I worked with Chester Kustarz at Duo Security. He was Head of Engineering in various roles throughout my tenure there (Director, VP, Director again after we were acquired by Cisco). Like many leaders who are cultural staples within an organization, there are stories and Chesterisms that float around Duo. Some I experienced and have retold, some I heard, and some are probably just made up. Regardless of their truth though, they are nearly all impactful in setting the tone and culture of the org.

One that I return to constantly is the following, told in Chester’s words.

We were trying to kick off a project. And someone looked and saw that the people had non-overlapping calendars for the next two weeks.

So they said, “Ok. I’ll schedule it for then.”

Wrong.

I say “What does it take for us to clear the calendar for tomorrow afternoon to get it scheduled? What about tomorrow morning? What about today? What about we walk over to the whiteboard right now and kick it off? This is important.”

The point is that we have to reframe our mindset. We have to have a sense of urgency. Pull it forward.

Companies don’t stop innovating because they become too big or bloated or outperformed. They become complacent. It happens to small companies too.

It’s important to have a sense of urgency. In particular this is true in startups, which as Paul Graham says are often “default to death”. The only path to success is to have a sense of urgency.

Reid Hoffman says it slightly differently.

You jump off a cliff and you assemble an aeroplane on the way down.

The point is that time is of the essence. Even when you’ve made it to profitability, you have a unique opportunity to seize that momentum and do more or go faster.

What’s powerful about the Chesterism above is that he doesn’t just say, “we need to have a sense of urgency”. His questions simultaneously model and will it into reality.

Pull it forward.