Letter to folks working with Bo (COO)

<aside> 💡 Context: We are a heavily async-based culture with an emphasis on writing our thoughts down, and Bo (Our Founder/COO) loves to communicate a via writing. Back in 2020 he started this letter (originally addressed to his team) about himself and how to work with him. This letter has been circulating throughout the company, is referenced a lot and played a major role for a lot of folks at CBH during their onboarding. It’s super enjoyable to read!

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Context: I wrote this originally for people on my team, but after thinking about it realized it might help anyone at the company who might be interacting with me even if it’s infrequently. As always, would love any thoughts/reactions. My inbox is always open for your thoughts :)

Hello, and welcome. I'm very excited to work with you on our mission of improving the lives of Healthcare Workers and Healthcare Facilities. Day in and day out, my goal is twofold: to serve our customers, and to grow the careers of those around me. I know that a strong, clear, and productive working relationship between you and I will contribute greatly to the time both of us spend at work.

It's with this goal in mind that I write you this letter - to help both of us achieve that relationship with intentionality. I guess, first a little background about me. We'd likely have chatted about our childhoods over lunch if we sat in the same office. In lieu of that, I'll write it here so you get a sense of me as a person - and I want to hear about your childhood too! Email me!

I grew up on the campus of a Science and Engineering university in mainland China in the 80s, where both my parents were engineering professors - nerdiness is in my blood. I moved to West Virginia when I was in elementary school, and got picked on a lot as a kid for my accent and being terrible at sports… but being a nerd was respected in my elementary school! It took me forever to realize this was no longer the case in the US.

I went to college in the midwest, majoring in Computer Science at the University of Illinois at Urbana-Champaign, and ran for and won a seat in the Student Senate. So, rather than the movie version of college, I pretty much spent my days either in the windowless basement of the Digital Computing Lab or knocking on doors for votes. Life of the party, I am - sigh.

I spent the first 5 years of my professional life at Microsoft in Seattle as a Product Manager. I learned a ton about what to do as a product manager, and unfortunately also learned a ton about what not to do in running large organizations. I then spent the next ten years founding and CEO-ing a Silicon Valley startup that brought digital investment advice to families across the country, before joining BlackRock.

I learned an immense amount from that 10-year journey, and we were fortunate to have the “classic” Silicon Valley experience from going through the incubator Y Combinator to raising venture capital from the biggest names in the valley I’d only ever read about (Sequoia Capital, the founders of Yelp and YouTube, etc) to being acquired. Both in running my own company and at BlackRock, I learned a lot about how to run large(er) organizations that I'm excited to use as a foundation for continued improvement here at Clipboard Health.

Outside of work, I play as much tennis as my body will allow and mostly spend as much time as possible with our two kids (a newborn and a two-year-old). We are such nerds that we named our first child after a class of fundamental particles in quantum mechanics, and our second child after one of the five canonical nucleobases in biology. The saving grace is both names are normal-ish sounding, I think :). With that background, let me start with What I Believe, which also helps explain some of my general expectations.

What I Believe & What I Expect

i.e. thoughts that ring true to me that have stuck with me through the years, that may help you understand me better and what I expect from both you and me. I'd love to hear where you might agree or disagree, have questions, and what you believe that's not on this list! I believe...

High Standards. First and foremost, I believe that setting high standards is the cornerstone of success. I have been the beneficiary of someone else's high standards time and again in my life, and seen myself achieve more than I thought I was capable of. Eventually, I got smart and just started setting very high standards for myself rather than waiting for someone else to do it for me. The last thing I want to do for you is to expect less.
Enforce high standards in your organization. It’s easy to say “I want to work with exceptional people”… if you believe that (and you must since you work here) is every single person on your team truly exceptional? If you don’t answer with a resounding yes… then the answer lies in yourself. You’re the leader of your team, this is 100% on you. Usually, it’s because it’s easy to say “I want high standards” but hard to do the dirty, awkward, and emotionally painful yeoman’s work to get there. This means going to each person on your team that’s a great person, hardworking, but just not exceptional, and saying “you’re good but not great, and only great people work on my team”. It means actually following through and firing that person, even though he or she is working really hard. (Hard work is necessary but not sufficient for success here). High Standards apply to more than just talent. High standards mean rejecting good but not great work products even though you’re close to the deadline. High standards mean not hiring that good but not exceptional candidate when your team is severely understaffed. It’s this kind of hard tradeoff that actually makes High Standards a reality and not just a poster on the wall. I write on our internal blog about managing to High Standards as I think it’s the most important thing we do.
Speed & self-sufficiency, loosely coupled. We are a small number of people working in a vast greenfield opportunity. Speed is underrated. Even though many blog posts have been written about going fast in a startup, it’s still massively underrated. To be fast you need self-sufficiency: as much as you can, we try not to take on dependencies (either internal or external) because we want to control our own timeline & quality. This means in practice if you can do it yourself don’t wait for someone else to do it because “it’s their job” or “it’s not my job”. Need to send an email newsletter? Fire up Mailchimp (or similar) and do it yourself. Need to write a Metabase query? Try it yourself first. We’re not a place where you hear phrases like “well, I had to wait for the BI team, and the User Research team, and coordinate the work” - we do the work here, we don’t coordinate other people doing work. Speed and self-sufficiency are supported by an organizational structure that is loosely coupled. If you’re client-facing, I hope that when a client comes to you with a problem you can fix it for them, immediately, rather than the common “let me open a ticket with department x”. If you’re in charge of a team, I hope your team has agency over accomplishing its goals. If I can do anything to help this be the case please come to me.
Hardcore. We look at other people in our world, like those in the storied Navy SEALs, and see what they're willing to do to be the best in the world and say "they are hardcore". We are equally hardcore. People on this team have 1) spent many hours a day for days on end working on a single math problem because it was that hard. 2) worked 100 hour weeks when needed as a young attorney in the middle of one of the biggest corporate bankruptcies in the US (not "I estimated I worked 100 hours" but "I wrote down and billed a client for each 15-minute increment of my day and they add up to 100 hours"). 3) Been the actual best in the world, placing first in national or international science competitions. Unlike the Navy SEALs we don't risk our lives, but we are just as hardcore about what we do.
We think from first principles. What's the goal? What constraints have we internalized that are unexamined? What assumptions have we made that are unexamined? For example, why do we "have no toes" in this company (as in, we never worry about stepping on someone else’s toes)? Because there's no customer problem to which the best solution is people in this company saying "I didn't do it because I didn't want to step on someone's toes". Thus toes don't exist, because we started with a clean slate and thought from first principles, rather than accept tradition or common practices unexamined. This helps us stay fearless and unencumbered - and yes, sometimes we have to discover best practices the “hard way” (from first principles) but I’m happy to pay that price. Something Elon Musk said in an interview stuck with me (paraphrased): I found out these rockets were crazy expensive, but when I looked up the cost of the raw materials it turns out only about 2% of the cost of the rocket is the raw material, so I thought 'well, almost all the cost is not in getting the atoms but arranging those atoms to form a rocket. So we just have to find a way to arrange those atoms more cheaply - that seems solvable'.
Your job is not simply to do "what Bo wants". Think of me not just as a manager but as an investor, and you're the CEO of your part of the organization. Your job is to create and execute a convincing plan to achieve your goals. This is good practice for when we're a public company and part of the S&P 500 because then investors will expect that from each of us (see advice from Sequoia about Board Decks as an example). If you find yourself reacting to my questions, thinking "I've never thought of that, hmm, let me think of the answer" somewhat often then that's not good. Ask yourself your own questions, use your questions to push your own thinking, that's a success.