Warren Buffet and Jeff Bezos talk a lot about that over time you end up with the shareholders you deserve. If you run your business in a short term way you are going to end up with short term shareholders. Similarly if you are clear about your long term priorities and principles - and you remain consistent to them - then over time you earn shareholders who will partner with you over the long term.

From an organizational standpoint I think this really applies. The right mindset is not how do you keep everyone happy but what kinds of people do you want to be really happy and how do optimize for them? How do you be the kind of leader they wished the organization had?

Think about this deliberately. Reframe the question from how do you keep people happy to how do you keep the right kind of people for your organization happy?

An example of this: We published a guide to our culture. We tried to write it in such a way that some people would read it and say this is not for me. We consider that success.

No product is the right product for every customer.

Before 100 employees you can reason individually about each person. Beyond that you have to be principle based and more methodical across the organization overall.

I think part of the value of having people join from other organizations is they are going to bring dissonance and friction. They will bring expectations, assumptions, and beliefs. Some times those will be wrong for your organization. And sometimes they will be right. The issues they encounter, or the deficiencies they observe are going to be blind spots that you have.

How do you know this is who we are as a company, these are the things we care about, this is who belongs and who doesn’t? I think it is a very difficult, subtle tension, and dialectic balance between your first principles and desires for the kind of organization you want to be. And the kind of organization that is going to be a good fit for you.

At Stripe we believe engineers working on customer-facing products have to have a good understanding how the customer uses the product, why the customer want this or that, and be willing to talk to customers. They have to be more than just an author of code. They have to be excited about understanding the customer need.

There has to be this ongoing reflection and incremental updating of your mental model based on what is working well, what did you expect to work well and didn’t, and what things did you not expect to work well and did.

[When called upon to make a decision] When we were 20 people I would think what is the best decision to make here. Now I often think why do we have to make the decision? The fact that we have to make this decision suggest maybe we are missing some principles or framework that would make the decision an easy one.

Example: We recently had a conversation about if a particular product was polished enough. I realized we shouldn’t be having that conversation. We should instead be thinking about what is our framework for deciding what level of polish a product needs to have at different stages of its life cycle.

Part of the essence of leadership is balancing twin forces. On one hand the empirical sense of what is working what is well and what isn’t. Not being too inflexible. And on the other hand being strict, and definite about the things that you aren’t willing to have vary. Being flexible but not too flexible. It is ultimately a subjective judgement call. That’s part of the reason leadership is hard.

A lot of things in life [and in companies] revolve around these very fine, highly ambiguous balancing acts.

Example: Being a micro pessimist but a macro optimist.

If you are overly cheery and think everything is awesome [lego movie style] about your day to day then you will miss really important problems. You will probably eventually fail because you didn’t fix things that demanded some urgent course correction. On the other hand if you are perpetually burdened and beset by challenges and frictions and problems – you will never able to inspire yourself [and others] to maintain the motivation to do whatever it is you are pursuing.

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