Understanding how to distinguish business wants from customers’ needs took me a while. While the lesson cost me a few bitter failures, it was worth it. Today, I can quickly sense when something is off, and teams are going in the wrong direction.

Let me share a success story where curiosity saved the day despite everything being set up to fail.

Start-ups are unique places. I love striving to create something new and disrupt markets. It takes a lot of courage to embrace the unknown, and that inspires me.

Years ago, I joined a start-up as the Head of Product. It was a funny title. I was the only product manager, but later, I understood why.

On my first day, the CEO astounded me. We met at a very unusual place for my onboarding—the hospital where his wife was recovering from food poisoning. He showed up soon after I arrived, and we went to a nearby cafe.

I was mentally prepared for a long meeting, but our chat didn’t last more than seven minutes.

CEO: “David. I will be brief. We have a culture of being straight to the point.”

Me: “Alright.”

CEO: “We’ve got US$10 Million as seed investment, and we burn US$1 Million monthly. Raising cash takes around three months, give or take. Our objective now is to prove market fit to raise more investment. In short, we have six or seven months. Otherwise, you better start searching for a new job.”

Me: “That sounds challenging. Tell me what’s between us and market fit.”

CEO: “Great question. You know we help car owners sell their cars without the red tape. They come to us, and we make an offer in an hour. That’s possible because car dealers bid on cars they want through our mobile app. But the thing is that no matter what we do, they don’t engage with our app.”

Me: “What do they say about the app?”

CEO: “They hate it. They dislike the look and feel and miss almost all the auctions. Here’s your mission: Redesign the app so we increase engagement by 30 percent. I don’t want excuses. I want it done. Deal?”

Me: “Got it.”

CEO: “I gotta go. We will talk in a month, and you can share your progress.”

I was tasked to redesign the app to increase engagement by 30 percent. Suddenly, my intuition kicked in.

What if the solution is wrong?

I had to understand how car dealers found cars they didn’t have. I wanted to organize a discovery round with the UX Designer and Tech Lead. This was in Brazil, so I was surprised that neither of them spoke Portuguese or were situated within the country.

How can you design something for someone you can’t communicate with? Well, someone had to talk to them. 

I’m not a user researcher, but I’m a curious person. I left my comfort zone and crafted an interview script with the team. We agreed I’d visit ten car dealers during my first week and share what I learned.

My first visit was the most interesting. As I arrived at the store, I prepared to present myself as the start-up product manager, but something else occurred to me. What if I pretend to search for a car I know they don’t have?

Car Dealer: “Hello, how may I help you?”

Me: “I’m searching for a BMW Series 3 Sedan. I love this car.”

Car Dealer: “Nice choice. It’s indeed a great car. I don’t have it now, but I might be able to find it. Give me 10 minutes. In the meantime, feel free to get a coffee or another refreshment. It’s on us.”

I wanted to see what the car dealer would do. First, he went to his 21-inch computer screen and searched for cars in portals. Then, he made a few calls. Although registered on our app, he didn’t bother checking it. After 15 minutes, he returned and said, “I’m sorry. I couldn’t find it, but I will call you back when I find it in a few days.”

I visited other car dealers, and the patterns became apparent. I switched between being a client and the product manager, and I learned:

It was clear to me that our app wouldn’t work as expected. I had to make a choice. Follow my boss and blame him once we screw up, or do what’s right and inform him after we reach results. I chose the latter.

As I shared the results with the team, we experimented with a few things.

We ran the above experiments for two weeks. We made a few tweaks and concluded it was worth combining a web platform with a wish list. We adapted the app to enable dealers to set a wishlist and receive notifications when their desired vehicles were in auction. 

It took us around two months to roll out the solution to everyone. Yet, the engagement doubled a month later and tripled four months later.

The CEO was getting ready to raise more funds and wanted to know how the team redesigned the app. When I told him we discontinued auctions in the app, he shouted, “Are you out of your mind? That’s not what I told you. The world is becoming mobile. Oh man, the investors will eat me alive.” 

Calmly, I said, “Listen to me for a minute. Our world is mobile, but the car dealers’ one is not. Our solutions are growing considerably due to word of mouth. You gave me a goal and a solution, and I focused on the goal. You can tell the investors the story of what we learned and how we tripled engagement in four months by doing what’s natural instead of what’s rational.”

Two months later, we had another US$50 Million invested.