Good salespeople have long dealt with stereotypes and generalizations that aren’t exactly flattering (or fair, really). We’ve all seen it play out: the irritated or downright rude email responses, the screened calls, the hang ups. It takes some pretty thick skin to push through the rejection and keep grinding.

But the fact of the matter is that sometimes, the skills it takes to do the job well can sometimes be perceived by people on the other end of the line as...well, pushy.

One of those skills is assertiveness. And yes, there can be a fine line between being assertive and being obnoxious. (Or worse: aggressive.) The key is being assertive for the right reasons — not getting someone on the phone or closing a deal, but instead, providing value to your buyer.

We’d argue that every single sales person needs some go-to assertive sales techniques in their toolkit. But first: let’s clear up any misconceptions about the definition of assertive.

What does assertive mean?

If we’re going by good old Miriam Webster’s definition, an assertive person is characterized by bold or confident statements and behavior. Which...okay. That’s helpful, but what are the kinds of actions that are associated with assertiveness?

In general, an assertive person may be more likely to speak up when they have an opinion or perspective. They may (relentlessly) seek out answers when they have questions. They typically aren’t afraid to express their thoughts and feelings, or to connect with and lead others. 

Why is assertiveness important in sales?

All of those things can be great attributes for a salesperson, if your head and heart are in the right place. 

Assertive sellers are direct and proactive. They are curious, wanting to learn more about their buyer — who they are, what they need, what they want to achieve as a professional and also simply as a person. They have a desire to deliver value to their buyer, and they come with a strong, informed perspective that they aren’t shy about sharing. 

Respectfully, of course.

Which leads us to an important point: Assertiveness starts to become aggression when it’s not combined with empathy, or active listening, or simply having your buyer’s best interests at heart.

4 assertive sales techniques you need to add to your repertoire

Being assertive is innate to some people, but it’s a skill that can be learned. A great way to become more assertive in sales is to start putting some tried-and-true assertive sales techniques into practice. Here are 4 of our favorites.

1. Bring a perspective

As we mentioned above, people with assertive personalities typically have strong perspectives. It doesn’t mean that they railroad others’ thoughts or opinions; it just means that they know where they stand and they’re not shy about expressing it.

One way to do that in sales is to intimately know your product or service. Not just how it works and all its amazing features, but the benefits and advantages and how they solve for your customers’ needs.

Then, take it a step further: believe in it. Selling is hard; selling something that you yourself are not sold on is even harder. Assertive sales people make it clear that they feel strongly about what they’re selling. 

Go beyond the product and think big picture: tap into your passion for your company’s mission, vision and values and leverage that. Sure, it might sound a little “fluffy,” but when you come to every sales conversation with conviction about how you can make someone’s work or life better, that’s a pretty powerful (and discernible) thing.

2. Reframe your questions 

Contrary to popular belief, “assertive” doesn’t necessarily mean loudest or most outspoken. Assertive salespeople also tend to be curious salespeople: they ask the good questions and they listen well. 

Many sales folks know which questions to ask; the problem comes with how they frame it. If you’re using aggressive question techniques, you are likely putting people on the spot or even offending them. Assertive question techniques, however, tend to be open-ended and “reflective” — i.e., they make your buyer think hard, reconsider their own perspectives and ultimately come to their own conclusions. For example:

  • Aggressive question: Why did you choose with your current vendor if they’re clearly missing the key feature you need?
  • Assertive question: Can you explain your team’s decision-making process when you engaged with your current vendor?

While aggressive questions lead or corner the witness, assertive questions seek to understand.

3. Be direct

Stop beating around the bush. Building rapport with your buyer is important, sure. But you’re both busy people, and at the end of the day, you’re not trying to make a friend — you’re trying to provide value and solve a problem.

Plus, buyers these days are savvier than ever before. They’ve done their research and they’re well informed. Be honest and upfront about why you’re calling them, then don’t be afraid to ask for what you need — as long as you’re clear and specific.

For example, instead of:

  • I was wondering if I could tell you a little bit about what we do here?


  • Do you have five minutes for me to share how we can increase your leads by 20%? 

4. Practice, practice, practice

Again, assertiveness isn’t something that you have or don’t have; it’s a muscle that you can build. Like so many other things in sales (and life), practice makes perfect.

Role playing with peers or managers is a great way to practice becoming more assertive. In addition to putting these other three techniques into play, you can also work on things like your delivery and tone of voice. Be sure to ask for specific, actionable feedback.

Recording your calls and playing them back is a great self-learning opportunity. You can also use them in coaching sessions and talk through what worked (and what didn’t) as you hone your assertiveness skills.

Learn how sales orgs across the globe are using Ambition’s sales coaching software to drive skill development and improve rep performance. Get a demo today!

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