From Aggressive to Assertive with 3 Ts

Often during our sales courses people ask me what's the number one skill of a successful salesperson. It must be assertiveness.

Assertiveness is not to be confused with aggressiveness. When you push your customer to buy based on your own reason (like you have to hit your target), you are aggressive. But when you push your customer to buy because it is in the customer's interest to buy, you are assertive.

There are 3 steps to be assertive in your selling:

Step 1: Teach

Here you teach your prospect not just about your product's features and benefits but challenge his assumptions. You also teach him how to take action base on what he desires.

Your teaching must offer an unique perspective and must be a two-way communication. That means asking questions and listening

Step 2: Tailor

After the prospect is taught on what is the right way to do things, you tailor what you have to what he desires. It means that you have to adjust your proposal and contextualize it to his needs. All these tailoring must lead to financial gains for the customer

Step 3: Take Control of the Conversation

Here you take control of the conversation by asking for the sale. You are comfortable discussing about money and you dare to pressurize the prospect to make a decision NOW. Various tactics including scarcity, scare and fear of loss are used. The point is you are pushing the prospect to buy not because you are desperate, but because you believe so much in what you are selling is good to the prospect that you cannot see yourself to be soft. We call this Assertive Selling.

So if you too want to close more sales and never end up with 'We'll contact you in due course" answer from the prospect, you need to be tough but not terrible. Be assertive and you'll get the sale. Related articles:

The Secret Under the Mattress: Why would a 79-year Man Bet So Big on 4D?

It was 2007 when we discovered his secret. While moving my father’s mattress, we found them: heaps and heaps of Singapore Pools 4D tickets. They were stacked in layers, a paper trail of lost hopes. What shocked us most wasn’t just the volume, but the stakes. He wasn’t betting a few dollars for fun. He was punting hundreds of dollars per draw—nearly ten times a month. At the time, my siblings and I were furious. Our father was a 79-year-old retiree. We wondered, with a mix of anger and confusion, why a man at his stage of life would need to win such "big money." What was he going to do with the money? We saw it as a reckless habit, a sign of poor judgment in his final years. Some of us would say, "If I were to give him money to buy 4D, why don't I use the money and buy 4D myself? At least I have better discipline". It has taken me two decades, and the experience of raising my own three grown-up children, to finally see the truth that was hidden under that matt...

Head Bleeding when the Chair Falls

The Weight of Silence: What Were We Really Arguing About? My earliest memories are punctuated by the sound of shouting. In 1970, when I was barely 6 years old, I stood as a small witness to the fierce quarrels between my father and my late eldest brother Kah Yang (he passed away in 1971 at the age of 17). As I grew up, these contradictions became the soundtrack of our lives, usually centered around our family's shoe shop and clothing stalls in Chinatown. In the court of family opinion, the verdict was almost always the same: my father was "wrong." He was judged as a man who didn't fulfill his role, who wasn't "burdening" enough for the family’s success. But as I look back from the vantage point of 2026, I have to ask: Was that actually true? Let me finally put to rest what my father did right: the truths that were buried under decades of criticism: Unseen Labor: He worked grueling, long hours. I remember him hauling boxes of goods and equipment to set u...

Business and Money Tips

Search This Blog