Hi, welcome to the team. I’m so glad you are here at $COMPANY.

It’s going to take a solid quarter to figure this place out. I understand the importance of first impressions, and I know you want to get a check in the win column, but this is a complex place full of equally complex humans. Take your time, meet everyone, go to every meeting, write things down, and ask all the questions – especially about all those baffling acronyms and emojis.

One of the working relationships we need to define is ours. The following is a user guide for me and how I work. It captures what you can expect from the average weekly working with me, how I like to work, my north star principles, and some of my nuances. I intend to accelerate our working relationship with this document. My intent with this artifact is to avoid suggesting how you should work.¹

Our Average Week

I’ve created a private Slack channel for the two of us to capture future topics for our 1:1s and provide a handy historical record of our discussion. We’ll have a 1:1 every week for at least 30 minutes except during HIGH ALERT (See below). This meeting discusses topics of substance, not updates. When you or I think of a topic, we dump it in our Slack channel.

We’ll have a staff meeting with your peers every week for 60 minutes, no matter what. Similar to 1:1s, we aren’t discussing status at this meeting but issues of substance that affect the whole team. Unlike 1:1s, we have a shared document that captures agenda topics for the entire team.

You can Slack me 24 hours a day. It’s my preferred communication medium. I like responding quickly.

If I am traveling, I will inform you of said travel in advance. All our meetings still occur if this is a professional trip, albeit with time zone considerations.

I work a bit on the weekends. This is my choice. I do not expect you to work on the weekend. I might Slack you things, but unless the thing says URGENT, it can always wait until work begins for you on Monday.

I take vacations. You should, too. Disconnected from work is when I do some of my best work.

North Star Principles

Humans first. Happy, informed, and productive humans build a fantastic product. I optimize for humans. Other leaders will maximize the business, the technology, or any different number of essential facets. Ideological diversity is critical to an effective team. All perspectives are relevant, and we need all these leaders, but my bias is toward building productive humans.

Leadership comes from everywhere. My wife likes to remind me that I wouldn’t say I liked meetings for the first ten years of my professional career. She’s right. I’ve spent a lot of time in poorly run meetings by bad managers. As an engineer, I remain skeptical of managers, even as a manager. While managers are an essential part of a scaling organization, they don’t have a monopoly on Leadership. I work hard to build other constructs and opportunities for any human on the team to be a leader.

I see things as systems. I reduce all complex things (including humans) into systems. I think in flowcharts. I take great joy in attempting to understand how these systems and flowcharts all fit and work together. When I see large or small inefficiencies in these complex systems, I’d like to fix them with your help.

It is important to me that humans are treated fairly. Most humans try to do the right thing, but unconscious bias leads them astray. I work hard to understand and address my biases because I understand their ability to create inequity. Those in power have a disproportionate responsibility to invest in historically disadvantaged humans proactively.

I am heavily biased toward action. Long meetings where we endlessly debate potential directions are often valuable, but I believe starting is the best way to begin learning and progress. This is not always the correct strategy. This strategy annoys those who like to debate.

I default to delegation. The delegation of increasingly large, complex, and high-risk projects to my team is the correct way to build trust and grow the team. If you feel a thing I’ve delegated to you is too large, complex, or risky, you should tell me, and I will help. You should know that I would not make this delegation choice if I did not believe you would be successful. I am always willing to help.

I believe in the compounding awesomeness of continually fixing small things. I believe quality assurance is everyone’s responsibility, and there are bugs to be fixed everywhere… all the time. This is everyone’s responsibility, and I will give you side-eye if I see you avoiding investing in quality.

I start with an assumption of positive intent for all involved. This has worked out well for me over my career. Yes, even when the sky is falling, and the humans are panicking, I will open the meeting with a joke.

I need you to know that sometimes we are on HIGH ALERT, and things will get strange and unpredictable. There is an exception to many of my practices and principles, which is when we are in a HIGH ALERT situation. HIGH-ALERT conditions usually involve existential threats to our product, team, and/or company. During this time, my usual people, process, and product protocols are secondary to countering this threat. If it is not apparent, I will alert you that I am in this state, along with my best guess, when we are done. If I am constantly in this state, something is fundamentally broken in my strategy. You should tell me this. I might be so busy that I need the reminder.

Feedback Protocol

Feedback (along with delegation) is at the core of building trust and respect in a team.

At $COMPANY, a formal feedback cycle occurs twice a year. The first time we go through this cycle, we’ll draft a proposed set of OKRs for you for the next review period. These are not product or technology OKRs but professional growth OKRs for you. I’ll send you these draft OKRs and upward feedback from your team before we meet so you can review them beforehand.

In our face-to-face meeting, we’ll discuss and agree on your OKRs for the next period, and I’ll ask for feedback on my performance. In our following review, the process differs thusly: I’ll review you against our prior OKRs and introduce new OKRs (if necessary). Rinse and repeat.

Review periods are one of many times we’ll exchange feedback. This will be a recurring topic in our 1:1s. I am asking you for feedback in 1:1s regularly. No matter how often you say you have no feedback for me, I will never stop doing this. Building a healthy feedback culture is a cornerstone of building high-trust relationships.

Disagreement is feedback; the sooner we learn how to disagree with each other efficiently, the sooner we’ll trust and respect each other more. Ideas don’t get better with agreement.

Meeting Protocol

I go to a lot of meetings. I deliberately run with my calendar publicly visible. If you have a question about a meeting on my calendar, ask me. If a meeting is private or confidential, its title and attendees will be hidden. The vast majority of my meetings are neither private nor confidential.

My definition of a meeting includes an agenda and/or intended purpose, the appropriate amount of productive attendees, and a responsible party running the meeting to a schedule. If I attend a meeting, I’d prefer to start on time. If I run a meeting, I will start that meeting on time. If it’s not clear why I am in a meeting, I will ask for clarification on my role in this meeting.

If you send me a presentation deck a reasonable amount of time before a meeting, I will read it and have my questions ready. If I still need to read the deck, I will tell you.

If a meeting completes its intended purpose before it’s scheduled to end, let’s give the time back to everyone. If it’s clear the intended goal won’t be achieved in the allotted time, let’s stop the meeting before time is up and determine how to finish it effectively.

Nuance and Errata

I am an introvert, and that means that prolonged exposure to humans is exhausting for me. Weird, huh? Meetings with three of us are perfect, three to eight are ok, and more than eight, you will find that I am strangely quiet. Please do not confuse my quiet with a lack of enthusiasm or engagement. Groups of humans are hard work for me.

I am bad at asking for help which is probably related to my introversion. When I ask for help, I probably should have asked for help earlier, and I’ve made the situation direr than needed. Sorry.

When the 1:1 feels over, and there is remaining time I always have a couple of meaty topics to discuss. This is brainstorming, and the issues are usually front-of-mind challenging topics that I am processing. It might feel like we’re shooting the shit, but we’re doing real work.

When I ask you to do something that feels poorly defined you should ask me for clarification and a specific call on importance. I might still be brainstorming. Your clarifications can save a lot of people a lot of time.

Ask assertive versus tell assertive. When you need to ask me to do something, ask me. I respond incredibly well to asking assertiveness (“Rands, can you help with X?”). I react poorly to being told what to do (“Rands, do X.”) I have been this way since I was a kid and probably need therapy.

When you say something complicated, I will often repeat it. I will say, “Let me tell you what I heard.” I have discovered the hard way that what is being said is often not what is being heard.

I can be hyperbolic, but it’s almost always because I am excited about the topic. I also swear sometimes. Sorry.

I love to start new things but I often lose interest when I can mentally see how the thing will finish, which might be weeks or months before the thing is done. I solve this by pairing with humans who are strong operators and who are very good at checking things off lists.

Humans stating opinions as facts are a trigger for me. When I hear this, I will often unexpectedly jump into a conversation to clarify that your opinion is just that… your opinion and not a fact.

This document is a living breathing thing and likely incomplete. I update it frequently and would appreciate your feedback.