Questions That Remain
Thinking about luck. Culture vs People. Leaving before it’s time.
Oh, you’re still here? I thought the story was over! I said Thank You, Slack.
But I suppose there is a bit more. Some questions that remain. Here are the top three that strike me as worth exploring. They proved consequential to the story but haven’t really been unpacked.
Thinking about luck — How much influence luck played in Slack’s journey and my own journey at Slack.
Culture vs People — How much of Slack’s success resulted from the people hired or the culture they operated in.
Leaving before it’s time — How I thought about leaving Slack and building up a life to head to, not just one to leave.
I had another question in there about money and MacGuffins that I’ll tackle in the next chapter. Turns out, it’s a bit bigger and needs more unpacking.
And what about you? Any questions you’d like unpacked? Leave a comment below or email me direct: sherrett@gmail.com.
Thinking About Luck
Sure, I think about it. But I struggle with this question sometimes because the answer is so unknowable. How much of Slack’s success depended on luck? How much of my personal success depended on luck? Unknowable. But also, a lot, I’d say.
From Michael Lewis’ Princeton 2012 Baccalaureate speech:
“This isn’t just false humility. It’s false humility with a point. My case illustrates how success is always rationalized. People really don’t like to hear success explained away as luck. Especially successful people. As they age and succeed, people feel their success was somehow inevitable. They don’t want to acknowledge the role played by accident in their lives. There is a reason for this. The world doesn’t want to acknowledge it either.”
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“Don’t be deceived by life’s outcomes. Life’s outcomes have a huge amount of luck baked into them. Above all recognize that if you’ve had success you’ve also had luck. And with luck comes obligation. You owe a debt. And not just to your gods. You owe a debt to the unlucky.”
Slack launched at just the right time to meet its market, at just the right time to have its market pull the product out of the team. Yes, Slack did all the things Slack could do to maximize its probabilities of success — great product, opinionated positioning, terrific public relations. All the pieces worked together in harmony.
Internet Relay Chat (IRC) sowed the seeds of Slack’s success by establishing much of the product model and conventions early Slack relied on. Web and mobile technology had advanced so a freemium trial model could work. Billions of people had an Internet connection. I could go on and on with factors that affected our success and proved essential.
Slack just basically appeared in the world at the right moment for a chance to succeed. If Slack launched a year earlier or later would it have succeeded to the same extent? I think it’s impossible to know but it’s also unlikely. It just hit right.
And in the same way that Slack appeared in the world at the right moment, I appeared at Slack at the right moment for me to have a chance to succeed. I got the contact from Rebecca to have the coffee with Stewart that led to my first job. I found valuable work within the scope of that first job to get to please sit next to the money, and that led to my second job, and then again my third and fourth and fifth jobs.
I never really knew where I was headed. My career isn’t a template for anyone to follow. If anything, it taught me to let go of the vanity that I had control over my direction. I did have some influence, but only some.
When I coach kids sports now I can see they often get frustrated or elated by things that happen in the game. An official’s call benefits them. A bounce leads to a goal against them. The outcomes big and small can be tipped one way or another by chance. The world has plenty of randomness in it.
In the face of that randomness, I try to get them to see the luck, acknowledge its role, then focus on just the things they can control: their effort, their attitude. They have 100% influence over those two things and no one else can do those things for them.
Then once they have ownership over their effort and their attitude, I ask them to own their part of their relationships — with coaches, with the other players, with themselves and with their parents too. Again, no one else can do this for them.
This isn’t a perfect model of how to operate in a world where luck continues to influence us. You still have to be able to see opportunities and be brave to try to seize them. You still have to be aware of probabilities and situations — when to push your luck and when to sit back. But I find it’s a good start.
And once you start to do these basics it’s amazing how luck can take care of itself.
Which Drove Which: Culture vs People?
The tendency with our first questions seems to be to assume it’s a zero-sum problem. People say things like, Slack’s success was 50% luck and 50% controllable aspects. The higher the perceived influence of luck, the lower the perceived influence of talent or hard work or smarts or jellybeans.
I won’t quibble with that here. Read the above section and you can see I think it’s not really a question worth spending a ton of time answering, if it’s answerable at all.
But I will strongly argue that the question of culture vs people is not a zero-sum question. It can’t be reduced to 50% culture and 50% people because each aspect of the opposition reinforced and drove the other. A better culture meant better people meant a better culture, and on and on.
So how much of Slack’s culture’s success was hiring the right people? Lots. How much was giving those people permission to be their best selves? Lots again. How much was the luxuries and freedoms we enjoyed — time, money, momentum — that acted as tailwinds? Bingo, bingo. Those all pushed us ahead too.
If you want to hire the best people, build the best culture. If you want to build the best culture, hire the best people. And, like planting a tree, the best time to do it was long ago, the next best time is right now.
Just think of your own career and how you’ve done varying levels of work in different cultures. Sometimes better. Sometimes not as good. You changed what you brought to the work and the work changed you. It was my experience that the people drive the culture AND the culture drives the people. It’s a bunch of complex and interacting systems that are somewhat opaque to their participants.
To put it into more concrete terms, ~80% of Slack’s investments every year (like almost all software companies) were in people: salaries and bonuses and benefits and desks and programs, etc. The biggest thing we spent money on was by far people. Like Soylent Green, Slack is made of people.
And consistently we saw that the top source of excellent new people joining Slack came from referrals from excellent existing employees. That virtuous cycle got started early and never in my time at Slack petered out. It didn’t depend on any cash kickbacks. It depended on Slack being an excellent place to work where people wanted to pull in more excellent people to work with. There was reputational contagion.
So it started with the people and they created the largest return on investment. And the people built the culture. Then the culture attracted additional people, who built new variations on the culture, that attracted more terrific people. There was no either culture / or people. It had to be both. And on and on. Chicken and egg.
Leaving Before It’s Time
Did I leave at the right time? Seven years and five jobs after I started? Maybe.
If I think of the through line of my work at Slack, I wonder: was my job consistently to be invisible and yet probing? To be the person doing marketing when we didn’t do any Marketing. To be the person doing sales before we had Sales. To help do a job and to be available to do new things when I found an adjacent space that needed something done? Partially, I think so. Or that’s how I found my belonging and created value.
At some point around 2018 I remember Stewart telling us that our opportunity was to be an N of 1 company — a Google or a Salesforce. We had the chance to create and own a large and growing market that touched a global audience. That was the size of the ambition we could reach. We could create a new digital way for people to communicate and work together. We were trending to be 2,000+ people. We went public. We crossed the $1-billion threshold of revenues.
Yet I found I was less excited about these goals and achievements. What did it mean to be an N of 1 company? We already were a verb in the vernacular.
The story I didn’t tell you about almost getting PIP’d in January, 2020 is that I was feeling pretty lackadaisical and doing a lot of questioning of my direction. If I no longer had to work for money, what did I work for?
I had to find new challenges to be excited about. I drew up a list of what I wanted to do and those challenges ended up being mostly outside of Slack. I used that list to create a portfolio of things to aim towards. I wanted to learn to play drums. I wanted to learn to fish on the ocean. I wanted to contribute to a better planet. I wanted to help people in my community. I wanted to be home with my family and not travelling.
I remember my last trip to SF in February, 2020, right before the COVID pandemic really ramped up. From seat 13F on the flight I watched the runway shrink below me. We crossed the water of Georgia Straight where the milky plume of the Fraser River lingered above the deeper saltwater. We climbed away from the forests and islands and reflecting water and all the places I actually wanted to be, and I knew I had to make a change.
That moment sticks with me as one of a few small realizations that I had to move on, and I had to leave before I was ready. Time ticked. Life passed and I had run out of spaces at Slack where I could be invisible yet probing. I had to jump into ambiguity, into seeing what I could do in a new life.
On that last trip I felt like I was saying goodbye to San Francisco, goodbye to that life, goodbye to Slack, goodbye to the person I had been.
One evening of golden sunshine I rode an electric-assist bike down Market Street with my teammate Chapman. We went to the Zuni Cafe and ate the bread and chicken salad I had heard of but never tasted. It was glorious and like my farewell dinner.
A week later travel shut down. Offices closed. We started disinfecting groceries before unpacking them and I started to build my plan for life after Slack.
Up next: Money as MacGuffin — Money can change things. Mixing with friends and family and kids. World’s smallest violin.
I like the idea of creating more surface area for luck. How does that happen? By showing up. Doing things. Meeting people.