This is a trial at a new type of post. I’m temporarily calling this the “Rubber Duck Series”. Based on the idea of rubber duck debugging (where a programmer tries to find the bug by explaining the code to a rubber duck on their desk), it’s essentially me trying to spot mistakes in my thought process by forcing myself to explain it out loud. Questions I ask myself in bold. Let’s see how this goes…

George Carlin was one of the greatest stand-up comedians ever. For my money, only Richard Pryor rivaled him. This is not something controversial I’m saying - just listen to other comedians talking about Carlin. So much respect cannot be faked, it must be earned. And Carlin earned it. Not only was he prolific, churning out a new comedy special every year, he was also a comedic genius.

If you don’t know who I’m talking about and are curious, you can watch him deliver his famous “seven dirty words” or reflect on the “save the planet” movement.

I’ve done so many Internet deep dives on Carlin, that I should have some kind of diploma to show for it. Sadly, they don’t give those out. But in one of those deep dives, I ran into the clip of Louis CK delivering a speech at Carlin’s funeral. It was like finding the pot of gold at the end of the rainbow. Louis happens to be my favorite modern day comedian, and there he was, paying his respects to Carlin.

It’s nice when you can find links between people you admire. It’s an interesting way to discover more about yourself, since whatever commonality they share is probably something you value in some way.

And there was Louis, holding back tears, clearly emotional, and trying to explain why Carlin had meant so much to him. And Louis tells the story of how it took him 15 years to build up a shitty 1-hour comedy routine that he absolutely hated. And the fear of realizing that, maybe, he made a mistake. A big mistake. Maybe he just wasn’t cut out for this career.

Louis describes how, at that point, he heard Carlin talking about writing. Carlin described how he just threw out his material every year and started from scratch working on new material for the following year. This idea scared the living crap out of Louis. “It took me 15 years to build this shitty hour - if I throw it away I’ve got nothing!”

But he tried it. And he became Louis CK.

Why did he try it?

You could argue there was a sense of urgency as he stared at a failing career. But it was purpose that pushed him through. Most people would have given up before, found a menial job, and taken a half-hearted attempt at happiness. What pushed Louis through was purpose. You can hear him talk about it.

“There was nothing else I wanted to do”.

When trying to change an organization, it’s purpose that generates momentum, not pressure or a new organizational design.

Are you saying it’s a bad idea to have leaders define a clear vision, like “one enterprise backlog and just feature teams delivering items from one backlog”?

It depends on context. That’s another link with the Louis CK story. Could you have saved him 14 years? Making him hear Carlin talk about throwing away material and starting fresh every year? I doubt it. He probably wasn’t ready to hear the message on year 1. His change process was slower. Artificially trying to speed it up would probably just generate more friction and have other un-intended side effects. I think the same is true for organizations.

A few weeks ago I wrote about the importance of scaling down organizational complexity. How when embarking on a change initiative, subtraction is the right mindset at the beginning, not addition. Don’t add a framework on top of garbage. Rather, start by removing the stuff you don’t need. You know, the famous “waste” everybody loves talking about. Scaling by simplifying.

Maybe you shouldn’t start by the solution. The new organizational design and processes. The shiny addition. Don’t even start by creating a sense of urgency. Nobody needs pressure. Start with a sense of purpose, as Kimber Lockhart eloquently suggests. That should be the guiding light. Your North Star.

Sure, purpose might change over time (Laloux’s evolutionary purpose idea), but if your purpose is clear, all the other big questions people want to rush to answer will be addressed in a just-in-time manner:

What is the product?
How do you handle budget in an Agile way?
What happens to Enterprise Architecture?
SAFe or LeSS?
...

As you simplify your organization and focus on creating cross-functional teams that are empowered to deliver value, you answer those questions only when absolutely necessary. And you revisit them often. Don’t discuss steps you cannot take yet, focus on the next step towards purpose, the one you can see, and wait for the options to emerge once you take that step. This is not rudderless, because you have purpose and It becomes the gatekeeper for all next steps.

Interestingly though, this goes against a lot of conventional wisdom on change. Where you start with a sense of urgency, create the big operational vision, and let that guide people through the process. Many famous consultants and book authors will propose some variant of this:

“Get leadership buy-in to the big vision. If they don’t buy-in, save your energy, go help another client.”

Do you like this attitude?

Not really. I understand it. I can see the argument for the defense - you have limited time, spend it trying to help companies willing to see the big picture. It will be hard enough already, at least pick an environment you have a chance.

But this attitude means you’re working with and changing only the companies that have little fear and a big appetite for change. That’s the minority. And those companies could probably figure out a lot by themselves with some lightweight guidance. Your coaching time could have been more effective (big picture) in another environment, where the speed of change must be slower because fear is predominant. Companies don’t want to get rid of their shitty 1-hour routine they have been building for the last 15 years either.

And getting rid of the fear, building trust and camaraderie, is a gradual process. Not a light switch you flip. And as a coach you need to guide them through this. Balancing the usefulness of doing some pushing, with the need to make them own the change, because that’s the only way it sticks. Which means you need to adapt to the speed the organization can handle change. And for large organizations with cultural and technical legacy, this takes time.

So it’s ok if the leaders don’t “get it” right away?

Trying to sell the promised land during a sand storm is not a winning strategy. At that moment people just want the sand out of their freaking eyes.

The important part is they are willing to experiment and change some things. It will probably go slow in the beginning, which is fine as long as it doesn’t stall. In large organizations, purpose has been buried under so much legacy, they need time to dig it out. Pushing them too far too quick will trigger too much fear on their side, followed by the inevitable return to command & control.