I think 37signals uses their own tool, Campfire to have the team in “one place” although physically they can be anywhere. Have you tried it, or do you use something similar? Or is it mostly one-on-one discussions one person at a time?

@Jarkko: Thanks Jarkko! I believe that freedom does make a difference. The real test is going to be with scale. Right now we only work with a short list of people on a regular basis. I’m hoping that this approach to team building is scalable.

It makes me think of the early united states. US democracy was a much different beast when it was young and had only a few participants. I’m hoping that a growing team will match growing resources and that we can some how avoid cliques. That said… how import is it that a team should try to avoid cliques?

Maybe the fact that you are all free to come and go, and are working together because you decide to do so makes all the difference?

I think that nails it on the head. It’s an issue of split personality. A strong team can’t be based of of schizophrenic expectations.

(BTW, we ask exactly those same questions when we interview contractors)

As a freelancer, I make an effort to take things to a more personal level and I think that has made all the difference – not only in building long term business relationships, but also with having a more authentic life where work and life don’t require 2 different personalities.

When I hire freelancers, I’ll ask “What are your goals? What do you need financially to get where you need to be and how can I help you get there?” I don’t remember a boss asking me this! But when two people who have their own businesses come together for mutual value, it’s a completely different experience.

Thanks again for an insightful and honest post!