Michael Lopp's Blog, page 32

July 14, 2016

How I Slack

Each Slack team I’m on has a different set of humans building their own unique communication culture. I’m actively on six teams: SlackHQ, Leadership, Destiny, two private nerd Slacks, and a private family Slack.


Three out of my six teams have 100+ active humans, 100+ channels, and are high traffic with hundreds to thousands of messages per day. The majority of my interaction centers on these teams and if I’m away from the keyboard for a few hours, my sidebar can be ominously full of unread channels and conversations.


sidebar1


In this piece, I’ll explain how I use the desktop version of Slack to sift quickly through these channels and conversations. If you’re on a Slack team with one channel and 10 humans, much of the following is going to feel like overkill, but there are useful optimization nuggets below. Important to note upfront that I am very lucky to be working at Slack. The following is full of my opinions, quirks, and neuroses and not those of Slack.


A Game of Microseconds


The rule has always been: if my hands leave the keyboard, I’ll screw it up. For years, I’ve written about the maddening imprecision of the mouse. With due respect to illustrators and other deft operators of the mouse, when I am required to use one, I am presented with too much optionality. It is the intrinsic power of a mouse that its defaults workspace is my entire desktop – each and every pixel is available to click whether it’s the right pixel or not.


I understand and appreciate that for novice users, the mouse’s broad optionality is perfect. It allows for curious unhindered exploration, but once a mouse teaches us the virtual landscape, once we understand how to work, a mouse’s utility fades and I need a clearly defined path to moving faster. There is no more important an area where I need to move quickly and efficiently than how I communicate.


Keyboard support is quite good in Slack. This is good news because my ability to quickly and efficiently find, triage, and respond to information within Slack is not a mouse task, it’s a perfect keyboard job. There are a handful of well-defined actions that literally instantly need to be at my fingertips. Let’s start with two related essentials:


Switch to my unread things ( CMD-K / Ctrl-K (Mac / Windows) ) If there is only one keyboard tip I want you to remember, it’s Cmd-K. The Quick Switcher is inspired by LaunchBar, QuickSilver and other handy context switching tools and it’s dead simple: hit Cmd-K and start typing the name of a person or a channel and when you see what you need, you can instantly jump to any context by hitting ENTER. If I’ve been away from Slack for bit, I hit Cmd-K and glance at the list in Quick Switcher. It’s a prioritized list of direct messages and unread messages.


Show me a recent conversation ( CMD-SHIFT-K / Ctrl-SHIFT-T ) Throw a SHIFT into Quick Switcher keyboard combination; CMD-SHIFT-K (or Ctrl-SHIFT-T on Windows) brings up Direct Message Quick Switcher. What I’m looking at here is a history of all of my single and multi-human conversations sorted by time. The more I work with an existing team, the more I find this conversation history useful. As single or multi-human conversations tend to be higher signal since they’re directed at me, this history is full of conversations between individuals and groups that I need at the ready for the next week.


Don’t Read Everything


My current strategy is to aggressively join channels. I don’t join every channel available, but the bar to get me interested in a channel is incredibly low. Any interest at all and I’ll join. With the current default Slack configuration, this can lead to channel sidebar proliferation, but here is my approach:



In Advanced Options on the desktop, I select the option to show only “My unread, along with everything I’ve starred.” This removes all channels with no activity from my side bar. This changes my default sidebar from LEFT to RIGHT.

comparison-small



After a few hours of activity, the unread counts build. So, I merrily Quick Switch my way through this unread activity. If I need to respond and I don’t have time or the answer, I will star the channel or conversation for a future response. This makes my sidebar a draft of my to do list. To date, this strategy has kept my sidebar tidy and under control in even the highest traffic teams.
Currently, there is one exception to my star policy and that is a “channel of importance”. The only channels which are starred are weekly 1:1 channels that I’ve defined as a running conversation of 1:1 discussions, decisions, and next steps.

There are times when I get behind, and when I end up in this state, the keyboard command I use is Ctrl-Esc. This marks everything read, but doesn’t do anything to my starred items. The FOMO inbox zero zealots in the audience just freaked out a bit. What if there something important in those channels? How do I know what’s essential without reading every single message? Wait for it.


My Sidebar is not my Inbox


For a large group of humans in a company using email, we believe that we’re doing each other a favor by making sure the TO: line of this very important email is populated with the correct humans and mailing lists. Also, protocol dictates the proper construction of the CC: line for the humans who are slightly less essential than the humans on the TO: line. We believe we’re doing the right thing because we believe this is the only way they’ll find this essential information.


This is incorrect. We’re lazy.


It’s not deliberate laziness; it’s tool induced laziness where we feel the need to blast every possible human with this essential piece of data because we’ve come to believe that email is the only source of truth. This makes our inbox a sacred place because it is our connection to our fellow workers. Conversely, we feel that if information is in our inbox, we have a deep compulsion to read it.


Three questions: How much time have you spent constructing mail filters for mails sent TO YOU that YOU REQUESTED that end up in folders that you NEVER EVER READ? For all of those emails actually in your inbox, how many did you read? Finally, how many days of your life have you lost simply worrying about your inbox?


My working and perhaps incorrect assumption in a Slack team is that if a piece of information needs to get to me, a qualified human will make sure I get it by either using the @name convention, sending me a DM, or creating a channel for us to have a longer running discussion of this essential information. Ctrl-Esc doesn’t delete a thing; it just marks it read.


Three More Keyboard Essentials


Further means by which I avoid the mouse:


Edit ( Up Arrow ) Anyone who follows me on Twitter knows that even with the fixed availability of the 78 keys on my keyboard, I excel at making typos. All the time. I completely drop entire words during caffeinated keyboard fury, and Slack messages are no exception. Hitting the UP ARROW in Slack allows me to edit messages. It is strange that this feature gives me so much joy.


Forward and Back ( CMD-[, CMD-] / Alt-[, Alt-] ) The defining characteristic of the keyboard that it allows me to move fast. Often I’ll blast right past a channel with an important piece of information that won’t be relevant until I’ve visited a few more channels. What was that channel again? Like a web browser, CMD-[ and CMD-] allow me to page through my channel viewing history. Handy for that piece of information that just zipped by but suddenly becomes important five seconds later.


Emoji reaction ( CMD-SHIFT-\ / Ctrl-SHIFT-\ ) I’ve resisted emoji for years. My opinion has been the same as my opinion of all messaging abbreviations. If you want to say something, take the time to write the words. Slack has changed my opinion about emoji, and the reason is, again, efficiency. There is a type of communication where all I need from you is the smallest of acknowledgments. I don’t need commentary or an opinion. All I need to know from you is: yes, I received this. Emoji reactions are the perfect low-friction way to deliver this acknowledgment. Here are my current top three Emoji and my internal mental translations.



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Published on July 14, 2016 08:27

May 11, 2016

The Cave Essentials

My favorite feature of my home office is the paint on the walls. It’s blood red. I’m talking deep scarlet burgundy. The ceiling is a single solid red, but the walls are a macabre mix of every horror film red on top of a slightly textured wall. When people walk in the office, it’s this color and texture they see and they often comment, “It feels so, well, oppressive.”


To which I answer, “There’s the door – right there.”


With respect to friends and family, my office is not for you; it’s for me. My office is not designed to welcome nor entertain anyone except me. It’s intended to be a place where I feel productively safe. Those blood red walls? There is not an ounce of horror in them for me. It’s my cave and a cave is a dark place hidden away from all to see. I wear those blood red walls like a warm blanket.


desk


There are three other essentials that, for me, represent a proper cave. They are:


Your forever desk. My primary location in my office is at my desk. As you can see from the photo, I have two 27” monitors – one is an iMac, and the other is a display. Family photos on the left. Secondary desk with the PS4 and laser printer on the right. You might not have even seen the primary desk at first glance which is surprising because it’s the most important part of the picture.


Everything on that desk will be replaced in the next five years. New iMac, new PS4. The family photos will be upgraded with the latest scholastic accomplishments. There will be more pens. That desk isn’t going anywhere.


A desk’s job is to build productivity, and for me, it achieves this by first providing an immense amount of clear working space. When I put my hands on the keyboard, I want nothing around them except a cup of black coffee. There’s space for memorabilia, but it is well outside my line of sight. Second, a desk must be built like a tank. The surface of my desk is two inches of solid wood. The legs and support beams are similarly sturdy. When I put my feet up on those beams, the desk doesn’t budge.


While I, too, take the desk for granted, there are moments when I stop and admire the slightly discolored oddly shaped patch to the right of my keyboard. It’s where I’ve worn through the finishing clicking and dragging various mice over the years. I run my hands over the surface of the deck. It’s smooth, but there are dents and divots. Some of those imperfections are stories, some are simply mistakes, but like a great bag, a desk’s character is one that improves with age.


A deep leather couch. True story. I owned the Pandora.com domain name many years ago. When I sold the domain for less money than you think to the company that became Pandora, I explained to my wife I wanted three things: whatever the fancy SLR camera was at the time, carte blanche to buy a shit ton of books, and a leather couch so deep that when leaned back, you crossed a time zone.


couch


The couch is from Restoration Hardware and it’s nearly four feet deep and almost seven feet wide. If I put my back squarely against the back cushion, my legs stick straight out like a toddler and I’m tall. When visitors sit down and discover this depth, they tilt their head, look at me, and are about say something snarky about feeling like a toddler, so I quickly explain…


“The door… it’s right there.”


This couch speaks to me. This couch says, “You. You there. You looked stressed and I have just the thing. Fire up Netflix, turn on a random Star Trek Voyager, lay down, and how about a quick snooze? Not interested in watching something? How about we re-read the Planetary Omnibus because we’re still not clear what the hell was going on there, right?”


If my desk is where I am productive, my couch in my cave is where I relax. Perhaps I am serendipitously productive or maybe I just find essential quiet between the thoughts on 28 square feet of leather.


Lovingly curated bookshelves. I’ve already waxed poetic about book shelves here. In preparation for this piece, I embarked on the weekend-long task of – once again – curating my bookshelves. If my desk is where I work, and my couch is where I contemplate, my bookshelves are my life resume.


bookshelf


The multi-day process of reviewing and sorting these books is not just organizationally cathartic; it’s a mental adventure where I perform a deep assessment of my current mental state. For example, multiple books on the craft of poker were removed from the shelf. Poker had a good long run – 5+ years – but during my last Vegas stint, I didn’t even think to visit the poker room. Those poker books – gone to goodwill. The writing shelf, the leadership shelf – all well stocked and full of decades of wisdom. The comic book shelf is now shelves as I’ve been on a very satisfying comic book kick for the past six months.


Unlike the desk or the couch, I don’t spend much time at my bookshelf, but like the desk and the couch, my bookshelf defines my office. These are the ideas and the words that I care about. I’ve spent thousands of hours of my time quietly contemplating each one of those books, often multiple times. For each one of these books, there are ten more that didn’t make the shelf. I could buy another bookshelf, but I enjoy the constraint of these 14 shelves. A book must distinguish itself in some way to make the shelf and when it does I want to see it every day.


A desk, a couch, a bookshelf all surrounded by blood red walls. This is the office I’ve designed for myself. I’m sitting here right now listening to Arcade Fire and appreciating that I prefer my coffee mug on the left – far away from the chaotic and spill-inducing movements of my mouse. The white stone polar bear is still sitting there, staring at me, reminding me that everything good that has happened to me is because I chose to write.


polar

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Published on May 11, 2016 07:13

May 3, 2016

Medium or WordPress?

As you may have noticed, I’ve been posting work to Medium for several months now. This started out as an experiment to see the magnitude of the reaction to successful pieces I’ve already written here.


The results? There are a lot of humans out there and many of them traipsing around Medium had never read these pieces. In general, an article that performed well here will play well on Medium provided that it hasn’t been posted here recently.


Folks have asked. No, I’m not done posting here. My policy is to continue to post all new content here and occasionally post pieces to Medium.


Now you know.


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Published on May 03, 2016 10:43

April 10, 2016

You Find People to Be Both Intriguing and Exhausting

I’ve been working on a talk about public speaking for a few weeks and I open with my worst public speaking experience. I tell the story of how I got up in front of the engineering team at my first start-up and had a full blown panic attack. Slide 7 of 15 – full stop. Couldn’t continue.


Most humans don’t like speaking in front of other humans and for me that situation is only exacerbated by being a self-identified introvert.


Thing is… I like public speaking. It’s a high. I get energy from the room and I’ve never been able to reconcile my introversion with this aspect of public speaking. Good news: outgoing introverts.


From The Muse – Outgoing Introverts Do Exist. Here’s one of the 10 signs:



It Actually Takes Less Energy to Say What’s on Your Mind Than to Make Small Talk


Introverts like talking about ideas or connecting authentically. Fake small talk bores you and drains your life force.


Yes. Right. Totally.


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Published on April 10, 2016 09:24

February 20, 2016

A Productive Space

Earlier this week a friend asked if I knew any 5-10 person start-ups that were doing interesting work in the productivity space. I knew a couple, but the always-full-of-opinion Twitter seemed like a good place to learn more, so I asked.


The following is a selection of the surprisingly number of start-ups that responded. I spent max five minutes looking at each and grabbbing initial thoughts. If they were in stealth mode and provided no pitch, I made up my own.


In one year, I’m going to return to this list and see who made it.


Here you go…


Airtable


My first job in technology was building databases, so Airtable resonates. It looks like it’s lightweight databases for regular humans. This is a noble cause, but I worry when a new service tries to be everything to everyone rather than focusing on a single clear use case.


Would I try it? Probably not. I use specialized services like Asana, but I suspect this would be a solid small business tool.


AskWonder


AskWonder appears to be a service where you can ask questions of qualified researchers – a personal research assistant. I signed up, but you’re asked to pick your industry and there is no “engineering” industry, so I picked writing. A simple interface allowed me to ask a question, so I did, “Who are the five most profitable publishers of technology-related books?”


I was then asked to supply a credit card for the $29.99 fee to answer this question. So I stopped, closed the window, and stepped away from the computer.


Would I try it? Nope. I’d use Google.


ClubHouse


ClubHouse is project management software that appears to be based on Agile. My impression is this is a crowded market where it is hard to differentiate. Also, I find it curious that in the past three companies I’ve worked at that we haven’t widely deployed these types of tools. There is certainly a market for this software, but it seems to be a personal choice for a team or two rather than an enterprise choice.


Would I try it? Not until I was at a start-up.


Coach.me


I’m already on Coach.me. It’s a combination of a tool to help you change/maintain habits as well as a tool to help you find a personal coach. As a serial evaluator of productivity software, I could definitely us the former. In terms of coaching, I’ve of the opinion coaching is a dish best served face-to-face.


Would I try it? Maybe, but not for coaching.


Meekan


Meerkan is a service I’ve always wanted, but one that is usually hindered by edge cases. It appears that Meekan is designed to work inside of Slack or Hipchat as a means of doing scheduling and other business activities. Bots inside of Slack/Hipchat. Yes. Good idea. Scheduling? I am biased by the fact that my schedule is crazy, but even with a less crazy schedule, the amount of human intervention necessary in scheduling a meeting with four humans is surprisingly high. I’ll explain.


Please schedule a 30 minute meeting with Ryan, Angela, and Tony on Wednesday. This is not a complex action. The bot needs to look at four calendars and find a common 30 minute slot on the next Wednesday.


But what if there isn’t a slot? Well, I’d guess the bot would helpfully find the next available slot. Hey Rands, there is no open slot on that Wednesday that all the participants can meet. What about 1:30p the following day?


Thing is… the meeting must happen. If it doesn’t happen, we likely lose $100k. Can I require a meeting to happen? Yes? Ok, how does a bot know which meetings are high versus low priority? And, by the way, we haven’t even talked about conference room availability.


No doubt that there is a large market for bots inside of Slack-like social spaces, but bots have yet to prove to me they can do more than very simple tasks.


Would I try it? Maybe.


Numerous


This is an app to help you keep track of all your numbers. They’ve created all sorts of interfaces to things that produce numbers and allow you to aggregate said numbers in one place.


This app stresses me out. I’m already at war with notifications on my phone and the idea that I’d build hooks into other services I’d use to give me more notifications appeals to the number counter in me, but no. So very no.


Would I try it? No.


Pingpad


The fact a good portion of the world still uses Lotus Notes (now: IBM Notes) tell us two things:



The world needs collaboration software;
Once collaboration software is truly adopted at scale, it’s nearly impossible to dethrone.

You might’ve giggled when I mentioned Lotus Notes, but take a look at your work life. Are you on Exchange? How about Gmail? It’s the same thing. A crap interface that you’re locked into because everyone else in the company is already there.


Meanwhile, apps like Pingpad offers real time collaboration on notes, lists, photos, and message, too. Their sizes allows them to actually evolve and innovate, but the more I stare at Pingpad, the more I wondering… isn’t this just Slack?


Would I try it? Maybe.


Small Wins


In stealth mode, so I get to dream on this one. I hope these folks are building a tool which allows teams of humans to broadcast and share wins across the team in an attempt both recognize excellence, but also to slowly replace the antiquated system of yearly or bi-yearly performance reviews.


Would I try it? Can’t tell.


Sortd


Kind’a excited about Sortd because I’m currently in a “use my inbox as a to-do list” phase. Gmail is designed by engineers so it has a bajillion knobs and dials to allow to me to adjust it… just so. This has resulted in a solid three weeks of close-to-inbox-zero, but the true test of any productivity is not the first three weeks of bliss, it’s what happens when something explodes. Reorg, unexpected travel, surprise resignation. The true power of your productivity is determined by it’s resiliency to the unexpected.


Sortd is Trello for Gmail. It allows you push mail to different lists like “To Do”, “Follow up”, or whatever list floats your particular productivity boat. Sortd merges your inbox with your to do lists and it appears to do it without imposing a lot of cognitive load.


Would I try it? Yes.


Superhuman


Kind’a excited about Superhuman too, but they’re all stealthy, so here’s their blurb:



Superhuman is not just another email client. We are rebuilding the inbox from the ground up to make you brilliant at what you do. We are specifically designing it for professionals and power users. Especially those with very demanding inboxes.


Superhuman is gorgeous. Blazingly fast. And comes with advanced tools and features that make you feel superhuman.


I’ve been waiting for a new view into my inbox for many years. Been mostly let down. Willing to be let down again.


Would I try it? Yes. Because email.


Canvas


(Disclosure: I’m an investor in Canvas.) Canvas is also stealthy, so here’s their blurb:



Writing is the best way we’ve found to communicate, especially at work. But all the existing tools we’ve used are stuck in the past. We deserve a product worthy of our everyday notes as well as our greatest thoughts. A hackable, opinionated product that’s made for us, developers and designers.


Would I try it? Yes. Because writing.

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Published on February 20, 2016 14:19

February 9, 2016

Operator is a monospace typeface from Hoefler&Co

From typography.com:



About two years ago, H&Co Senior Designer Andy Clymer proposed that we design a monospace typeface. Monospace (or “fixed-width”) typefaces have a unique place in the culture: their most famous ancestor is the typewriter, and they remain the style that designers reach for when they want to remind readers about the author behind the words. Typewriter faces have become part of the aesthetic of journalism, fundraising, law, academia, and politics; a dressier alternative to handwriting, but still less formal than something set in type, they’re an invaluable tool for designers.


I’ve dropped Operator Mono into both Sublime and Terminal. A monospace typeface needs to be readable and without a lot of opinion. After brief usage, Operator Mono easily meets both requirements.


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Published on February 09, 2016 11:11

February 4, 2016

I ask how they were treated

I’ve been fretting about the role of lead of leaders. I have a good rubric for understanding and evaluating front line leaders, but lead of leaders is a very different gig that requires a different set of leadership muscles. Briefly and incompletely, they need to be better at:



Delegating work
Influencing
Decomposing vision into strategy
Executing that strategy
Building of new leaders

This article documents interview questions of CEOs – some useful material here.


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Published on February 04, 2016 08:18

February 1, 2016

The Illusion of Competence

My favorite moment playing hockey is literally a moment. The puck gets passed to me just behind the net, I look up across and I ask myself a simple question, “Hmmm, what am I going to do here?”


In less than an instant, I do the following:



Who are the two closest players on the opposing team? What is my impression of them? What are their weakness?
What is the right path to start my approach? Charge down the middle? Hang right? Hang left? What are likely obstacles in each direction?
How fast? Sprint now or wait until I have more data?

And I execute. Cut back behind the net because Eli, their forward is sloppy at right turns and is left-handed. Sprint — because there is room mid-rink.


The plan is never executed as I expect because in hockey everything changes in a moment. So I get to do it all again “Hmmm, what am I going to do here?” Melissa, my forward, is ahead of the play and, wow, can she skate, but remember – left handed. Lead her a bit and then bolt to her left because she’s going to need an outlet pass in about seven seconds.


The outside observer sees none of this. They see a singular fluid motion as I travel from one end of the rink to the next, they nod their head and think, “He makes it look so easy.”


Let’s be abundantly clear. I am a nerd and that means for most of junior high and high school, the idea of team sports gave me the shakes. I much preferred the anonymous confident solitude of video games and BBSes. I ran cross country and I did some swimming, but neither of those involved anything resembling teamwork. You ran, you swam. Someone added up the points and declared a school the winner.


Do you know what I did in order to appear competent at hockey? I played a lot of fucking hockey — for years. Now, I do have NADD which means I have a singular ability to apply myself to understanding a thing, but it was still months before I could skate with any sort of competence and it was years before I performed anything resembling a move on the rink.


That’s the illusion of competence. By making it look easy, you fool them into thinking it’s not hard. And that’s a pleasantly aspirational idea. The idea that there is somehow magic that is going on to make the complex simple.


But it’s always hard work.

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Published on February 01, 2016 07:16

January 31, 2016

Average Tenure is Nine Months

I’m not sure what is more surprising. There’s a dog-sitting start-up in Seattle called Rover or:



The average tenure of a developer in Silicon Valley is nine months at a single company. In Seattle, that length is closer to two years.


I’d like to see the source data on this assertion. Not the existence dog-sitting start-up part.


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Published on January 31, 2016 09:42

January 26, 2016

Powerful people are terrible at making decisions together

Via Corinne Purtill on Quartz:



The higher the concentration of high-ranking executives, the more a group struggled to complete the task. They competed for status, were less focused on the assignment, and tended to share less information with each other. Their collaboration skills had grown rusty with disuse.


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Published on January 26, 2016 07:47

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