· Letter

If You Know the Objection Is Coming, Why Are You Waiting For It?

Why the best founders say it before anyone else does.

Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.

A sales leader I respect told me a story recently that I have not stopped thinking about.

Early in his career, he gave a keynote to a room full of CEOs. Big companies. Experienced operators. People who had been running businesses for decades.

He got bad marks. Negative reviews.

The feedback? “There is nothing new in his talk.”

And he was furious. Not because the feedback was wrong. Because it was right. There was nothing new. But the whole point was that they already knew this stuff and were not doing it.

The problem was, he did not say that upfront. He let the audience sit there for an hour thinking they were hearing old news. By the time they left, the objection had already formed. Too late to fix it.

From that day forward, he addressed it on slide three. Before anyone had time to think “I already know this,” he told them: “You already know everything I am about to say. The question is whether you are doing it.”

The objection died in the room. Every time.

Most founders wait for the pushback

Think about the last time you introduced something new to your team. A new process. A new system. A new expectation.

You probably presented it, answered questions, and moved on. And then, three weeks later, you started hearing the resistance. “This does not work for us.” “We were already doing this.” “I do not see the point.”

By then, the damage is done. The objection has calcified into a belief. And beliefs are much harder to shift than reactions.

The fix is embarrassingly simple. If you know what they are going to push back on, say it first.

Disarming the objection is strategy

When you launch a new sales initiative with your team, you know exactly what is going to happen. They will start strong. Energy will fade. Some people will question whether it is working. Others will quietly stop doing the work and hope nobody notices.

You know this because it happens every time. With every team. In every company.

So why not say it out loud on day one?

“We are going to start strong. Then energy will dip. Some of you will wonder if this is worth the effort. That is completely normal. It happens in every company that does this. The difference between companies that grow and companies that stall is what happens after the dip.”

Now when the dip comes, it is not a crisis. It is a checkpoint. Something you predicted and prepared for.

This applies everywhere, not just to internal initiatives

Pricing conversations. Say the price is high before the client does. “This is not the cheapest option. Here is why it is the right one.”

Sales proposals. Name the risk before the buyer raises it. “You are probably wondering whether this will work for a company your size. Here is what happened with three companies exactly your size.”

Client onboarding. Tell them what the hard part will be before they hit it. “The first month will feel easy. Month three is where the real work starts. We will be here for that.”

In every case, you are doing the same thing. You are showing the other person that you understand their experience better than they do. That builds trust faster than any case study or testimonial.

The question worth asking yourself this week

What objection are you currently waiting to hear from your team, your clients, or your prospects that you already know is coming?

And what would change if you said it first?

Because the best sales leaders, the best founders, and the best account managers do not wait for the objection. They disarm it before it forms. And the conversation that follows is entirely different.

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Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.

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