face is critical.

To develop this type of mindset, you need to start by treating yourself well. Here, I’m talking about the basics: 

  • Getting 7–8 hours of sleep per night
  • Eating healthy, nutritious foods
  • Getting at least 30 minutes of exercise 3x per week
  • Reducing your alcohol consumption

I get it… 

“Work hard, play hard!” Right? 

Sort of. It’s great to have fun and celebrate your success, but it’s equally important to treat your mind and body well. Remember, that’s going to give you a better mental makeup. 

This is critical. Take it from someone who ignored this for many years.

Once you’ve laid the foundation, you need to have a plan for when the inevitable bad day, week, or month happens. 

It’s called adversity, and you need to embrace it rather than fear it. Adversity is something that helps you get better at every step in your sales career. When you come up against a bad day or week, ask yourself these questions:

What would [Insert Your Role Model] do in this situation? How would they talk about it? Would they get frustrated or create a plan and blast through this mess?

What am I learning right now from this adversity? How will I use this learning to decrease the likelihood that this happens again? 

How will I talk about this adverse situation several years from now? 

Likely, the one adverse situation you’re experiencing now won’t be the end of the world. So slow down and walk through the questions above. 

  1. Unplug from the frustrating moment. 
  2. Jot down the answers. 
  3. Read them back to yourself. 
  4. Gain some perspective. 

The last, crucial way to create positivity in your sales career is by surrounding yourself with others who exude this same mindset. 

If you look around your sales floor, there are likely groups of people who are crushing their quotas and loving life — as well as folks who are missing their quotas and spend their time talking poorly about the job and the company. 

Do yourself a favor and avoid anyone who has a cancerous attitude. 

I cannot say this enough. Even if your closest friend on the floor is a negative person, you need to avoid them at all costs. 

Go find the group that’s doing a great job, and sit with them. Feed off of their energy. Learn from them. Learn how to motivate yourself.

This is a lesson that you should follow at every step in your career.

Coachability

Alright, we’ve laid the foundation for success through a positive mindset. We’re eating healthy, exercising, getting good sleep, and we’re surrounded by successful, happy people on the sales floor. Now it’s time to accelerate learning, and this comes from the coaching you’re receiving in your role.

Often, when you get coaching, it’s going to push you outside of your comfort zone. You’re going to be asked to try something different than you’re doing it today, and it’s going to make you feel uneasy. 

You HAVE to be willing to be coached. 

Scripts, objection handling, and closing techniques that come from your manager are likely being used for a reason. They work. 

So when you’re receiving coaching, make sure you’re open to it. Trying something new once and declaring, “It doesn’t work!” — that’s a surefire way to continue missing your quota. 

When you receive coaching, privately, at home, apply it in a role play setting. Work on it with your peers on the sales floor. Do it until it feels comfortable. 

Before you ultimately practice on your prospects, build your confidence in safe scenarios where you can screw it up as often as you’d like. 

Curiosity

The single, most consistent trait I see in top-performing salespeople is curiosity

They proactively seek out coaching, knowledge, and educational opportunities. They sit near top performers and listen. They ask to silently audit ten of their cold calls or three of their demos. They take notes and ask a lot of questions. 

Want to know how to write a better sales email? How to handle a specific objection? Go find someone on the floor and get the answers you are looking for. 

Want to know why you lost a deal to a competitor? Go to their website and learn everything you can about their product. 

Be curious enough to understand why you succeed, but more importantly, why you fail in many situations.

When you are perpetually curious and you’re always asking questions, you’re going to collect a ton of information that’s useful. Put it somewhere! 

Create a personal playbook for success. What works on the phone, email, social? What are your favorite objection techniques? How do you beat certain competitors? What’s your best follow-up advice? 

Document all of this for yourself and study it. Over time, the playbook will evolve and change as you get better! 

Work Ethic

Last, but certainly not least, is work ethic. This trait is 100% in your control — and you need to understand how valuable it can be, especially when you’re early in your career or not hitting your quota.

Regardless of what people tell you, there is value in the statement, “Sales is a numbers game.” While I agree it’s not ALL about numbers, the more at-bats you get, the more likely you are to succeed. 

If you’re not doing well, commit to the following changes in your daily routine:

  • Start your dialing 15 minutes earlier
  • Reduce your breaks for lunch, water cooler talk, etc., by 15 minutes
  • Stay 15 minutes later than you normally do

Even if you just do this for one month, and you’re making 5 dials every 15 minutes, that’s 15 extra dials per day, or 300 extra dials per month. 

Sales is a compound game, so this stuff adds up! 

You might find that doing this for just one week or one month gives you the extra at-bats you need to catch back up to your peers or successfully hit your quota. It’s worth it to put in the time now. 

The great thing about developing this work ethic today is that it will be extremely helpful for the rest of your career. As you move further and further up the ladder, working hard to solve challenges will become more of the norm. Developing this trait early is incredibly helpful for every stage of your career. 

Step 2: Level Up Your Discovery Skills

When I’m talking to salespeople about critical parts of their sales methodology, I tend to hear a lot about “closing business” or “getting the deal across the line!” While I agree that these are important, I’d argue that your likelihood of closing deals starts at the very beginning of your sales methodology. 

It starts with asking great questions and truly listening to the responses your prospects give you. 

I can’t tell you how many calls I’ve been on where a salesperson asks me discovery questions and then proceeds to show me features of their solution that don’t align to my answers or what I’m looking for. 

It’s infuriating because it’s so easy to avoid. Let’s talk about how.

First of all, discovery isn’t something that you do at the beginning of a call because your manager told you to do it. Discovery is meant to do exactly what the word says: discover! 

The best way to do that is to come prepared to the call ready and willing to listen, and gather information that helps you actually help your prospect make the best choice for him or her. 

To start, questions should generally be open-ended. I like some of these when I’m just getting to know my prospect:

  • What business problem are you trying to solve when looking at different software?
  • What have you tried in the past to solve this problem? How did it work? What do you hope this new software will do differently?
  • In terms of priorities for the business, where does solving this problem currently rank?
  • How do these purchasing decisions usually get made? Who is involved in ultimately choosing the vendor you work with?
  • Has budget been an issue in the past when choosing software to solve this problem?

There are hundreds of questions you could ask, so these examples are just a few I like, because they help me get information to position my product or service effectively. 

What I’m generally looking for is an understanding of their true business challenge, how important it is to solve for them, what they have tried to do before and why it hasn’t worked, how they make decisions and if they have enough of a budget. 

Once you have those answers, make sure you continue to do additional discovery throughout the call. You might hear the prospect say something later in the call that doesn’t align with the answers they gave in the beginning. If that happens, make sure to drill down and truly understand this new piece of information. 

“Jim, I think I heard you say that you’re currently trialing software for call recording, but in the beginning of the conversation you mentioned marketing being the #1 priority. I want to make sure I understand the priority for your business. Do you mind expanding a bit on which of these is currently most important?” 

Having good, active listening skills will allow you to go deeper into discovery throughout the entire call and navigate your demonstration to match true business need.

As you move into your product or service demonstration, you should have a clear understanding of what’s important to your prospect. The demonstration should map exclusively to solving those problems. 

Don’t show fancy, cool features just because you like them! Show the prospect what they need to see to be successful. I like using “tie-back to benefit” as a way to remind the prospect why you’re showing them each feature. 

“Jim, looking at my notes here, you made it very clear that acquiring new customers through social media was important to your business this year. You also mentioned that it needed to be automated, and not something your staff had to focus on all day. This part of our software that we’re looking at now, is going to do just that. Let me show you how it works to acquire those customers, and then we can both agree at the end if the automation meets your needs. Sound good?”  

Actively listening to your prospects to gather relevant information is a skill that takes some time to master. If your company has recording software, spend some time listening to top reps. If they don’t, saddle up to someone who is successful and start learning how to do great discovery. 

Step 3: Get Comfortable with Rejection

I’ve worked with some of the top salespeople in software over the last decade of my career, and rarely have I seen someone close at a rate higher than 40%, which means that even the best salespeople experience rejection more than half of the time. Yikes! 

When you’re prospecting, it’s likely you experience rejection even more often, like 90%. How the heck do you keep persevering when there is so much rejection? The answers to this question will help power you towards success in your career. Here are four surefire ways to do just that:

Expect Rejection On Every Call

Given the numbers we just talked about above, you should expect that you’ll be rejected on nearly every outreach and most of your demonstrations. Superstar salespeople understand that rejection is part of the game. 

They know exactly how many “no’s” it takes to get an emphatic, “yes!” Each no just gets them closer to their next scheduled demo or next sale. That’s the right mindset for sales

Don’t Take Rejection Personally

In part 1, we discussed the appropriate positive mindset required to be a top-performing salesperson. That mindset can get beat down over time as you experience more and more rejection. 

Remember…

Don’t take it personally! When a prospect tells you no, they aren’t rejecting you as a person. They are rejecting this one particular attempt at outreach. Analyze what went poorly in this attempt and live to try again. 

Know Rejection Leads To Future Acceptance

When a prospect tells you, “No,” true professional salespeople hear, “Not right now.” The best at handling rejection analyze what went wrong, and learn from the prospect about their failures. 

Maybe it was price. Maybe it was that they don’t understand the benefit. Maybe it was just bad timing. Either way, great salespeople note what went poorly and use that information to reach out later down the road and have another shot. 

Have A Big Enough Pipeline Not To Care

This last one is my favorite… 

True superstar salespeople have such a robust pipeline of ideal prospects that they just don’t care about the lost opportunity. They move the deal out of their pipeline once they experience rejection, because they have many other deals that look better and will help them achieve their number. 

Remember, the more deals you have, the less rejection hurts.

If you’re a salesperson who is developing great habits, asking your prospects great questions and listening, and you laugh in the face of rejection… you’re almost there. Let’s put it all together with an incredible sales process that will deliver strong, predictable, quota crushing results. 

Step 4: Have a Strong, Predictable Process

If you’re working at a company that has a robust sales process in place, start by asking yourself if you’re following that process the way you’ve been taught. 

If you aren’t, now is the time to get on board. If your company doesn’t have a strong process, then it’s pretty easy to create a personal process that works for you and delivers predictable results.

To start, I like to identify the key inputs required to achieve your desired outcome, then work backward.

So, for this example, let’s assume you have a quota of $50,000 in annual recurring revenue to achieve. The first thing we want to know is what the average revenue is for each deal that you close. 

Let’s say each deal that you close is worth $10,000 on average. We know that you need to close 5 deals to hit your quota. 

deals to hit quotaNext up, I’d want to understand what percentage of opportunities that you demo, end up closing. Take a look at each of your last 6 months of performance. How many demos did you complete inside of each month, and how many closed? Let’s say the number is one in four, or 25%. 

Percentage of demos that closeIf we need to close 5 deals, then we now know it will require 20 completed demos. 

Demos neededOnce you understand this, it’s important to look back and see the percentage of demos that were scheduled that actually ran. I call this “stick rate” or “show rate.” Let’s assume that 65% of your scheduled demos show up to join your meeting and get a full demo. If that’s the case, we know you need roughly 31 demos scheduled to achieve your demo performed goals.

Scheduled demos needed

Now, let’s back it up another step and check the number of daily activities through calls and emails that are required to book a demo. 

If it takes, on average, 40 activities to book one demo, then we know it’s going to take 1,240 activities this month to achieve the demo scheduled rate you need to succeed. 

Daily activities neededOk! We’re getting somewhere. Here’s what we’ve discovered so far:

  • 1,240 activities
  • 31 demos scheduled
  • 20 demos performed
  • 5 closed won
  • $50,000 in ARR

This is your battle plan. 

But, we’re not finished yet. Now it’s time to dive into each of the metrics to understand why someone moves from one stage to another and how to increase the likelihood that more prospects do. After all, we’re here to crush quota, not just hit it. 

Work with your manager or one of your sales operations people to understand the “strike zone” for each of the metrics above. 

 

What is the “Strike Zone”?
Strike Zone is that defined time when prospects are more likely to move to the next stage.

 

For instance, your sales ops person might tell you that, on average, prospects who book a demo with you get 11 touches, but you’re just averaging 8 per prospect.

Sales Ops predicts that by going deeper with more touches on a smaller prospect pool, you can actually reduce your activity to demo ratio to 35 instead of 40. 

They might share with you that when a demo is scheduled within the next 48 hours, it will actually show up at 75% rather than 65%. You might find out that after doing a demo, if you schedule a follow-up call within 72 hours, your close rate moves from 25% to 30%. 

Remember, sales is a compound game! 

Let’s look at our new funnel now that we have our strike zone data:

  • 1,240 activities
  • 35 demos scheduled
  • 26 demos performed
  • 8 wins
  • $80,000 in ARR

Look at the difference you’ve made by understanding what behavior impacts the conversion rates in your plan. Even if you can move conversion rates by 2–5% up and down the funnel, you win! 

When you combine this type of process-based thinking with strong coaching, the sky’s the limit. 

How to Get Better at Sales

To truly get better at sales, you must have a long-term outlook. Habits and skills sometimes take a few years, but often can take decades to formulate. 

If you’re not hitting your goals and you want to begin the process of getting better, the four steps above will absolutely put you on the right track to succeed. Building strong habits, listening, accepting rejection, and having a strong predictable sales process is just the beginning. 

Justin Welsh

Justin Welsh is an entrepreneur & advisor to high-growth SaaS companies. His previous work experience includes serving as the SVP of Sales for Los Angeles-based PatientPop, where he grew the business from $0 to $55M in recurring revenue in less than five years. During his tenure, PatientPop was named Entrepreneur's 16th most entrepreneurial company of 2018, one of Silicon Review’s 50 Fastest Growing Companies, and BuiltIn LA's #2 out of 100 best places to work. Before that, Justin was the 10th hire and spent five years in various revenue leadership roles at Zocdoc. You can learn more about Justin at www.theofficialjustin.com.