Hi, I'm so glad we are working together. To make this an awesome relationship, there are some things I thought you should know about me. Keep in mind that this document, like myself, is a work in progress. Issues and pull requests are welcome! I will try to keep you updated as I make changes.

Here are my main responsibilities at the moment as CTO and Integrator:

1. I help shape our company's long-term strategy and vision, but ultimately my job is to ensure that all teams across the organization are working together to realize this vision.
2. Create an environment for all employees to do their most impactful work and lead their most fulfilling lives. I aim to build a system that aligns individual aspirations with our company's needs and objectives. I want to ensure that you're where you want to be and growing at your desired rate. If I do this well, I hope we can work together for a long time. And if the day comes when that alignment is no longer possible, I want you to look back on Denim as one of the best places you have ever worked.
3. Provide context on priorities, why things are a certain way, why we do certain things, and where we want to go. I have a lot of our company's historical and "global" context, so by sharing it with you, you can make the best decisions for the company.
4. Temporarily handle high-priority and complex issues for which we haven't hired or trained someone yet. My goal is that, eventually, I make myself redundant.

In general, I am always available on Slack. Since most of my work is internal, I'll only check my emails once or twice daily, so that's generally not the best place to reach me.

Sometimes, I will dump information to you on Slack because I'm thinking about it right now, but I don't necessarily expect you to respond immediately. If it is unrelated to something we recently talked about or if it's really early, really late, or on weekends, please respond when it's most convenient.

I expect you to set your Slack "notifications preferences" based on your working hours. If it is truly an emergency, I will "notify anyway". I have done this maybe two times in the last year. I believe this is the best way for us to feel comfortable detaching.

I am notoriously bad at unscheduled phone calls and text messages since my phone is generally on silent to avoid distractions.

In a fully remote setting, it is often hard to tell how strong a person feels about a certain idea. We want to encourage people to share their thoughts freely. However, when the CTO makes a statement, it might be perceived as a strong directive when it is just a mere suggestion. Below is how I try to use "flashtags" in my statements.

• #fyi or #idea: I haven't spent a lot of time thinking about it. You can read it or not. Act on it or not. No response is needed or expected.
• #suggestion: Here's something I would do if I were you. But, I'm not you -- and you own this, so your call. Just consider it and weigh it against other things you're considering. I won't be offended if you go another way. A quick reaction/response would be appreciated (so I can learn what kinds of suggestions are useful/valuable), but is not necessary.
• #recommndation: I've thought about this a lot. It's kept me up at night. I dug in. I think I understand the tradeoffs. You can choose not to take the recommendation, and go your own way, but please do it for good reasons.  Please dig in a bit yourself and have a well-reasoned rationale for why you don’t want to take the recommendation. Please don’t ignore or dismiss it out of hand. A response (either way) is politely requested.
• #plea: We don't like issuing edicts or directives. But...please, please, please just do this. Trust works both ways, and I need you to trust me on this. If you still feel compelled to resist, something’s not right, let's huddle.

If I make a statement where the intention isn't clear, feel free to ask if it's a #idea or #recommendation.

0. My Mornings: Reserved mostly for my "deep work" time, preparing for meetings that day, or taking external meetings. Many of my best ideas are thoughts I have during a morning workout.
1. Strategy Monday: This is where I have my "Strategy" meetings to set the pace for the week. This usually includes Exec Session and OKR Check-ins.
2. Deep Work Tuesday: This is for me to work on my big "rocks" for the week.
3. 1:1 Wednesday: This day is for our personal growth. This is where we will have most of our 1:1s (see below). We can also schedule working sessions on these days.
4. Working Session Thursdays: This time is for us to work on the business. I am available to help with your team / department goals. I can provide feedback, share context, help problem-solve.
5. Staff Friday: My ideal Friday will be to lead a productive staff meeting, and have a series of skip-level 1:1s in the afternoon, and get some deep work in before the weekend.
6. Weekend Review: Usually, on a Saturday or Sunday, I will spend a few hours reviewing our KPIs and OKR updates to help me share context and prioritize the next week.

For us to sync up our calendars, I would encourage people who report into me to have a calendar schedule that allows us to keep Wednesdays and Thursdays open for collaboration.

Time is our most important asset. I am a firm believer in being prepared for meetings. If you can, please do as much pre-work as you can so the meeting is more productive. In addition, I expect that you are fully engaged (no slacking). If you feel like this meeting isn't relevant to you, you can drop off.

In general, we have two types of meetings:

This is where we focus on company issues. We use this time to solve some problem, share information, or make a decision. We should know what the goal of the meeting is before meeting.

For these meetings, I would appreciate you sending me context beforehand, and if you do so, you can expect me to be prepared and fully engaged during the meeting.

This is where we focus on you. You tell me what's good or bad. Tell me how I can make your life easier. A good framework is tell me things you want more of, less of, or to stop. We should focus on things beyond the moment like your personal / career development.

I want to avoid this being a status update on your projects since I should be able to get status updates through other channels. However, we can certainly talk about some of the challenges and problems you are working through.

I would also appreciate it if you could share any feedback with me during this meeting. Tell me how I am doing. I may share feedback with you too.

We should feel safe delivering feedback to each other. There will never be any punishment associated with delivering or receiving feedback. If anything, we reward that. I think feedback should:

• Include positive and negative
• Be delivered as real-time as possible
• Have the intention of helping the other person grow
• Address the behavior or action, not the person
• Be actionable

• If it's something tactical, I will most likely tell you as I notice it. It will probably be unstructured. These will be more like Learning Moments, so feel free to ask questions to clarify. (ex. Hey this might be a better way to do X,Y,Z...)
• If it's something behavioral, I will try to find examples and synthesize it a bit more. This will likely occur in our 1:1s, feedback circles, or quarterly check-ins.

• Be direct, calm, and serious. If it is delivered jokingly, I might not take it seriously or think it's a real problem.
• I appreciate things when they are delivered in a rational, not emotional way.
• Help me understand the why and help me come up with a solution.
• If I seem defensive, it's more likely because I am trying to understand the rationale, not because I'm getting upset.

In addition to the company values, here are some things that I personally value.

• Deep work: I think that to be really innovative and deliver excellent quality work, we need to have uninterrupted time. I will try to respect your deep work time so let me know if I'm bothering you.
• Resourcefulness: Sometimes we need novel solutions. Sometimes we just need to look it up. For things we can look up, always try to find resources before reinventing the wheel or asking someone else what to do.
• Be forward-looking: It's more important to me that an issue never happens again than it is to fix it right now.
• Be thoughtful and complete: Have a complete understanding of how it works. Know what the second and third-order consequences are.
• Be intentional and proactive, not reactive: We have too much to do for any of it to be random. Intentionality is important to make sure we get the results we want.

In order for me to delegate effectively, there are three things we need to be aligned on. I will try to articulate these three things, but if you feel like they aren't there, please help us get there.

1. I need to trust that you deeply understand the problem that we are trying to solve. It should be clear what the "success criteria" is. This is not "what needs to be done" but "what is the outcome or result if we do it well".
2. I need to trust that you have the "will" AND "skill" to do the job exceptionally well. If you don't feel like you have the ability to take it on, I can help make sure you have proper context and resources, and share how I might approach it.
3. I need to trust that you have the right priority and urgency levels for the work that needs to be done. We need to align on what is most important at the time. This is especially important since we often have more work than time so we need to be able to prioritize effectively.

These are things I am currently working on. If you notice any of these things, let me know.

• During stressful / meeting-heavy days, I might be pretty curt. Don't read into brief replies too much. I'm probably just trying to quickly solve the problem.
• I might get anxious when things seem clear to me, but aren't clear for others. PLEASE don't let this discourage you from asking questions. Chances are I am just frustrated that I am having a hard time articulating my thoughts.
• Sometimes when I really want to understand something, I go into "digging mode" and ask a rapid series of questions. Don't worry, you're not under attack and it's okay to tell me if you don't know or unsure. This happens often when there is a bug in the system or if I'm trying to understand a concept or product feature.
• I am very prone to typos, especially when I am responding from my phone or typing quickly. If a sentence doesn't make sense, there's a good chance I just typo'ed something. You should definitely ask for clarification. If there are typos in this doc, let me know!
• As an engineer / builder / designer at heart, I tend to throw out solutions rather than focusing more on the success criteria or outcome. If you feel like I'm throwing out a solution (especially a bad one) please ask me to clarify what the success criteria or outcome is. I am always open to better ideas and I want to empower you to come up with solutions.

If you see me not living up to anything in this document please let me know. It’s possible that I’ve changed my mind (👍). More likely I’m dropping the ball (👎). Either way I’d like to know.