Management There are no hacks

The Way I Heard It Was…

We’re a team. There’s a mountain that no one has ever climbed before, but you – in your bones – believe we can. More importantly, you can stand in front of us, point at the mountain, and tell us the compelling story of how we’re going to climb that impossible peak.

You talk with your hands, you raise your voice at precisely the right times to punctuate your thoughts. Your pauses build tension. You’re not talking about yourself, you’re talking about all of us and how we are going to collectively achieve this impossible task.

Your story is engaging, but light on specifics. We don’t care because we all desire to achieve the impossible and, more importantly, we just love the way you tell this story. We believe you. This belief washes away the perceived need for concrete next steps. We are emotional beings; your manner and delivery has convinced us to follow you on an impossible task.

This is vision. You are using all your leadership skills to describe a vision.

There is still a mountain to climb. How are you actually going to perform this herculean feat? Thankfully, we have you. Now you begin to plan.

You start with questions: How big is the mountain? What obstacles are we aware of? Where is the top? What is the best path to climb to the top? Are there alternative paths? How many hikers do we have and how fit are they? What are their respective strengths and weaknesses? What is the best configuration of humans to perform each task? What contingencies are we going to need to build for unexpected developments while hiking?

It’s an endless list of questions, so you first determine what questions are critical, which are important, and which are nice to have. Second, you hand the task of answering many questions to humans on your team. You do this by first reminding us of your vision, explaining the relative importance of the questions, and defining when you need to know an answer. Each time, without fail, you finish with I trust you to do this important thing.

You learn not just from the answers, but from how the team discovers answers. Their discoveries update your mental model of not only how we’re going to achieve this impossible task, but also the abilities and nuances of the humans we will need to depend upon.

Conflicting opinions. Confusing data. Unexpected developments. Interpersonal conflict. We sometimes miss the bliss of the vision and despair. I’m not sure I can do this. You respond immediately, “It seems an impossible thing. Of course it’s hard, but we are going to do this together and I’ll explain how.”

And you do.

All of the answers have developed into a draft of a credible plan. You find trusted advisors with whom you test the particulars of the plan — these advisors unabashedly tell you the truth. You eagerly listen to their truth. You iterate. Finally, you stand in front of all of us, describe the vision once more and then tell us how we’ll execute on the plan with a well-defined strategy.

“We are going to climb this mountain. Thanks to all of your hard work, we now have a strategy. We know each part of the climb, how we’ll be organized, and how we’ll tackle each day.” You draw the mountain, you draw the planned trail, and you draw signs along the trail to describe how each step of the climb will go.

We have lots of questions. You eloquently and completely answer our questions, which builds our confidence. We are still scared because no one has climbed this mountain before, but as we stare at the picture we built together we believe it can be done.

This is strategy. You are using all your leadership skills to define a strategy that supports a vision.

We begin the climb.

The execution of the plan, the tactics, is the hardest part, but no one will believe this for a while. We’re optimistic, full of energy, and chasing an ambitious, compelling vision. We’re laughing, patting ourselves on the back, and climbing. We frequently look at the plan that we’ve built, read the signs, and follow the directions. Step after step.

As each day passes, we discover small flaws in our plans. Unexpected developments that our strategy did not take into account. We stop, regroup, and share thoughts on how to proceed. You listen, ask questions, and make a quick decision. We nod – satisfied – and keep climbing.

Days pass and we continue to discover the unexpected. The frequency of the unexpected begins to concern a small group of us. You can hear despair and you show up quickly to talk directly to us. You remind us of the vision. You remind us that no one has done this before, for good reason. It’s not that other humans weren’t smart or organized enough, it was simply that they didn’t believe in the impossible. And we do.

Your words and enthusiasm calm some of us, but others will never come back to belief. They will continue to climb, but the magnitude of the task will never be less than impossible. They will not finish the climb with us.

Disaster strikes. Not just an unexpected development, a complete and total disastrous surprise. Worse, the disaster shines a light on the simple known fact that this task is impossible and our strategy is now clearly, woefully flawed.. All of us are rattled. Including you. Someone asks, “Should we turn back?” and the deep murmurs of agreement show the degree of despair and disbelief within the team.

This started as tactics. You were using all your leadership skills to execute tactics that supported the strategy to achieve the vision. Now you must use judgment if we are to succeed.

Judgment. The accumulation of all of your experiences into wisdom. Readily accessible, informed inspiration. Judgment isn’t just what you rely on to make a decision; judgment tells you when a decision exists. Are we going to stop or continue? What are the costs of each? How much do we risk if we continue? What do we forever lose if we stop? Is now the time to decide?

As you stand in front of us, hearing the echoing murmurs of despair, you make a decision because you are accountable for this journey and while most believe accountability means responsibility, you understand accountability means “required or expected to justify actions and decisions.” Justify to whom? To us. To give account. To tell the tale of why we are here. To justify why we need to complete this impossible task. To make the decision to continue and to explain in understandable detail what changes we’re going to need to make to achieve our goal.

You make your decision. We are going to continue. You explain your decision. And this is how we’ll proceed differently. You repeat the vision, you repeat the now revised strategy and supporting tactics. You feel you’ve done this a hundred times, but you’ll do it a hundred more before you’re done because each human needs a different thing to hold onto at different times in their journey.

Wild enthusiasm is gone. Belief is shaky. Your words can’t prevent a few from turning back, but those who stay take a deep breath, remember why they are there, and start climbing again.

Small steps. Climbing. One step at a time.

The first disaster is far behind us now. The second one, too. More members of the team have left, but others have now joined because they’re inspired by our ambition and also because it’s become well known that we are still climbing.

There are two more disasters ahead of us, but in six short weeks, we’ll reach the summit. The impossible will have been achieved. No one believes this right now. We are singularly focused on the task at hand: the act of taking each small step. The most important thing we do is take another small step.

There are no hacks. There are no silver bullets. The way that you are going to achieve this impossible task is by continuing to climb.

Management Find joy in crushing your ignornance

Ask for Help

In 2018, I wrote How to Rands, which seemed like a good idea at the time. Someone else came up with the idea of the manager readme, and the idea of writing a document regarding how I worked seemed like a helpful exercise1.

I shared the document with the executive team at Slack, and the Head of People commented on this clause:

I am an introvert and that means that prolonged exposure to humans is exhausting for me. Weird, huh? Meetings with three of us are perfect, three to eight are ok, and more than eight, you will find that I am strangely quiet. Do not confuse my quiet with lack of engagement.

“That explains a lot,” he said… ominously.

As a person with a twenty-year-old blog, various YouTubes of me around the world talking about leadership, and podcasts, you might assume “extrovert.” Nope, no, never. Each of those communications mediums might be considered a coping mechanism because I much prefer sitting here in the Cave quietly banging on my keyboard versus actually talking with humans.

As a leader, you might assume that introversion is a professional liability, and you’d be partially correct. It’s taken years of hard work to develop skills that fill the extroversion gap (like public speaking), but the single most significant impact of being an introvert is I don’t ask for help.

Introduction to Logic

Back to UCSC. With my second attempt at programming successfully behind me, I’m in my second year taking Introduction to Logic. It sounds like a computer science class, but it’s not; it’s a philosophy class. We were introduced to the traditional theory of syllogism, contemporary symbolic logic, the relationship between logic and language, and the nature of scientific reasoning.

It’s not a stretch to understand why this is part of the computer science program. Binary or Boolean logic shows up all the time when you’re hacking away at that code. The problem is that the surface area of Introduction to Logic’s was vastly more extensive and far more complex than I expected. Think word problems, except all the words are symbols.

No problem. Going Full Pascal on this sucker. Focus. Intense focus. Confident answers to every question, right? Maybe. With programming, I had exposure to the concepts over years of tinkering with computers. With logic, I was being exposed to entirely new forms of thinking. The validity of deductive inference, the strength of inductive inferences, and the study of logical paradoxes. When the first quiz arrived, I only felt confident in 50% of my answers.

Going Full Pascal was not working, so I reached the professor during office hours. He was a fine lecturer, but when I asked my questions, he gave me that non-verbal judgey look of “How are you not getting this?” that only an introvert can read… and dreads. The teaching assistants were traveling in a similarly unhelpful orbit.

Post-quiz, I was uselessly applying my intense Full Pascal focus when I looked across the lab and saw John Zorne, a college mate. Well, might as well say hello rather than spinning my wheels here figuring out logic.

“Hey, John” I walked up behind him.

“Oh hey…” he wasn’t happy.

“What are you working on?”

“Oh. I, uh, just bombed my first quiz in Intro to Logic. I can’t figure this stuff out.”

Misery loves company. I sat down next to him and plopped my 50% complete Introduction to Logic quiz. “Me either.”

We compared notes on the class. Professor was an entertaining lecturer. He was engaged and funny. He was also confirmed awful at 1:1 discussion. Yes, the teaching assistants were similarly unhelpful. The quiz seemed fair, covering topics we’d discussed, but the complexity of the problems seemed beyond what we’d discussed. Applying our knowledge of lessons and completed homework learned was not working. I glanced at his failed quiz and realized he’d successfully answered problems that baffled me.

“Problem 8. I had no idea how even to start. How’d you do this, Zorne?”

And he showed me. I didn’t understand at first, but he drew a clear line from what I did understand to this particular problem as discussed the problem. After 15 minutes of swirl, Problem 8 was no longer a problem but a solution.

He grabbed my quiz and picked a problem I successfully answered, and we repeated the process of teaching each other. After a few more successful discussions, it became clear that we each had 60% knowledge of the class to date with maybe 50% overlap. Combined, we had a workable knowledge of the class to date.

Zorne asked, “You want to work on the homework?”

“You bet I do.”

After-class study groups. Tutoring. Randomly bumping into a classmate in the library. I’m sure you did all of these very logical activities to support your learning. Not me. Remember, introvert. I am far more comfortable with the incredibly shortsighted strategy of suffering in solo silence. Zorne’s offer to work together on the homework wasn’t the first time someone had offered to help, but it was the first time I accepted.

If you’re thinking to yourself, “How dumb,” I’m happy to inform you that in terms of the range of stupid things I did as a teenager, this squarely goes in the “Not actually that heinous” portion of the stupidity spectrum.

Ideas Get Better with Eyeballs

An inability to ask for help is not the domain of introverts. We certainly make it a more laborious mental process, but in any group of humans where there are those who know and those who are learning, the latter population is hesitant to ask for help because they don’t want to appear dumb to those who have clearly figured it out.

This is ludicrous. Those who know would greatly benefit from teaching those who don’t know, and those who don’t know would equally benefit from learning.

Yeah. We’re in a hurry. We have a deadline. Everyone is scurrying around so competently. In this hurry, we create the erroneous perception that stopping to teach is somehow slowing the team down when the reality is that we are not just investing in future speed, but in team health: the selfless act of teaching is one of the greatest accelerants to building trust in a team.

Thanks, Zorne.


  1. If this is the first time you’ve heard of this idea and are excited, let us clarify what a manager readme IS and IS NOT. It IS an opportunity for you to explain what you believe and how you work as a leader. It IS NOT how you dictate to your team how they should work. 
Management Increasingly Pointlessly Tactical

The Hotel Giraffe

The 9th floor of The Standard located in Greenwich Village of New York City. Pre-pandemic. I wake up mid-day and a full-sized giraffe stands in the corner of my hotel room. The view of mid-day downtown Manhattan is obscured by a full-sized living breathing giraffe. This animal is staring at me.

Blink.

This situation makes complete sense, but I have questions. How did the giraffe get in my room? It wasn’t here when my head hit the pillow for my mid-day nap. It kind’a make sense though, right? The Standard’s hip and quirky. I can see them delivering a mid-day giraffe, but I have continued concerns. Do I have to feed it? How long will it be here? Who cleans up after a hotel giraffe?

Ten minutes pass. A hotel giraffe stare down. More questions. Who is going to make the first move? Are giraffes dangerous? Herbivores, right? How is a threatened giraffe going to act? In a hotel room? I’m dreaming, right?

I try to wake up.

Three Numbers

At my last gig during a particularly stressful time at work, I started asking folks four questions. On a scale of 1 to 10 (1 == low, 10 == high):

  1. How stressed are you right NOW?
  2. What is your IDEAL stress level? Ideal meaning the stress is useful and not debilitating.
  3. What is your MAX stress level?
  4. What behaviors do you see in yourself when you close or at MAX?

My answers at the time were:

  1. Now: 7
  2. Ideal: 4
  3. Max: 9
  4. (See below)

What I like about this set of questions is they frame a personal story about stress. Everyone knows what stress is, but we process and use it in different ways, we have different tolerances, and we have different coping mechanisms.

When someone answers these questions, I always have follow-ups because everyone’s stress assessment and coping strategy is intriguingly different. At the time I was asking folks, I was hanging at a seven and had been there for almost a month. With stated ideal of four, that seven was a growing concern because a seven means I start to exhibit the behaviors that show up when I’m close to MAX. These behaviors include:

Lossiness: I become unreliable. I miss on commitments and I’m not aware I’m doing so until reminded after the miss which leads to…

Irritability: Small annoyances have a disproportionate effect on my mood. I have strong negative reactions to small developments that I normally easily shrug off. Then I start to become…

Increasingly Pointlessly Tactical: Stuff is dropped, I’m grumpy, so I start to make lists. Lots of them. On these lists I draw boxes that I expect someone to cross off diligently. I become militant about the state of these lists and these boxes. This show of force gets everyone’s attention, but all the boxes in the world don’t answer the question Why are there checkable boxes in the first place? IT DOES NOT MATTER. THE BOXES. THEY MUST BE CHECKED. And when they aren’t there is…

Rage: The final straw. When we’re not all following my irrational unspoken script, I get rage because of my totally unrealistic expectation that everything must proceed exactly to plan. Problem is, after almost three decades of leadership experience, we’ve never followed the script. The script changes every day. This is how I know I’m close to peak stress. I’ve forgotten that a significant part of my job is competently and quickly acting when we go off script.

As leadership advice goes, I don’t recommend rage. It feels good for a half a second before you experience instant regret. Also, once you’ve raged, you’ve got two situations to resolve: the core issue and the damage you’ve just unnecessarily inflicted on your team.

The Stress Math

I wrote the first draft of this chapter late in 2019 intending it to land with the new book. I cut it during the final edit because the piece was half formed. Recent world events have the topic of stress on my mind even more and I realized that while my four questions are intriguing, they don’t paint a complete picture regarding stress.

The stress behaviors ring true for me, but in staring at the better part of a year of an increasingly terrifying and broken world, I’ve been thinking about the constituent parts of stress. To me, stress is an accumulation of:

  • The thing that is stressing me out right now. It’s probably why I am thinking about stress. It’s obvious. It’s visible.
  • All the non-front-of-mind stressors. If I stop and think about it for a moment, there are an obvious handful of other stress developments in my life. Large and small, but all contributing to my overall feeling of stress.
  • Finally, there are the deeply buried things. I know these exist because even during normal stress-light times, I find myself dropping straight to rage on random unexpected situations. Why do I drop to rage? Well, my best not-a-psychologist answer is that situation nudged a deeply buried stressful topic for me. What topic? No clue. Is it contributing to my overall stress? You bet.

My forthcoming advice for both detecting and handling stress is unchanged given the wide variety of stress that exists, but an opening thought as you interact with your fellow humans: without reflection, you don’t know how stressed you are and neither do they.

Leading Stress Indicators

Rather than explain how to climb out of the rage pit, my advice is: Don’t drop into the rage pit in the first place. Seems like obvious advice, but we humans are stimulus-driven creatures. There are those of us who believe we are truly not alive until the risk of failure is an imminent dangerous threat… unless the consequences are significant. I am, unfortunately, often one of these short-sighted emotional humans.

When you combine this stress proclivity with the fact that in any moderately sized group of humans there will always been curveball off-script non-Pandemic situations with stress creating potential, you might resign yourself to believing that a high level of stress is unavoidable, but you’d only be partially correct. No amount of planning can prevent all of stressful situations from occurring, but we can make strategic investments to prevent our default reaction from being more stressful.

I do so by making four obvious and consistently daily investments in myself: exercise, sleep, food, and time. I exercise regularly, I get a consistent amount of sleep, I plan and eat healthily, and I carve off time to do the housekeeping of the intangible.

This is not an article that explains to exercise, sleep, eat, and find creative time. This article documents how I know when I am not making these investments. These leading indicators are my warning signs. You, sir, are not prepared for when it hits the fan and it always hits the fan.

Food

I remember discovering coffee at my first software intern engineering job at Borland. College. It was likely a morning after a late night in the dorms. A late night. A late late night. As I blearily stared at my screen, I remembered my parent’s daily coffee habit. Coffee. Coffee can help, right? So I tried a cup.

Instant productivity. Where have you been my whole life? Fast forward to four months later and I was drinking coffee all day. Like any good drug, the more I took, the more I needed to achieve instant productivity. It was around this time that I discovered the jitters.

4pm. Sixth cup of coffee? Shaking. Little sweaty. Neither debilitating, but neither familiar. The moment is memorable because it was one of the first times I discovered the non-alcoholic health consequences of poor food and drink management.

The coffee jitters calibrated me to being aware of the consequence of what food and drink I was consuming. This is what too much caffeine feels like. Turns out coffee (especially decaffeinated coffee) is also an appetite suppressant which means I was also skipping meals. 3pm was regularly rolling around and I had a horrifically delicious Egg McMuffin six hours earlier, no lunch, and six cups of coffee. Why can’t I think? I’d dart to the car, head to Wendy’s (best fries), inhale a burger, and thirty minutes later, my head would clear.

An extreme example, for sure, but these extremes have a beginning, middle, and end, and once I knew how hungry began, I learned the importance of avoiding those beginnings. A breakfast before 9am, lunch – always – and at roughly the same time, same for dinner. No coffee after Noon.

What’s the consequence of missing a meal? It’s not a disaster, but it’s a very small early warning sign. Why am I unable to perform the simple act of feeding myself? More on this shortly.

Exercise

The most important work I do is when I am not working. I’ve already written about this elsewhere calling this work Anti-flow. If Flow is productive focus, then Anti-flow is a productive lack of focus.

Biking continues to be my chosen exercise. I’m averaging 35 miles per week which regularly includes four to five thousand feet of climbing in my treasured Santa Cruz mountains. 35 miles of biking is somewhere around four hours on the bike. That’s four unscheduled hours which unless I’m riding with a friend, it’s me, myself, and I.

I call this my most important work because it is during this unstructured time that I find elegant next steps to my hardest problems. These aren’t solutions to the biggest challenges on my plate, but inspired next steps that I rarely find when everyone stares at me on the video conference expecting immediate inspired leadership. Even more addicting is the inspiration that comes during the ride that continues for hours after the ride completes. I am fired up to solve all the things after a ride. This is the end of millions of years of evolutionary biology loudly telling me, “When you take care of yourself, your body will reward you.”

In the prior section on eating, you will notice I didn’t mention an obvious important aspect: nutrition. Of course, if you are paying attention to when you eat, you should pay equal attention to what you eat. Similarly for exercise, I am not going to highlight the hopefully obvious fact that a consistent exercise regimen has a vast array of positive health benefits.

If I miss my goal for a week of exercise, the downside isn’t immediately noticeable. A bit disappointed in myself. As we’ll learn in a moment, I probably won’t sleep as well, I find that I won’t eat as healthily, and I’ll have a similar question as when I skip a meal, “What is preventing me from exercising?”

Sleep

Unlike a skipped meal or a lack of sufficient exercise, a single night with insufficient sleep is a haze over my entire day. It’s obvious dullness of the mind that isn’t hard to miss. I tell myself that I’m functional, but my decisions are slower, complexity is daunting, and my default mindset is, “Just make through the next couple of hours.”

This is not the type of sleep situation that concerns me.

The more devious sleep situation is the one where I get slightly less sleep than I need for a couple of weeks. Good time to point out that I’m not a doctor, but I do know after stumbling around in this body for a great many years for me that around seven and half hours of sleep is ideal for me. Your needs are likely different.

Six hours. Seven hours. Six and a half hours. I don’t wake up in a haze. I wake up pretty easily and mostly refreshed. For the first day and maybe the second, but after a couple of weeks of slightly less sleep, I begin to feel quietly mentally thin. It’s all the same symptoms as one bad night of sleep except less so. Just a little hazy. Just a little mentally slower.

Why am I sleeping less? I’m either having difficult falling asleep, waking up in the middle of the night, or waking up early in the morning and then staying up. When one or more of these sleep patterns emerge over multiple nights, I start to ask the core question which will bring us back to our beginning: what’s keeping me up?

Deeply Buried Things

Remember the hotel giraffe? The question is: why am I so tired in the middle of the day that I’m dropping into REM (“dream”) sleep. Obvious answer: I have a bit of jet lag, right? Wrong. For me, jet lag sleep when traveling West to East means it’s easy to stay up late and hard to wake up early. Mid-day hotel giraffes? Something else is out of equilibrium. What is out of whack?

Well, I haven’t ridden my bike in two weeks? Why? Late night fire fighting. How have I been eating? Consistently. Lots of calories. Lots of salt. And usually walking hither and fro.

As I lay there in The Standard thinking, I realize what the hotel giraffe is telling me: Yes, you are tired from the flight, but you were tired before you even got on that plane. You normally sleep on planes, but you didn’t because your list of things to do is impossible. You will never get it done and you didn’t actually know that until a giraffe showed up in your mid-day hotel room.

So go fix that.

Rands Important or Urgent?

I Think in Flowcharts

The most valuable part of a long bike ride is the second 30 minutes. The first 30 are spent settling into a groove, finding the right pace, and clearing my head. I know this is done when random interesting ideas start showing up, as I’ve written about before. There are three categories of exciting ideas:

  1. Stop now. Instantly tell Siri to create a reminder. If Siri isn’t working because I’m off-network, I’ll stop my bike and type my reminder. The idea is that important.
  2. Disposable. Interesting idea, but not worth capturing yet. Maybe it’ll come back later?
  3. Greatest hits. These are disposable ideas that keep come back on subsequent rides.

One of my great hits for a couple of years has been building a flowchart regarding making big decisions. Not small decisions, big ones. As with all complicated people things™, I see these situations as flowcharts. An obvious set of steps, branches, and logical conclusions. Flowcharts give me a sense of control when it’s hitting the fan.

(click on the image for a larger version)

Management I preach delegation a lot

Going Full Pascal

First-year of college at UCSC. First computer science class. Introduction to Programming. The language: Pascal.

Failed it. Failed it badly. Knew I was going to fail it halfway through the class.

This was my chosen profession. I’d been a grocery store clerk, a butcher, a video store clerk, the guy who backs up the system to tape drives on Saturday, and a bookseller. I wanted to be a computer scientist, and I failed my first class… badly.

There were situational reasons. First-year in college. Adjusting to living in a dorm. Meeting all sorts of strange new people. The distractions were innumerable, but the real reason was character.

This is how I work. I walk into a situation, and I’m furiously trying to figure it out, “Which situation is this?” I am parsing the people, the words, and the mood, and I’m searching for familiarity. I am not calm until I find this familiarity, and when I do BAM Ok, what’s next? How do we make progress from here? Let’s go. Like… now.

You think this results from years of being a leadership type who is constantly thrown into random situations where I am required to build situational awareness quickly, and you’d be partially correct. Here’s the rub: I’ve always been this way.

Voracious consumer of information, professional introvert, and ownership of a painfully short attention span. Combine all those, and you get me: usually well-informed, very aware of what those other shifty humans might be plotting, and probably already thinking about something else. Ta-da.

There are situations where this particular set of skills is advantageous, particularly in situations where I have relevant experience. In these situations, I can hit the ground running, quickly assess, and equally quickly get us moving in a credible direction.

There are an equal amount of situations where my skills/habit put me at a disadvantage. Which takes us back to Pascal.

Incapable of Achieving Your Dream

I’d programmed a bit on my Atari 400 and a lot on my Apple ][ and IBM PC, but this was hacking. Slowly trying to figure out how it all worked, copying code snippets out of magazines, and attempting to convince myself that I understood how a computer worked. When I arrived in my first computer science class, my prior experience gave me the impression that the class was “been there, done that.” It looked like code, so, yeah, I understand what’s going on here.

When it quickly became apparent that I didn’t know what was going on, I didn’t ask for help (introvert), nor did I focus on solving the core problem (short attention span). I missed the basic rules of how a programming language is structured. Essential details that I’d never seen before. When it came time to demonstrate applied knowledge, my YOLO shenanigans failed me. Worth noting: I was moderately successful in high school with YOLO shenanigans. Hustle. Bluster. Call it what you want; you can’t hustle your way through the necessity of hard work.

UCSC at the time had an option where there were no grades. You could select a written evaluation, and while I do not remember the specific words, I vividly remember how it made me feel: “The thing you’ve wanted to do all your life. You are incapable of understanding, let alone doing the work.”

Deep breath. New strategy.

Next semester. Different professor, but same course. First day and every day, I took copious notes. First homework assignment. 25 problems. I answered every problem, and if I had a hint of confusion about my answer, I went back to the book and re-read the section to make sure the answer was understood and defensible.

Next week, the professor announced a separate extra credit lab where we’d learn a new language called “Scheme.” Totally optional. I signed up. First tutorial, there were 10 of us in the lab. Scheme, a language based on recursion, was confusing. I never missed a lab.

Next week. First programming assignment, which included a bonus objective. I wrote the code, and I obsessed about the bonus objective. Ten points for the assignment. I got 12 total with the bonus. Eventually, our first test. 100 points possible. I got 110 for answering the Scheme extra credit question.

Every week.

Fast forward to the end of the semester. Our final programming assignment was a contest to see who could design the most efficient version of an algorithm. Work together as a team. Ask for help. I took the assignment to my extra credit lab, which was now just the Teaching Assistant and myself talking about Scheme. I told him about the contest, and we spent the lab whiteboarding different approaches. The result: a contest win and more sweet, sweet extra credit.

My grade-less report card still sits in a drawer in the cave. The phrase I remember, “Best in class.”

Deep Vertical Knowledge

This article is not how I became an amazing software engineer. My academic ups and downs at UCSC continued. Data Structures blew my mind. C++ blew my confidence. When I started at Borland, I was a below-average junior engineer. Improving steadily over the years and in awe of those talented humans around me who made it look so easy.

Seven years later, when I became a manager, I was average again. The learning cycle restarted. Sitting here now, years later, I am very clear I have strengths and areas I need to invest in. Took years to figure that out.

As a leader, these days a senior leader, I preach delegation a lot. It’s the complicated act of giving accountability for the work to others. You often delegate works you know you could complete, but your job as a leader is to give others opportunities while also learning how to coach and guide them towards the essential lessons better learned via experience than lectures.

Delegation is an art. When handing off a set of work to another human, it needs to feel like support, not avoidance. Well-executed delegation feels like a vote of confidence. Poor delegation looks like abdication. Great, my manager just handed me a disaster. Now what? Poor delegation re-enforces the perception that managers are out of touch and unaware of what is going on.

This article is about preventing this perception and understanding when it is in your best interest to Go Full Pascal. Contrary to what I suggested earlier, Going Full Pascal isn’t just hard work because the work should always be some version of hard. Going Full Pascal is when it is necessary to work hard and acquire deep vertical knowledge so that you understand every single nook and cranny of the complicated situation in front of you.

This is not a move you attempt in every situation; it’s the one you keep in your back pocket for when the sky is falling, and you don’t need to prop the sky up; you need to prevent it from falling ever again. You’ll know you’ve done this when you’re done, and everyone sees the solution, and they clap. Loudly.

Not Micromanagement

A few years ago, I revised my thinking about managers continuing to code. I went from “No way” to “Stay programming limber.” Like coding, you can send deeply confusing messages to the team when you Go Full Pascal. You’re always one poorly formed sentence from signaling to the team that you’ve Gone Full Micromanager.

How to avoid the micromanager label? That’s another important article. Today I want to remind you that just because it says manager in your title doesn’t mean you are absolved for doing the hard work of deep vertical knowledge.

I’m built to be a competent leader. I seek information so that I understand how the world works. My introversion has made me into a good listener because you talking is less scary than me talking. My short attention span means that chances are, when you speak to me about what I’m working on, I’m giddy excited because I seek stimulating situations that hold my attention.

I’ve become a better leader because I know when my skills and habits are a detriment. I’ve come to understand bias and how it impacts my team. I’ve worked hard to be a good public speaker who conveys excitement and speaks slowly and clearly. I have objects on my desk right now that I hold in my hand to remind me to focus my attention when it wants to wander.

And I know when to Go Full Pascal.

Management One paragraph in a very long story

Feedback is a Mirror

You have an internal storyteller, and they are always telling you a story. Today the story is, “Almost done with all of my bugs. There were ten at the beginning of the week, but now I have two. One of them is hard, but I’ll figure it out. The other, I’m sure, will be a breeze. When these are done, I am going to spend some time working on my prototype for the next release. Can’t wait.”

This narrative serves many purposes. It gives you direction (Here’s the work I need to do), priority (This is what is important), and motivation (And here’s my reward when I am done).

Here’s the thing: this narrative has strong bias. It is biased in your favor and is world-class at focusing you on what is important, interesting, and compelling versus what is boring, hard, or frightening. Go back and read the fictional narrative. What is the inner voice trying to get you to ignore? Two things: the hard bug (We’ll figure it out!) and the unknown bug (I’m sure it’ll be a breeze!).

That hard bug? It’s really hard. In fact, you’ve been dreading it for two weeks because your spidey-sense is telling you it’s the end result of a poor architectural choice you made six months ago. It’s not a bug; it’s feature work. And that it’ll-be-a-breeze bug? Your inner voice literally lies to you here. It’s the last on the list because it’s the hardest. There’s no scenario where it’ll be a breeze.

None of this dialog occurs outside your head. None of this behavior is wrong or weird. It’s just you getting through your stuff today like everyone else, but today of all days, James, a co-worker, is talking with you in Slack and out of nowhere jokingly types, “Yeah, but you always underestimate the worst bugs by 10x. That’s why you’re always last.”

James is joking, but you feel every single word.

One of the many benefits of feedback is that it breaks your ongoing inner narrative. It breaks it. It mentally forces you to stop in your tracks and consider the feedback not because you want to but you are incapable of ignoring it. The feedback is that compelling.

Confusingly, this reaction applies equally to constructive, helpful feedback as well as toxic unhelpful criticism. In each case, your brain stops and cannot proceed until you’ve somehow processed this new bit of information. You see that they see you, and now… you see you.

If it’s constructive feedback, you feel it. He’s right; I avoid the hard bugs because I worry they are critiques of my possible prior poor architecture decisions. In the best scenario, you process and act on the feedback. In the worst scenario, you rationalize it away and leave yourself unchanged.

If it’s destructive feedback, you really feel it. The other person designs the feedback to cut deep. That’s their intent. I’m not going to explain the motivation of these humans, but please note their nefarious intent is to land the sucker punch, and it somehow landed. Amongst their toxicity, there is something you heard. When I am in this scenario, I attempt to push the toxicity aside, look in the mirror and ask myself, “Why do I care?” There is always an unintended lesson.

Here’s one lesson: when constructive feedback stops you in tracks, it feels like your entire world is this feedback. You aren’t this feedback. It’s a sliver. A thread. One paragraph in a very long in-progress story. You are a fully formed human full of skill, will, flaws, strengths, good days, and bad ones, too.

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.