THE STORY AS I HEARD IT WAS Stewart Butterfield likes games and has twice attempted to build a commercially viable online game. The first one was called Game Neverending. Built during the first generation of the internet, it was not a success. But one aspect of the game appeared valuable: sharing photos.
The company that built Game Neverending, Ludicorp, pivoted and built Flickr for the world. Butterfield sold Flickr (at 40 people) to Yahoo! and remained there as the GM for four years. Upon leaving Yahoo! he made his second game attempt with Glitch, with his company Tiny Speck. Web-based, artistically delicious, and weirdly clever, Glitch didn’t find a viable market. As Butterfield attempted to return investors’ money, they asked, “Do you have any other ideas?”
He did.
In building Glitch, the team had hacked on a version of Internet Relay Chat (IRC) to make it more useful for team collaboration. They could not imagine building anything else without this janky communication tool, so they chose to build the janky communication tool from the ground up—and that changed everything.
Pivoting and rebranding the company, they built a beta in six months. They signed up 8,000 companies in 24 hours and quickly discovered they’d built the fastest-growing piece of enterprise software in the history of the galaxy. They called it Slack.
I was in love with Slack long before Stewart mailed me. It was not that I was a longtime IRC user—it was just obvious to me that communication among teams must evolve. It could be much faster to find, contact, and communicate with another human. There would be less time lost endlessly managing an inbox. We would finally build a living repository of knowledge. Problem was, I loved my current job.
Stewart wrote, “And Michael, what harm could it possibly do to talk?”
What possible harm indeed…
My title when I was hired at Slack was Vice President of Engineering. My prior role at Pinterest was Head of Engineering. Titles, as we learned in the introduction to Act II, vary by the culture, but the responsibilities are the same. Unlike at Pinterest, at Slack I shared senior engineering leadership responsibilities with cofounder and CTO Cal Henderson.
I was in an executive role at Pinterest for almost two years. Slack probably thought I was an “experienced executive leader.” As it turned out, two of those words were correct. The first and the last.
It takes three years—minimum—to become competent at a new job. Three years minimum. This meant that when I arrived at Slack I was still 12 months from truly understanding and being competent at the role of executive.
Why am I telling you this at the beginning of the third act? Two reasons. First, you already knew leadership was hard, so why make it harder right out of the gate? Second, you won’t believe me anyway until you’ve seen with your own eyeballs how long it takes to become proficient at a complex job.
The sense of distance that started when you became a manager of managers is truly impressive as an executive. You are now responsible for an entire business or organization, which means not only are you far from the work, but you’re far from the teams as well. Oh yeah—and you’re accountable for all of it.
This responsibility is accompanied by the toughest aspect of the executive role, which is that fires burn faster uphill. When something catches fire on one team, there is a manager there who hopefully competently handles the fire. Sometimes they can’t. The fire gains strength and speed, and it’s escalated to their director, who with their additional experience can often put out the now significant blaze. Sometimes they can’t. Sometimes the magnitude of the disaster is beyond the ability of your whole team, so they escalate it to you.
As an executive, the majority of unexpected situations you’ll face are prequalified five-alarm fires. They are the worst possible version of the situation. And that’s just Monday.
Strange, right? So, what do executives do all day? Fight fires? Yes, but our primary job is fire prevention. What combination of people, products, and processes is necessary to build the highest-quality product? Figuring that out is the easy part of the executive’s job. Here’s the hard part: what combination of people, products, and processes is necessary to prevent fires from existing?
In our third and final act, we’re going to consider the small things you can invest in as an emerging executive. We’ll take a long look at how politics is affecting your organization and how communication is or isn’t flowing across the company, and we’ll finish with my defining leadership principle.