Management This. Forever.

You are Going on a Quest

The most common conversation I’ve had during the last three start-ups was the growth conversation.

Some version of: “Rands. I am here. How do I get there?”

For leadership-minded engineers, there are four career paths available to you. I will describe three briefly, and then I’ll talk about the fourth one a lot.

The first three career paths for leadership-minded engineers are CEO, CTO, or VP of Engineering.

If it strikes you a little saccharine or aggressively optimistic about showcasing these executive’s roles to an engineer who just graduated from the University of Waterloo with barely a year of experience under their belt, remember two things. First, the amount of career opportunities at a rapidly growing start-up is a lot. Double-digit hiring for multiple years means there are monthly new leadership opportunities. Second, unlike other large companies, the CEO, CTO, and VP are visible actual humans instead of “Person Who Keynotes from A Far.” This makes substantive discussion regarding these working humans aspirational and informational, as you can see with your own eyeballs how these leaders work.

The common response to my initial explanation of the three roles is silence which is expected. The person sitting across the table probably wasn’t thinking about becoming the CEO, but now they are. They are still wondering about tangible and actionable next steps for their career, but they are, more importantly, lacking a helpful framework to think about their growth. Good news, I’ve just introduced the beginnings of this framework.

CEO. Her job is the whole gosh-darned company, whether that’s product, engineering, people, real estate, legal… I could go on because the list is everything. A CEO is accountable for every single moving part, and if the human sitting across from me wants to head in this direction (the vast majority do not), then my advice is to get out of engineering. You’ve already spent at least five years of your life becoming a qualified engineer. If you aspire to run the whole show, you need to get real experience in other parts of the organization. A small leap is product management; a larger leap is running a non-engineering function like customer support.1

CTO / VP of Engineering. I can’t describe the role of CTO2 without describing the role of VP of Engineering. At a start-up, the CTO is responsible for building the machine. The product. The service. Whatever this particular company brought into being and is now selling. This could have easily been the founding VP of Engineering, but in my experience, the early engineers with leadership aspirations gravitate more towards the CTO title because it’s… shinier.3

At less than 50 engineers and without many managers, the CTO quickly realizes she needs to scale the leadership strata at the company. Still, she also knows she loves building and doesn’t aspire to lead the process, product, and people stuff that has suddenly become all that she does.

Enter the VP of Engineering. The CTO built the machine. The VP of Engineering’s job is to run the machine. Whether they are peers or the VP works for the CTO, the division of labor is roughly the same: the CTO is accountable for the technology (current and future), and the VP of Engineering is accountable for the humans who build the product, the process they develop to get that job done, and the politics (good and bad) with other teams who all significantly contribute to delivering the product.

My brief career advice for each role matches these responsibilities: if CTO lights you up, then the opportunities we’ll find for you are deeply technical and increasingly complex. We need you to stay profoundly technical and in touch with the engineers (regardless of title) who deliver bleeding-edge relevant work. If VP is the role, the opportunities we’re looking for are still engineering-focused, but we’re looking to use the other side of the brain. Work with growing the humans, the signing of process accords with other teams, defining culture, and building useful communication bridges across the company with essential partners.

The above framing is intended to start a career conversation, and after having several hundred of these, I can confirm the framing works to get a conversation started. How that conversation twists and turns is a function of the human across the table, the company’s culture, and the current leadership opportunities at the company. It is the first of multiple conversations, with each one finishing with a clear spoken-out-loud commitment to “This is what we are going to do next.”

This. Forever.

You’re right. I said four roles. Thanks for paying attention.

The fourth role is by far the most important. It’s the role the vast majority of engineers will follow in their careers, and I’m going to call it “This. Forever.” The role you have right now is the thing you are going to do be doing forever.

Yup. You read that right.

Facts. The vast majority of engineers will not become engineering managers. It sure hasn’t felt that way for me for the past two decades, where I’ve spent my time building the leadership detritus to mint new managers out of necessity.

Unsurprisingly, engineers begin to believe the only path is that of management in these start-up scenarios. It’s the only way to maintain relevance in a rapidly evolving situation from everything they’re seeing. As a primary contributor to this erroneous perception, I apologize. We managers shine so much light on management’s necessity that we forget that leadership comes from everywhere.

And chances are you going to be doing this… forever. The name of the company might change, you’ll have a new manager now and then, and the product will have a different name, but the work you’re doing now is the class of work that will dominate your work life for years.

A depressing thought? Not when you remember you’re on a quest.

Poetry, Not Tasks

I just had a birthday. My wife wrote a very nice birthday card where she listed things she liked about me. Item number four on that list read, “How you are always on a quest.”

She’s right. At any point in my life, you could ask me, “What quest are you on?” and I’d instantly have an answer:

  •  Growing an American Chestnut.
  •  Making sure I don’t miss out on this Internet thing.
  • Figuring out how humans make decisions.
  • Explaining leadership to engineers in a helpful way.
  • Getting the hell out of a no-win job scenario.
  • Writing and publishing a book

Some of those quests were finite and understandable. Others were subjectively hilarious, but, again, if you stop me in the hallway and ask me, “Rands, what’s your quest?” I will tell you.

Notice. None of those quests read “Become a VP.” I indeed spent a lot of time thinking about what it’d take to become a VP, but the quest wasn’t the title. The quest was a cascading series of quests of advancement that gave me the confidence to believe I was qualified or that helped me build a network of humans over the years, so leadership opportunities appeared. When the interview request finally landed years later, it was an important event that resulted from a variety of quests.

Quests are actionable. They are understandable. They aren’t tasks. They are work with a bit of poetry. They are always front-of-mind, and if I’m not on a quest, my wife can confirm that my only goal at the point is, “Find a quest.”

A title is a sign-post. It tells you where you are. A title is a comforting reminder of where you are, but what is more interesting is where you are going next and how you will get there. This will involve a quest. I stand firmly behind my career title opener because it begins a vital conversation; it’s starting a story with the human across the table, not about what title they want, but what quest they need to begin.

  1. I’ve done this before. I was accountable for the people team, marketing, and the cafeteria. I was horrifically bad at all three.
  2. There are companies where the CTO title has been a parking lot for valuable engineering leaders who we can’t let go of and aren’t doing anything.
  3. There’s a variant to CTO, which I’ll call “Chief Architect.” Both of these roles aspire to keep banging on keyboards and inventing more products and technology. The difference between the two roles is that the CTO is willing to wade into some politics and is willing to do some people work, but the Chief Architect wants absolutely nothing to do with this work. That’s cool. Keep inventing.
Tech Life You've been warned

Doomscrolling at Scale

WARNING: The contents of this article might adversely affect your information consumption habits.

A few weeks back, the sitting President incited domestic terrorists to storm the Capitol, so they did. For reasons I still don’t fully understand, this was a relatively straightforward process for the insurrectionists. It was also an incredibly well-documented events thanks to both journalists who risked their lives documenting the riot, a soon-to-be elected official who – fascinatingly – live-streamed his illegal participation, and, finally, the domestic terrorists themselves who were looking to boost follower counts by posting images of their illegal acts in real-time.

The real-time nature of January 6th lent itself to observation via social media. As it became clear the domestic terrorists were breaching the Capitol, I was glued to Tweetbot, my favorite Twitter client, looking for the latest developments. Years ago, Twitter put limits on their API, effectively lobotomizing third-party clients. This meant within Tweetbot, I had to sit and wait for slow manual refreshes of the latest tweets on the insurrection. And there were a lot of tweets. It was a rapidly developing, incredibly well-documented event, and it was clear I was missing content as I sat there glued to Tweetbot waiting for my horrifically slow insurrection updates.

The obvious answer was to move either Twitter’s mobile client or move to their website. As I was at my desktop during this failed coup, I moved to Twitter’s website and remembered what I learned years ago: their website is hot garbage.

Twitter Aside: I am thankful for Twitter for banning Trump. It was three years late.

If you haven’t been to the Twitter website, go there now and tell me what you see. I’ll tell you what I see: a lack of place. There’s a promoted tweet dominating half my screen. I see some tweets from people I know, but a robot locked in a basement somewhere decided the order of this particular timeline, so I don’t trust it. The order of a timeline is defined by – wait for it – time. Not robots. Yeah, I get Twitter is trying to help by enhancing the quality of my feed. Yeah, I know it’s configurable. Still, I’d prefer if they spent their valuable cycles patrolling the feeds looking for humans actively working on toppling democracy. Thanks.

I poked around a couple of other parts of the website and was similarly baffled and lost. The Explore section is surfacing trending topics but is mostly ads. It says this section is for me, but none of these topics are click-worthy. What about notifications? This is broken into three sections: All, Mentions, and Verified. The All section is an aggregated set of notifications on things I might be interested in. Again, smooshed into time-ignorant irrelevance by the robots in the basement.

LET ME BE CLEAR WHAT I WAS LOOKING FOR AT THE TIME OF THIS EVENT:

  1. I wanted to see the tweets of those I followed as quickly as possible.
  2. I was very interested in the tweets of trusted humans who were sifting through all the same stuff I saw to find the most engaging tweets.
  3. Finally, I was interested in a keyword search of ALL tweets, but I needed an effective way to reduce noise to find a signal.

After a few hours of reload misery, I remembered TweetDeck. In the back of my head, my impression of TweetDeck was it was for companies who wanted to slice and dice the Twitter firehose into different useful feeds. For example, I’m assuming that many airlines use TweetDeck to proactively do customer support when a stranded traveler tweet rages. I’ve been that tweet rager. I’ve appreciated it when the airline attempts to be helpful.

Installing TweetDeck immediately improved my information consumption. TweetDeck not only defaults to time-based ordering of my tweets, but it also refreshes automagically as it’s part of Twitter and not subject to the lobotomized 3rd party APIs. TweetDeck also provides a multi-column format where you can look at multiple feeds. I’ve since forgotten the default set-up, but it was something like my friends feed and notifications feed.

Problem solved. Real-time doom. Many columns. This is great. Really great. Except TweetDeck didn’t allow resizing columns, and the maximum width was frustratingly narrow. I’d be able to consume far more tweets if they’ve just let me make… those columns… a bit…. wider.

The question was: why was TweetDeck giving me so much space for more columns? It tortured me, so I decided to make some more columns.

OH
MY
GOD
I SEE IT

Some relevant facts:

  1. There are a lot of humans on Twitter, and they are tweeting a crap ton of both informational, opinions, and uselessness.
  2. There are (or were) talented engineers who know/knew that there are humans like me who would want to build and run advanced queries against the entire Twitter fire hose because THAT’S WHAT THEY WANTED.

They did. The ability to build and run random queries exists. You can do it in Twitter, but in TweetDeck, you can build these queries and have them presented as different columns of constantly refreshing tweets.

It looks like this:

From left to right, the columns are:

  1. My time-based friend-based Twitter feed.
  2. Notifications: likes, retweets, replies, and follows to my Twitter activity
  3. Reporters: this is a Twitter list, which is a collection of Twitter accounts that I’ve curated.
  4. Keyword search on “inauguration”
  5. Keyword search on “#BREAKING”
  6. Keyword search on “youtube.com”

Notes on these columns:

  • The list feature in Twitter has been around for a long time, but it wasn’t until I saw it in the TweetDeck context to understand the value. These reporters’ tweets show up in my time-based feed, but I am often missing things in that feed. I don’t want to miss these humans tweets.
  • Simple keyword searches can be problematic because they predictably return a crap ton of results. Shortly after the President committed the impeachable offense of inciting a riot, I started a column for the “25th amendment”. This was full of noise until I discovered I could set engagement filters on the column. Only show me tweets that have at least X retweets, likes, or replies. Setting this to 5 likes immediately decreased the noise. For particular noisy settings, setting a higher engagement threshold helped a ton.
  • The “#BREAKING” search is abused a bit but has revealed some gems in the past weeks. It was that column where I discovered the rumor that the PGA would strip Trump of his PGA championship. Ya’know… because he incited a riot. On the Capitol. As the President of the United States.
  • There is a slew of other filtering options, including location, language, and a bunch of different knobs and dials to allow crisp filtering of your columns. Go explore.

At a time where, well, shit is going down, I am thankful for TweetDeck. A side effect of my newly found doomscrolling at scale are the columns which are not filtered by my friends. The keyword search columns are regularly showing me opinions I disagree with, lies designed to terrify, and other popular tactics of those who are more interested in fear than facts. I mute some. I block others.

However, I am discovering brand new humans. Who are fired up and good to go. I’m in awe of the work of journalists seeking and reporting the truth. There have been some good Bernie memes, too.

My doomscrolling has calmed since the inauguration. Nothing is fixed, but we are heading in the right direction. If you follow me on Twitter, you’ve noticed the tone has been uncharacteristically political. That’s not changing. One of the many lessons I’ve learned over the past four years is the seductive power of lies. I’ll be using every tool at my disposal to remind everyone of the power of the truth.

You’ve been warned.

The Important Thing Three acts

The One About Small Things, Done Well

In our 44th episode, we walk through the first chapters of Lopp’s 3rd book. Learning to deal with endless meetings, understanding The Situation™, and learning that people often just want to be seen. Spend 45 minutes with Lyle and Lopp talking about important things.

Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

Rands Don't think. Don't analyze. Don't assess. Just be scared.

Fear is a Liar

He says things so sweetly. He knows all your failures. He remembers your emotional scars. He sounds like you. And he craves your attention.

The Thursday after the election, I woke up, grabbed my phone next to the bed, and scanned the latest news. We were still two days from announcing the winner of the election, but there was good news. Some media site had called the election, and the hourly trends on ballot counting in Pennsylvania looked very promising.

A sigh of relief. The briefest moment of early celebration in a year where celebration was scarce. I shared this relief with close dear friends, and the reaction was swift and crushing, “Don’t celebrate. Let me explain to you in great detail how this is going to go simply horribly.” And then they explained the terrifying opinionated detail.

Fear is a liar.

She knows what scares you. She was iteratively designed over billions of years to prevent you from being eaten by a cave bear. She’s still around. She has impressive controlling strength over you. She sounds helpful. She sounds smart. She moves so fast.

Early in the pandemic, I was part of a hastily thrown together Zoom interview. The host opened with a softball, “How are you?”

A guest, “Spent the morning doomscrolling.”

An internal mental giggle. Yeah, it was the first time I’d heard the word: doomscrolling. It perfectly described a regular act for me. Sitting down at my favorite device and just soaking in the doom, the fear. Pick a topic: elections, racism, democracy, civil unrest, or a pandemic. It’s trivial to find a steady flow of content to confirm and stoke my worst fears. I do this daily.

Fear is a liar.

The early builders of the Internet had a hit on their hands. They quickly realized they had two critical challenges. A lot of data was being generated by humans using the Internet, and there was an infinite gold mine buried inside that data. Billion-dollar data storage, management, and analysis businesses emerged to tackle these challenges.

Machine learning also flourished as businesses learned how to use machine learning to look at vast data sets and learn. What were they learning? Very simply, these ‘robots’ learned to predict things that you like with increasing precision.

Correction. It’s not like. It’s engagement. How likely are you going to engage with a piece of content? The content could be a link, advertisement, but – important point here – it’s not relevant whether you like the content or not; it’s whether you engage. The more you engage, the more signal you send, the more data you create, which means more data for the robots to learn from, which means they do an even better job find more engaging things to click on.

I’m delighted and a little in awe when Instagram presents me with pitch-perfect advertising. I spent the first fifteen years on the Internet, avoiding engaging in all advertising, but Instagram ads are good. Really good. Why yes, those navy blue leather boots are precisely what I want. Right now. It’s magical. It’s nice that Instagram made my shopping experience better. Still, it’s horrific that the same mechanisms have created a generation of humans who believe doomscrolling is anything but compulsive consumption of weaponized fear.

And fear is a liar.

You’re worried about something. Very normal. Very human. You have a moment, so you sit down with your favorite device and take a gander at your friend’s activity, whether that’s a social network, a messaging thread, or any number of means that keep us connected.

What are they up to? They’re worrying, too, because there is a lot to worry about these days. One friend found a particularly worrisome piece of content and has shared it. Oh dear, how worrisome. You click on the link (engagement), read the opinion (not facts) piece, and it echos your worry, so promptly share it with another group of friends (sharing) who need to read this critical content.

Every sentence, every action in the prior paragraph, involves creating useful data for the robots to figure out more what this group of humans cares about to push more engaging content targeted explicitly at these humans.

Those who peddle fear understand precisely how these robots work and have come to expect how you will react. They throw a thousand lies into a social network and let the robots do their work. Humans react, robots notice and adapt, and the peddlers of fear create a fear-based echo chamber where they’ve discovered the very best lies that will efficiently engage the broadest audience.

We’re talking about a planet full of humans mostly unknowingly generating data that robots are sorting, filing, analyzing, and search for that one piece of content that instantly engages you. These robots don’t care if that content is a new pair of boots or a lie.

Those who peddle fear are counting on the fact that your reaction is fear and that you’ll get mad and want to take action. Quickly. Urgently. Irrationally. They don’t want you to think; they want you to hate. They want to divide. They want you to believe the act of consuming, engaging, and echoing anger, fear, and hate is a productive act.

Don’t think. Don’t analyze. Don’t assess. Just be scared. Hate an amorphous someone. Fear.

The thing is – if you choose…

Fear is a teacher.

I think of that bully in my 6th-grade class who randomly stood up during lunch, walked across the courtyard, and bullied me. First, I was scared, then I was embarrassed in front of friends, and then I was mad.

Today. Many years later, it’s the only thing I remember about the 6th grade. It’s a permanent mental scar, but I’ve chosen to learn from that scar. I’ve thought about what it means to be a bully, how they are motivated, and how they should be treated. I now treat them appropriately. Quickly and with directed informed purpose.

I act because I’ve considered, I reflected, and I’ve learned. This is the bizarre gift of fear: it teaches you. It ferociously highlights a situation where you must pay attention. It’s an unforgettable opportunity to learn when the danger passes because you absolutely do not want to be here again. That’s the lesson.

Fear is a teacher.

He says things so clearly. He understands you completely. He knows what motivates you. He speaks with confidence. And he wants you to be safe.

Fear is a teacher.

She knows how to get your attention because she knows what scares you. She was there when it happened. She remembers how you got that scar and she wants no further harm to come of you. Fear is a reminder that it’s time to learn and then act.