How to Win Bigger Clients With Better Questions: What Won Us #TeamSeas Wasn't Technical. It Was Listening

People sometimes assume we won the #TeamSeas project because of our technical skills. That's not what won it.

When MrBeast and Mark Rober's team came to the table, they were planning to raise $30 million to pull 30 million pounds of trash out of the ocean, in front of tens of millions of people. Their previous campaign had gone down shortly after launch, so uptime was the concern from day one.

What won that project wasn't technical opinion. It was listening. I heard what mattered to them, asked the right diagnostic questions, and built the system around their actual concerns instead of my assumptions.

Why most pitches don't land

Most service business owners walk into a sales conversation ready to talk. They've got their process, their experience and their best examples lined up, and they want to show the client how good they are.

The problem is that the client isn't asking how good you are. They're asking whether you understand their problem, and you can't show them that by talking. You can only show them by asking.

When you lead with what you do, you're guessing at what matters to them. When you lead with questions, they tell you, and then everything you say afterward lands, because it's about them.

What the right questions sounded like

The team came in with a clear list of what they needed. Handle large donations, handle tens of thousands of transactions, and stay online no matter what. Most people would have started talking about the website at that point.

Instead, I started asking questions.

What's the lowest donation you'll accept? Who's your merchant? Who's hosting it? What customer service tools do you have? And you said the last campaign went down for 24 hours. What actually happened?

None of those questions were impressive on their own. But each one uncovered something they hadn't fully thought through, and by the end of the conversation they could see risks they didn't know they had. That's the moment a client stops evaluating you and starts trusting you.

Listening is a skill, not a personality trait

A lot of owners think they're good listeners because they're polite and let people finish their sentences. That's not the same thing.

Real listening in a sales conversation means you're paying attention to what the client is worried about underneath what they're asking for. When a client says "we need it to stay online," they're really telling you they're scared of a public failure. When a client says "we need more leads," they might really be telling you they don't trust their current marketing to work.

The words they use point you to the question you should ask next.

How to ask better discovery questions

Build around their concerns, not your assumptions

Once you've listened, the recommendation almost writes itself. You're no longer pitching your standard package. You're solving the problem they just described, in the order that matters to them.

That's exactly how we approached #TeamSeas. Their biggest fear was the site going down in front of the world, so the foundation came first. Everything else was built around that. The site never went down, they raised more than $30 million, and when campaign leadership started planning the sequel, I was one of the first calls they made.

That kind of relationship doesn't come from a great pitch. It comes from a client feeling understood.

What this means for your next sales conversation

Before your next call with a potential client, write down five questions you'll ask before you say anything about what you do. Make at least one of them about what went wrong last time, and one about what success would look like to them.

Then go in with the goal of understanding, not convincing. If you understand the problem better than anyone else they've talked to, you won't need to convince them of anything.

Frequently asked questions