We think of organizations as a way to coordinate work and get things done, which is true enough. But at the same time, every organization is a bundle of contradictions and conflicts.
For example, an organization must have a way to attract and retain members, or it will cease to exist. At the same time it must constrain people’s behavior, or it won’t be able to get anything done. This means any organization has the oxymoronic goal of being an attractive prison.
I’m collecting organizational paradoxes for a potential book.
I will be updating and revising this list over time. If you have any paradoxes to share, or stories that illuminate any of the paradoxes I’ve listed here, or if you’d like to offer counterpoints or contradictions, please do! I’d love to make this list as comprehensive as possible.
Here’s what I’ve got so far:
When you ask for help, you get more work to do.
This is my third book. I often turn to social media for help when I’m dealing with a new or tricky topic. Often, when I ask for help, someone gives me a new book or article I need to read, giving me more work to do. So even though my goal is to lighten the load, I end up with more work!
I also saw this dynamic in my company, XPLANE, when we were growing very fast in the 1990s. As people became overloaded with work, they asked for help, so we hired new people to give them a hand. But these new people couldn’t really help without training, and guess who needed to train them? That’s right, the people who were already overloaded with work. So by trying to help them we were actually just making more work for them.
Which leads me to another paradox:
When things start to get better, they seem to be getting worse.
Take the example of the new people in my company who needed training from the overloaded experts. The way we eventually ended up solving this problem was to set aside two hours a week as dedicated training time. We did our best to make it fun, with drinks and snacks and a playful attitude, but there was no disguising the fact that, in the short run, this made us less productive as a group. It’s like the man in the story who is so busy sawing that he can’t take time away to sharpen his saw.
When things start to get worse, they seem to be getting better.
From 1990 to 1997, when digital cameras were being introduced into the marketplace, Kodak stock doubled, from about $45/share to more than $90/share, partly because they sold off their chemicals, medical diagnostics and household products businesses to focus exclusively on photos, partly because they expanded their mini photo labs into emerging markets like Russia and China.
From 1975 to 1985, as Japanese car companies were rapidly taking over the US car market, GM stock more than doubled from about $30/share to about$80/share. Everything was fine in Detroit for a long time. Troubling news from Japan was discounted for twenty years before it was taken seriously.
Why? When a company focuses its efforts on executing today’s business model, and ignores R&D and investment in the future, revenue and profits initially go up. Things look great. But ignoring the future has consequences and those chickens will eventually come home to roost.
The more you coordinate and communicate about work, the less you get done.
Time is finite. The more time you spend coordinating your efforts, the less time you have to do the actual work. Think about the amount of time spent in planning in most organizations.
Here’s a concrete example from my own experience:
In the early days of my company we had a Monday morning meeting that everyone attended. Everyone would share what they had accomplished the previous week and what they were going to work on in the upcoming week. That meeting was part of the magic. Everyone knew what everyone else was working on, we all understood the business as a system, and we could all see the connections between what we were doing and the larger goals of the business. We could also how we could help each other, make each other’s jobs easier, eliminate unnecessary work, and so on.
As the company grew, that Monday morning meeting started to get unwieldy. First, it started getting longer. What used to be a half-hour meeting stretched to an hour, then two hours, then the entire morning. About this time, the meeting got to be too big for any of the rooms in the office. We had to rent out the second floor of a nearby coffee shop.
At some point we realized that we were facing a tradeoff. The more time we spent on communicating, connecting and coordinating our work, the less time we had to actually do the work. If we continued to grow without changing anything, we would get to the point where maintaining our connectedness would continue to squeeze the time we could be productive.
The more you do, the less you can do.
As you take on more jobs and tasks, your overall workload increases, which means you have less time to spend on each job. Not only that, you need to spend more time coordinating and switching between tasks, leaving you even less time to do each one.
And the bigger the project, the more people get involved, which in turn makes the project even larger and more complex. This results in more time spent on meetings and coordination activities, which usually means less time on the project itself.
When a project falls behind, a common response is to schedule more status and update meetings, which means there’s less time to move the project forward. Another response to late projects is to add more people, but this is only likely to make it even more late, because those new people will have to be brought up to speed — a dynamic that is examined in depth in The Mythical Man-Month by Fred Brooks.
Let’s say you want to deliver excellent service to customers and you want to be very quick to respond to their support requests. The more time you spend helping customers, the less time you have to improve the product or service you are helping them with. Over time, customers can end up more disappointed, precisely because you are spending so much time helping them.
The reward for doing good work is more work.
Do a great job at work and you’ll be rewarded with more projects. Do a poor job and you’ll get less work. Be agreeable and people will ask you to do more. Be difficult and disagreeable and people will leave you alone. 
This is related to the Peter Principle: When you do a great job at something, you tend to get promoted. If you do well at that job, you get promoted again. Eventually you will reach a job where you are unable to perform well, at which point you will no longer be promoted and will remain in that position indefinitely. The net effect is that managers rise to their level of incompetence.
Tools designed to increase productivity decrease productivity.
Smart phones and the web has given us a plethora of new tools that promise to increase our productivity: Calendar apps, to-do list apps, collaboration tools, and so on. But as the number of productivity tools increases, the time we need to spend learning the tools, looking for better ones, updating them, using them, and switching between them, takes up so much time that our productivity ends up going down instead of up.
Attempts to increase control reduce your control.
In many cases, trying to increase your control of a situation reduces the amount of control you have over the situation.
In the early days of the industrial revolution, employer attempts to increase control over workers led to the rise of labor unions.
In Ferguson, Missouri, police attempting to control protestors only succeeded in making the protests more severe, causing an escalating spiral of anger and violence that only started to subside when police stopped trying to control the situation and started to focus on more systemic change (like requiring police to wear body cameras).
This is a common phenomena. People don’t like to be controlled and manipulated. So attempts to control them often result in resistance. It isn’t always loud, active resistance like we saw in Ferguson. People can resist in quiet and subversive ways that you may not even know about.
Keeping yourself in business can put you out of business.
As a business, obviously, one of your goals is to stay in business. So it would seem to be common sense that you don’t try to put yourself out of business. However, the nature of business is constant innovation. So if you don’t put yourself out of business, sooner or later, someone else will.
This screams against just about every natural self-preservation instinct. Most businesses have very strong organizational defense mechanisms to avoid behavior that would jeopardize the business at all.
For example, Kodak invented the digital camera in 1975, but film was the center of Kodak’s profitability, and the company’s internal defense mechanisms were so strong that the digital camera eventually disrupted Kodak’s business from the outside rather than from within.
The less money you have, the more you can innovate.
We tend to think that bigger is better when it comes to budgets. But the fact is that the greatest innovations have been launched by people with scarce resources. Xerox had tons of money and in 1970 they set up a center for innovation, XEROX PARC (Palo Alto Research Center) to imagine the office of the future. And they did. Imagine it, that is. But those great ideas were made real by others. Apple was launched by two guys in a garage. Facebook and Microsoft were launched by college kids. AirBnB was started by two guys who couldn’t afford the rent on their San Francisco apartments. EBay started out as a computer programmer’s hobby.
Scarcity drives creativity. Big money kills it.
Organizations will preserve the problem to which they are the solution.
Unions, for example… were a brilliant solution to the problem of capital management, which tended to exploit uncapitalized workers. But over time as capital increased in complexity, unions complexified as well, until unions needed management. The two became one system — union/management. So now the problem with unions is that they are locked into the old framework, the old system. They inadvertently perpetuate the continuation of the problem (management) they are the solution to because as long as unions exists, companies feel they need management to offset them, and so the two became co-dependent. In effect problems and solutions tend become a single system.
Defense contractors would go out of business if countries stopped fighting wars.
The U.S. Congress. Just think about it for a minute.
The more important the decision, the less informed the decision-maker will be.
The more important a decision, the higher it will typically be escalated in an organization. The higher it goes, the more it will be removed and abstracted from the actual situation and the problem that needs solving. This means decisions are escalated to people who know less and less about what’s actually going on.
Attempting to solve a problem can make it worse.
Sometimes by trying to solve a problem, you only make it worse. For example, we develop antibiotics to combat bacteria, but the more we use antibiotics, the stronger the bacteria get. In fact the strongest bacteria in existence today live in hospitals for exactly this reason. It’s estimated that 5 to 10 percent of people who are hospitalized are infected with something else while in the hospital. According to a New York Times article, “The Centers for Disease Control and Prevention estimates that roughly 1.7 million hospital-associated infections, from all types of bacteria combined, cause or contribute to 99,000 deaths each year.”
You want peace, so you spend money on a strong defense. This money strengthens the companies who make weapons, which benefit most when the weapons are used and need to be replenished. So in the interest of peace, you are strengthening the enablers of war.
Even the simple act of focusing on a problem can make it worse.
Mental health therapy, for example, often asks people to review and examine the things that are troubling them, which can make them loom larger and larger. The more we seek to cure phobias, the more time and money we spend on them, and the more phobias we discover. By focusing on the problem we enlarge it. Attacking a terrorist group gives it more combat experience, making it better at fighting. It also increases the international attention paid to the group, helping it gain more followers, members and sympathizers.
The solution to many problems is an opposite problem.
Let’s say you see the problem in these terms: your workplace is too rigid, too inflexible. Leaders are overly authoritarian. Work is too structured. People are divided in silos and can’t easily collaborate with each other. What do you do? You want to make the workplace more flexible. You want leaders to be more collaborative. People should have more freedom to do their work as they see fit. People should be connected, so they can more easily collaborate across divisions.
Now imagine you do these things. This gives rise to another set of problems. Now people are saying that leaders are indecisive, there’s no structure to the work, and it seems too disorganized. People are interrupting each other and talking too much when they should be working.
I saw my company oscillate between these two poles for many years. At one point my little company had as much paperwork and bureaucracy as a Fortune 500 corporation.
The bigger things are, the harder they are to see.
The things you ignore are the things that are the most fundamental and obvious. Rarely do you notice the air that you breathe. The ground that you walk on. The culture in any organization is one of these invisible things. Culture manifests itself in your unconscious behaviors and routines, the things that you do without thinking about them. It takes time, energy and attention to notice it.
For example: Xerox invented the PC but failed to execute due to culture.
Just because something is true doesn’t mean the opposite can’t also be true.
The Yoruba people tell the story of Eshu, who walked down a road wearing a hat which was black on one side and white on the other. After he had passed, the people working in the fields on either side began to argue about the color of Eshu’s hat. In some versions of the story they annihilate each other. In other versions Eshu simply comes back and shows them their folly.
You can confirm this one just by reading through the paradoxes above and considering their opposites. Sometimes things are easier to see when they are bigger. Sometimes the solution to a problem is not another problem. And so on.
There is a core paradox here that gets to the heart of this problem:
The more you know, the less you can see.
In order to do anything in the world, you need to make judgments and decisions about what to do. Experience can be very helpful because the more you know about something, the easier and more quickly you can make judgments and act. But the world is always changing, sometimes in ways that are hard to perceive. So the very expertise that enables you to diagnose issues and act quickly can also close your mind to possibility and blind you to things that are right in front of you.
Patterns may seem familiar, but no two situations are alike. The context matters, the history matters. The more confident you are, the more careful you should be. It’s in those moments of overconfidence that the most catastrophic mistakes are made. Think about Custer and the Little Big Horn. Think about the Titanic.
The resolution to this problem is to be mindful, to pay attention to what’s going on in the moment.
But this resolution creates the other half of the paradox: Mindful attention will help you see new possibilities, yet if you were to perceive everything as if it were completely new, you would be like a baby, unable to function at all.
There is a common military saying, “The Generals are always fighting the last war.” The idea here is that Generals were once foot soldiers, and the bulk of what they learned in combat was during the last war. The lessons they learned in that war may or may not be valid in the current war. World War I was a trench war fought mostly by infantry, so the French built the famous Maginot Line, a seemingly impenetrable defense. But in World War II German troops simply went around it.
In the 1904 Russo-Japanese War, Japan conducted a surprise attack on the Russian Fleet, which sealed a quick victory. But the attempt to repeat this strategic victory by attacking Pearl Harbor failed miserably.
In his book The Future of Management, Gary Hamel reports a conversation he had with senior executives in a big American auto manufacturer. He asked them why, after 20 years of benchmarking studies, the company had been unable to catch up to Toyota’s productivity. Here’s the answer he got:
“Twenty years ago we started sending our young people to Japan to study Toyota. They’d come back and tell us how good Toyota was and we simply didn’t believe them. We figured they’d dropped a zero somewhere — no one could produce cars with so few defects per vehicle, or with so few labor hours. It was five years before we acknowledged that Toyota really was beating us in a bunch of critical areas. Over the next five years, we told ourselves that Toyota’s advantages were all cultural. It was all about wa and nemawashi — the uniquely Japanese spirit of cooperation and consultation that Toyota had cultivated with its employees. We were sure that American workers would never put up with these paternalistic practices. Then, of course, Toyota started building plants in the United States, and they got the same results here they got in Japan — so our cultural excuse went out the window. For the next five years, we focused on Toyota’s manufacturing processes. We studied their use of factory automation, their supplier relationships, just-in-time systems, everything. But despite all our benchmarking, we could never seem to get the same results in our own factories. It’s only in the last five years that we’ve finally admitted to ourselves that Toyota’s success is based on a wholly different set of principles — about the capabilities of its employees and the responsibilities of its leaders.”
There’s a human tendency to perceive what you believe.
The stranger or more dissonant something seems to you, the more likely that you are encountering something new that you may be able to learn from. Things that are truly new to you may very possible seem to be in contradiction with things you already “know.”
Why all this talk about paradox? It’s not to confuse you or just to be a jerk. It’s because finding and recognizing paradoxes fuels the power to rethink, reframe, and see more than one side of things. As soon as you become comfortable with one way of seeing things, someone will point out truth in the opposite point of view.
Paradoxes can be clues to understanding deep and abiding conflicts, and confronting them directly may sometimes help in the search for resolutions. Niels Bohr once said, “How wonderful that we have met with a paradox. Now we have some hope of making progress.”
Liminal Thinking — the art of creating change by understanding, shaping, and reframing beliefs — can make you more successful in working with paradoxes, complexity and change.
If something has worked forever, it’s bound to stop working sooner or later. The world co-evolves and nothing can stay on top indefinitely. The longer things have been going well, the more fragile they are likely to be. So, as Lieutenant General Hal Moore said, “when there’s nothing wrong, then there’s nothing wrong, except that there’s nothing wrong. That’s exactly when a leader must be most alert.”
 Matt Manuel.
 Pollack, Andrew, Rising Threat of Infections Unfazed by Antibiotics, The New York Times, February 26, 2010.