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Everybody’s Crazy: Why Management is Hard (And What to Do About It)

Photo by Artem Bali on Unsplash

The Weird Thing

Every so often, when I was running an engineering organization, a new manager would come and find me. “Person X just did this weird thing!!”, they would say. “I thought I knew how to work with them!! Now I have no idea! What’s going on??”. The “weird thing” could be suddenly getting angry, or insisting that a clearly sensible goal was unreasonable, or abruptly heading off for a vacation for three weeks.

“Person X” could somebody in the team, but could also be a founder (“I’ve had a great idea about this feature you’re about to ship”), a CEO (“I want everybody here this weekend”), an executive (“I was watching my wife/husband use the product on Sunday and…”), a peer (“no, we’re not doing that thing we agreed to”). The common theme was unexplainable weirdness, and the surprise that “reasonable people” could suddenly go off the rails.

After having this scene play out repeatedly, I began to refer to it as the “Everybody’s Crazy” moment: the moment when the true business of working as a manager became visible.

An aside about management and leadership: in my experience, management and leadership are not separate. To quote Andy Grove (via Kim Scott in Radical Candor), “management and leadership are like forehand and backhand. you need both to win”. For simplicity I will refer to the business of running a group of people as “management”. I you prefer “leadership”, perform an on the fly substitution. If you have a great word that combines both, email me!

Managing With the Wrong Model

About People

Managing people with the expectation that they will behave rationally leads to surprise, disappointment and, very likely, frustration. Yet this expectation is often embedded deeply, and unconsciously, in people who run organizations.

As a coach in the tech industry, I work with founders who are baffled why their product organizations can’t build exactly what’s in their head; VPs who struggle to understand why their clear, deeply logical explanations of the future are met with bored silence; CTOs who know they are just rightabout everything (and they often are), but don’t understand why people get upset when they make their case.

The problem is people. They’re a mystery.

And it’s no wonder they’re a mystery. From kindergarten onwards, we are stuffed full of facts and explanations, models and structures. If we’re in the tech industry, we probably did just fine, probably thrived, learning beautiful models and increasingly complex explanations through high school, college and on into our career.

But we are taught nothing, or very little, about how people work, who they are, what they need. How many of us ever had a class explaining what an emotion is, what its effects are, where it comes from, how to deal with it? The closest we got was probably somebody telling us “not to get emotional” (which, unfortunately, for a human being isn’t possible).

About Management

The history of management as a discipline doesn’t help. Management began in the nineteenth century with the need to organize large groups of people to service machines. Machines enabled massively scaled production! Scaled production equaled prodigious economic growth! A new model! But this required people to move from the free-form business of agriculture to the rigid structures of manufacturing. Which meant rules, measurement, goals and consequences. Better rules and measurement lead to better productivity, greater scale, higher profitability. Management became the craft of making all that happen, and over a hundred years or so, it got sophisticated, entrenched and celebrated.

Despite being wildly out of date (the term “knowledge worker” was coined in the 1950s), this original “management mindset” lingers as a kind of cultural memory, weirdly resisting attempts to shift it (Emotional Intelligence, Lean Startup, and many others).

The critical values for a tech company are no longer repetition and regularity. When necessary, they’re important (hi, Tesla!). But the criticalneeds for growth are creativity, insight, deep understanding of craft (coding, marketing, selling, finance), and the ability to fluidly and continuously re-invent our markets, our companies and ourselves.

Rules and measurement are necessary. But if people were simply rational actors, we could set the OKRs, write the task lists and then check our email occasionally, dozing at our desks as the team cheerfully got everything done.

How the Crazy Shows Up

A client of mine asked me about their CEO a week or two back. “Why does he do that?”, they asked. “He knows it jerks the whole team around. He knows it’s not good for the company!”

He’s a person. He has his crazy. Coming to grips with the crazy in people, understanding it, dwelling in it, making it work, is the real job of management.

How The Crazy is Built In

People are driven by two systems: emotional and rational. This is a simplification (of course), but a very powerful one, and over centuries, thinkers, psychologists and neuroscientists have dug hard into how these two systems relate, which is dominant, which brain regions apply to each system, where an “emotion” lives, how a moral code comes about and much more.

The model I have found most useful comes to us from Daniel Kahneman in “Thinking Fast and Slow”. He describes, with decades of experimental evidence, in how the two systems show up in our behavior and relate to each other.

System 2, Meet System 1

What Kahneman calls “System 2” (the “rational” system) is structured and slow. We use it to build spreadsheets, OKRs and task lists. It’s how we make tables of “pros and cons”. It causes us to add up time estimates, set deadlines, and think they will be met.

Crucially, we are usually under the impression that System 2, our rational system, is in charge,.

“Everybody’s Crazy” moments happen because we’re expecting System 2, and we get System 1.

“System 1” is lightening fast, unstructured, and driven by highly sophisticated pattern-matching. We judge and respond emotionally to a person’s facial expression far faster than we can think. We will get furious (or happy!) many seconds before our rational system has a chance to catch up, because a combination of words and tone hit a pattern that has a significant meaning for us. The pattern may have been built as we were growing up, from friends, a traumatic or wonderful experience — in the moment, we don’t know. The pattern matches, and we react.

System 1 Runs the Show

System 1, our “emotional system” (experts may quibble with the name) is our “crazy” — a set of triggers, beliefs and patterns that have a meaning all of their own: a personal meaning completely independent of logic and rationality.

Unlike our rational system, our emotional system is almost completely invisible to most of us, and even less visible to those around us. And we are not experts in managing it. We have decades of training in our rational system, and almost none (most of us) in our emotional system.

Our emotional system runs the show. In many ways, it is the show.

When the CEO I mentioned above jerks his team around, he’s being driven by his emotional system (almost certainly). Perhaps he values chaos at some level. Maybe the beautiful buzz of new ideas overwhelms him and he has to see them built. Maybe he is, at some level “comfortable” with having his team be irritated. Who knows? Probably somebody should ask him…

The (Invisible) Elephant and the Rider: A Useful Metaphor

Metaphors are good. They allow cognitive systems work with complex problems. A metaphor that helps come to grips with the two systems is suggested by Jonathan Haidt: our cognitive mind is a rider of an elephant — our emotional system — and thinks he is in control. But the elephant has other ideas:

I’m holding the reins in my hands, and by pulling one way or the other I can tell the elephant to turn, to stop, or to go. I can direct things, but only when the elephant doesn’t have desires of his own. When the elephant really wants to do something, I’m no match for him.

The elephant is strong (and, I would add, for most of us, invisible): we will spend more money when we’re feeling good, hire people because they “seem right”, and build things just because we want to build them, throwing away all market fit evidence in the process. (This is startup failure mode #1, by a country mile, incidentally, despite Lean Startup, Agile and all the rest).

Photo by C Rayban on Unsplash

A Better Model of Management: Being Fluent in Both Systems

My goal in writing this is to radically change the balance in how we think about management. Management is not singularly, or even primarily, a cognitive pursuit. It requires a skillful and discerning use of both cognitive and emotional talents and tools. It requires us to be fluent in both systems:

  • A manager has to set goals, which means brilliantly clear, rational thinking. And then she has to communicate those goals in such a way that they resonate with the team, which means engaging with emotion, story, and relationships.

  • A manager has to run meetings, which means building and controlling the structures of agenda, timing and summary. But which also means deep, conscious listening, authentic speaking, reading the room, allowing conversation to flow, and truncating time-wasting communication with empathy and compassion.

  • A manager has to speak truth to power, being able to compress complex issues into tight, compact messages, whilst at the same time broadcasting the emotional energy that’s driving the need for truth.

Throughout the day, a great manager is constantly balancing emotional skills — self-understanding, human connection, communication — with cognitive insight and creativity — building models, breaking down decisions, checking progress against to-do lists. The two skill-sets go together.

Management Learning: Building the Toolkit

I’m going to assume that learning the cognitive toolkit is well covered. Anybody in even a starting management position is likely to have good analytical skills, and be encouraged to make them better.

What is necessary is an approach to building a toolkit for the emotional system: a path for building a more subtle understanding of the elephant, and more ways to guide it. The framework below is intended as a set of high-level, repetitive steps to build a comprehensive toolkit over time:

Awareness: Seeing The Elephant.

The good news is that humans have a built-in debugger. The debugger is awareness. When we focus our awareness on our emotions, our patterns, our reactions, they become increasingly visible.

  • This can begin very simply. Ask yourself, as you go through your work: what am I feeling? what do I really want to say? how is my body reacting? What are the other people in the room feeling? What is the emotional temperature of this conversation?

  • Just asking yourself the questions will begin to make the working of your, and others, emotional systems more visible.

  • The power of awareness is not a secret. Meditation in all its various guises, is fundamentally a discipline for focussing awareness, known for thousands of years. Yes, it helps calm you down, sleep well and stop yelling at the dog. The point of it, though, is to learn to see: yourself, your patterns, and those of the world around you.

  • Find a meditation practice (“Search Inside Yourself” is a good start. So are Headspace, and Calm). You will sleep better, and kick the dog less. You will also be learning how to use your debugger, your attention.

Apply a Model

Your cognitive mind can work when it has something to grasp onto, and it grasps onto models, structures and symbols. Simply naming your emotion (“I am happy”) allows your cognitive mind to start work: now I know I am happy, how is that going to affect my decision-making? how am I expressing that to my team right now


Our brains are built to be rewired. Anything we repeat, carefully and frequently, moves further into our unconscious, rapid-response emotional system.

The Work of Management

As you gradually grow your toolkit, the work of management becomes seeing the interplay of both systems clearly, and reaching for the right tools from each side of the toolkit at the right time.

A conversation which is going badly off the rails requires managing emotions, connection and relationships. Building a business model requires clear, intense cognitive attention. You can (of course!) build a business model out of hope, or anger or excitement. That’ll drive the momentum. But evaluating how it matches technical or business futures is a rational task. Confusing the two isn’t going to end well.

Any management situation has a rational and emotional component. The art is seeing what the mix is, and wisely choosing the appropriate tool from a (hopefully) every-growing set.

Everybody’s Crazy. Management is Hard. Hard Things are Worth Doing

Management is hard because everybody is at least a little bit crazy, at the mercy of their emotional system, their own personal elephant.

Being a manager is to discover that craziness and help it become skillful, alive and aligned with the work. It is very essentially about understanding people, in all their brilliance, energy and weirdness.

Our work is not our life, but it is not separate from it either. A great manager is a wise, skillful guide who makes a great difference to both. Have that as a goal.

(A Note: I use this “two systems” approach as the basis for my coaching, and will be continuing to describe it in posts over the next few months. Sign up below if you’re interested in how it develops. And: interested in coaching? Drop me a line).

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