Introduction to The Three Envelopes

For those familiar with the comedy world, The Aristocrats might ring a bell. It’s an old joke where the basic setup and punchline stay the same, but everyone has their own version of what happens in between.

IT and management have something similar: The Three Envelopes.

The details change depending on who’s telling it, but the basic story is remarkably consistent. A manager inherits a troubled project and three envelopes from their predecessor, with instructions to open them one by one whenever things go seriously wrong.

It’s an old management joke, but anyone who has spent enough time around corporate IT will probably recognize some uncomfortable truths hiding inside it.

So let’s open the first envelope.

Chapter 1: Meet the Envelopes

A New Beginning

The Three Envelopes story begins with a new manager taking over a troubled project from their predecessor.

Along with the usual handover comes one final piece of advice: there are three numbered envelopes waiting in the desk. When things go seriously wrong, open them one at a time, and in order.

Sooner or later, as tends to happen in IT, something goes seriously wrong.

“Hey Jack, I’m the one that did this before you. Should anything go awry, you’ll find three envelopes in the top right drawer. Open them in sequence,” says the mysterious voice from the past.

“I’ve got everything under control with these,” thinks Jack. But do I? The envelopes stand as his so-called safety net. But what’s inside?

The First Envelope: Blame the Predecessor

Soon enough, the project runs into trouble. Deadlines slip, problems surface, and questions start being asked.

Time to open the first envelope.

“Blame your predecessor.”

It’s an effective strategy because there will almost always be inherited problems to point at. Decisions were made before you arrived, technical debt already existed, and perhaps the documentation isn’t quite what everyone hoped it would be.

And for a while, it works. The new manager gets some breathing room, and everyone agrees that the previous management clearly left a bit of a mess behind.

Until the next crisis arrives.

Chapter 2: Reorganize

The Second Envelope

Eventually, blaming your predecessor stops working. You’ve been in charge long enough that the problems are now yours.

Another crisis arrives, so it’s time for the second envelope:

“Reorganize.”

Teams move around. Responsibilities change. Reporting lines are redrawn. Departments are merged, split, renamed, or moved under different management.

Sometimes a reorganization is exactly what an organization needs. But sometimes it creates a lot of visible change without actually fixing the problem that caused the crisis in the first place.

Everything Changed, Except the Problem

This is where the Three Envelopes joke starts becoming painfully familiar to anyone who has spent enough time in corporate IT.

The organization chart may look completely different. People have new managers, new responsibilities, and perhaps even new job titles.

But underneath all of that, the same technical and organizational problems can still be sitting there waiting for the next crisis.

And eventually, there is only one envelope left.

Chapter 3: Management Insights and Anecdotes
Avoiding the Envelope Carousel

Not everyone wants to play the management game.

Andrew has spent much of his career on the engineering side and has deliberately avoided climbing too far up the management ladder. That also gives him a good seat from which to watch the familiar cycle of new managers, reorganizations, changing priorities, and eventually another new manager.

There are engineers who would probably make excellent managers but simply don’t want the job. They prefer solving technical problems to dealing with the politics and organizational maneuvering that can come with management.

Sometimes the best way to survive the Three Envelopes is simply not to be the person opening them.

“At engineering level, sure. I’ve seen many engineers have the potential to become great managers, but they choose not to partake in never-ending rat races.”

The Entertaining Escapades

Of course, management changes don’t always follow the neat Three Envelopes script.

Andrew recalls one manager who had developed a reputation for being particularly difficult to work with. Blaming predecessors and playing the usual management games only works for so long, and eventually the organization decided it was time for another change of management.

Then there are the stranger ways people manage to leave an IT job. In Romania, one IT professional apparently helped things along by insisting that the computer monitor on his desk belonged to him and that he should be allowed to take it home.

Not every departure requires three envelopes. Sometimes a monitor will do.

Conclusion: The Third Envelope

Eventually, blaming your predecessor stops working. Reorganizing doesn’t solve everything either. And when the next crisis arrives, there is still one envelope left.

“Prepare three envelopes.”

That’s why the joke has survived for so long. Managers change, organizations reorganize, and every new arrival inherits decisions and problems from the people who came before them. Sometimes those really are the cause of the problem. Sometimes changing the organization really does help.

And sometimes, a few years later, someone else is sitting at the same desk explaining what the previous manager got wrong.

Whether you’re opening the envelopes or watching from the engineering side, you’ve probably seen your own version of the story.

Just hope you never need envelope number three.