My User Manual

"Perseverance is Where the Gods Dwell”

I first came across the idea of User Manual in an article titled The Indispensable Document for the Modern Manager. At the time I was managing a fully distributed team of designers, developers, and marketers.

I've been managing remote teams since 2010—I thought I had it all figured out—except the same problems kept coming up over and over again. Penning this document was an attempt to communicate my expectations and idiosyncrasies to my team. Ultimately it improved our alignment and helped us get everyone rowing in the same direction.

Introduction

Welcome to the User Guide for Working With Me. This is a living breathing document that will change as I learn more about myself and how I can best support others. The purpose of this document is to give you a no-holds-barred look at how I think, how I take action, and how I perceive the behavior of others. I encourage you to write your own user manual so that we can better trust and understand each other—and therefore improve our working relationship and the outcomes we achieve together.

On Communication

The way I communicate is a demonstration of my beliefs, experiences and skills. My perspective on communication in the context of our work includes the following beliefs, ideas, philosophies, and expectations:

The sole purpose of products is to create joy for or provide value to people.
Communication is oxygen.
Communicate well and communicate often.
Communicating well means being specific and direct. Honesty and candor are the foundation of a relationship supported by trust.
Respect the hierarchy of communication so that you can get what you need from others (Most urgent → least urgent): Call → Email → ClickUp → Slack
I like fast turnaround and acknowledgement on all communication. If I comment on a task in ClickUp, Figma, Notion, or another system and I ask a question, I expect a response even if it’s just a quick “got it” or “on it” type response. Your response, however short of simple, relieves a lot of anxiety that I have around miscommunication.
I expect that you’ve organized and taken action to close the loop on whatever we discuss. You should be taking notes, organizing and prioritizing on your own.
The benefits of working remote are numerous, the pitfalls are many. For this reason I require a response to direct, high urgency questions within 60 minutes during your normal working hours. (You must be available during agreed “office hours” see your team’s specific user manual and our culture book for more information.) If you are a contract team member this rule does not apply though we know you’ll do your best to be responsive and timely. This idea must be balanced with the next one.
Async communication is important to me and anyone else doing deep work, creative work, etc. I don’t expect immediate responses. Timely != immediate.
If you don’t respond to requests during office hours in a timely manner (within 60 mins) I’ll assume you’re doing something other than working at your desk/computer.
Close the loop on ANYTHING we discuss. Small, large, important, unimportant—anything. If we discussed it I expect you’ll be making a note and following up with me to let me know how things went, if you need help or other resources, what your next steps are, etc.
I will get frustrated if things fall through the cracks or I have to follow up on something more than once.
Convey your ideas and challenge the ideas of your teammates (and my ideas)—but always bring your reasoning along with your ideas. If you challenge an idea, be able to explain your logic. Data AND anecdotes based on gut feeling and intuition are welcome.
Short, concise, and SPECIFIC communication works best. Be direct. Do not worry about politics or hurting my feelings. If you lack candor I will assume you are hiding something, this will erode the trust in our relationship.
Be aware of the personalities and emotional capacity of your coworkers. To be understood, speak their language. To be heard, communicate through their experience.
Ask questions. Especially early on in a new project or when working with a new client, adding a new feature, etc. If you do not ask any questions I will assume you are not engaged and that we are somehow misaligned. The quality of your questions will tell me a lot about what I can expect from you in terms of future performance.
My communication style is forceful and at times disagreeable. My goal is to always be respectful and conscientious. This is more a reflection of my passion re: what we’re working on than my disapproval of you, your work/performance, or your ideas. Do not misequate my passion with displeasure. If I have an issue with your work I will be very specific in my criticism. If you disagree I expect you to push back.
I don’t like yes men or yes women. I need truth seekers who do not fear giving negative feedback or calling bullshit when it’s required. I can smell bullshit a mile away and if you are a brown-noser or people pleaser you won’t last long in this environment.
Be clear, specific, and assertive about what you need from me to be successful.
Be punctual.
I’m impatient. I want things done yesterday. Progress inspires me. I’ll do my best to be as patient with others as possible—while balancing our need to move quickly and get things done.
I expect you to communicate forcefully—passionately. If you temper yourself or couch your opinions I will interpret that as a lack of trust and/or confidence. It’s up to both of us to work hard at building a trusting relationship so we can openly share our thoughts, ideas, and opinions.
I believe data is valuable, but I believe in the instincts of talented, experienced, and passionate people as well. We should be customer driven and data informed—do not blindly follow data, use the compendium of experiences you’ve accumulated over time to make good decisions.
Ask: how could this data be misleading?
Ask: how could this feature/idea/campaign fail?
Ask: where could I / We be wrong?
Ask: what’s the best/worst potential result?

On Reporting

Establish a reporting cadence of once per week—or earlier in the beginning of your tenure with the company.
Higher frequency reporting means tighter feedback loops. Tighter is better.
Report in a direct, concise, and specific manner. Brevity is a sign of clarity.
Reporting should be framed in the context of your progress against a plan, project, objective, KPI, etc.
Include qualitative and quantitative information in your reporting.
Keep it simple.
Always report bad news quickly and directly. This takes courage—we need to build trust and confidence in each other to enable open and free communication of poor results, unintended consequences, etc.

1 on 1s

Keep a historical record of the things we discuss during one on ones, Google Docs, or Notion works well for this.
I value the time we spend together—come prepared by reviewing what was previously discussed and have an understanding of any open loops that you may need to discuss.
Bring all of your problems, complaints, concerns, etc. This is the best time to air your grievances.
Once per quarter we will formally document performance.

First 6 Months

Early on I’ll work closely with you until you earn my trust. This could easily be interpreted as micromanagement, however, once I trust you I will give you the space you need to make decisions and execute on your own.
Autonomy is important here, we want you to operate like an owner and think like an entrepreneur. People are more important than process.

Feedback From Me to You

I expect you to clarify feedback and get an understanding of how to take action to resolve any issues presented during feedback.
Ask questions to get clarity on next steps or how to change your behavior or improve your work.
I will be as direct and detailed to drive home my point.

Feedback From You to Me

I’m always available. Yes, always. Your communication, questions, or feedback is important to me.
The more specific the feedback the better.
I will propose solutions or alternatives for most of the feedback you provide, but not all of it. I'll do my best to explain why I make the decisions I make.

Me as a Resources to You

Be assertive in letting me know what you need to be successful.
Be clear when you require company resources—if you want to purchase something present a solid case for what you need. EG. I need $x for y-thing which would add value in this way, etc.

Hiring and Managing Your Team

Establish and maintain a clear dollar weighted org chart. Hierarchies work—but flatter is better.
Maintain descriptive job responsibilities, roles, objectives, and KPIs.
Always be recruiting.
At the end of the day the only thing that matters are our people and our customers.
I’m extremely results oriented. Focus on outputs not inputs.
Our most important roles are not driven by process. Creativity, leadership, soft skills, etc cannot be created with process.

Contribution to Strategy

Strategy is the oxygen of our business.
Your job is not only to perform the functions of your role but to contribute to the broader strategy. You ideas, opinions, vision and feedback matter.
Dedicate time to understanding the inner-workings of our organization, industry, and customers beyond the scope of your role—it will serve you well and it will make all of us better.
Cumulative knowledge accrues internally when everyone is actively engaged in meta-thinking–EG how will my work affect the future of this organization.
Look for ideas outside of our competition and industry—have funnel vision not tunnel vision.

Logistics

Communicate personal boundaries and I will respect them.
I like to have after-hours conversations about strategy, ideas, roadmap, etc—this feels more like play than work for me.
I enjoy caffeine fueled after hours dinner where we discuss our grand vision.
I’m usually available on weekends, if something is urgent I’m available 24/7.
I generally take time on Sundays to recharge or work on passion projects.
If you go on vacation make me and your teammates aware of what could go wrong.
Live and die by your calendar. Be organized. Time is our scarcest resource.

Drives Me Crazy

Long winded discussion with no goals or objective, no context, and zero specificity (EG small talk, bullshit, etc).
Keeping me in the dark. Going quiet. Lack of consistent communication. If you go silent for a long period of time I start imagining bad things—I’m inventing reality. Avoid this. Communicate progress more often.
You don’t propose solutions to problems. If you have zero ideas, or zero curiosity about what we’re working on we will have a very short lived relationship. I strive to create an emotional and intellectually safe environment so that we can make mistakes, share ideas (even bad ones), learn, and grow.
Fail to follow through—I’m a great starter and I surround myself with people who are excellent at follow through. Do what you say you’ll do and be aware of over-committing. Don’t voluntarily burn out.