Chapter 12. The Enemy
The $150,000 mistake, the discovery of critical and unfixable architectural flaw three weeks before shipping, and the Really Bad Hire (aka, we’re being sued).
These are not screwups,[2] these are fuckups, and they aren’t about to happen—they’re here. They’re guaranteed. When you discover them, the air leaves your lungs, the back of your head tingles, and there’s an odd metallic taste in your mouth. Your mind goes blank except for the crisp mental picture that is a fuckup of your own making.
Initial personal discovery is shocking, but what I want to examine is secondary discovery. This is when your boss learns of the fuckup, and you shouldn’t be worried whether there’s an odd metallic taste in his mouth; you should worry about who he’s about to turn into.
Management Transformations
Ideally, your boss is the levelheaded type, and he’ll manage your fuckup cleanly and easily using his years of experience, but fuckups knock people off their game and out of their comfort zone. Fuckups create unusual stress, and stress can mutate normally sane people into unrecognizable caricatures of themselves. Let’s talk about some of them.
The Interrogator
The Interrogator’s approach is an endless stream of questions: “When did the customer first call?” “Who triaged the bug first?” “What were the results?” “How did we proceed from there?” It goes on and on.
What’s annoying about the Interrogator is that he actually only wants to ask one question—THE question—but he’s putting you through the paces to build a sense of context. This stream of questions will demonstrate the relevance of the one question. The one question is the only question that matters, and when it shows up, it’s time to start the meeting.
While you’re being grilled, I want you to remember this: the Interrogator is blowing off steam while asking the endless list of questions. This process of question and answer is laborious, but with each piece of data you convey, you have an opportunity to paint a more detailed picture of your fuckup and increase the chance he can help.
There are Interrogators who don’t actually have one question that they’re driving toward, and these managers need managing. If you’re 27 questions into your 1:1 with no clear direction and a total lack of context, it’s time to dig in your heels and ask, “Hey, Boss, what are you really trying to figure out here? Are you just pissed, or are we trying to make progress?”
The Prioritizer
Meetings with the Prioritizer start with a complete inventory of the to-do list for your team. He wants to know everything that you’re planning to do to resolve the fuckup, and if this list doesn’t exist or isn’t complete, you might as well reschedule the meeting, because there is no other way to satisfy the Prioritizer.
With that list in hand, the Prioritizer will now put you through the agonizing process of prioritizing every single task on the list. If he’s in a really bad mood, he’s going to want to talk through your mental process of prioritization for each task. What he’s doing is sniffing for a lack of knowledge on any of these tasks, and if he finds it, you’re screwed because any lack of knowledge or confidence this close to the fuckup erodes his confidence that you’ve actually got a plan.
Unlike the Interrogator, there is no obvious point where you’re going to understand, “Oh, this is what he wants to know. This is the plan.” He wants to know everything. Your fuckup has him freaked out, and his reaction to this is to gather as much data as possible. Feels like micromanagement, right? It is. More on this in a moment.
The Randomizer
The insane version of the Prioritizer is the Randomizer. This is the manager who is going to swoop into the situation with good intentions, but he’s mostly going to randomize the team with his endless good intentions.
The warning signs of the Randomizer are easy to recognize: his marching orders to address the fuckup change every couple of hours. You might not initially see this, because the Randomizer is the boss. His sense of passion and urgency is intoxicating because everyone wants to get to the other side of the fuckup. They want to succeed. After the third drastic change to the plan of action, the team is going to start scratching their heads and thinking, "How is running around bumping into shit actually helping us?”
You job as the minion of the Randomizer is to get back into the 1:1, close the door, and see if you can summon the Prioritizer. Your boss should be your strategic muse, not your tactical nightmare.
The Illuminator
The Illuminator is on the same mission as everyone we’ve already talked about, but he’s subtle about it. You may not even know the Illuminator is in the room when you show up for your 1:1. I love the Illuminator. I love being the Illuminator.
See, you fucked up. The Illuminator isn’t going to interrogate or prioritize you for an hour; he is elegantly, calmly going to get you to realize the magnitude of the fuckup and also get you to suggest a reasonable course of action. In fact, you’ll be proud of yourself halfway through the meeting when you slap your forehead and say, “Wow, this is what happened and this is what we should do!”
The transcendent Illuminator experience is when you don’t realize the Illuminator is gently mentally course-correcting you and providing silent guidance. The cherry on top is, even if you do see this management manipulation, you realize, “Oh, he’s trying to help.”
The Enemy
On the opposite side of the spectrum of the Illuminator is the Enemy.
Like the Illuminator, the Enemy isn’t going to reveal his colors immediately, but unlike the Illuminator, he will not revel in silently providing guidance; he loves going on the attack. The Enemy is pissed. The Enemy is angry about your fuckup, and the Enemy believes that dragging you through that anger is a useful learning experience.
Here’s the terrifying reality regarding the Enemy: unlike all the other personalities I’ve talked about, the Enemy is not on your side. As long as your fuckup didn’t involve breaking the law, your manager is part of your team, and even if he’s furious with you, he should always be trying to lead and trying to help because you are his responsibility.
If the Enemy shows up, your fuckup has now doubled in size. You’ve got a fuckup and you’ve got a manager who doesn’t believe in you. My hope is that the Enemy is a mood; it’s the peak fury of your manager’s reaction to your fuckup and, fingers crossed, it should fade into a calmer personality. Still, even when it does, you need to figure out why your manager doesn’t trust you when he’s freaking out.
The M Word
Yes, everyone except the Illuminator is a micromanager, and while being micromanaged sucks, see, you fucked up. It’d be great if your manager remained even-keeled, but we humans are a squishy, moody bunch, and how we react when a fuckup is thrown in our laps varies by the day.
Whether you’re being interrogated, randomized, or prioritized, you need to remember two things.
First, it’s your job to figure out how to bring your calm, levelheaded boss back into the room. Every personality save for the Illuminator is looking for the same thing: explain to me what we’re going to do to fix this, why this is a fix, and when is it going to be done?
Second, as you stare at this strange person who was your boss, you need to remember that people with more experience can teach, you can learn from them, but you might need to wait for it.
While you wait for the storm to pass, might I suggest a healthy dose of proactive fuckup triage? Unless you’re working for the Enemy, your boss will eventually help, but long-term success here will be taking an active role in understanding the full scope of your fuckup and determining what needs to change to make sure it never happens again.