Ted’s feeling pretty good. He sits across from me in the conference room and says, “Program launch is solid. We’ve been working on the details for almost a month. We vetted the concept with all the affected teams and made tweaks, and now they’re fine. The only step left is sending the announcement to the whole company.”

“Nice work, Ted,” I say, “Huge amount of work.”

“Thanks.”

“You’re not remotely done.”

Ted, “Pardon?”

A Test of Character

In the 23rd Century of the Star Trek universe, there exists a test for cadets on the command-track of Star Fleet. Via Memory Alpha:

The test primarily consisted of the cadet placed in command of a starship. The ship would soon receive a distress signal from the Kobayashi Maru, a civilian freighter within the Klingon Neutral Zone that had been heavily disabled. Being the only ship in range, the cadet usually either chose to withdraw from the rescue mission or enter the neutral zone and rescue the vessel in risk of violating the treaties. The ship would then be confronted by Klingon battle cruisers which typically engaged in a firefight.

The punchline? It is virtually impossible to win the scenario. The cadet cannot simultaneously save the Kobayashi Maru, avoid a fight, and escape the Neutral Zone intact. The test is one of character and decision-making.

A critical part of a manager’s job lies in their ability to appropriately act in unusually complex, unexpected, and perhaps no-win scenarios, but you know what’s better? Not getting in those situations in the first place.

A System Failure

The daily life of a manager is full of unexpected developments. The daily stand-up where you discover you’re a month late on a feature. The 1:1 where Justin first tells you his shields are down. The random conversation in a hallway where you discover the first hint of an impending professional disaster. These discoveries are standard operating procedure, and they never stop. Good luck.

A Kobayashi begins innocuously. A simple communication. A non-hasty and thoughtful launch of a program. A well-designed and well-tested feature now available to 100% of your customers. You’ve done this before, and you are not going through the motions which make the reaction… jarring.

A Kobayashi erupts immediately. The swift response starts with someone raising their hand virtually or otherwise and what they say or type immediately differentiates this situation from your unexpected daily developments. You think, but do not say, “Oh. Shit.”

If you are finding this piece uncomfortably vague and have no idea what I am talking about, I humbly suggest you stop reading right now because the rest of this piece will continue to read vague and unhelpful.

A Kobayashi is a system failure, and you understand this when the first bit of feedback arrives and it’s a combination of:

• A complete surprise,
• An intense adverse reaction,
• Via a population of humans raising their hands in protest who you did not expect,
• Including a new piece of critical information you had no idea belonged in this situation.

A Kobayashi is a system failure because the usual means of getting important work done in a group of humans failed spectacularly. A reorganization that felt obvious and non-controversial. An HR program that appeared a win for everyone. A well-intended disclosure of information planned to build trust on the team. The potential situations are endless, and the only true consistency is the two words. Your words. And there are two.

“Oh. Shit.”

A Perfect Kobayashi

The unfortunate truth of Kobayashi’s is the best way to prepare for them is to experience them. To do so, let’s create a hypothetical program that I’m about to launch. All good projects have a code name, so let’s call this one: The Good Place¹.

These are the hypothetical specifics of The Good Place. It’s a company-wide program I’m launching later this month. It will only affect 5% of the engineering team and the affected folk’s day to day lives are mostly unaffected for a quarter. After that quarter, they’ll need to make some changes to how they work, but, hey, they have three months to prepare. No problem.

The Good Place shares attributes with all Kobayashi’s. Specifically:

• It affects a broad set of diverse humans.
• It represents an unfamiliar or significant change to how those humans work.
• It’s initial perceived success depends on how the affected humans react to the change.
• It looks a lot like work I’ve done the past.

Combined those attributes create the perfect Kobayashi. My guard is down, the change is hard to digest, and I’ve underestimated the number of affected humans. Since success is dependent on initial perception, when that larger than expected reaction emerges, I go into extreme denial and start lying to myself.

• It’s just a couple of people. It’s not.
• It’s just a misunderstanding. It’s not.
• It’ll blow over. It won’t.

This is the bad place.

A Proper Preparation

A useful article document on how to move into damage control mode and deftly handling this no-win scenario seems like a good idea, but wouldn’t it be better if this article explained how to not get into this situation in the first place?

Super.

My Kobayashi prevention protocol is conveniently the same process I follow for any significant change on the team. Let’s begin:

Frame the situation via a written artifact. You need to create a presentation or document that clearly explains what is going on, why it is happening, what success looks like because of this change, how we are going to measure success, and how anyone can give feedback on this development. This is simply a draft, and it’s going to change a lot before you’re done.

Vet the draft plan with three no-skin-in-the-game trusted humans. Take your draft and give it to three humans who are not affected by this change and who you trust to tell it to you straight. If there is only one piece of advice you should follow in this entire piece, this is it. Unaffected trusted humans are the ones who are most likely to see the obvious flaw in your plans and who are also eager to tell you about these flaws.

Write down a list of all people and teams that you expect will be affected by the change. This exercise is the first step of building out a communication plan, but right now it’s a sizing exercise. Write the list. Ok, how many folks are on it? Five? Just five? Why are you still reading this article if we’re talking about five affected people? I’ll tell you why. You can smell the larger-than-expected impact. Your spidey-sense is tingling. How many humans will really be affected? Not just direct, but indirectly. Humans who care about the directly affected humans. Humans who will have a strong opinion about the change. Humans who are going to raise their hands and speak. Yeah, put them all on the list, return to your three trusted humans and vet the list.

Draft your communication plan. With your framing and vetted list in hand, it’s time to operationalize this program. It’s called a cascading communications plan because you start with the most affected humans and slowly work your way towards less affected humans. Here’s the order of operation:

1. A pre-flight meeting with affected humans in a 1:1 situation. Face to face, you are going to walk the directly affected human through the framing. The rule is: no one who is directly significantly affected by this change can learn about this from anyone but you.² I call this pre-flight because there is a non-zero chance that one of these humans is going to point out an obvious flaw in your plan. I’m not talking about being unhappy about the plan; I am talking about a strategic error in your framing and/or roll-out. Plan for changes to your framing.
2. A walk-thru with small groups of “persons of interest” through the framing with Q&A. It’s little less personal in a group setting, but the goal is the same: gauge reaction and, if necessary, make adjustments to the framing.
3. A presentation with Q&A to affected teams either team by team or all at once. By this point, you will have vetted the plan with trusted advisors, affected humans, and persons of interest. This is the first presentation where you are unlikely to make changes based on feedback from the audience³. At this point in the process, the questions that show up during Q&A will be the ones you’ve heard a couple of times. Nailed it.
4. An announcement to the entire team or organization depending on the size of the program via presentation, an email or Slack.

Have you ever sat at your computer with a huge message that you need to send to the team and you can’t hit the SEND key? You know why? You smell the Kobayashi potential of this message. You can sense there is an essential angle that you did not consider. There is one person who has critical feedback that you have not heard. You will know that you’ve done everything you can regarding Kobayashi prevention when it’s trivial to hit SEND.

A Prediction of the Unpredictable

Like most principled leadership applied with consistency, your reward for all of this Kobayashi Maru inoculation is nothing. Nothing happens. No one raises their hands. There is no drama. The team looks at your framing, crinkles their forehead, and then says, “Yeah, that makes sense. What’s next?”

No one celebrates when nothing happens. We all know when something significant goes wrong because suddenly everyone rushes around with great ferocity. Heroes and heroines appear when something goes wrong. They work for three days straight. We award spot bonuses for this exceptional effort. There are no spot bonuses for averted disasters because they are the results of capable leaders competently doing their job.

I, like Captain Kirk, don’t believe in the no-win scenario in business. There will always be system failures large and small in complex groups of humans combined with rapidly changing stacks of technology. There is win inside of each failure because there are lessons. There are essential discoverable lessons within each failure, and these lessons are essential new additions to the playbook we use to prevent that failure from happening again.

That’s how you win.