Ask yourself hard questions. Questions for which you fear the answer.

Ask questions you’re afraid to hear the answer to.

Ask questions that unsettle the rest of the organisation. Questions that would make even your CEO uncomfortable, because the mere possibility that there is an answer would suck the air out of the room and leave everyone speechless.

People who ask hard questions are often pushed to the margins, or fired. Not because of the question, but because many people don’t want to hear the answer. It hurts to hear what you don’t want to hear.

Then there are the “experienced” professionals who don’t even dare to challenge the status quo. Nobody is foolish enough to risk their job.

But for a business, a lack of uncomfortable questions is just as much of a problem. Without good questions, there is no innovation.

Innovation is proportional to hard questions

A company’s capacity to innovate is directly proportional to three things:

1. How many hard questions get asked.
2. The courage to answer them.
3. At the end of the day, the ability to execute on those answers.

If you’re one of the few with the courage to change things, you’ll have to learn to ask hard questions, and to deal with the lack of courage of the people around you. It isn’t easy. It never was, and it never will be.

Don’t chase the “yes”

I love asking hard questions, and I allow myself to ask them every day. But I confess I wasn’t always good at it, and it caused me a lot of trouble in my career.

Here is what I learned. My mistake was trying to get people to say “yes” and agree with me.

If you’re leading a controversial project, believe me: it isn’t essential that everyone agrees with you, but it is critical that nobody opposes you. You don’t need everyone to say “yes”. You need to make sure nobody says “no”.

It may sound subtle, but it makes all the difference.

For every “no” you get, work to understand the objections, the challenges and the concerns behind it. Only at the end of the process, when nobody is saying “no” anymore, go looking for the “yes”.

Good ideas get better when questioned

Good ideas are hard to ignore. Good ideas survive the test of time. Good ideas gain strength when they’re questioned and, to many people’s surprise, they even get better.

Good ideas prevail, simply because they are good.

You have only one job: make sure your idea isn’t ignored, keep collecting feedback, and keep improving it.

What if we built our own private cloud?

This year I allowed myself to ask a hard question: what if we built our own private cloud?

Gradually, we took apart every “no”, including the ones from our own team. For every criticism, we learned something and improved.

A project that started with the goal of cutting costs turned into a fantastic continuous build platform, and became a fundamental part of how we innovate.

The result: lower costs, better systems, and a real step forward in our ability to innovate.

Woovi’s success with Pix comes from the fact that we didn’t stay on the margins. Through many mistakes and successes this year, we got more right than wrong.

What’s yours?

What is the hard question that keeps you up at night?

I first told this story on stage at the Dell Technologies Forum. Thanks to Diego Puerta and Bruno Luiz Assaf for the invitation, and to Eduardo Darim, Marcelo Marchel dos Santos, Rosangela Souza and Amauri Barros for the conversation that inspired it.