How to Be a More Assertive Salesperson

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Good Morning! It's National Drink Wine Day - as if sales reps needed another excuse to pour one up after a full day of cold calls. At least today we can officially call it ‘celebrating a national holiday’ instead of ‘Tuesday’. Cheer’s to the holiday! Now let’s get into it. 👇️ 

• Why you should be more assertive 🤝 

• Your personal AI executive assistant 🤖 

• Ask a ‘curiosity question’ ✍️ 

• 6 unconventional negotiation tactics 👀 

• Sales jobs & a meme 😂

Why You Should Be More Assertive in Sales

You know those hardcore sales influencers that go viral for saying aggressive things like ‘you need a six pack to be on my sales team’?

As I’m sure you know - those outrageous sales tactics don’t actually work in B2B sales. 

I mean… imagine being on a sales call with a CEO and saying something like: “Are you going to let this $100K purchase price stand in the way of you and your dream future? Didn’t think so….sign here.”

While these aggressive sales tactics don’t work, being assertive in sales does.

Being an assertive sales rep is effective for getting deals closed faster and weeding out the unqualified tire kickers.

So today, we're breaking down how you can start being more assertive in your sales, and close more deals this year. 👇️ 

Assertive vs Aggressive

Aggressive reps try to control the conversation: This is what you need and here's why you need to buy now.

Assertive reps guide the conversation: Based on what you've shared, here's what I think would work best. What are your thoughts?

One tries to force a decision. The other helps shape thinking.

Get Comfortable With Uncomfortable Responses

Here's what most reps miss: Being assertive starts with being honest - even when it's uncomfortable.

It's okay to say:

• No, we can't do that - without an explanation

• I honestly don't know, but I will find out - instead of making something up

• We might not be the best fit - rather than forcing a bad deal

• I've changed my mind based on new info - instead of sticking to an outdated idea

When you become comfortable with saying things that aren’t always popular or feel natural, you provide truly honest answers and guidance to your prospects.

Four Ways to Start Being Assertive

1. Own the Risk Conversation

Most reps try to hide potential challenges or roadblocks.

Assertive reps bring them up first:

Before we go further, you should know that implementation typically takes 30 days. Some companies want it faster, but rushing usually causes problems. What timeline were you thinking?

The sooner you can bring up or uncover the potential downsides or ‘risks’ that come along with what you’re selling, the better you can control the sales process.

2. Ask Better Questions

Instead of surface-level or Yes/No questions, go deeper and open ended:

Weak: Do you have budget for this project?
Assertive: What needs to happen for this project to get funded?

Weak: Would you be the decision maker for this project?
Assertive: Walk me through how purchasing decisions like this typically get made?

3. Speak Human, Not Jargon

Technical language doesn't make you sound smarter - it makes you harder to trust.

Instead of: Our solution leverages cutting-edge AI algorithms to optimize your workflow efficiency metrics.
Try: We help your team get more done by automating the boring stuff.

Assertive reps don’t need to hide behind corporate fluff. Be direct with the language you use.

4. Build Trust Through Transparency

Being assertive means being upfront about your intentions:

I'm sharing this pricing now so you can decide if it's worth continuing our conversation. Does this align with what you were thinking?

This doesn’t mean you need to tell them you’re trying to sell them the entire time. But you can be transparent when you’re trying to help them in their buying process.

Remember: Assertiveness isn't about being pushy. It's about being confident enough to be honest.

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