A Fresh Design

Dear Friends:

How should we organize Circles, the company?

With a fresh design in front of us, this is a nice moment to reflect on how to organize. How do we align everyone involved in Circles to crush the mission? How do we build a culture that is effective and fun? How can we build quality that scales?

I’ve reflected on practices from M5 I’d repeat, things I could improve, things that never felt right. I’ve read some books, had some chats, and am planning to visit a few companies. There’s a lot of innovation going on in the world of organization design.

Here are a few questions…


Mission was one of the most powerful forces at M5. But there were structural tensions. The owners’ “other” mission was to sell the company for a high price. The minute we split up equity, the hour we sold a piece to outside investors, and the day we all realized the shares had become valuable, was when heads turned away from the company mission. How can we keep all eyes on one ball? When faced with learners that can pay $15/month and learners who can pay $115, who will the organization decide to serve?


We had some good managers at M5. But managing is an awkward, clumsy, inefficient thing. I’m looking into the new wave of companies that are doing without. Is this possible? Would it be cool? Can we please live without performance reviews?

Staff Functions

I love building culture, but I am on the record as describing a human resources department as a speed-bump on the road to success. I spent weeks every year budgeting and planning – even producing a 100+-page plan once. But Laloux’s description of companies that have moved from “predict and control” to “sense and react” really resonated. Could we scale Circles into thousands of employees with only a handful in HQ?


We played with this fire at M5. For example, we tried to put all of our service issues in plain view. It was powerful, but also hard. At scale, publishing requires rigorous systems. How far can it extend? Will baking it in from day one make it any easier? It always felt weird that salaries were not public, when people were always talking about them. And, uggh, the side-deals. But should pay be public?

Political Correctness

See “transparency.” Am I going to be able to play nasty but great rap songs at company meetings? Does being comfortable at work require rules?

Homes and Offices

The evidence for working at home is strong. Even at this pre-company stage I see the temptation to hire wherever the talent lives. But if culture is so important, can you really build culture effectively with a distributed workforce?


I’m sure people don’t work harder when they are paid more. People work for autonomy, mastery and purpose. Even salespeople. Stock options are an icky mess in most cases. But we need reward systems that reinforce the mission and give everyone a chance to benefit when their work builds value. And are fair. While we made a lot of people a lot of money with M5’s sales, I don’t think I came close to getting this right.

Look, there’s lots of big questions. Let’s see how far we can get in the pre-company phase figuring some of this stuff out before we launch.

I’m so excited to be talking to you all about this. Thank you again for being part of this conversation.