How to Improve Self-Esteem in Sales: 12 Techniques to Try

Sales is hard.

You know it. Your family knows it. And (if you’re lucky) your employer knows it too.

And despite the high potential earnings a successful sales career rakes in, the profession isn’t growing as much as other jobs.

For many, it all has to do with rejection. Rejection is, of course, a given in this industry. And some reps take it more personally than others.

But then there are the standouts.

You know the type—they get rejected just like everyone else, sure, but they’re always quick to bounce back. They’re confident and self-assured, but never cocky. And when they speak to prospects, they’ve got this natural magnetism. This ability to instantly ease skepticism and let buyers know, “Hey, you can trust me on this.”

What’s the secret? Self-esteem.

And with a bit of work, you can cultivate a healthier sense of self-worth by following just a few proven techniques.

In this guide, we’re covering how to improve self-esteem using The Increasing Self-Esteem Framework. Inside, we examine three core pillars to promoting self-confidence while looking at 12 proven techniques you can start using today. We’ll also take a closer look at the best benefits of upping your self-worth on the job.

Let’s dive in.

What Is Self Esteem?

Pride, confidence, self-assurance, dignity—there are many words to describe self-esteem. But what does it all mean?

Simply put, self-esteem is your general sense of self-worth. It’s how much you value your thoughts, emotions, and actions. And it’s influenced by beliefs about yourself as well as the beliefs you think other people hold about you.

Your self-esteem doesn’t just affect your you-focused feelings though. That opinion you hold about your own value permeates through and influences so much more in your life. Self-confidence, whether low or high, affects:

  • How you interact and connect with others.
  • Risks you’re willing to take.
  • Goals you’re driven to make.
  • Motivation and ambition.
  • Decision making.
  • Physical and mental health.
  • And much, much more.

Ultimately, your self-confidence affects nearly everything in your life because self-esteem is directly connected to how you move through the world.

Having poor self esteem and living your live via a series of negative beliefs can make the challenging and difficult situations that you'll find in a sales role much tougher than they need to be.

Self Esteem Stats

Low self-esteem and a lack of confidence can be devastating professionally. Here are just a few stats to prove it.

  • Nearly 4 out of 5 women (79%) and more than 3 out of 5 men (62%) experience a lack of confidence in the workplace. (ResumeLab)
  • Low self-esteem workers are 3X as likely to experience high stress on the job and professional burnout. (Do Low Self Esteem by Johnson et al.)
  • Individuals with high self-esteem from blue-collar families earn $7,000 more per year than their less confident peers. In white-collar classes, high self-esteem professionals earn a whopping $28,000 more than their low-confidence peers. (Self-Esteem & Earnings by Francesco Drago)
  • Nearly all employees think confidence is important for a successful job search (99%), believe they perform better on the job when confident (98%), and feel happier at work when they’re more confident (94%). (Indeed)

Why Is Self Esteem Important for Salespeople Specifically?

Now, self-esteem is integral for a healthy personal life and a successful professional one. That much is clear, and dare I say obvious.

But why is it so critical for salespeople in particular?

And why is knowing how to improve self-esteem a real game-changer for career-minded reps looking to grow?

Well, it turns out there are three reasons in particular:

  • It makes you rejection proof
  • Buyers want to spend time with winners
  • Your confidence rubs off on prospects
  • More positive relationships with customers and colleagues
  • Reduction in negative habits

A) Self-Confidence Makes You Rejection-Proof

In the world of sales, you’re bound to get rejected at some point. That’s just the nature of the business.

And in reality, your product isn’t going to be a fit for 9 out of 10 prospects you talk to.

But what defines an effective sales rep isn’t so much how many times they get rejected. Instead, it’s how they respond to that rejection.

Do they lose motivation because of a “no”? Do they lose faith in their proven processes? And do they see that negative response as a judgment on their own abilities and worth as a sales professional?


Do they let that rejection roll off their back? Do they continue to power through each day? And do they tell themselves, “Hey, it’s just business”?

A healthy amount of self-confidence makes it easier to recover from rejection and get back on the horse.

And given how sales and rejection go hand-in-hand, getting this benefit alone is worth a small fortune in this business.

“If you look at it from the point of where do you get the confidence and the motivation to go out there and to be successful, you have to address the individual's fear of being rejected and failing. And that is a constant. No matter the technology, no matter the age.” – Interview with Samuel D. Osborne, Educator & Author

B) Buyers Want to Spend Time With Winners

There’s no point in denying it—confidence closes deals.

And I don’t mean the overly confident reps. The ones that wear diamond-encrusted watchbands, are quick to name-drop and tell you all about their wins, and promise their product will change your entire life (hint: it won’t).

Instead, buyers are attracted to reps that know what they’re talking about, that are clearly and undeniably smart, savvy, and successful.

They want to know that when they listen to you, their business is bound to grow. And they want to be better off because of your relationship.

Do you know how you communicate that feeling? You guessed it—by demonstrating self-confidence.

C) Your Confidence Rubs Off on Prospects

Trust is obstacle #1 for sales reps.

And as you’ve probably already figured out, buyers are often inherently skeptical of any sales professional or pitch, no matter how good it is.

In fact, a study from HubSpot found that just 3% of people consider salespeople to be trustworthy, beating out only stockbrokers, politicians, care salespeople, and lobbyists.

But when you know how to improve your self-esteem and speak confidently about the product you’re selling, you build trust. You go from being a simple scammer, a snake oil salesman, to an expert your buyers can turn to for valuable information and services.

And the more your buyers trust what you have to say, the more likely they’ll be to close a deal with you. Simple as that.

The Increasing Self Esteem Framework

Now that we’ve covered why growing your self-esteem is so important (especially in sales), let’s dive into the meat of it all—how to be more confident.

There are tons of books, seminars, and courses on the topic. And if you get lucky, you might find one that works for you.

However, the truth of the matter is that growing your self-esteem is hard. For many of us, self-defeating behaviors are ingrained into every thought and emotion we have. They’ve probably even been that way since early childhood.

But when you put in the consistent and concerted effort, you can learn to be more self-confident on the job. You just need to know how to do it.

That’s why I created The Increasing Self-Esteem Framework, built specifically for sales reps. This 3-step framework (and 12 proven practices) is simple. Just:

  1. Increase Your Self Trust
  2. Increase Action Taking
  3. Increase Flexibility

1) Increase Your Self Trust

At the core of the framework is boosting your self-trust.

Self-Trust: Having the mindset that whatever comes your way, you will be able to handle it. Someone with a high degree of self-trust feels safe in relying on their own mental, emotional, and physical abilities to tackle life’s difficulties.

If you can’t trust yourself, others won’t trust you either. And when you lack self-trust, you often feel conflicted—your wants and needs pull you in one direction, and your self-doubt pulls you in the other. Until you can trust your abilities, you’re always going to feel unsure.

A lack of self-trust often doesn’t happen all at once. Instead, it’s a slow degradation caused by consistent self-denial. Maybe your truth was made wrong by family, friends, or society as a whole. Or maybe you’ve just gotten so used to going against what your heart told you because it was more convenient than to listen.

5 Self-Trust Boosting Practices

No matter where your lack of self-trust comes from, there are ways to fix it. And the five self-trust boosting practices below are a fantastic start.

As with anything to do with relationship building (regardless of whether that relationship is with us or with others), boosting trust should be seen as a war of attrition as opposed to a war of annihilation.

In other words, do as many of these practices as often as possible, and let them grow with time. There is no one-size-fits-all, immediately actionable silver bullet that will help you build a bone-deep sense of self-trust overnight.

Do your best to be compassionate and patient with yourself as you cultivate your self-trust. This process will take time. But trust me—it will be worth it.

1. Spend Time With Yourself

Just like any relationship would struggle to thrive if the people in it didn’t have any quality time together, so too must you spend quality time with yourself.

Make time to reconnect with yourself—your thoughts, your feelings, your desires—on a regular basis.

If your schedule is so tightly packed that you don’t have any moments of quiet and solitude, then your self-trust has likely suffered.

Do you go to bed with a racing mind? Thoughts shooting at you from every angle, begging for your attention? Then you might be overdue for some quality ‘me-time.’

The better acquainted you are with yourself, the more you’ll start to recognize yourself as an individual with true value.

2. Make a Self-Like List

While your life’s choices shouldn’t be led by external validation, we all crave validation of some kind. And one form of validation that we often underutilize our own validation.

That’s why making a list of things you like about yourself can be so powerful.

Take out a piece of paper (yes, it has to be something you can physically write on) and get started. Write out at least fifty things. Anything goes—from past experiences and accomplishments to personal qualities, aspects of your relationships, and unique abilities.

It’s challenging to believe that others like us for who we are if we don’t first like ourselves for who we are. So grab the bull by the horns and give yourself the validation that you may, at times, be seeking from others.

3. Take More Risks

One of the best ways we can build self-trust is by regularly challenging ourselves.

Regardless of whether or not we succeed in accomplishing the task, just the mere act of giving ourselves the challenge grows our self-esteem and self-trust. Doing so sends the message that we are someone who is worthy enough to be challenged with difficult things in the first place.

Ask out that attractive person you have a crush on. Initiate that difficult conversation with someone who you have been meaning to clear the air with. Go after that job you want. Push yourself in your physical exercise goals. Move forward in your life and claim what you want.

All of these types of actions build self-trust. You merely have to be willing to accept the challenge and do your best in the face of it.

4. Reward Yourself

When you deprive yourself of rewards, your brain gets hard-wired to not give you the motivation you need to accomplish your goals.

That’s why it’s so important to regularly reward yourself for your accomplishments.

Whether you’re rewarding yourself for one of your goals being achieved or you’re just gifting yourself a reward because you’re a badass who deserves nice things every once in a while, rewarding yourself is a necessary habit to get into.

5. Mark Down Your Achievements

So often our wins (both big and small) get lost in the hustle and bustle of daily life. And so often we forget about everything we’ve accomplished over the past week, month, year, decade.

The more we forget about what we’ve achieved, the less we remember our abilities in the face of adversity. And the less we trust ourselves to overcome new challenges.

That’s why since 2013, I’ve kept a running list of my monthly wins. From professional goals like becoming a best-selling author on Amazon to personal ones like learning how to do a backflip on flat ground, this ever-evolving list is a powerful self-trust booster.

If I’m ever doubting my abilities, I just thumb through these accomplishments and my self-trust is restored.

That’s why I recommend keeping an achievement list for every single one of my students. And it’s why you should start building yours today.

“One of my favorite things that I recommend to my clients is to create a journal. Call it your wins journal. So every time you have a win, small, medium, or large, write it down. Like, “Woohoo, celebrate! Today I talked with John DOE at Google, and he's always super excited about bringing our stuff into his company.” Write that down. So when you do get caught in these anxious moments, go back to your wins journal, like, “Oh yeah, that happened. That was real. Reminding yourself that you are good at what you do. You are enough, you've got this.” – Interview with Michele Molitor, Coach, Hypnotherapist, & Imposter Syndrome Expert

2) Increase Action Taking

One of the core influencers of a healthy self-esteem is your ability to take action.

When you take action, you’re taking control. You’re pushing closer to achieving your goals. You’re influencing the world around you. And you’re building up more and more confidence with each new win.

But taking action doesn’t come naturally. After all, we as humans tend to favor the path of least resistance. What’s going to be easiest for me?

As a result, this skill takes a bit of work to develop.

But once you do develop it, you’ll feel more confident in your abilities. And you’ll know that with some elbow grease and consistent pushing, you can build the life you want.

So, let’s take a look at a few ways to turn yourself into an action-taker.

Fear Is Normal (So Use It)

Most people think that to be brave is to not feel fear. That bravery is simply not feeling afraid, to be fearless.

This is not true.

In reality, being brave is to feel fear…and act anyway. It is to act in spite of fear.

Taking action when there’s no fear doesn’t require any bravery. In circumstances like these, it isn’t hard to take action. Instead, it’s rather easy. After all, what’s holding you back if not fear?

So, if you’re wondering how to take more action in life, the first thing you need to understand is that it’s okay to be afraid.

When you start to feel your heart flutter, your mind fogs up, and your palms begin to sweat, don’t panic. Instead, recognize this as an opportunity to become braver.

And remember that fear is normal. It just depends on what you do with that fear—act on it or succumb to it.

Exercise Your Daily Courage

Courage is like a muscle. If you stop using and training it, it atrophies. Just like a bicep, quad, or calf.

Now, this doesn’t happen overnight, mind you.

But as time passes, it becomes more and more obvious you’ve lost your courage. And by the time you’ve realized what’s happening, you now find yourself succumbing to self-doubt in situations you would have breezed through years ago.

To maintain (and increase) your courage muscle mass, you need to use it. You need to train it every week. And if you make it a habit of avoiding stressful situations, you’re going to become less and less courageous.

Your courage muscle is going to atrophy.

Your comfort zone is going to shrink.

And in the end, you’ll be unable to take action in even the most minor stressful situations.

On the other hand, if you keep training your courage muscle on a daily basis, you’re not only going to maintain it. You’re also going to reinforce it (especially if you make sure to increase the difficulty of your training by increasing the level of required bravery to take action).

Focus on the Consequences of Not Taking Action

Like a lot of people, you probably focus way too much on the negative consequences of your taking action. When it’s time to act, you start to invent all sorts of stories in your head on the premise that you’re going to fail.

Not only does this lead you to focus on destructive thoughts which are going to make you feel less able to succeed. But it also keeps you from taking action by making you afraid—more afraid than you were at the beginning.

You’re so afraid of the consequences that you might suffer by taking action that you don’t make a move at all. And that means you miss out on the benefits of acting.

Now, if you want to focus on negative consequences, there’s a better way…

Instead, start focusing on the negative consequences of NOT taking action rather than on the negative consequences of taking action:

  • The regrets of having done nothing
  • The shame
  • The disappointment in yourself and your abilities

By focusing on what you’re going to feel if you DON’T take action, you’re going to feel a strong and compelling urge to make your move.

Build Your Self-Image

We tend to live up to the identities we create for ourselves.

The self-proclaimed strategists ponder their moves before striking. The person who introduces themselves as an avid swimmer sticks to their daily laps. And the entrepreneur who can’t talk enough about their businesses will risk it all to see them succeed.

We become what we see ourselves as.

And when you see yourself as an action taker, you tend to start instinctively responding to situations as one.

This will become natural the more you act in response to challenges.

But you can get started by shifting your own perception of yourself from a problem avoider to an action taker. Start seeing challenges as opportunities. And if you find yourself thinking about ways to get out of difficult situations, tell yourself, “That’s not what I do now. I take action!”

The more you do it, the easier it gets.

“Success isn't about working harder, because people go, ‘I’ve got to work harder.’ It's not about that. It's about doing the consistent action on a daily basis.” – Interview with Marx Acosta-Rubio, Business & Lifestyle Strategist

3) Increase Flexibility

“If you want to make God laugh, tell him about your plans.” – Woody Allen

Life is unpredictable. And more often than not, a plan (no matter how perfect) will fall apart when the time comes to execute. Everyone makes mistakes. And your environment is constantly changing, especially in sales.

But when you can increase your ability to be flexible to the inevitable issues that will crop up in life, you reduce your chances of being affected by them. And in fact, you can even benefit from those issues if you’re particularly clever with your pivoting.

Whether it’s starting a new job, taking a new class, or getting married, being cognitively flexible helps us to grow and get along better with others.

The Biological Basis of Inflexibility

An area of the brain called the anterior cingulate gyrus (ACG) tends to be overactive in people who have difficulty with cognitive flexibility. Located in the front part of the brain, the ACG is involved with shifting attention.

When the ACG works well, it allows us to focus on something, let go, and then shift to focus on something else. However, when it’s overactive, there is a tendency for people to get stuck.

This is what happens when we become cognitively inflexible—we start down one path mentally and then refuse to change direction.

The good news is that there are some simple strategies you can incorporate into your life to help you become more flexible and adjust more easily to change.

3 Techniques for Becoming More Cognitively Flexible

So, how can you improve self-esteem by boosting cognitive flexibility?

Below are three techniques in particular that’ll help you get better at going with the flow and adapting to tricky situations.

1. Practice “Thought Stopping”

An important part of gaining control over your repetitive thoughts is to become mindful of them when they occur—and then practice the simple technique of thought stopping.

To pull this off, try envisioning a red stop sign when you identify any destructive thoughts. And imagine saying to yourself: STOP!

The more you practice this, the more you’ll start feeling control over these thoughts.

You can also use a more physical approach by putting a rubber band on your wrist and snapping it when you catch yourself in a loop of negative thinking.

No matter which technique works best for you, the important thing is stopping those thoughts dead in their tracks. Before they can do any more damage.

“The more mentally fit you are, the faster you are able to actually go from what's a very natural human response to challenge and stress, and be able to shift out of it and get to a positive, more clear, calm, laser-focused, discerning perspective on everything.” – Interview with Adam McGraw, CRO at Positive Intelligence Inc.

2. Document Your Options & Solutions

One of the best methods I’ve found for dealing with negative thoughts and boosting flexibility is writing things down.

When thoughts are floating around in our heads, they’re abstract. They’re like shapeless, undefined blobs.

But when we put them down on paper, they become concrete. And that helps us look at them more rationally, decide if they’re valid, and choose whether or not to act on them.

Try writing down:

  1. The thought that’s stuck in your head.
  2. What you can do to help offset the thought.
  3. Things you have no control over with regard to the thought.

When everything’s all down on paper, you’ll likely be surprised at how different things look compared to when it was just in your head.

3. Think Before a Knee-Jerk “No”

Some people have the tendency to say “no” automatically—even before thinking about what was asked of them. This can be especially problematic in relationships. It is limiting and unnecessary to always dismiss ideas or deny your partner his or her requests.

It’s a nasty habit that, when gone unchecked, can easily leech over to your professional life and sabotage working relationships (and career prospects).

To help with this, before responding to a question, take a deep breath. Hold it for three seconds and then take five seconds to exhale. And while you do so, actually consider what the best way to respond would be.

Sometimes a quick break from automatic responses is enough to drive serious change and promote more cognitive flexibility in life.

Wrapping Up

In my experience, there are three things that determine your success in sales. First, having a product or service you truly believe in. Second, focusing on providing value, not just making a sale. And third, having the self-esteem to sell confidently, competently, and consistently.

With a healthy self-confidence, you’ll be able to push through rejection, attract more buyers, and build trust quicker than ever.

And if you know how to improve self-esteem using The Increasing Self-Esteem Framework, becoming a confident sales rep is a snap.

Just work on:

  1. Increasing Your Self Trust
  2. Increasing Action Taking
  3. Increasing Flexibility

Changing your views on yourself and the world around you doesn’t happen overnight. But if you put in the work to use the techniques in this framework as much as you can, you’ll find yourself becoming more confident every day.

And a year from now, you’ll look back with amazement at how far you’ve come.

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