A Slack Story: Next Steps
Sometimes I listen. Sometimes I don't.
In my last note I asked you for your feedback — tell me what you’d like to see next from A Slack Story.
Many of you excellent readers did just that, and I’ve collected that feedback below. (Disclosure: many = 9.)
But I’m not going to really listen to it. I know. I’m sorry. Sometimes I listen to feedback. Sometimes I don’t. To quote Stewart: “¯\_(ツ)_/¯”
So what am I going to do? I’ll tell you below the feedback. If you’re impatient, skip ahead to the spoiler header, A Slack Story: No Next Steps.
What you said you wanted next from A Slack Story
It was only 4 questions. My mom didn’t even answer. So let’s get to it.
Question 1: What should happen next?
The breakdown from the suggestion options:
0% — Keep pushing. Same format.
22% — Publish with new format: shorter / longer / more visual
44% — Bring in guest conversations
0% — Become a podcast.
0% — Pause / Stop.
Everyone else decided to choose the Other option and write in something.
11% — Put it all in a book! I think this is where I assumed you were going. With a big fat Slack logo on the cover. It reads like an odyssey so I think it could be a compelling book.
11% — Just keep writing. Do whatever it takes for you to keep writing.
11% — Unclear. I think it depends what stories you have left to tell and what your goal is. If you want to continue growing, maybe moving to a more discoverable format will help. Maybe another option is to just consult with high growth startups on how to scale as successfully as you did. Coffee with Slack Man!
Reflection
No one said Keep pushing. Same format. No one said Pause / Stop. No one said Become a podcast.
So don’t keep doing the same thing. And don’t stop. And don’t do what everyone else seems to be doing. So what then?
Bring in other guest voices (44%) in a new format (22%). Right. That’s some solid direction.
Question 2: What’s the #1 reason you picked his? (Write anything.)
As a long form answer, I’ll pull out a few bits of feedback folks had to share here.
Very descriptive. Which is good. It does say “Slack Story” on the tin. But you can also have some format where you are prescriptive. Write a book?
Because I think you could be equally "successful" at any of these... just depends on what you want to accomplish and what you're excited about.
The primary sources have been my favorites — photos, screenshots, excerpts, etc. lets add humans!
I want to hear the counter parties’ perspectives of the specific situations where you shared your thoughtful interpretation and hypotheses.
I know James. :)
Reflection
First of all, thank you. I’m very lucky to have such a wonderful and generous group of readers.
A book, eh? I mean, maybe? I don’t feel a ton of attraction to the publishing process, especially its timeline and the necessity for promotion. It’s very time intensive.
The primary sources have been my favourites, too. It’s such a fun story to be able to reflect on and share small, inconsequential or quotidian items from.
Counter parties would be excellent to include into the larger story.
Question 3: What do you like most about A Slack Story?
I thought about this question as a way of asking what I got right in A Slack Story and what I needed to keep focused on to continue. It was a multiple choice question so folks could check multiple options.
The bottom 3 options were free-form responses folks added into the Other field so I’ve added snippets of them below:
It wasn’t trying to create grand narratives but reveals the specific ways this group of people at that time thought through and worked through the business tasks (e.g. go public, do sales, etc.) in your ways.
Thoughtful/reflective was the most compelling for me. Super easy to read too.
The fact that I know you personally makes the story more engaging.
Reflection
I makes me really happy to see that the work I put in on the writing and storytelling are recognized by folks. Additionally, that folks found it thoughtful / reflective.
I had quite a few times in the writing where I approached a topic and wondered how much I should say about it. I had to make a judgement call.
And hello to whoever knows me personally! I’m happy to know you and to get your feedback, though I made it this whole process anonymous so you’re still under the shroud for me. But hello!
Question 4: Do you have a question for me?
Another long form answer, so another chance to excerpt the superb responses folks had. I’ve tried to answer them in-line, as JS.
Q: What did you leave out?
JS: Lots! And, probably, not enough. It was still 123,421 words. Around ~330 pages in a paperback book. Too long!
Q: Based on your story and the parts you attribute to Stewart (quotes etc.) and the myths I have heard about him (is he a practicing Buddhist?) I want a whole chapter on him. Could Slack have been born without him? How much of a visionary is he? He feels wise to me, I want to know how much of a mentor he was to you, if at all. Is he a wise person?
JS: Yes, Stewart. He’s a great character and I feel really lucky to know him. I tried to share bits about him while respecting his privacy. I’m sure Slack would not have been born without him. I don’t subscribe to the single genius theory of Slack, though he is a great visionary with lots of wisdom. I’d say he wasn’t a mentor so much as a guide on how to operate. Is he wise? I think you’d have to ask him and he’d probably say he doesn’t feel wise many days. But he probably is. Time will tell.
Q: How did you create a work/life balance and keep a sense of your personal self separate from your work self, especially in those early days when you were basically moving or doing whatever Slack asked of you? I ask because I didn't quite realize how much of myself I was giving to Slack until I had the opportunity to slow down a bit during the pandemic and reflect. Curious about your experience!
JS: Work/life balance: ha! Good one. My family definitely helped a ton with keeping a personal self. My wife is the background star of A Slack Story and my life. And having kids helped too. Kids just don’t care about software companies, sales calls, meetings, deadlines. They want to go to the park or have lunch or get to swimming lessons.
Q: i’d love a thought piece on how much of the slack journey was good fortune vs. right decisions and people. looking back, what would have happened in a shittier market, with a shittier leadership team? do these counterfactuals matter?
JS: This would be interesting. I tried to tackle it a bit but I don’t think I’m the right person to write it. I think it would take much broader understanding on the influence of luck, and more academic research. I’m just a lucky beneficiary of the time and place I lived.
Q: tell us about watching from the outside since leaving. whats it like to see slackbot in a superbowl ad?
JS: Wait, what? Slackbot had a Superbowl ad? Hmm. I think the easy answer here is to be offended or outraged. But that might have been a good choice for the folks making the choices at the time. Chances are they’re smart and capable and buffeted by many forces to make that a complex decision like that. I don’t know! I haven’t seen it or looked in up. Okay, now going to look it up. Oh. Double hmm. Mr Beast. Not to my taste. But don’t let my yuck ruin your yum.
Q: Long pants or shorts?
JS: Always shorts as much as I can.
Q: How's Vancouver these days?
JS: Blooming with cherry blossoms. You only can live in one place at a time and I feel lucky to be able to choose this place.
A Slack Story: No Next Steps
I should have called this whole post A Slack Story: No Next Steps. Because that’s where I’ve landed. There won’t be any new parts, as far as I can tell right now. Sorry.
Why?
I felt like I was living too much in the past. I’d told the story — memorialized it, reflected on it, written it over the course of 2 years (1 year of drafts, 1 year of polishing, recording, publishing).
I felt happy with that process and results and work, and sometimes it’s best to leave it at that.
I did have a whole interview series dreamed up though. I recorded intro music. I had a schedule of guests.
It was going to be called the 3 x 3 Interview. The format: 3 questions for the guest from me, 3 questions for me from the guest. That’s it. Less than 20 minutes per interview. The intro music in triplets.
The format even came from one of the practice interviews I did with Kim Graves. It was her name and her idea. (Kim! Please take your excellent idea and run with it if you ever want. It’s not for me to do.)
Put it another way, I guess I’m taking my own advice and Saying No Nicely.
I’ve spent some time sprucing up the existing chapters of A Slack Story — interlinking them to make reading easier and so anyone discovering a portion can then choose their own adventure to other portions. But this will be the last official post for A Slack Story. As far as I can tell.
So What’s Actually Next?
More writing! And I’m really excited about it. I walk down the street and hear characters’ dialogue. Little bits of every day detail find their way into what I’m working on.
It feels really alive and it’s another totally different kind of story for me: a murder mystery / detective novel. The White Rabbit Detective Agency.
At some point I may share some of it here.
(Unsubscribe link in the footer to spare your inbox.)
Until then, thank you very much! I need to practice my drums.




