What do I do when my boss keeps making things worse?

Worse then worse?

I recently gave a presentation titled "Worse Then Better" that explored the Hero's Journey and how we put off the difficult in favour of the secure and comfortable. At the end, I was asked a provocative question: What do I do when my boss keeps making things worse?

Climbing that steep slope

Imagine two extremes. The first boss is happy with the status quo and focuses on consistency and predictability. The second boss is Elon Musk.

Working for Elon Musk is famously demanding. Gwynne Shotwell, COO at SpaceX, Elon's rocket company, has wrestled with this situation: "First of all, when Elon says something, you have to pause and not immediately blurt out, "Well, that's impossible," or, "There's no way we're going to do that. I don't know how." So you zip it, and you think about it, and you find ways to get that done." [SpaceX's plan to fly you across the globe in 30 minutes, Gwynne Shotwell - https://youtu.be/Dar8P3r7GYA]

She realized that while it was her job to keep the rocket company running smoothly, it was his job to keep it ambitious. These are conflicting impulses. "Every time ... people were getting comfortable, Elon would throw something out there, and all of a sudden, we're not comfortable and we're climbing that steep slope again."

It is difficult to argue with the incredible results that have been achieved at SpaceX, thanks to Elon's restless nature. But just as all kings are men, but not all men are kings, Elon is an incredibly demanding boss, but not all incredibly demanding bosses are Elon. This leaves us with two possibilities.

High pressure, high output

First, the person asking the question might be working in an environment that is high pressure but adaptive, achieving great things. The second possibility is that the environment is both high pressure and maladaptive. Instead of working hard to achieve great things, the team is working hard while being undermined by ineffective and capricious leadership.

Elon Musk can be tough on morale, but it's hard to argue with the results at SpaceX and Tesla, so by that measure his approach is adaptive. On the morale front, there are countless stories of Elon creating what is described as a toxic environment, but those who stay, stay for the results, despite the gruelling workload and environment.

Managing up - or out

The second scenario calls for some conscious "upwards management".

When the boss shows up with new ideas, review the current workload and the challenges your team faces. Create a project pipeline that clearly shows how much is under way to make plain how substantial the existing workload is. This can help establish the need for more people and funding.

Encourage your boss to identify success criteria for each project, emphasizing the significance of bringing projects to a successful conclusion. Identify in advance why a project could be cancelled and what lessons must be learned to extract value from the effort.

This might work to mitigate the impulsive nature of the assignments your boss is doling out. At the very least it's good fodder for the resume when you look for work elsewhere.