Letter to folks working with Bo (COO)

• What I Believe & What I Expect
• What I say or do that some can misinterpret
• Communications
• Getting ahold of me
• One on Ones
• Meetings
• Responsiveness
• ToDos for Version 2:

What I Believe & What I Expect

1. 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.
2. 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.
3. 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.
4. 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.
5. 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'.
6. 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.
7. Our company is like a minor league baseball team on its way to the World Series. As we get bigger (i.e. advance through the season) the problems get harder, the organization we manage gets more complex, and the competition will get more skilled, requiring each of us to get better quickly. This has been put articulately by others as “the same performance that earned an Outstanding last year will only earn an Okay this year”. To get better, great athletes do a lot of studying game film, training, and nutrition work off the field. For us, operating the business is "on the field", so we have to manage our own "off the field" work to make us great. This is not about the hours you work, but about doing the intentional efforts beyond just running the business to make ourselves better.
8. Discipline. Something a friend who invests in startups said once stuck with me, and I'll quote it here (she eventually made that talk into a blog post): "After a founder sends me two or three update emails, I can immediately get a sense for whether or not that company will succeed. Some send an email and then you don't hear from them again for four months. Others use different formats or metrics every time. Or they say that revenue is the top priority in one meeting and then say they're focusing on engagement and redesigning the app in the next. That's not an update, that's an excuse. If revenue isn't where it needs to be, admit that you have an issue to your investors, your team, and above all yourself so you can start getting back on track." Each of us leads our own team and/or scope of initiatives, and holding ourselves (and each other) to a high standard of discipline is a key compounding effect that makes our organization stronger every day.
9. Hard work. Each of us is given a limited and unknowable amount of time on Earth. This company is a collection of people who have each decided that they want to spend this phase of their lives becoming great business operators, and in so doing dramatically improve the lives of workers in the largest part of our economy: healthcare. We start with the nurses and nursing assistants who get paid very little to do the yeoman's work of caring for patients that is the foundation of good healthcare. As hard as any of us work, I'm constantly reminded that our customers, the nursing assistants, work far harder at far greater risk to themselves on the front lines, and get paid far less. That perspective reminds me to never complain, and get back to work. I constantly ask: can we be doing more for them? Can we do more today?
10. Go faster. Speaking of our limited time on Earth, everybody gets the same 24 hours, but some people can get a lot more done than others. Every step we take in every project we do, every requirement we impose on others, has a Time Cost that oftentimes people don't account for correctly. Time Cost should show up on our credit card statement because it is a real cost. I believe in deciding proactively when to pay and when not to pay that cost, what I buy with that cost, and when to save others around me that cost.
11. Touch the ball more. Years ago I read that the best soccer camps for developing youth prodigies into professional players focus every day on only one metric: how many times did the player touch the ball. Not number of goals scored, not number of games won. This stuck with me because it rings so true that the most foolproof way to get better at anything is to get more reps. For software engineers, reps are getting more code you wrote or bugs you fixed into the hands of customers to see what broke and what lessons you can take away. For P&L owners reps are getting more ideas into the marketplace more quickly to see which ones yielded the improvements to your core metrics you hoped for. The best way to write a good essay is to write ten bad ones in a row and then turn in the last one. What is it for you? Can you get faster tighter feedback loops? Can you "touch the ball" more? Get started. Nothing beats getting started. Right Now.
12. Read, a lot. Here I'll quote from the memoir of a retired military commander. "Reading is an honor and a gift from a warrior or historian who—a decade or a thousand decades ago—set aside time to write. He distilled a lifetime of campaigning to have a "conversation" with you. We have been fighting on this planet for ten thousand years; it would be idiotic and unethical to not take advantage of such accumulated experiences. If you haven't read hundreds of books, you are functionally illiterate, and you will be incompetent, because your personal experiences alone aren't broad enough to sustain you. Any commander who claims he is "too busy to read" is going to fill body bags with his troops as he learns the hard way. The consequences of incompetence in battle are final. History teaches that we face nothing new under the sun." Mattis, Jim. Call Sign Chaos (p. 42). Random House Publishing Group. Kindle Edition. I also remind myself not to oversteer based on one or two books I read recently, no matter how much that book may have “really resonated” or seemed to mesh with my (limited) experience. I wouldn’t want to be led into an amphibious assault by a commander who only read one book on amphibious assault. By the same token, I know that my team (you) wouldn’t want to be led by someone who’s only read one book on management, hiring, or marketplaces. Your teams deserve the same.
13. Metrics & Customer Conversations together are the ultimate Arbiter of Truth. I call this “Facts not Adjectives”. Metrics are the ultimate measure of whether you understand your business. Customer Conversations are the ultimate measure of whether you understand why your business is the way it is. Metrics tell you what is happening at scale, and may point the way to figuring out why. Customer Conversations driven by curious people revealing the actual root cause of exactly why something is happening and pointing the way to even deeper insights & ideas to fix it. And the two interweave to form a strong fabric: customer conversations can be backed up or disproved in the metrics; metrics can be corroborated or contextualized by customer conversations. The opposite of Metrics & Customer Conversations is… adjectives. Phrases like “major issue”, “substantial impact”, “is a well-oiled machine”, etc. are all adjectives. I don't trust adjectives. Adjectives obfuscate and overly simplify a nuanced and messy reality, and it's in understanding that nuance and messiness that real economic value is created. If you dig into the Metrics yourself, have the Customer Conversations yourself, you’re likely to notice specific subtleties and intricacies that others can't see that lead to specific solutions. Push through the phase where you think in adjectives and go directly to thinking in specific Metrics and specific Customer Conversations.
14. Great leaders traverse multiple levels of abstraction and detail quickly and repeatedly. Nothing is "above" them, and nothing is "below" their notice. Have you talked to a customer lately? Tried to book them into a shift? Is your plan for your business ready for review by the Board of Directors? How about the public markets (i.e. can be included in our future filings with the SEC)? If we continue to succeed, we'll be there far before you think we're ready - no company is really ready for its IPO - so let's get started practicing now.
15. Know your business cold, inside and out. There's a difference between 1) "I should know that, but I don't", 2) "I can't get at that info, but I have been pushing on the work needed from other teams [i.e. Engineering] to get it, and in the meantime here's what I was able to jury rig together to get a range for that number", and 3) "it's unknowable". Very very few things are in the 3rd category, and we should have intellectual honesty about that.
16. I believe in asking lots of questions. What are we not thinking about that may limit our success? What will disappoint a customer? Asking pointed questions is how we push each other to ever higher standards of high-quality thinking. Our “The Working Backwards Document: Guide, Examples And How We Approve Initiatives” is a manifestation of this.
17. Clear and precise goals. Not just for your organization for this quarter, but for everything we do. What's the goal of the meeting? What's the goal of this email? What's the goal of this blog post? The more precise our goals are, the more likely we are to actually get what we want. I believe in extremely high precision, and admitting what you don't know or haven't thought it through, rather than letting imprecise thinking hide behind imprecise language. Writing is thinking. Precise language is precise thinking.
18. Think for the long term. What will you want to have done when it's 3 years in the future and you're looking back at this problem/opportunity/moment? Imagine the Ideal Impossible answer, and work backward from there. SpaceX realized that the Ideal Impossible way to make rockets cheaper was to make them reusable, even though entire nations had been unable to achieve this. Today, their rockets landing themselves is so routine it doesn't even make it onto the news.
19. No plan survives first contact with reality. So, you know, run towards getting contact with reality!
20. What got us here won't get us there. We experiment. This means the way we operate, even our org structures, are all experiments. Nothing is permanent. We start with how we can best improve the lives of our customers, and run whatever experiments are needed at every phase of this company to get there. For example, if I ask someone else to tackle a problem that I've also asked you to tackle, it's not because I don't believe in you. It's because I think the problem is big enough that it's worth running multiple experiments side by side. Imagine if in Physics or Chemistry the entirety of the human species ran only one experiment at a time...
21. Self-awareness. I believe all of us, especially those of us in leadership roles, must work hard to cultivate high self-awareness. This means being curious about how you're being perceived and looking around you and outside the company for ways to improve yourself and your org. This means knowing your motivations, sharing that with others to help them understand you. Know your weaknesses, be brutally honest with yourself about them and how you're improving, and don't look away. Acknowledge your insecurities (at least to yourself, and ideally to others around you), and know when insecurities might be driving your thoughts or actions. Let's be honest, we all have insecurities. As a leader, it becomes hard to realize the way your voice seems to boom louder than every other voice in the room - so speak quietly. You get used to people withholding their opinions until they hear what you have to say - so try to speak last. People are afraid to bring ideas to you, afraid to dissent, afraid to engage - so you must proactively and intentionally help your organization counter-steer this tendency. All of these things can and do happen even to the most well-intentioned leaders. You have to work consciously and actively to fend off its corrosive effects - this is something I’d only give myself a C+ on, but I work on every day.
22. Assume positive intent. If ever you or I find ourselves thinking "hmm… I could interpret what he or she just did in two ways" let us both strive to use the most positive intent interpretation. I will always assume you're a good person moving quickly, with a lot on your plate, doing your best. I hope you give me the same graciousness in interpreting my actions. That said, please tell me. The fact that something I did could be misinterpreted is very useful for me to know!
23. Growth Mindset: it's not about whether you're good at something today, but about getting better quickly. When you get a numerical evaluation, whether by me (on our 1 to 5 scale), by our customers (i.e. NPS, CSAT), or by the market (i.e. Revenue, Churn) think of that first and foremost a feedback loop. Like seeing the answer key after you completed a math quiz - that you got the question wrong doesn't mean you're "bad at math" (i.e. a permanent judgment of talent or worth). That you got the question wrong just reveals an opportunity to practice, push harder, and get better (i.e. "that I missed this question about eigenvectors just means I need to practice, it's a temporary condition").
24. Own the Outcome. This means don’t complain about another team without them present to hear it (thus it becomes feedback that helps them get better, not complaining behind their backs). This means don’t think your agency or control ends at the boundaries of your own team - you can have great influence on others and you should cultivate and wield that influence in service of our shared customers. And remember that your loyalty is to our mission and our customers, not to your direct reports. We stand shoulder-to-shoulder as if we are scientists in front of a chemistry experiment, not “depending on our people” when you get feedback from others or when an experiment didn’t work, but working together with your peers to figure out what will work and how to achieve success together.
25. Solve a problem once, you've kicked the can down the road. Solve a problem and put systems in place to ensure it stays solved is better. Solve the problem, and put in place systems to guard against future problems of this general type or with a similar root cause is best.
26. Speaking of finding root causes… I believe in asking "why" at least 5 times in a row. I pretend that I am explaining why something happened to a very inquisitive five-year-old (i.e. myself). After every sentence, she asks "yeah but why is that" or "ok but why then did that thing happen". It teaches me really quickly whether I have a deep understanding or not, And motivates me to go get that deep understanding.
27. You'll hear me refer to the Rude Board Member on my shoulder - someone who's smart and speaks their mind without any sugarcoating. This is a way for me to constantly remind myself and those I work with that decisions need to make sense at the company level not just at the level of a person, team, or department. I oftentimes will say out loud in our meetings, "I think Rude Board Member might say..."
28. You'll also hear me refer to the Busy Customer on my shoulder - a healthcare professional or healthcare facility employee who's super busy is really depending on us and speaks their mind. I want customers to be spiritually present in each conversation, in each of our minds, as we work on their behalf. Busy Customer reminds me that the reasons we make a decision or answers we give internally that would draw frowns from a busy customer if she was in the room are by default poor and deserve extra scrutiny. For example, we're not solving a problem right now because some other internal team is busy? Bad answer, busy customer doesn't care about your internal politics. We're making a product decision that's not ideal in anticipation of some future feature coming down the road? Bad answer, busy customer doesn't care about your future roadmap. Etc.
29. Finally, I expect you to be great because I believe in you. I expect this list to be just the beginning of a much longer list you'll keep for yourself and hold yourself (and me!) accountable to. I believe you're capable of greatness - that's why you're here. My job is to be a helpful person on your professional journey. Okay, with that backdrop, let's talk about… things I say some folks might misinterpret.

What I say or do that some can misinterpret

1. I sweat the details, a lot. The difference between Good and Great is often a collection of very small details. This means I’ll often ask very detailed questions or make very detailed suggestions. I’m not trying to micromanage you; I’m not telling you you have to do it my way. I am instead holding your work to a high standard (see #1 above) and using questions or suggestions as conversation starters. For example, during a spec review for an iOS mockup, I might ask “why does this button filter the Table View rather than jump to a place within the Table View”? Please don’t think to yourself “why is the COO getting involved in what this button does”… it’s because I care. What I’m hoping you’ll say is “I thought of that too, but what you’re missing Bo is that…” which helps me learn and helps ensure we’ve thought through the details on behalf of our customers. Please don’t take that as “Bo wants the button to do X” - you’ve been thinking about the spec for days, I’ve been thinking about it for minutes, how would I know? :)
2. I have a lot of ideas, suggestions, and opinions. They are all conversation starters, that’s all. Things I say are not somehow more important because they happened to come from me. Treat it like you would input from any other internal stakeholder or customer, and filter it through your own judgment. You own the outcome, you're graded on judgment. Some of us have scars from working with past high ego bosses; you should be safe here. I try to have an extremely low ego, but I'm not perfect, please tell me when I'm not meeting my own standards.
3. Some folks are more contemplative than others - if you are, and I pepper you with questions, it's okay to say "let me think about it and I'll get back to you" and write me something later (but tell me when to expect your response, and of course follow through) if that's how you think best.
4. I sometimes swear. It's nothing except that I'm really passionate about something we're talking about, and a bad habit I picked up. I'm working on trying to tone it down.
5. Want feedback? Ask me. My written feedback has been called more useful than my verbal feedback. I struggle with giving clear enough negative feedback in person, because I care about how you feel, so force me to give you a number/grade/rating on a numeral scale and that'll push through my weakness here. I'll also include a numerical rating in all written check-ins (i.e. if we do one at day 30, day 90, mid-year, end of the year), so remind me if I fail to do that.
6. Me asking "when will this be done" is not necessarily me asking you to "do it faster". You set your own deadlines, just communicate your plan & schedule (written if at all possible). You drive. That said, I will sometimes think you can go faster, so our customers' lives improve earlier and you get more reps. In those cases I'll say simply "I think we can go faster"… but as mentioned above, as a conversation starter!

Communications

Getting ahold of me

1. Call me on Slack. Anytime. Seriously. No need to warn me or ask me, no need to first Slack me and say "can I call". A huge part of my job is to be here for you so that you can be here for our customers. I truly value each effort you make to reach out. We run a 24/7 company because patients get sick and need care without regard to what the clock on the wall says. We're also a distributed team hailing from seven countries and more than seven time zones. If you're afraid of calling me because "it's too late where Bo is"... don't be. I work weird hours, and it's my responsibility to turn off my ringer if I need to, not your responsibility to predict my schedule.
2. If you call, Slack, or email I will try to get back to you the same day, though sometimes it'll be the next day. I return calls first, then slacks, then email, so feel free to use that to your advantage depending on urgency.
3. You are always welcome to drop a meeting on my calendar. Anytime. Everyone in the company should be able to see my calendar - not just when I'm free and busy, but what exact meeting I'm in with whom (please tell me if you can't; then I must have inadvertently broken it).
4. I very much appreciate your responsiveness and strive hard to be similarly responsive to you. That said, this is an Area of Growth for me. Please don't hesitate to tell me if I'm not being responsive enough to enable you to do your best work. I will not in any way take it personally.

One on Ones

1. 1:1's are for you, to be driven by your agenda, and secondarily for me (I might have a few agenda items at the end). Think of 1:1's primarily as Board Meetings where you're the CEO and I'm a member of the Board. Your agenda, your plan, I'm here to help by whatever you need: a thought partner, by pushing your thinking, by helping you get access to talent/capital/other resources inside and outside the company.
2. We might meet 1:1 daily, weekly, monthly, or quarterly. It's up to you. I won't be offended if you turn up or down the frequency, and vice versa please don't be offended if I do either. Usually, it'll be because other projects on my plate are consuming more or less time, and shouldn't be read as a judgment in any way of you or our working relationship.
3. Don't wait for our 1:1 to roll around if there's a conversation we could have now that's urgent, or will enable you to do great work faster. Like I said earlier in this letter: touch the ball more, go faster, get more reps. I'm here to help you do that.

Meetings

1. I believe meetings are expensive, and get more expensive at the square of the number of people involved (more people get pulled from doing Deep Work to attend, still only one person can speak at once so less is learned from each attendee, every person in attendance becomes de facto unresponsive to customers).
2. Meetings are a tool, like a hammer.
1. Each meeting has a goal. The goal of a meeting is never "to have the meeting", just like the goal of a construction project is never "to hit something with this hammer".
2. By the same token, I don't mean any offense if I ever decline a meeting, cut a meeting short, or propose that we don't have to meet and propose an alternative tool. I'm essentially saying "hey how about a drill for this project, not a hammer" not "I don't value your efforts" (which some people can interpret). No offense is meant.
3. Our standard for meetings is high.
1. Every Meeting Has A Document. "Document" can be a spec ready for review, a well-thought-through JIRA ticket, a full set of mockups, or a project on Asana where there are written updates to all or most Items. The key to all these is that the writing (and necessary thinking) has been done ahead of the meeting by the organizer. This is because writing engenders high-quality precise thinking, reading is a faster way to absorb deep content than listening, writing is more effective at "getting everyone on the same page" (I mean, literally), and written records keep us all accountable and can be easily disseminated broadly to those who couldn’t be there.
2. If the meeting starts and not everyone has written their document (or section thereof), then we simply cancel and reconvene later. Better to have a high-quality meeting tomorrow than a low-quality meeting today (note I said tomorrow, not next week).
3. Meetings have action items and should be judged by all attendees by the quality of the action items and their on-time completion rate. If a recurring meeting (literally the only type of meeting more expensive than a regular meeting) isn't getting a good completion rate on items, you should probably fix it or stop the meeting series and find another tool.
4. A suggestion: if the meeting's only purpose is to "check-in" on an initiative, you can probably do it in written form. Haven't tried it? Try it! Would love to hear what you think.
5. That said, want to bat an idea around? Call me. Call a friend. Rubber Ducking helps some people think (including me), and I'd love to help in any way I can.

Responsiveness

ToDos for Version 2: