"Is anyone here working on the internet?"

This is what David Hyser, Chief Digital Officer at Citi Retail Services, asked his manager at his first job in 1997. Of course, it sounds like a silly question to ask now, but at the time, the internet's utility to blue chip businesses was just a concept that many knew nothing about.

David was intrigued enough to ask if anyone was working on the internet, even as vague of a question as that was.

A big part of David's job is to take new ideas and concepts and turn them into reality. It requires a certain level of discipline to make this happen when you're not the only one impacted by the decisions your team makes.  

David provided me with some real insight on how entrepreneurs can make better decisions and become better leaders.

Here is what I learned from David Hyser.

Take friction out of the process.

It could be the "uberfication" of everything, but every leader I've interviewed insists that reducing friction is the path to successful leadership and startup growth. Hyser had similar thoughts on reducing friction.

"Even though we're a large company, our retail services division is focused on helping our retailer partners sell goods and services to their customers with as little friction as possible, with customer value and security at the top of our priority list," says Hyser. "We're a chameleon operating under our partner's brand in many respects, and that's why our seamless integration within our partner's business is critical to our joint success."

I remember my time as a project manager, and although my job description never said it, my number one goal was to reduce friction for every team that I worked with. It didn't matter what technology I had at my disposal, I had to remove the friction on how decisions were made.

For entrepreneurs creating breakthrough products, think about how much friction it takes to use your product or service. Break it down and remove as much as you can.

Work within your constraints, but continue to push the limit.

I had a habit of pushing the capabilities of those around me and pushing them to be better. Often times I would find the edge and then get a tersely worded email or a private meeting letting me know I crossed the boundaries. 

The best innovators embraced their constraints, but found ways to still push the limit. They didn't just resist at all costs.

Hyser had similar advice, except he calls it "Up and to the right," a reference to an alignment framework that his team developed to empower confident decision making. 

"You have to find your north star and consider every option and decision you make within the context of whether that's helping you move up and to the right, without being paralyzingly specific about a pre-ordained path. Every member of the team needs and deserves a framework that empowers them to make daily decisions with confidence vs. feeling it necessary to seek escalation and validation of every decision -- so long as you're staying true to the framework, and every decision moves you closer to your core objectives," says Hyser.  

Don't overthink every decision. Be comfortable not knowing everything.

I was sitting with a mentor recently discussing a new business idea. He interrupted me halfway through my spiel and told me to stop overthinking and just do it.

He was right. I had the right components in place, but for some reason, I didn't start executing on them. I was waiting for something that was never going to happen.

"When you stop being super prescriptive about everything, more things will start working for you and your company. There is more than a defined list of possibilities. Embrace not knowing everything," says Hyser. "What we've done well here at Citi is creating a framework for making decisions without getting multiple levels of approvals. This allows us to move faster with confidence."

Celebrate the finding of failure.

Hyser truly believes that the only way to find the edge is to cross it. I laughed when he said this because I had the same experience when working as a consultant for my clients.

Now, I only choose to work with people who will embrace failure. I once had a manager tell me that "failure was not an option," and that was a sign for me that things weren't going to end well.

This is refreshing advice to hear. For many entrepreneurs, we've been trained by working at corporations that didn't celebrate failure. If you failed, you were wrong and you will be penalized for it.

Thank you David for taking time out to help entrepreneurs and leaders who are looking to make an impact on the world.