Missionary vs Mercenary
How to answer the key question — What is Slack? The missionary vs mercenary model of startups. Working with Stewart. Finding a 3rd way. Meatball restaurants don’t last.
The first Slack Vancouver office had no plumbing so we washed our dishes in the bathroom sink. Hot water rarely reached that bathroom so we just boiled water in the office kettle when things got too grungy to wipe clean.
Because washing the dishes was such a chore, each of the 3 of us (Stewart, JR and me) had our own set of cutlery that we kept on our respective desks. When one of us got fed up with the state of the office we gathered all the office dishes to be washed. It was an unspoken agreement that suited how we wanted to work.
About once a week, in the middle of the afternoon lull, one of us would boil water and spend 10 minutes on the task of washing the office dishes. I can still see Stewart up to his elbows in suds in the bathroom sink while talking with the bank on speaker phone set beside the sink.
I had stolen my set of cutlery from a restaurant whose menu featured mainly meatballs. Stewart and I ate lunch there one day. We wanted to get out of the office and have a chat. We had to start making some progress on the marketing tasks that were piling up.
As was our usual pattern, we talked about life, current tech news, travel – anything to set the stage and avoid the real thing that was on both of our minds. I liked asking him broader questions and I think he appreciated getting them. It wasn’t all work all the time. It wasn’t all “businessman things.”
Chatting more broadly gave his mind a short break, something to interrupt the hamster wheel. But the thing we were avoiding talking about was almost always the current work we were doing and how it was or wasn’t getting done.
And in general, Stewart and I hadn’t found ways to work particularly well together when we worked closely together. This came down to the fact that we each wanted control over the work. I tried to obtain that control through process. Stewart held out against the process, or rebelled against it or just generally ignored it. That made for some challenging times.
After all, I was a hired gun on a 3-month contract. He was the boss leading the company. Shouldn’t I have known better?
Silicon Valley lore
There is a classic bit of Silicon Valley lore that all entrepreneurs are missionaries. It gets repeated because it’s flattering and it also contains some portion of truth.
The classic presentation of the Missionary vs Mercenary model comes from John Doerr, the legendary venture capitalist at Kleiner Perkins, who invested in foundational tech companies like Netscape, Amazon, Intuit and Google — an amazing track record. He may have a pretty low profile in the general public but to anyone with a passing interest in the societal and commercial impact of technology, John Doerr is Silicon Valley royalty. Whole books have quite rightly been written about him, and by him.
In Doerr’s 2007 presentation to the Stanford School of Business entitled Entrepreneurs are Missionaries, he outlines his model for thinking about founders in Silicon Valley.
“…an entrepreneur does more than anyone thinks possible with less than anyone thinks possible, in whatever field they're working in, and importantly, at least for my values and those of my partners, entrepreneurs are not mercenaries. They're missionaries.”
…
“More differences between the mercenaries and the missionaries? Well, the mercenaries are opportunistic, always interested in the pitch and the deal and they're kind of sprinting for the short run. As opposed to the missionaries, who are much more strategic. They're focused on the really big idea – in forming a partnership that will last and they know that this business of innovating is something that takes a long time. They look at it more as a marathon.
The mercenary is obsessed on the competition. They create a kind of aristocracy of the founders. They're not inclusive of the rest of a team, and they're really driven by their financial statements. As opposed to their mission and value statements, for example. Or obsessing on the customers.”
The model proposed by Doerr is a classic duality. Either you’re a missionary or a mercenary. It’s black or white. Hot or cold. Left or right. You need to choose your approach (or have the approach choose you). The two approaches are in opposition to each other. The missionary is the hero.
Being a Mercenary
When I started at Slack I was a consultant trying to prove my worth. I had a 3-month contract to do. So, pretty clearly, I was a mercenary — a professional hired to do a job.
Stewart was the CEO trying to balance so many things at once, one of which was managing me, this damned marketing consultant with my questions, my ideas, my demands. As I was coming to learn, he cared so much about everything he had to do. All those “businessman things” he talked about. He knew he had to do them and he wanted them done his way, particularly any kind of public facing communication. Yes, dear reader, it would be safe to say that Stewart angled towards the missionary side of the duality.
So there were many days for me that I would characterize as wandering days — days spent wondering what I should do or could do to get the work done that I had been hired to do. It obviously needed to get done. I obviously had been hired to do it. I obviously also needed Stewart participating and onboard with my work. He had done all the marketing before I’d been hired and wanted to be deeply involved in any new marketing. And yet.
Sure, I found many things to work on in the meantime. There was no shortage of tasks that I could do. I knew how to do consultant work about process and preparation and describing the problem and proposing approaches. Not actual work. Work about prospective work and around existing work.
But my recollection of those early days at Slack is largely waiting for Stewart and waiting to get down to doing the real work I had been hired to do. I think it’s safe to say I was not a great mercenary.
The fate of meatballs
The meatball restaurant we visited went out of business or became something new before we could return. But on that one particular day we visited, alone on that particular patio, after we had gotten through our small talk, I remember eating meatballs and caesar salad with Stewart, and finding that we were in sync.
Perhaps we’d found a third way to bridge the divide between missionary and mercenary? Time would tell. I knew somehow I had to find a new way of working with him. So I was trying new things.
And it helped that by then I had some familiarity with Slack because I had been using it for hours every day. I started to see the really compelling parts of what it could offer to prospective customers. Stewart and I shared articles back and forth on ways of launching, ways of thinking about products. We had ideas we bounced off each other. We started to build a shared topography of what we could do and where we wanted to go. We started working well together.
And pretty quickly I realized we weren’t alone. We had customers. People that we knew and who turned out to really like to use Slack, once they started to use it. We started to hear back from friends and contacts we’d coerced into using Slack. They had tons of suggestions on how to improve the product, and that proved perfect. It meant they used the product and liked it enough to speak up. They were engaged. They had complaints and feedback and it felt glorious, even if they only numbered in the dozens, maybe the hundreds at the time. Despite the missing features or clunky bits, real people were using Slack and kept using Slack once they got started.
The problem was the level of coercions needed to get them started. These were the warmest prospective customers we would ever find, and it still was really hard to get them started. To compound our problem, it took multiple people to get started on Slack at the same time for it to work. As we said internally at the time, the single-player experience sucked.
So we had both the cold start problem (why would I use this if there’s nothing in here to use it with?) and the multi-user problem (who would I use this with if the people I communicate with aren’t on it?). There was a huge amount of friction to get people to begin using Slack and to get their teams using it. They had email. They had chat. They had file sharing. Another tool could be the answer?
But even before that, before we could ask people to use the product and get their teammates using the product, we had a positioning problem. The key problem I’ve mentioned before: what the heck was Slack? It wasn’t email. It wasn’t file sharing. It wasn’t project management software or help desk or task management.
All these crowded software categories existed and bulged with competitors. But we didn’t want to get slotted into those categories. It was like restaurants. Categories existed: pizza, sushi, quick service, casual family. Meatballs? We definitely didn’t want to be a failed meatball restaurant.
Our goal was something both smaller and bigger. Smaller, in that Slack needed to start out and compliment all the other software people were already using. Bigger, in that we wanted to create a whole new category of software and a better way for teams to work together.
So how do you tell people about something new that’s small and big at once? That’s new and familiar? That’s incremental to what they use but then replaces much of the functionality of those tools? How could we give people some compelling story that they could describe to someone else, and that made them look good, and got them to try our product, with all (or at least the majority) of their teammates?
We didn’t know any of those answers, yet. But we knew we had to find out or we were sunk before we’d launched. Our survival hinged on getting our story right.
In many ways, though we didn’t talk about it at the time, Slack had inherited the Glitch problem – a great experience once you experienced it, but an experience that didn’t fit into any of the existing containers in your brain.
Over meatballs on that restaurant patio, Stewart and I didn’t necessarily know the answer to the key questions, What is Slack? We had clues and ideas and needed proof outside of our collective brain space. We needed a way to learn which of our stories would work best, and we needed some proof. We needed to “get out of the building,” as Steve Blank says in Four Steps to the Epiphany.
So we came up with a way to test a bunch of positioning options and get some proof: landing pages. We’d trial our ideas away from the warmest prospective customers with the coldest ones — random people on the web.
How did we do it and what did those landing page look like and how did they perform? We’ll dig into all that in the next chapter.
Menschy
As a sidenote here, I wanted to unpack a bit more an idea I’ll come back to a few times later in this project.
Remember how I hinted at a third way of working in a startup? Not mercenary, not missionary, but something else? It’s an idea I’ve thought about a lot since my time at Slack, since I’ve had a chance to reflect on the bigger picture and how my roles fit in over the years.
And I’ve come to think there is a third way to be that I would call “menschy,” derivative of the yiddish word mensch — “an honourable person.” It’s the best word I’ve found so far to describe the best version of the role I had a chance to play.
Not a missionary. Not a mercenary. A mensch. I don’t want to dress this concept up too much or be too self aggrandizing about it, but it’s the most apt way to describe the approach that worked best. When I did my best work and when that worked served people best, I lived up to a menschy approach.
What I had to do — and what I think anyone in any situation of high uncertainty and high pressure needs to do — was find the work that needed to get done and do it as well as I could. It was to help other people — teammates, customers, prospects. It was to live up to the descriptors of a mensch — strength, integrity and honour or compassion. It was to be human and humane. That’s what I aspired to.
I wasn’t a founder. I couldn’t be a missionary. I’d joined 8 others at Slack who had all been part of the Glitch failure. That experience tempered and dedicated and bonded them to each other and to the larger mission of Slack.
And I also wasn’t a hired gun. Or, at least I didn’t want to be, though that was mostly my role to play at the time. Mercenary values didn’t feel right. I wasn’t going to go on to be a marketing consultant at other startups. I wasn’t looking for the highest bidder. I wanted to belong at Slack and really commit to making it be as good as it could be.
But I found I needed to add elements of both missionary and mercenary into my approach to make it work. I needed to have the dedication and purpose of a missionary. I needed to have the clear headedness and bloody mindedness of a mercenary. I needed to have a focus on a mission. I needed to deliver concrete results. I needed to hold on tightly. I needed to let go lightly.
I didn’t have the word menschy in the early days of Slack that I’m describing in this chapter. But I did have the feeling that I needed to find a better way to work with Stewart, and to work with the Slack team. I needed to serve the mission of the company and I needed to deliver on the goals of my contract. Was I able to balance those opposite demands?
That’s something to cover in the next chapter, where we get down to doing some of the actual work.
Up next week:
So, what is Slack?
Knowing we didn’t know. Creating 5 options to answer the question. Learning about each option. The MAYA principle. Finding our tone and market.