the curtain opens on act one
A software manager is brought into a doomed project. It is hopelessly behind, the requirements have changed so often they are effectively kept in chat history instead of JIRA, and Office Space references and memes pepper every conversation. The previous manager resigned.
When they get to their new office, their predecessor is clearing out their desk. “I’ll only be a minute. By the way, I left you something,” says the old manager. After the predecessor leaves, the new manager has a look around, and discovers three envelopes in the top drawer of the desk.
- The first envelope is labeled, “Open when in trouble;”
- The second is labeled, “Open when in even more trouble;”
- The third is labeled, “Open when all hope is lost.”
Well, they research anti-patterns in software project management; they talk to everyone; they identify the key players; and they go to leadership with a clear explanation of what the problems are, what’s realistic to achieve, and what needs to be done.
To their surprise, leadership goes along with things and tells them to make whatever changes they need. They institute daily builds; they lead stand up meetings, they deploy rapid iterations; and the team starts tracking velocity. Two months later, at the quarterly review, they present their progress: Velocity is 200% of the previous rate, morale is up, and they’re going to get 80% of the previous functionality done with less than 90 days of slip off the impossible schedule.
There is silence, then leadership tells their that this is unacceptable. Sure, they agreed they could institute change. That’s their job. However leadership did not approve any compromise in scope or delivery date. This is a competitive business, and there are thousands of qualified managers looking for a job who can come in and get things done. Do they want to admit they can’t do their job?
Leadership lays down the law:
“We have assigned a product manager to discuss AI integration with your technical lead. And the VP of Marketing needs to talk to you. We have made a commitment to all-singing, all-dancing Agentic AI, and he needs a forty-minute presentation explaining how your project will be built on top of a platform created by this new company our investors made us buy last week.
“You look pale. Is there a problem?”
trouble
The new manager goes back to their office in a quandary, then they remember the first envelope. They open it, and inside there is a three by five card inscribed, Blame Me.
They go back to leadership a day later with a gdoc emphasizing how the project was way off track, how the architecture was fubar, how morale was poor, and how requirements were incorrectly documented. They don’t blame the previous manager directly, but they do identify various management techniques and best practices that were not enforced prior to their joining the project.
They will work the team to hit the date, but the commitments made by the previous manager were done without actually checking to see whether the team could deliver or making any changes to actually hit the new dates. After some huffing and puffing, leadership buys off on delivering 80% of the promised functionality with a 45 day slip in the delivery date. Whew!
Things go along well for a month, until the Hawthorne Effect wears off–that inevitable clawback of early gains. The numbers slip, morale goes down the toilet, and the team goes into survival mode, avoiding responsibility for anything and pointing fingers at each other… and the new manager.
even more trouble
Well, the first envelope helped, maybe the second one will help as well. The new manager opens the second envelope, and inside there is another three by five card inscribed, Reorganize.
The manager declares that the team needs to split into pairs along architectural lines, and has the ticket system reconfigured since individuals are no longer responsible for the end-to-end coding of features. The Hawthorne Effect restarts, morale is improved thanks to ‘A change is as good as a rest,’ and the work gets back on track.
Things go along quite well under the new system until two weeks before the original due date. Leadership calls the new manager in in and asks them to chair the release planning board, there will be a major customer release in two weeks. The new manager reminds them of the 45 day slip they negotiated.
“No,” leadership tells them, “We agreed on you delivering 80% of the functionality on the original date, and the remaining 20% of the functionality 45 days later in release 1.1. Furthermore, we are entering into a strategic agreement with Microsoft and you will need to ditch integration with our acquisition and port the work to Microsoft’s platform instead.”
all hope is lost and the curtain falls
Well, it’s back to the office to have a good long think. The new manager opens the last envelope with shaking hands. The advice on the card is of little comfort: Prepare three envelopes.
An earlier version of this old story was published in 2008.