The Parable of the Airplane

Lindsay Jones is a friend of ours who is a professional theatrical sound designer and composer.  He spends his life flying around the United States, hopping from production to production, and he’s full of crazy (and true) stories about air travel. Here’s one of our favorite stories:

It’s 6 a.m., we’re all boarded on the plane and ready to go. The captain comes on the PA system and explains to us that, somehow, someone has overfilled the fuel tank by 10,000 gallons. Now, I’ve flown on planes for a long time, and I didn’t know that such a thing was possible. I mean, if I overfill my car by a gallon, I’m gonna have gas all over my shoes, right?

Well, so anyway, the captain then says that we have two options: we can either wait for the truck to come suck the fuel back out of the plane, which is going to take over an hour, or twenty people have to get off the plane right now to even out the weight.

No one moves.

Now, there’s this guy across the aisle from me in first class, and he is absolutely livid. He reminds me of Frank Burns on M*A*S*H; he’s just super indignant and sputtering everywhere, demanding to know who’s responsible. It’s an amazing showcase, it’s like he’s Margaret Dumont in the Marx Brothers movies.

So, he grabs his wallet and pulls out this massive wad of cash! And he’s like “I cannot be late for this meeting!! I will give $40 to any person who gets off this plane right now!”

Sure enough, people take him up on it. He gives out $40 to 20 people (which is $800 in cash, by the way!) and they all leave.

So, now we’re all set and we head out to the runway, and the captain comes back on the PA again. The plane’s computer has stopped working. No one knows why. Now we gotta get towed back to the gate.

Frank Burns is apoplectic. I mean, seriously, I thought he was gonna have a stroke. He’s cursing and screaming. Everyone else is just looking at each other.

We get back to the gate and this guy is demanding another flight. They offer to book him on the 9:30, which is too late. He’s like, “Isn’t there another flight before 9:30?”

The gate agent is like, “Well, there was another flight at 8, but it’s all full now. They’re closing the doors now.”

And he’s like, “Full?! Whaddya mean it’s full? There’s not one open seat on that plane?!?!?!”

The gate agent is like, “No sir, that plane was wide open until 20 passengers showed up out of nowhere and took all the seats. They were the happiest passengers I’ve ever seen, they were laughing all the way down the jet bridge.”

It was a very quiet ride on the 9:30 flight.

This story is, of course, about trade-offs.  Although most of this book focuses on various technical trade-offs in engineering systems, it turns out that trade-offs also apply to human behaviors. As a leader, you need to make decisions about what your teams should do each week. Sometimes the trade-offs are obvious (“if we work on this project, it delays that other one…”); sometimes the trade-offs have unforeseeable consequences that can come back to bite you, as in the preceding story.

At the highest level, your job as a leader—either of a single team or a larger organization—is to guide people toward solving difficult, ambiguous problems. By ambiguous, we mean that the problem has no obvious solution and might even be unsolvable. Either way, the problem needs to be explored, navigated, and (hopefully) wrestled into a state in which it’s under control. If writing code is analogous to chopping down trees, your job as a leader is to “see the forest through the trees” and find a workable path through that forest, directing engineers toward the important trees. There are three main steps to this process. First, you need to identify the blinders; next, you need to identify the trade-offs; and then you need to decide and iterate on a solution.

Identify the Blinders

When you first approach a problem, you’ll often discover that a group of people has already been  wrestling with it for years.  These folks have been steeped in the problem for so long that they’re wearing “blinders”—that is, they’re no longer able to see the forest. They make a bunch of assumptions about the problem (or solution) without realizing it. “This is how we’ve always done it,” they’ll say, having lost the ability to consider the status quo critically. Sometimes, you’ll discover bizarre coping mechanisms or rationalizations that have evolved to justify the status quo. This is where you—with fresh eyes—have a great advantage. You can see these blinders, ask questions, and then consider new strategies. (Of course, being unfamiliar with the problem isn’t a requirement for good leadership, but it’s often an advantage.)

Identify the Key Trade-Offs

By definition, important and ambiguous problems do not have magic "silver bullet" solutions.   There’s no answer that works forever in all situations. There is only the best answer for the moment, and it almost certainly involves making trade-offs in one direction or another. It’s your job to call out the trade-offs, explain them to everyone, and then help decide how to balance them.

Decide, Then Iterate

After you understand the trade-offs  and how they work, you’re empowered. You can use this information to make the best decision for this particular month.  Next month, you might need to reevaluate and rebalance the trade-offs again; it’s an iterative process.  This is what we mean when we say Always Be Deciding.

There’s a risk here. If you don’t frame your process as continuous rebalancing of trade-offs, your teams are likely to fall into the trap of searching for the perfect solution, which can then lead to what some call “analysis paralysis.” You need to make your teams comfortable with iteration.  One way of doing this is to lower the stakes and calm nerves by explaining: “We’re going to try this decision and see how it goes. Next month, we can undo the change or make a different decision.” This keeps folks flexible and in a state of learning from their choices.

Your Mission: Build a “Self-Driving” Team

Coming back to Bharat’s quote: being a successful leader means  building an organization that is able to solve the difficult problem by itself. That organization needs to have a strong set of leaders, healthy engineering processes, and a positive, self-perpetuating culture that persists over time. Yes, this is difficult; but it gets back to the fact that leading a team of teams is often more about organizing people rather than being a technical wizard. Again, there are three main parts to constructing this sort of self-sufficient group: dividing the problem space, delegating subproblems, and iterating as needed.

Dividing the Problem Space

Challenging problems are usually composed of difficult subproblems.  If you’re leading a team of teams, an obvious choice is to put a team in charge of each subproblem. The risk, however, is that the subproblems can change over time, and rigid team boundaries won’t be able to notice or adapt to this fact. If you’re able, consider an organizational structure that is looser—one in which subteams can change size, individuals can migrate between subteams, and the problems assigned to subteams can morph over time. This involves walking a fine line between “too rigid” and “too vague.” On the one hand, you want your subteams to have a clear sense of problem, purpose, and steady accomplishment; on the other hand, people need the freedom to change direction and try new things in response to a changing environment.

The Cycle of Success

When a team tackles a difficult problem, there’s a standard pattern that emerges, a particular cycle.  It looks like this:

Analysis

First, you receive the problem and start to wrestle with it. You identify the blinders, find all the trade-offs, and build consensus about how to manage them.

Struggle

You start moving on the work, whether or not your team thinks it’s ready. You prepare for failures, retries, and iteration. At this point, your job is mostly about herding cats. Encourage your leaders and experts on the ground to form opinions and then listen carefully and devise an overall strategy, even if you have to "fake it" at first.³

Traction

Eventually your team begins to figure things out. You’re making smarter decisions, and real progress is made. Morale improves. You’re iterating on trade-offs, and the organization is beginning to drive itself around the problem. Nice job!

Reward

Something unexpected happens. Your manager takes you aside and congratulates you on your success. You discover your reward isn’t just a pat on the back, but a whole new problem to tackle. That’s right: the reward for success is more work…and more responsibility! Often, it’s a problem that is similar or adjacent to the first one, but equally difficult.

So now you’re in a pickle. You’ve been given a new problem, but (usually) not more people. Somehow you need to solve both problems now, which likely means that the original problem still needs to be managed with half as many people in half the time. You need the other half of your people to tackle the new work! We refer to this final step as the compression stage: you’re taking everything you’ve been doing and compressing it down to half the size.

So really, the cycle of success is more of a spiral (see Figure 6-2). Over months and years, your organization is scaling by tackling new problems and then figuring out how to compress them so that it can take on new, parallel struggles. If you’re lucky, you’re allowed to hire more people as you go. More often than not, though, your hiring doesn’t keep pace with the scaling. Larry Page, one of Google’s founders, would probably refer to this spiral as “uncomfortably exciting.”

The spiral of success is a conundrum—it’s something that’s difficult to manage, and yet it’s the main paradigm for scaling a team of teams. The act of compressing a problem isn’t just about figuring out how to maximize your team’s efficiency, but also about learning to scale your own time and attention to match the new breadth of responsibility.

Important Versus Urgent

Think back to a time when you weren’t yet a leader, but still a carefree individual contributor.    If you used to be a programmer, your life was likely calmer and more panic-free. You had a list of work to do, and each day you’d methodically work down your list, writing code and debugging problems. Prioritizing, planning, and executing your work was straightforward.

As you moved into leadership, though, you might have noticed that your main mode of work became less predictable and more about firefighting. That is, your job became less proactive and more reactive. The higher up in leadership you go, the more escalations you receive. You are the "finally" clause in a long list of code blocks! All of your means of communication—email, chat rooms, meetings—begin to feel like a Denial-of-Service attack against your time and attention. In fact, if you’re not mindful, you end up spending 100% of your time in reactive mode. People are throwing balls at you, and you’re frantically jumping from one ball to the next, trying not to let any of them hit the ground.

A lot of books have discussed this problem.  The management author Stephen Covey is famous for talking about the idea of distinguishing between things that are important versus things that are urgent. In fact, it was US President Dwight D. Eisenhower who popularized this idea in a famous 1954 quote:

I have two kinds of problems, the urgent and the important. The urgent are not important, and the important are never urgent.

This tension is one of the biggest dangers to your effectiveness as a leader. If you let yourself slip into pure reactive mode (which happens almost automatically), you spend every moment of your life on urgent things, but almost none of those things are important in the big picture. Remember that your job as a leader is to do things that only you can do, like mapping a path through the forest. Building that meta-strategy is incredibly important, but almost never urgent. It’s always easier to respond to that next urgent email.

So how can you force yourself to work mostly on important things, rather than urgent things? Here are a few key techniques:

Delegate

Many of the urgent things you see can be delegated back to other leaders in your organization. You might feel guilty if it’s a trivial task; or you might worry that handing off an issue is inefficient because it might take those other leaders longer to fix. But it’s good training for them, and it frees up your time to work on important things that only you can do.

Schedule dedicated time

Regularly block out two hours or more to sit quietly and work only on important-but-not-urgent things—things like team strategy, career paths for your leaders, or how you plan to collaborate with neighboring teams.

Find a tracking system that works

There are dozens of systems for tracking and prioritizing work.  Some are software based (e.g., specific “to-do” tools), some are pen-and-paper based (the “Bullet Journal” method), and some systems are agnostic to implementation. In this last category, David Allen’s book, Getting Things Done, is quite popular among engineering managers; it’s an abstract algorithm for working through tasks and maintaining a prized "inbox zero." The point here is to try these different systems and determine what works for you. Some of them will click with you and some will not, but you definitely need to find something more effective than tiny Post-It notes decorating your computer screen. 

Learn to Drop Balls

There’s one more key technique for managing your time, and on the surface it sounds radical.  For many, it contradicts years of engineering instinct. As an engineer, you pay attention to detail; you make lists, you check things off lists, you’re precise, and you finish what you start. That’s why it feels so good to close bugs in a bug tracker, or whittle your email down to inbox zero. But as a leader of leaders, your time and attention are under constant attack. No matter how much you try to avoid it, you end up dropping balls on the floor—there are just too many of them being thrown at you. It’s overwhelming, and you probably feel guilty about this all the time.

So, at this point, let’s step back and take a frank look at the situation. If dropping some number of balls is inevitable, isn’t it better to drop certain balls deliberately rather than accidentally? At least then you have some semblance of control.

Here’s a great way to do that.

Marie Kondo is an organizational consultant and the author  of the extremely popular book The Life-Changing Magic of Tidying Up. Her philosophy is about effectively decluttering all of the junk from your house, but it works for abstract clutter as well.

Think of your physical possessions as living in three piles. About 20% of your things are just useless—things that you literally never touch anymore, and all very easy to throw away. About 60% of your things are somewhat interesting; they vary in importance to you, and you sometimes use them, sometimes not. And then about 20% of your possessions are exceedingly important: these are the things you use all the time, that have deep emotional meaning, or, in Ms. Kondo’s words, spark deep “joy” just holding them. The thesis of her book is that most people declutter their lives incorrectly: they spend time tossing the bottom 20% in the garbage, but the remaining 80% still feels too cluttered. She argues that the true work of decluttering is about identifying the top 20%, not the bottom 20%. If you can identify only the critical things, you should then toss out the other 80%. It sounds extreme, but it’s quite effective. It is greatly freeing to declutter so radically.

It turns out that you can also apply this philosophy to your inbox or task list—the barrage of balls being thrown at you. Divide your pile of balls into three groups: the bottom 20% are probably neither urgent nor important and very easy to delete or ignore. There’s a middle 60%, which might contain some bits of urgency or importance, but it’s a mixed bag. At the top, there’s 20% of things that are absolutely, critically important.

And so now, as you work through your tasks, do not try to tackle the top 80%—you’ll still end up overwhelmed and mostly working on urgent-but-not-important tasks. Instead, mindfully identify the balls that strictly fall in the top 20%—critical things that only you can do—and focus strictly on them. Give yourself explicit permission to drop the other 80%.

It might feel terrible to do so at first, but as you deliberately drop so many balls, you’ll discover two amazing things. First, even if you don’t delegate that middle 60% of tasks, your subleaders often notice and pick them up automatically. Second, if something in that middle bucket is truly critical, it ends up coming back to you anyway, eventually migrating up into the top 20%. You simply need to trust that things below your top-20% threshold will either be taken care of or evolve appropriately. Meanwhile, because you’re focusing only on the critically important things, you’re able to scale your time and attention to cover your group’s ever-growing responsibilities.

Protecting Your Energy

We’ve talked about protecting your time and attention—but your personal energy is the other piece of the equation.  All of this scaling is simply exhausting. In an environment like this, how do you stay charged and optimistic?

Part of the answer is that over time, as you grow older, your overall stamina builds up. Early in your career, working eight hours a day in an office can feel like a shock; you come home tired and dazed. But just like training for a marathon, your brain and body build up larger reserves of stamina over time.

The other key part of the answer is that leaders gradually learn to manage their energy more intelligently. It’s something they learn to pay constant attention to. Typically, this means being aware of how much energy you have at any given moment, and making deliberate choices to “recharge” yourself at specific moments, in specific ways. Here are some great examples of mindful energy management:

Take real vacations

A weekend is not a vacation. It takes at least three days to "forget" about your work; it takes at least a week to actually feel refreshed. But if you check your work email or chats, you ruin the recharge. A flood of worry comes back into your mind, and all of the benefit of psychological distancing dissipates. The vacation recharges only if you are truly disciplined about disconnecting.⁴ And, of course, this is possible only if you’ve built a self-driving organization.

Make it trivial to disconnect

When you disconnect, leave your work laptop at the office. If you have work communications on your phone, remove them. For example, if your company uses G Suite (Gmail, Google Calendar, etc.), a great trick is to install these apps in a "work profile" on your phone. This causes a second set of work-badged apps to appear on your phone. For example, you’ll now have two Gmail apps: one for personal email, one for work email. On an Android phone, you can then press a single button to disable the entire work profile at once. All the work apps gray out, as if they were uninstalled, and you can’t “accidentally” check work messages until you re-enable the work profile.

Take real weekends, too

A weekend isn’t as effective as a vacation, but it still has some rejuvenating power. Again, this recharge works only if you disconnect from work communications. Try truly signing out on Friday night, spend the weekend doing things you love, and then sign in again on Monday morning when you’re back in the office.

Take breaks during the day

Your brain operates in natural 90-minute cycles.⁵ Use the opportunity to get up and walk around the office, or spend 10 minutes walking outside. Tiny breaks like this are only tiny recharges, but they can make a tremendous difference in your stress levels and how you feel over the next two hours of work.

Give yourself permission to take a mental health day

Sometimes, for no reason, you just have a bad day. You might have slept well, eaten well, exercised—and yet you are still in a terrible mood anyway. If you’re a leader, this is an awful thing. Your bad mood sets the tone for everyone around you, and it can lead to terrible decisions (emails you shouldn’t have sent, overly harsh judgements, etc.). If you find yourself in this situation, just turn around and go home, declaring a sick day. Better to get nothing done that day than to do active damage.

In the end, managing your energy is just as important as managing your time. If you learn to master these things, you’ll be ready to tackle the broader cycle of scaling responsibility and building a self-sufficient team.