Rands It's hard to have nice things on the Internet

Just Hard Work

I started this piece in late November. It’s a piece I usually write Christmas as a kick-off to the new year. The precise process by which this yearly piece arrives is a mystery. Probably the mental reset that comes with the New Year. So, what’s with the first draft showing up before Thanksgiving?

As I wrote earlier, I’ve been turtling since the US Election. Mostly avoiding all news, standing up and politely walking away when the conversation sways towards politics, deeply diving back into a video game legend. You know. Classic avoidance.

I’m also writing a new book about — wait for it — that’s right, leadership. This topic was inevitable, but since the election, I’ve been wondering whether there is something original or new to write, given the current circumstances in the United States.

Probably not.

Like many friends, I’ve chosen to focus my efforts on family, community, and work. Attempting to comprehend, let alone influence, the larger narratives on the planet strikes me as a particularly futile effort in what appears to be a post-literate society.

So, at the beginning of this year, I want to tell you a small leadership tale about the Rands Leadership Slack and why it works.

The Rands Leadership Slack is a community I created on June 1st, 2015. It’s, yes, a Slack, and as of this writing, it has almost 35,000 members. Over 5,000 of those members are active every week. There are over 800 public channels, and while many are focused on the craft of leadership, there are hundreds of non-leadership channels. I now play a game where I wonder, “Is there a channel for X?” I find said channel and over 100 members are usually already chatting about the topic.

While I am proud of this blog, the Rands Leadership Slack is the most impactful thing I’ve built outside my family and job. Thousands of community members discuss and learn from each other every day.

And it’s hard to have nice things on the Internet.

Here’s how we do it.

Endless Hard Work

First, there was a bit of luck. I was pretty quick to see Slack would be a good tool for this type of community, but Slack, by choice, was not designed for community. The free plan is designed to give you a taste but not a scalable community. After 90 days (or a certain number of messages?), you must pay to see your history. This was Slack’s chosen business model.

I spoke at Slack before I became the VP of Engineering, and they graciously agreed to comp me a pro edition of Slack with no restrictions. They don’t do this anymore. Don’t ask. This generosity allows us to see the entirety of Rands Leadership Slack, which gives the community memory and history.

Second, there is endless hard work.

I use the process for each application, which you can read about here.

  • Receive an email from an applicant.
  • Read the email and determine if they can follow directions.
  • If they can’t, send them a follow-up email that explains the directions again. This is a template. I don’t type this each time.
  • If they can follow directions, send them the invite plus the onboarding directions, which ask them to read the Code of Conduct. Set their profile image to anything but the default, and once logged in, introduce themselves on intros and drop me a direct message on Slack.
  • If new members directly message me (I feel 40% of the new members do this), respond briefly but thoughtfully.

There was a window where existing members could invite new members, but as I wanted everyone to experience the same onboarding, all applicants now follow the same process. My estimate is that I’ve sent around 39,000 emails (roughly 10% of invited applicants never joined).

39,000. Spread that over nine years, that’s not huge amount of daily work, but it is a process I have consistently followed for almost a decade. Many applicants who are aware of the size of the community assume there is either a small army of admins who handle this or that we’ve got robots doing the work. We don’t. It’s just me. 39,000 mails.

While the size of the community is an essential aspect of the community, this is not what makes it valuable.

Listen, Understand, and Learn

Given the by-design upfront choice not to open the floodgates on user growth has never been outrageous; it has been steady. This gentle and mostly predictable user growth means that social breakdowns that occur when many strangers are suddenly shoved together don’t occur… as fast.

Around the five thousand-member mark, we had the first community request for a Code of Conduct. We had the first serious issue with a member where it was clear that I, the only admin at the time, would need to act. But how? And based on what? My random judgment? At that time, I had this aspirational but erroneous belief that because it was a leadership community, members would bring their best leadership skills to the table, and the Code of Conduct or other cultural artifacts were unnecessary.

My resistance to calls for a Code of Conduct and subsequent additional requests for a formal administration team was impressive… and delusional. I was in New York at the time and spending multiple hours each morning with requests for comment from the community when I finally threw up my hands, found what looked like a good Code of Conduct on the Internet, branched it, touched it up with a smidge of Rands™, and sent it to the complainers.

“Happy now?”

“Yes.”

wut.

The magnitude of the impact of the decision to create our Code of Conduct dwarfs my decision to keep growth sensible by designing a robot-unfriendly complex application process. The fact that it exists addresses many initial concerns of the community. Its regular use in conversations within the community gives us a useful playbook for deconstructing complex people issues. Most of every week since the Code of Conduct landed, I’ve used to explain a bit of this community to another member. Most months, I take time to edit it to help clarify the thinking laid out in the artifact. Policy changes land in the document multiple times a year because I do what I initially failed to do when the community asked for its existence — I listen.

When I realized the single best feedback source on what the community needed was the community, my job became obvious. Not enforcer, but educator. This feedback does not arrive conveniently. It’s usually packaged inside high drama. Two or three, or fifty members are ready to fight. Tempers are often high. When they show up, I clench my jaw and remember that while they might not know it, they are teaching me about the community, and I have to listen to understand the lesson. I have to empathize with the concerns, but not so much that I participate in the often heated emotions. My job is to ask questions to gather as many perspectives as possible. Finally, I must decide: “Does our Code of Conduct help resolve this situation? Or does it need to evolve?”

I need to find the lesson and then do the work to teach that lesson to everyone else.

Lead Peacefully

One of the favorite lines from the Code of Conduct:

“As a leadership community, we believe peer-to-peer discussions, feedback, and corrections can help build a stronger, safer, more informed, and more welcoming community.”

I interview and hire a new set of admins every two years, and within a few months of their start, a new conflict emerges in the community. As new admins, they ask me for advice, and I point them at this part of the Code of Conduct and ask some version of it: “Did you see if they attempted to resolve the situation themselves? It is a leadership Slack, after all.”

“But shouldn’t we help?” they ask.

“We are helping by suggesting they use their leadership skills to attempt to resolve this situation by themselves.”

It’s easy to make instant emotional assumptions about other humans, especially after decades of training on social networks. Our culture asks members to do the work, step outside of themselves and consider the perspectives of others to find a lesson they might not have seen. It doesn’t always work, but it’s where we start.

RLS will celebrate its 10th anniversary later this year. It is the highest-quality, most inclusive, and most authentic leadership community on the planet.

And it only took one hack: Hard work. All the time.

Happy New Year.

Management Impending doom. Just the hint of it.

Managing Up

My problem with the phrase “Managing Up” involves a hard-earned historical observation regarding its weaponization. The helpful version of this practice is a clear understanding between you and your manager that there are uncommon, intriguing, or worrying developments that you — without hesitation — share with your manager.

Isn’t that their responsibility, as well? It is. Also, wouldn’t you expect them to have significantly more of these observations because their observational blast radius is larger? They do. Do we call this “Managing Down”? Gross. No, we call this bi-directional effective communication, which is a mouthful. This is also only half of a correct strategy.

“Managing Up” is problematic because it often describes a subset of humans who perform this task, believing, “I am artisanally selecting the most important bits of information to share upwardly because my judgment is incredibly sound.”

This is not what they are doing. What they are doing is manipulating perception. They have a specific selfish narrative they want their manager to build, so they carefully select a subset of the truth and market it as the complete picture. They believe their manager is so busy and soup tasting that their interpreted version of the story will become canonical.

Bad news, truth tweakers. A competent leader will source their facts. They will share that partial story with a trusted other not because they don’t trust you but because a story must defend itself, stand up to scrutiny, and prove its worth. They don’t do this because they don’t believe you; they do this because it’s perfectly reasonable communication hygiene. When they discover you’ve delivered half the story, they will quietly ask themselves, “Why half? Are they trying to save me time, or are they trying to lead me astray?” One occurrence of this behavior is no big deal. A small error. Two occurances? Is this a pattern? Probably not. Wait, three? Ok, why are they deliberately choosing to tell me a dubious version of the truth?

Managing up. If you were drawing a word cloud of dubious management-related phrases, chances are, “Managing Up” would be proximate to “Kissing Ass.” To me, “Managing Up” has that “your boss’s job is more important than yours” feel, which pisses me off.

Your boss isn’t more important than you; it’s different. You are responsible for yourself and the professional well-being of your team of seven engineers and your product. Your boss is responsible for her job, you, your six peers, their 57 respective employees, and the four products. That’s 72 humans and five products if you’re keeping count.

As you move “up” the organization chart, the amount of responsibility that weighs on a manager increases significantly, and, yes, this does mean they often make more money than you, but that is often because they have more years of experience. This experience allegedly means they can complete a more diverse set of work at vaster scale because they are you in 5-10 years, but — I remain steadfast — it’s different work.

But each of you has equal responsibility for sharing information.

Essential Information

Okay, thanks for letting me vent. With that out of the way, let’s get practical.

The amount of aggregated information you need to do your job increases as a function of the magnitude of your responsibility. This means you must become adept at finding, confirming, understanding, and passing it along in the correct direction.

That’s what you’re looking for — information that has passed through the bright minds of your team, where they’ve coalesced the vast amount of information they see into informative, crisp narratives. One challenge is they know you have six other leaders doing precisely the same thing, so they need to prioritize and choose which narratives to share.

What’s important to share? I’m glad you asked. There are three areas where the information requires constant vigilance:

  • Projects — the things you build, the large tasks you complete, and the significant work involving many humans.
  • People — all the humans around you in every direction helping you complete the projects.
  • Politics — the connective communication that binds all the humans together — easily manipulated for good and evil.

In this piece, I will explain the projects, people, and political developments you always want to share — no matter what. While I will strive to make this complete, there is one type of development you must always report:

Unexpected developments. A situation appears in front of you, a non-threatening one but unexpected. Strange. Something is up, but you can’t discern the backstory story or the intent. It is unfamiliar. Tell your manager. Now. Just a brief note. A heads up. It’s probably nothing — it usually is — but there is a chance your manager’s context plus your suspicions equals additional clarity.

I want to start by acknowledging a fundamental professional tension. Your managers want you to believe you can do your job without them (which everyone wants, by the way), but when you fail to keep them informed about important developments within the team, it looks like you don’t know how to do your job (which no one wants, by the way). Confusingly put, neither you nor your manager is doing your job correctly when you’re sharing too much or too little information.

Here are the areas:

People

  • A significant unexpected change for a key individual on the team. Life situation, odd conversation that doesn’t add up, or, again, a perception that something is up.
  • Major successes. It needs to be communicated even if it was supposed to happen like this for them. Exceeding expectations is worth noting. Every time.
  • For humans on your team, with an agreed-upon growth plan you’ve shared with your manager, you report minor successes against this plan. Failures, too.
  • Anytime ever that anyone ever thinks about saying the words or phrases “Human Resources,” “People Team,” or “Legal.” Even if they claim to be joking, the fact they are thinking of these teams is a fact that must be shared.

Projects

  • A significant positive or negative development on a critical project. Not the resolution but the observance of the development at first sight. This is even more critical when your manager has a professional stake in the project’s outcome.
  • Projected-related gossip from external high-trust parties. Might be gossip. Might be an early warning system. Could be political. Keep reading.
  • Achieved milestones. Missed milestones. Contributing factors and recommended fixes are appreciated for those missed milestones, but waiting until these are perfectly defined is often a tactic motivated by not wanting to share bad news. The sooner I hear bad news, the more I can help.
  • Impending doom. Just the hint of it. A slight smell in the air.

Politics

  • Interesting developments on external teams where we have a project dependency.
  • Gossip, rumors, and lies about the project. Yes, much of this information is false, but the fact these rumors are wandering the hallways is news. Folks are spreading this misinformation for a reason that is worth discovering. True story: there are humans out there who insert lies into the organizational bloodstream to see the reaction. They call this pressure testing, and these humans are jerks.
  • Just. Plain. Weird. Yeah, it’s a catch-all. Yeah, it’s the hardest to define, but sometimes people say the darndest, strangest things, and rather than scratching your head and staring at the ceiling, tell someone else this weirdness and see what happens.

Do all this consistently with your manager and team; again, you’re working with half the information.

Managing Sideways

My actual problem isn’t with “Managing Up” or “Managing Down”; if you do this well, you’re still only working with half the necessary information. You and your manager collectively represent half the information required to do your job. HALF.

Look to your right. Look to your left. That’s the other half, and you’re probably ignoring much of it. It took me a couple of decades to properly value horizontal relationships and their context. Why? Because everyone kept asking me if I was “Managing Up”. [facepalm] My manager told me what to do; they set my compensation, so I managed the relationship because they managed me.

People, projects, and politics. Your relationship with your manager represents half the information you need, half the context. It doesn’t mean you can’t do your job, but it’s not a stretch that you are missing critical developments because of the absence of this context.

If you don’t believe me, it’s because the lesson hasn’t been hammered into you by the path of senior leadership, where you become increasingly distant from the measurable familiarity of hands-on work and become adept at building a sense of satisfaction and productively finding, confirming, understanding, and passing along critical information.

And you are not doing this alone.

Rands Seek understanding

The Cleanse

I’m in the midst of a media cleanse. This started before the election when I canceled my Washington Post subscription. Jeff Bezos can do whatever he wants with the Washington Post, and he’s 100% correct that I don’t trust large media organizations.

After the election, I removed all news sources from Feedly except the Atlantic because I find their writing informative and compelling.

A friend calls this turtling. Pulling your head inside your shell and hiding. It’s quite comfortable here. With most of my free time, I’m leveling a dragon Holy Priest in World of Warcraft. #ama

Next on the list is Twitter. Since it was sold and turned private, my engagement has been significantly lower, and my follower count has shrunk as the humans have moved off the platform, but quite soon, I’m deleting my account. My finger has been over the DELETE button for a few days, and I’ve wondered why. Two facts: First, there are thousands of folks with whom I share stuff there. I can see they are there via much reduced but real engagement. Second, I have just under 20k tweets since 2007 that, upon review, tell an interesting story… at least to me.

I’ve downloaded the complete archive, and I’m sad to say I’m about to create a bunch of 404 errors when my corpus of tweets vanishes from Twitter. Why? This is my content, and I don’t want whatever Twitter has become to benefit from its existence. I’ll share the archive here at some point, but for now, I’m cleansing.

Like FaceBook before it, Twitter turned into something else. They both, early on, felt like a means of connection. Unfortunately, building that social graph allowed these businesses to target you and your engaging, clickable content expertly. What was a means of connection turned into hot, juicy, bite-sized content. Over the past two decades, this practice has made us intellectually lazy because these media services are paid not on the quality but the quantity of service. More clicks, more engagement. Truth and facts. Optional.

And what was a clever means of connection turned into a raging stream of clickable things.

So, bye, Twitter. I’m late to the funeral, but better late than never. It was fun before it got terrifying.

While I am profoundly turtling and have little desire to see a path forward, I have two related observations:

First, the lack of healthy debate on most social media is one of the core issues with the platform. Humans must disagree, but these platforms do not provide a proper bi-directional medium (or set of tools) for these debates. It’s liking, then not liking, then yelling, then ALL CAPS, and NOW I’M UNFOLLOWING YOU and YES BLOCKING BYE.

Debate is a tricky act between two humans who can both speak, listen, understand, and possibly evolve. Two humans. Often, there will be more, but let’s keep it simple and assume it’s two. Both humans are required to do this, and in the primarily anonymous world of social media, it’s normal not to consider the other human a human. They are the last thing they wrote that you disagree with. There is no relationship; it’s simply the last thing they posted. And how do you feel about that post.

The stakes are higher in person. You have to stare at that human in the eye, especially after they say something you don’t like. So, what do you do? You can’t yell, you can’t ignore them, and you certainly can’t block them, so what is your move? Mine: seek understanding. Put on that empathy hat and try to understand why they’re saying what they’re saying. That’s the first step. There are many more — read the book.

The continual failure to do this in social media results in a growing echo chamber where the humans agree, and those who disagree are quickly voted off the island. Some of these echo chambers are low stakes. Think about your favorite sports team. Those fans are aligned on what’s important. Who needs debate? The only debate we care about is what $OTHER-TEAM we hate the most. Go $OUR-TEAM.

There are higher-stakes echo chambers, too. Use your imagination here.

Second, it’s not a short or medium-turn fix to what ails us, but I am curious about investing in local and independent news organizations. Large media organizations have to compete with social. They desperately need those clicks, and that means mimicking the patterns they see in social. The headline must engage in one second or less, or it will be forgotten. It’s an economy of attention, not understanding or truth.

Local media has taken it on the chin for decades because social media consumes advertising dollars. Local media has withered without that support, with remaining big media sources bending to social media engagement patterns. The idea of investing in local media news organizations is because they report on the events that happen in my neighborhood. This makes them more human to me. They have skin in the game because, like me, they live here. My problems are their problems, which means we have a solid foundation to start to understand.

How do I go about this investment? Where do I start?

I don’t know. I’m turtling. For now.

Rands That's curious

Hold Your Breath

Hi. I’m stressed, too. Here are random thoughts on this from the beginning of November 5th, 2024 — election day:

  • Today, a convicted felon and failed businessman (six bankruptcies!) slash narcissist slash twice impeached politician who does not believe in democracy, who called for and achieved an armed insurrection, and who lies compulsively is the Republican nominee for the President of the United States.
  • While the presidency is at stake today, winning the presidency is only part of what is decided tomorrow. There are countless House and State elections, State Supreme Court, and other Statewide offices on the line tomorrow, which leads me to a strangely comforting thought…
  • There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

Hmmm. This is just stressing me out more. Let’s try something different.

That’s Curious

If you ride a Waymo, they’ll flip you off.

Waymo is an autonomous vehicle available in San Francisco. No driver. All robots. I’ve taken ten rides so far, and it’s a coin flip if someone gives me the finger. There’s the folks on the street. Other drivers. Really, anyone might flip you off.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the middle finger might include the following:

  • Anger with a service that will make a bunch of jobs irrelevant.
  • Abstract anger with the general idea of artificial intelligence and what it might present to the human race.
  • Fear. Pure fear of the unknown. We, as a species, have an impressive history of doing incredibly stupid shit because we’re scared.

Fear is natural. It’s equal parts rationality and irrationality. Shoved together instantly when you are quickly presented with a suddenly unfamiliar situation. It’s your brain flipping the high alert switch because you don’t know what to expect next, and the stakes appear high.

So you react. Fight or flight.

And then you flip off the robot car.

Cool.

There’s another emotion you can experience in a car, and that’s road rage. This is the moment you’re behind the wheel, and another driver cuts you off. In a second, you go from calmly driving down the highway to a vicious, rageful human bent on the destruction of this other.

In an instant.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the rage might include the following:

  • Surprise, your calm drive to work was suddenly interrupted.
  • Anger at this anonymous whoever interrupted your calm drive to work and threatened your safety.
  • Finally, and full disclosure on this one, I did research here; you’re probably male and either already stressed about something else and/or have higher levels of impulsiveness and aggression on the road.

Understanding that, as a human being, you can have these real and immediate visceral reactions is essential because these reactions are being exploited daily1.

On Curiosity

I mostly ignored the mid-terms. I ignored it because most of the content generated that cycle wasn’t news; it was carefully constructed incendiary entertainment posing as news designed to get me to flip off someone. It was not designed to inform but to get me to react. Quickly and emotionally. No reason. Fight or flight. I chose flight.

This political season, I’ve been all in. Since last November, I have completed one small act each day. This can be a donation, or this can be an action like writing and editing this piece. At the outset, I had a blank slate regarding what I knew. I spent a lot of time understanding how political payment processing works. I built a remedial understanding of the critical issues in each swing state and read about the intricacies of voter suppression. Curiosity is a feedback loop. The more I learn, the more I can inform and target my actions. It’s delicious. Information is empowering.

And calming.

Elections have been gamified. The stories from major media outlets are designed to get you to engage and not to think. In fact, they’d much prefer if you forwarded that link with that clever headline to all your friends… who cares if you read it? We need the clicks. We need that sweet advertising revenue.

Campaigns run the same playbook, but they don’t need your clicks; they need your money, and that means they must convince you, scare you, and motivate you with an artisanally crafted crisis tailored to get you not to think but to flip off the robot car and then donate as frequently as possible.

The Big Lie

The only vaccination I know to the incessant barrage of memes, rage, and compelling lies is education. One of my daily acts has been educating myself. When someone makes a bold claim on the news or social media, I take the time to understand what they are saying and the history behind it. Many of these research adventures have led me to the darkest chapters of United States history, where I’ve learned that this group of oppositional humans has always existed. Its election deniers in 2024; in 1865, after losing the Civil War, unrepentant Confederates were sent to Washington as senators and representatives.

Congress refused to seat them and drafted part of the 14th Amendment “to perpetuate, as a constitutional imperative, that any who violate their oath to the Constitution are to be barred from public office.”

I didn’t know that. Now I do. We both do.

The biggest lie they propagate is devious and deflating. It’s the idea, the feeling, that there are many — more of them than you. They do this by being loud and outrageous, minimizing those they consider less. They want you to think they are legion because they know they are less. There are more of us than them. Not Democrats or Republics, but decent, kind, and thoughtful humans. I’m talking about people who want the best for others and are willing to do the work to help each other.

So, today. Vote, then stop watching the feeds. Turn off the TV, which is more entertainment than news. Don’t worry. The results will find their way to you. I guarantee it. While it does, take time to teach yourself something. Go deep. Call someone you know is stressed and ask them how they are doing. They’ll laugh nervously. That laughter, that’s stress transforming into relief. You helped. Briefly. Call another person? Sure. Do 15 minutes of your favorite exercise. Even better. Your brain does its best work when it’s working out; today, you need your best work. Tomorrow, too.

There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

But there are more of us than them.

Now breathe.


  1. Oh, Waymo? They delivered absolute magic. Try it. It will exceed your expectations and give you a glimpse into a possible future where serious crashes are significantly reduced because 94% are caused by human error. There will be unforeseen consequences, upsides, and downsides, but as a super fan of progress, Waymo is on a short list of moments I know I’ve seen a compelling future. 
Writing Be ok with that

Your Writing

  • Less than 1% of your writing will be life-changing.
  • 3% will be trivial to write.
  • 4% will strongly resonate with others in a way you didn’t expect.
  • 5% will be quite good.
  • 15% probably should’ve never been published.
  • 26% will elicit a reaction you did not expect. Positive or negative.
  • 28% will become vastly better because you chose to edit.
  • 30% will start as one piece but finish as another.
  • 40% will be good solid writing.
  • 45% will do much worse than you expect when published.
  • 60% of your writing will never be finished. Be ok with that.
  • 100% of your writing is worth your time. 1

  1. Thanks to the folks at the Rands Leadership Slack for reviewing an early version of this piece.