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Three Ways Lack of Assertiveness Hurts Your Sales Results

6 November 2026 by Colleen Stanley

The Corporate Executive Board, now part of Gartner, conducted research involving more than 6,000 salespeople. One of the top five profiles identified was the Challenger rep, salespeople who were assertive in controlling the sales conversation.

When I read those results, I thought, “Finally! Assertiveness, an emotional intelligence skill, is being recognized as a critical selling skill.”

Lack of assertiveness shows up in several areas of the sales process, however, many sales managers don’t recognize it as the real problem. They continue to teach and reteach selling skills when the focus should be invested on developing the salesperson’s assertiveness skills.

Assertiveness is the ability to state what you need nicely, without offending others.

Assertive salespeople win more business because they are comfortable setting expectations, asking difficult questions and qualifying opportunities.

Here’s three examples of how low assertiveness impacts sales results.

#1. No clear next step. Sales managers preach the importance of getting a clear next step on the calendar. Simple enough until the prospect says something like, “Connect with me in a couple of weeks.”

The non-assertive salesperson defaults to passive selling behaviors and goes along to get along for fear of looking pushy. “Okay, I’ll reach out in a few weeks.”  Then they end up in chase mode, looking like a stalker.

The assertive salesperson takes a different sales approach stating what they need nicely. And what they need is commitment from the prospect for the next meeting. “Happy to connect in a couple of weeks, however, let’s get a date on the calendar. Otherwise, we are going to end up in email tag or voicemail hell.”

It’s an easy qualification step because committed prospects will agree to setting a date on the calendar.

#2. Practice proposals. A salesperson meets with the prospect. It’s a pleasant meeting—but there really isn’t a burning goal to achieve or a problem to solve.

However, the prospect says, “This sounds interesting…could you put something together?” The non-assertive salesperson defaults to passive selling behavior. “Sure…happy to do so.” When they meet to review the proposal, the salesperson hears objections such as, “This is more than we want to spend. Not sure if the time is right.” Chalk up lack of assertiveness to another practice proposal and another inaccurate sales pipeline.

The assertive salesperson will nicely call out the sales elephant in the room. “Mr/Ms prospect, I appreciate that you’d like me to write up recommendations. However, I’m not sure I’ve really heard enough reasons for you to make a change or invest. What am I missing?”  

One of two scenarios will occur. The prospect starts selling and convincing the salesperson on why they need to make a change OR the prospect admits, “Yes, you’re right. The timing isn’t good. We’ve got bigger priorities.”

Assertive reps close more business because they only work on qualified opportunities.

#3. Budget. You’ve taught your team to uncover the investment necessary for your services. (Can you imagine a realtor showing you houses without knowing your budget?)

Logically the salesperson knows this is a qualifying step, however, when the prospect says, “Just put something together…we don’t have a budget” the non-assertive salesperson goes along.

They put together a proposal only to hear, “This is way more than we can invest.” Another practice proposal on the sales books.

The assertive salesperson is comfortable asking further questions. “Not unusual, most people don’t have a budget, however, companies with similar challenges and goals generally invest between X and Y. Is that inside or outside of your range?

I had to learn this lesson when I was struggling to uncover budgets, I gave a mentor the excuse that people just didn’t know how to invest in sales training. He paused, looked at me, and asked a great question. “Well, if they don’t have a budget, how can they tell you it’s too high.”

Gulp. My lack of assertiveness was the culprit.

So how do you improve lack of assertiveness?

Sales leaders, lack of assertiveness often comes from self-limiting belief systems. “I don’t want to look pushy. I don’t want to rock the boat.”  This type of self-talk is linked to the fear of losing the sale.

Here’s the reality: You can’t fix a self-limiting belief by teaching another selling skill.

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