Assertiveness Training Framework: Cultivating Sales Confidence

Few things are as frustrating as having a gamechanger idea, only to be overlooked and ignored when you try to bring it up.

It’s soul-crushing.

It’s maddeningly infuriating.

And more likely than not, it’s all your fault.

If you want to be taken seriously, to command the respect of those around you, and to be even remotely successful in sales, you need to be assertive. But developing an assertive mindset isn’t as easy as a snap of the fingers. In fact, doing so takes work—and quite a bit of it.

This guide shows B2B sales reps like you how to cultivate this mindset using my Assertiveness Training Framework. And with it, you can harness the massive benefits (both personal and professional) to becoming more assertive.

What Is Assertiveness Training?

So, what is assertiveness training?

Assertiveness training is essentially any activity or exercise that helps you become more self-confident, a clearer communicator, and a champion for your own rights.

This interpersonal skill will help instill assertive behavior which is an incredibly powerful trait of selling high performers.

That being said, assertiveness is not about being overly aggressive (think sales reps that are too pushy, arrogant, and abrasive).

Instead, it’s the mindset that what you have to say matters. And you have the right to take care of yourself, achieve your goals, and be respected for the expert you are.

5 Benefits of Assertive Communication in Sales

There are some very real benefits to cultivating an assertive mindset with the help of assertiveness training.

Benefits like:

  • Closing More Deals (Duh) – You don’t get the sale if you don’t ask for the sale. When you lack assertiveness, you lack the confidence you need to push through the awkward yet entirely necessary stages of closing a sale. But as you become more assertive, you’ll find yourself closing more often.
  • Having More Authority – The more authoritative you appear, the more likely buyers will be to listen, value your opinion, and look to you as a trusted expert. Consequently, you’ll find yourself having more influence over not just whether they buy but also what they buy.
  • Voicing Your Good Ideas – So many sales reps keep their mouths shut, even though a good-as-gold idea popped into their head. Here, a lack of confidence is again the culprit. A more assertive rep won’t feel out of place offering up good ideas when they have them.
  • Better Communication – Tiptoeing around an issue may seem like a good way to soften a blow and keep on your buyer’s good side. But in B2B sales especially, being clear and to the point is a better way to communicate. Your buyers will appreciate you saying outright what you think.
  • Higher Self-Esteem – Last but not least, a more assertive demeanor will also help boost your self-esteem. That, in turn, leads to greater job satisfaction, a higher earning potential, and ultimately a happier, healthier home life.
  • Avoiding aggressive behavior – Self confidence and assertive behaviors close deals. Getting angry at your prospects at best stalls the, at worst ruins relationships.

The Assertiveness Training Framework

Clearly, there are some very real, tangible benefits that come from being more assertive in sales. Some of those benefits can boost your commissions. While others help you reach your personal potential.

No matter which perks you hope to gain the most, the fact is you need to know how to improve assertiveness before you stand to benefit from it.

And that’s where The Assertiveness Training Framework comes in.

This framework breaks down into six principles of becoming more assertive:

  1. No Excuses For Your Behavior
  2. Help or Not? It’s Your Choice
  3. Yes, You CAN Change Your Mind
  4. Go Ahead, Make Mistakes
  5. “I Don’t Know”
  6. “I Don’t Care”

And when you learn how to implement each, you’ll be on your way to reaping all the advantages (professional and mental) that greater assertiveness provides.

1. No Excuses For Your Behavior

You have the right to offer no reasons or excuses for your behavior. 

During childhood, we were expected to explain why we took certain actions to our parents, teachers, and other authority figures.

And at the time, it made sense. Doing so allowed those authority figures to explain why our choices were good or bad. They were learning experiences.

But as adults, we no longer have to explain that why to others. And we do not have to justify our actions if we don’t want to.

You do not need to respond to someone's questions. It is perfectly okay to say you do not like something and then move on from that comment without explaining anything.

You shouldn't need to attend an assertiveness training course for this point. If you have decent communication skills and keep your mouth shut, you won't feel the need to flood your conversations with excuses.

If somebody asks to borrow your car and you don’t want to give it to them, you shouldn’t feel the need to make up some kind of story, white lie, or exaggerated truth. Instead, it’s your assertive right to say, “No” and leave it at that.

How To Be More Assertive Pro Tip: Learn to take responsibility. No excuses doesn’t mean blameless. If anything, it means you’re even more responsible for your actions. You need to decide if your actions were right or wrong, correct or incorrect.

If you’re in the wrong, take ownership and apologize. But if you’re being pressed to say sorry for something you were in the right for, you do not need to offer up any excuses.

Assertiveness Training Exercise: Start Spotting Excuses

Learn to identify excuses before they come out of your mouth. Oftentimes, excuses are automatic. In times of adversity, our brain instinctively passes the blame onto something else to protect us.

But if you rely on those excuses, you take control out of your own hands. Plus, you hurt the buyer rapport you’ve worked so hard to build.

So next time you run into an issue with a prospect, try to identify the excuse you’re about to default to and stop it from leaving your lips. Then you can determine if you even need to justify your behavior at all.

“The easiest way to become an action taker is the first time that excuse pops up, show it who's boss.” – Interview with Ryan Stewman, World Leading Sales Expert

2. Help or Not? It’s Your Choice

You have the right to decide if you will (or won’t) find solutions to other people’s problems. 

This one is probably the toughest assertiveness training step to master. But it’s also perhaps the most important.

You need to learn to say “No” to solving other people’s problems. This is a key assertive behaviour once you start saying no in a calm and positive way.

You are ultimately responsible for your own psychological well-being, happiness, and success in life. And as much as we might want to do good things for one another, we are not responsible for other people and their problems.

But when we get too sucked into helping others (especially when it’s to our own detriment), we’re allowing ourselves to be manipulated. Enlisting our help might be a quick fix. But in the end, it’s often the other person that needs to go through the work, sweat, and pain to rearrange their own life.

For example, imagine your sales manager asking you to work late on a Sunday because they procrastinated. Maybe some of you won’t have to work too hard to imagine this scenario. They may even convince you that you should help because you’re a part of the team.

Don’t be fooled here—you have the assertive right to say “No” to this. In the end, it’s their problem, not yours. And they should be the ones to fix it.

How To Be More Assertive Pro Tip: Understand the power of “Me” thinking. We’ll talk about this more in-depth later. But don’t forget that ultimately, we’re all responsible for ourselves.

And if a team member or even a buyer presents a problem and asks you to solve it, think about whether you want to help, whether you should help, and if helping will somehow hurt your well-being.

Only then should you decide whether to offer aid.

Assertiveness Training Exercise: Get Comfortable With No

This exercise is simple—start saying “No” more.

That’s it.

If you’re invited to an after-work party that you just don’t want to go to, say “No” instead of reluctantly going.

If you’re asked to stay late when you’ve got plans that’ve been in the works for months, say “No” rather than caving.

And don’t feel obligated to give excuses either! Remember the previous step.

The more you do it, the easier it becomes.

“One of the big things in sales is you can't control how people are going to react to you. You can only control what you put out there.” – Interview with Nina Purewal, Best Selling Author & Founder of Pure Minds

3. Yes, You CAN Change Your Mind

You have the right to change your mind.

For some reason, one of the worst insults you can hurl at a politician is that they’re a “waffler.” They say one thing in a press conference. But then another later in their career.

They’ve changed their mind. And doing so is supposed to be interpreted as being spineless, incoherent, or unprincipled.

Now, I’m no fan of politicians. But I’ve never understood why this is such a bad thing.

We don’t have access to all the evidence, all of the time. And when new evidence comes to light, it’s natural—even more, it’s beneficial—to change your mind in light of that new evidence.

This is especially important in a fast-paced business environment like sales. Variables change all the time. And what was a given about a deal or a lead will often flip and turn the knowns on their head.

If you are rigid in your responses to these changes, you can’t react as well as you should. And that can lead to blown contracts, angry prospects, and poor performance overall.

As the old saying goes, “The green reed which bends in the wind is stronger than the mighty oak which breaks in a storm.”

How To Be More Assertive Pro Tip: Follow the “strong opinions, loosely held” mindset. This mindset was (and is) used by business behemoths like Steve Jobs and Mark Zuckerberg. Essentially, it means to be passionate about your beliefs but also open to re-examining them in light of new evidence.

Courage and humility are key here. And in the end, the outcome is wisdom.

Assertiveness Training Exercise: Adopt a Growth Mindset

There are two mindset types: fixed mindsets and growth mindsets.

A fixed mindset characterizes someone who thinks our intelligence and talents are innate. Some people are born smart. Some are born brave. And some are born the opposite. There’s not much they can do to change that.

A growth mindset, on the other hand, means that you believe your intelligence and your abilities can be developed. We learn from our misjudgments rather than being doomed to repeat them. And we have the power to learn to be better.

Next time you’re faced with a challenge, don’t say, “I can’t.” Say, “I can’t yet.” Learn from your failures. And know that you can always become better.

“Do you have a growth mindset? It doesn't mean being positive about everything, it means saying you're open to learning.” – Interview with Beth Benatti Kennedy, Business Leadership Coach & Author

4. Go Ahead, Make Mistakes

You have the right to make mistakes.

“Let he who is without sin cast the first stone.”

No one is perfect. And no matter how smart, skilled, and charismatic you may be, you’re going to make mistakes.

It’s important to remember, though, that everyone else is in the same boat. We all make mistakes. And since everyone does, you shouldn’t have to feel like you need to hide them.

It is your assertive right to make those mistakes and not to tear yourself down (or let someone else tear you down) because of them.

You are not uniquely terrible or especially flawed if you screw up.

And in fact, making mistakes is often the only way you learn. So if you aren’t making mistakes, you aren’t trying hard enough to grow.

How To Be More Assertive Pro Tip: Take immediate action to correct your mistakes. There’s value in recognizing you aren’t perfect. But using that recognition as a crutch to not fix a situation or improve is a problem. 

So if you do make a mistake, be sure you’re putting in the hard work to rectify it. 

Assertiveness Training Exercise: Own Up To Your Mistakes

If there’s one thing that pisses everyone off, it’s when someone passes the blame onto something else.

Unavoidable tech problems, an accident on the road, a sick loved one—those are all reasonable excuses. But when the excuse is because of a mistake (a misquoted price, an incorrect product spec, an overlooked proposal detail), that’s when you have to own up.

The instant you feel an excuse bubbling up in the face of your own mistake, resist the temptation to pass the blame. Your buyer will respect you more for it. And at the same time, you’ll get a nice boost to your own self-respect too.

“I think people, in a truly visceral way, [byuyers] want to see themselves in everybody that they talk to. And so I think if you're a super-polished salesperson in suit and tie, you never miss a beat and you're crossing your I's and dotting your T's and you never screw anything up, almost nobody sees themselves in you, right? Everybody's screwed something up. And owning that is really important.” Interview with Peter Von Burchard, VP of Sales & Customer Success at Wistia

5. “I Don’t Know”

You have the right to say, “I do not know.”

This one is huge for salespeople. Especially salespeople that work with a particularly technical product or service.

Despite what many in the public think, sales isn’t about bullshitting. It’s not about trickery or cons. Instead, it’s about problem-solving. And if you’re not providing the right information, your solution won’t fix the issue your buyer’s trying to solve, leading to low satisfaction, damaged trust, and zero loyalty (this is bad stuff).

Rather than rattling off a white lie, it’s actually better to say you don’t know the answer to a question.

If it’s a specific product detail, don’t fudge the numbers. Instead, say, “I don’t know” and then assure them you’ll find out the answer.

If it’s an unrelated question, don’t be afraid to say, “I don’t know” and then shutting up.

But just because a prospect asked a question doesn’t mean you need to have the answer, especially if the question was downright stupid to begin with.

How To Be More Assertive Pro Tip: Cut the bullshit excuses. In the face of the tension created by questioning buyers, we often feel like we have to come up with an answer. And if we don’t have that answer, we may offer up excuses. 


When you throw out a load of excuses, it’s obvious you’re shifting the blame away from yourself. As a result, you come off as disingenuous and someone not to be trusted. And that can hurt your deal’s chances of success. 

Instead, be forthright. And if it’s a credible question, simply say, “I don’t know but I’ll find out for you.” Easy. 

Assertiveness Training Exercise: Say It More

Easy exercise here—get comfortable with saying “I don’t know” more often. Cut the excuses. Be direct. And don’t feel nervous about not having an answer.

Just like saying “No,” this one gets easier the more you do it.

So get to practicing.

“If you're doing the right thing for long enough, if you help enough people for long enough, people will stick up for you. If you are full of BS and you're spinning these white lies that might seem harmless in the moment, you've got nothing to fall back on.” – Will Barron in Interview with Daniel Disney, Author, Speaker, & owner of The Daily Sales 

6. “I Don’t Care”

You have the right to say, “I don’t care.”

Finally, your needs, goals, and interests are your own. And just because someone else is worried about an issue doesn’t mean you have to be too.

You tend to find this in the workplace a lot. Random people will tell you how you can become more efficient, or you can become more of a team player, for example. But when it comes down to it, your sales target is based on your actions and work alone.

You should not be forced to care about the stresses, accomplishments, or methodologies of others.

If you’re missing out on some real benefits from collaboration, then that’s on you. But if it’s all about feigning interest for the sake of “harmony,” you shouldn’t feel obligated to care.

How To Be More Assertive Pro Tip: Understand that you are not your team. You are told from a young age that you should “play nice.” That you should want to work in a team. That you should want to help other people. That “a rising tide raises all boats.” And there might be a slight grain of truth in this over the long term.

However, in the moment, you have the assertive right to say, “I don’t care.” You have the right to take responsibility for your own actions. And you have the right to let other people—even team members—deal with their own issues while you deal with yours.

Assertiveness Training Exercise: Set Your OWN Goals

Piggybacking off the pro tip, you should set your OWN goals rather than basing your potential off the goals others set for you.

For instance, team goals might be helpful for reporting performance to the C-suite. And the goals your manager sets for you are probably based on those larger goals.

But the best goals, the most informed goals, and the most rewarding goals are the ones you set for yourself.

This isn’t to say you should outright ignore the other goals, of course. But setting your own goals will help keep your cares and the cares of others more separated.

“Goal setting is also extremely personal. Some people might set a goal to be debt-free and they feel great about that. Other people set goals to accumulate assets, to buy cars. Some people want X number of dollars in the bank. Everybody's blueprint's different. Everybody's life is different. It's supposed to be. So that's another thing. We can’t get into trying to judge ourselves by how somebody else has decided to live their life.” Interview with Duane Marino, Sales Strategist & Author

Wrapping Up

To be successful in sales, you’ve got to be assertive—there’s no doubt about it.

Only an assertive rep will:

  • Actually ask for the sale.
  • Have the confidence to steer a prospect towards the better product.
  • Be able to achieve the professional and personal accomplishments they deserve.

When you’re assertive, you achieve more. You earn more. You live more.

And when you follow the six principles of The Assertiveness Training Framework, you can gain the confidence and self-respect you need to be more assertive, both in your personal and professional life.

  1. No Excuses For Your Behavior
  2. Help or Not? It’s Your Choice
  3. Yes, You CAN Change Your Mind
  4. Go Ahead, Make Mistakes
  5. “I Don’t Know”
  6. “I Don’t Care”

Now it’s time for you to start doing the work to be more assertive. Just follow the steps, implement the pro tips, and use the exercises as much as you can.

And before you know it, you’ll have the confidence and clear communication skills you need to take your sales game to the next level.

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