Onboarding Reading and Things to Do

Created By
Ben Denny
Last updated
January 31, 2022
Reading time
15 mins
A few weeks ago, Bo Lu (Clipboard Health’s COO) approached me with a new project: Rewriting some of our onboarding documents from the ground up.

Our current documents, he said, had a flaw: they had mostly been written by people in the company who were well past the onboarding process. In effect, they had to some extent forgotten what it was like to be a new employee in our workplace - and once everything seems normal to you, it’s hard to focus on the important differences between our company and other workplaces.

I think he’s right. I come from a non-conventional work background, and some of my former workplaces placed very different levels of value on things like independence, curiosity, and effective communication. For me, everything here is a little different and I know firsthand that it can take more than a bit of energy to get used to a new culture and a new set of expectations.

For some of you, this will be your first time working in a start-up environment, so it’s really relevant to know that start-ups don’t survive unless they have speed and flexibility in a way that most established or traditional companies just don’t have. This means a lot of communication - you will need to be more in other job roles and departments than you might be used to. It also means that job roles tend to be less defined, and you will find yourself touching a wider variety of projects and roles than you ever have before.

For some of you coming from start-ups this might be a more familiar environment, or it might not. Not every start-up is a well-run utopia - there are plenty of bad management techniques and bad internal culture to go around. It might be that you have to unlearn some old knowledge or pick up something new to be effective here.

Everyone’s onboarding ramp is a different length - mine is very long. I’m having to learn a lot of things. I’m having to change the way I think about how I go about my job. You might start out closer and have fewer things to learn or change, but there’s still always going to be a need to adjust - not only during onboarding but as the company changes and evolves as well. You might start even further from where you need to be than I am, but let me tell you: that’s not a downside here. There’s time and support to get you where you need to be - your job is to take advantage of that.

Instructions and Expectations

This document is intended to pull together some of the most critical information we have about who our company is, what we do and you will ultimately be successful here. We require all new hires to read this information as part of their onboarding because we believe in transparency and telling you exactly what we expect right out of the gate so there are no surprises down the road. For each section, there are some bolded questions for you to answer. Please complete each question as you complete the reading to ensure you can leave thoughtful, detailed responses. These responses help us gauge not only your own understanding of what you have just read, but also help us to continually improve our onboarding process.

We look forward to reading your responses, and most importantly, we want to welcome you to our team!

These readings should be completed as part of your New Hire training path in Leapsome, and need to be done within your first 10 days (this is when it will be most impactful 😃).


This document takes a look at various writing from both inside and outside the company that we feel does a good job of letting you know who we are, what we value, and what kind of values and behavior will work best to help succeed at Clipboard Health. Don’t just read them, though - each section includes space for you to express your thoughts on the ideas you’ve just absorbed. Writing about what you just read will not only help you organize your thoughts on us, but it will help us learn a little bit about you and how we can help you feel comfortable, prepared, and effective.

What Is Culture?

Almost every workplace at least talks about company culture. What they mean varies place-to-place, ranging from “the exact way we expect you to behave at all times” all the way down to “sometimes, we have Taco Tuesday events”. Knowing exactly what “company culture” means and how it affects you in your day-to-day work is a big deal, and it’s something you will want to get a handle on as soon as you can.

What is Culture? by our CEO Wei Deng explains exactly what we mean when we say “culture” at CBH, and gives some insight into what motivates the culture we have and want to build.

Questions about “What is culture”?

  • What does Wei feel culture is at the most fundamental level? How will you be able to tell what our culture is at a company level or a team level?
  • How does CBH’s concept of culture differ from your last position? Is it better, worse, or about the same - and how?
  • Every company has a document saying what their culture is, but not every company lives up to it. Let’s say you saw some place where our statements on culture didn’t match up with the actual reality of our company - say we were rewarding bad behavior of some kind or otherwise working against what we say our values are. What would you do?

Company Values, Beliefs, Expectations, and Habits

As What is Culture implies, it’s impossible to understand our culture without understanding the values that culture is built from. This article takes a look at the values that permeate everything we do and everything we build - more than anything else, this is who we are at a fundamental level. Understanding these values did a lot to help me understand what was expected of me - what mattered, what worked best, and how I should be thinking about my work.

I’ve been at some companies that had a list of values that was just a piece of paper - I read it once when I started the job, and then it never came up again. I can’t stress enough that this isn’t the case here. Every one of these values matters to CBH as a company, and they come up constantly - in meetings, in emails, and in our approach to every project we tackle.

If values matter (and they should!) they naturally flow into expectations and behaviors. It’s nice if we talk about high standards, but we also need to flesh that out in terms of what those standards are and what you can do to meet them Bo writes explicitly about those expectations and behaviors in his Letter to folks working with Bo, not just for us but also for leadership. Where you might need more information to do something, leadership is available for that; they commit to getting back. Where you might need time to think about an idea, you have it. There are expectations on both sides - leadership commits to giving you tools and standards to live up to, but expects you to use those tools to meet the standards set.

Questions about “Company Values, Beliefs, Expectations and Habits

  • Pick one value from the list that you believe is important but you find you struggle with in some way. Which is it? How do you handle it?
  • You are going to have a lot of interaction with coworkers and colleagues that affect you and your ability to do good work. What’s your game plan for when you run into a situation where
  • someone isn’t living up to our values, especially when not doing so is hurting your work or the goals of the company?
  • Is there a value that’s important to you personally that you don’t see included? What is it, and why is it important to you?
  • Look at the “What I Believe & What I Expect” section of Bo’s article. What does he expect regarding speed? What does he think about ownership of your part of the organization? What does he believe about “getting more reps”?
  • We believe you should have expectations for leadership to live up to their own standards. Bo has sections about what to expect from working with him and communicating with leadership - is there anything missing there you’d like to see? Are there any behaviors you’ve found useful in other leaders you’d like to see adopted here?

Don’t just say no

It’s easy to point out a problem with an idea, but it takes effort to find a solution to a problem that works. CBH is all about being fast and effective - as a startup, we have to be - and letting problems persist where active effort and thinking would let them solve is death for a company like ours. Don't just say no; say yes to something else is a short piece from Bo about not letting ideas die on the vine.

Questions about “Don’t just say no”

  • What is the expectation in terms of turning down ideas? What do you do when someone brings you a clearly unworkable idea?
  • In the article, Bo quotes Eugene Wei as saying “Bureaucracy is just institutionalized veto power growing linearly with organizational size.”. What does that mean for a growing company that doesn’t address the issue?


Bo talks Institutions at CBH about institutions, relating them to municipal infrastructure like roads or sewer systems. These are the things we build into the way our company does business - actions we take regularly and the people in charge who make sure they get done This creates a consistent “the way we do business” expectation people can rely on - in a way, the sum of our institutions is who we consistently are. Intentionally building ourselves into something good is important.

To add a bit to what he said, institutions aren’t always built intentionally and aren’t always good. Just as with culture and our values, this is easy to talk a big game about in the company knowledgebase and then otherwise ignore. If we do that, we end up with institutions that are integral to how we do business that are counterproductive and make us worse. In the same way, it’s important that we intentionally build good institutions, we have to be careful to avoid unintentionally building bad into our business model if we are to reach our goals of who we want to be and how we want to serve our customers.

Questions about “Institutions”

  • What are some unhealthy institutions you’ve seen established? What would you do if you saw one here?
  • What are some institutions you’d like to see built at the company that you haven’t seen here yet?

Know your numbers

Most good habits aren’t automatic - some take special effort, and some come about as the results of other good habits maintained over time. Bo touches on that topic in Story: Alfred Lin and "know your numbers", where the key idea is being able to express where your project is in as much detail as needed when asked.

We’ve all had an experience where we were caught unprepared by someone asking about a project we were working on. But ideally, this doesn’t happen - if you are truly immersed in your work and interested in what you are doing, you do “know the numbers”. If you are taking full ownership of your project, knowing the details come out of that naturally.

Knowing the details of your work is an indicator that you’ve provided yourself with the information you need to move forward - you know where you are at, and you know what your goals are. This isn’t just something you need “to impress the boss”, it’s also an important self-check; if you find you couldn’t explain your project at a moment’s notice to someone asking, you immediately know you have an opportunity to review and improve until you can and be that much more prepared for success.

Questions about “Know Your Numbers”

  • What tools and habits do you use to keep yourself up to date on your projects? How effective are they at keeping you up to date? What room for improvement do you see?
  • If someone asks you to explain where you are on your project in detail and you can’t, what do you think that tells them about you and your ownership of the project?

Writing is Thinking

We believe that “writing is thinking”. This doesn’t mean we expect everyone to have professional-quality writing in their skill set, but reflects on how we view the action of writing: it reveals the thought process and how completely you’ve considered your situation in a way that casual thinking and speaking just don’t do. This isn’t just lip service - a lot of your coworkers and colleagues are here because they were able to communicate well through writing (myself included). It’s something we think is important to how we do business, and it’s a skill we value more than most companies you’ve encountered.

But why do we value this one skill so much? Think about if you had to sit down and describe something you find beautiful in writing. This could be the grand canyon, a significant other, a flower, or anything you love. Could you really “paint the picture” of what’s special about your topic to someone if you only had a few minutes to do so? Could you get all that complexity across?

Don’t feel bad if you couldn’t; that’s part of what the writing process is about. Feelings are sometimes deceptive - we can feel we really understand something and still find that the sudden need to put it down on paper reveals parts we didn’t understand as well as we thought we did. But in writing them down, we can see those gaps and fill them. This isn’t just about explaining things to others - it’s about explaining them to ourselves, as well.

We think this applies to our work just as much as it does a beautiful landscape, if not more. Do you know where you are at on your project to the extent you could clearly communicate it in writing? If not, writing it down will show you why and what you need to do to be able to. Once you’ve got the writing piece in place, you can use that understanding to communicate better in any medium - not just in writing, but verbally as well.

Again, we don’t expect everyone to have perfect word choice - we aren’t all writers. Here’s a quote from Steven Sinofsky’s piece above:

Writing can be difficult for some, for sure. That is why it is important to focus on the function, not the form. Don’t be afraid to help people (especially as a manager) through the process of the “basics” of writing.

We are a lot more concerned about the function than the form as well, and we’ve found that clean, complete thinking translates into functional writing even if it doesn’t end up looking particularly pretty. We are also willing to help - if you need help developing the skill, let us know - we will be glad to help (My email is ben.denny@clipboardhealth.com, and I’m available to help any time).

Questions about “Writing is Thinking”

  • How well do you think you are currently able to communicate through writing? What room for improvement do you see?
  • How often do you use writing as a tool to improve your thinking? What benefits or drawbacks have you seen to putting down your thoughts on paper?
  • When we say "writing is thinking", what do we mean? Why is writing different from just carefully thinking about something?

Letters From New Team Members

We are always looking for the best perspectives, and usually the best viewpoint on a subject comes from someone close to the issue - the person with their hands dirty doing the task knows about it in a way that someone far away from the subject can’t. We also want different perspectives - different people have different approaches and get different lessons from the same subject matter.

That’s why I’m writing this document in the first place; I’m new, too. Another person who is just starting with us at the time I’m writing is Eli Zamora, who put together Top 5 tips for starting your journey at CBHfor us. I’m glad he did - he has cool insights I didn’t think of and he presents them in a different way than I could. We are building a library of similar letters at our Letters of Advice from 'New' CBH-ers (and how to document your own experience) from people from all over the company - as they join, we get the lessons they learned and we all get to grow. Read several of these - they are short but packed with insight that will help you as you move forward.

You later will be asked to do the same thing - maybe with onboarding, but maybe by writing something related to your particular skillset and place in the company that gives someone else an edge and a perspective they otherwise wouldn’t have had. Accumulating that kind of knowledge is a huge value to all of us - it makes us faster and smarter than we could be ourselves.

Questions about “Letters From New Team Members”

  • Pick out a couple of tips from one of the letters you read and let us know how they changed your thinking - what was something you didn’t expect? What’s something you really like? What’s something that maybe makes you nervous, or that you have more questions about?
  • You are going through onboarding too - what’s a tip you would add to Eli’s list? If you can’t think of one, that’s good too - what’s a question you have that you would make into a tip if you knew the answer?

Things to Do

Besides all the reading, we also want to make sure you get through some tasks this week that will help you get familiar with the company and how we do business. Most of the tasks are conversations - in a remote environment, it’s incredibly important that we intentionally emphasize communications. We want to make sure you know who is available to help.

Getting Plugged In

Every job is a bit different, and one of the harder things about starting a new job is figuring out the dynamics of your team and coworkers. This can be especially challenging in an entirely remote environment - it’s easy to feel isolated from people who aren’t physically present, and it’s hard to figure out how to work with someone you aren’t “with”. I’m the kind of person who is especially susceptible to feeling out of place in a new job, and making connections with the people I’ll be working with as soon as I could did a lot to help me feel more at home.

We want to make sure you get plugged in, so you can feel comfortably a part of Clipboard Health as soon as possible. One way we do this is by making sure you have a few meetings on your calendar as soon as possible - these can be with team members, your leadership, or anyone who is related to or interacts with your job role. The main goal is to make sure you are establishing relationships; we want you to know who you can go to for help or with questions and to have colleagues and friends you can interact with on a personal level.

Questions about Getting Plugged In

  • There’s a good chance we’ve already set up a few meet-and-greet meetings for you, but if we haven’t, reach out to a few people this week and find a time you can have a web meeting and introduce yourself. Try to walk away with something useful from each meeting, whether that is a resource you can use in the future, a person you can reach out to for assistance when you aren’t sure how to proceed, or a piece of knowledge that will be useful in your job.
  • What stood out to you about the people you met with?
  • Tell us about something useful you took away from your meeting - what was something you learned, or a resource you discovered?
  • Do you have any more meetings planned for the future as a result of the meetings you’ve already had?

Attend an All-Hands Meeting

We have a weekly all-hands meeting to keep everyone plugged into the overall pulse of the company. The format of the meeting is flexible to allow for the needs of the week, and while there are some things we try to keep consistent there’s often a good deal of difference between meetings. If you’d like to know a little bit more about what to expect, we keep recordings and slides from previous meetings here - feel free to review a few.

If you don’t already have a calendar invite for the all-hands meeting, let your leadership or Jesse Ferrigno know so we can get you on the calendar.

Questions about “Attend an All-Hands Meeting”

  • What was something you learned or took away from the meeting? How will it be useful to you?
  • What was the focus of this week’s all-hands meeting? How was it relevant to your position?

Write About Your Experience!

We love people in the company learning from other people. The last step in this document is very purposefully for after you’ve completed it - we want to hear from you about your experience joining CBH, and what you learned. You might be the first person joining in your role since we started this, and if so what you write will help everyone who came after you; they can share in your insights about our culture, what you’ve learned about how your department works and how you found your place with us socially.

We could write something to try to explain the same things, but we wouldn’t capture what you have: your own perspective on what Clipboard is like right now, as seen from your eyes. So write something - format it however you want. Make it as long or as short as you like. Just let people know what you learned as you joined us. When you are done, submit your letter and we will get it added to the library!

↓ Featured Articles

Internal Articles

What is Culture?
7 mins
Wei (CEO)
Letter to folks working with Bo (COO)
24 mins
Bo (COO)
Top 5 tips for starting your journey at CBH
10 mins
Eliseo Gil Zamora
High Quality And Fast
15 mins
George Markoulakis (CPO)
Onboarding Reading and Things to Do
15 mins
Ben Denny
Letter to Engineering Manager Candidates
5 mins
Bo (COO)
Our leaders are also excellent individual contributors
2 mins
Bo (COO)
Building for Scale
4 mins
Mike Cook