My User Guide

If we understand how our teammates communicate, work, and learn best, we’ll be more happy and effective as a team. Maintaining a User Guide allows people to understand how to work with you. That’s why I have every member of our team at Retriever build and maintain their own User Guide.

And there are substantial side benefits. It prompts introspection and fosters self awareness.

Below is the exact User Guide that I share w/ my team at Retriever. It’s tremendously helpful in quickly acquainting new colleagues with me and my working style — including my habits, quirks, and gotchas.

Note: this User Guide is very targeted to my role and my team at Retriever. Likewise, you should consider your context and audience, and target your User Guide accordingly.

Stedman’s User Guide, as Retriever CEO


  1. I process things visually. I need to see written notes to get my bearings, maintain attention, and keep track of where we’re going.
  2. I am a direct communicator. Please let me know if this style does not work for you and I will modulate it.
  3. Please explain things to me on a call, not on Slack.
    • I probably don’t have context for whatever you’re working on, and a 1 min call will allow you to give me the context that I need to help you out.
    • If it’s not worth getting on a 1 min call to discuss with me, it’s probably not worth asking me about anyway!
  4. I LOVE feedback. Critical feedback is great. There are things I’m messing up every day and if you don’t tell me, I probably won’t improve.

Things that you should know about me:

  • ⚠️ Communication style
    I’ve been told that I can be “intense”. If you feel I’m too direct, or intimidated, please let me know, and I will try to modulate during our discussions! That said, I am probably best suited to work directly with folks who respond well to my intensity. Please understand that even if I come off that way, it is coming from a place of enthusiasm and energy rather than aggression.

    Another key to my directness is that I think it’s the best way to get to the truth. Underpinnings of this view:
    Disagree and Commit
    Harmony vs Productive Conflict

    I also talk loudly. I grew up talking loudly because my mother is very hard of hearing and she needed us to speak up. If I’m speaking too loudly, you can let me know!
  • ⚠️ Take notes during our meetings 
    I don’t trust my memory — or yours. So I want a written record of the important stuff. This means, if we’re having a meeting, I want notes taken. If I can trust you to take good notes, I will be much more at ease, and you will get more out of me in meetings.
  • ⚠️ Context switching
    I’m bad at it. If you need something from me that’s urgent, ask to get on a quick call to explain it (not on Slack). Otherwise, make a task in Asana with a due date of Today and rest assured that I will look at it.
  • Convince me with data 
    I make complex decisions with data. e.g.) If we’re trying to decide how many people to hire next month, I need to see 1. a forecast of our growth, and 2. a forecast of our current team’s capacity to absorb that growth. The answer (how many people to hire) should be in line with those two things. The reason is that – when we’re making decisions under uncertainty – it’s important to articulate what we don’t know, and to try to be as precise as possible in the face of that uncertainty. When you start to layer uncertainty on top of uncertainty, it only takes small errors in each forecast to yield huge errors in the overall output. Back to the hiring example, if we’re a little over on our growth forecast, and a little under on our capacity forecast, then we can easily end up hiring too many people, which is very costly to us. Before making long-term strategic decisions, I need to see a model that justifies our decision.
  • Timing/Schedule
    • I like working at night. You’ll often get pings from me in the wee hours. There is no expectation that you respond to these at night or that you likewise develop nocturnal habits.
    • I’ve never been productive in the afternoon. Unless I have fixed engagements, I prefer to take a few hours in the afternoon to exercise, think about high-level strategy, or meet with people/take calls.
  • Closed-mindedness
    I’m conservative in the sense that I prefer to “stay the course”, and tend to be pessimistic about exciting new endeavors. I will often try to pick apart an idea even if I’m excited about it. Don’t let that discourage you; on the contrary! A good idea will stand up to the scrutiny.
    • In part, this conservatism is learned. We tend to succumb to “grass is greener” bias, and want to pursue the “shiny new” thing. I want to counteract that bias. This makes me err on the side of pessimism when considering new initiatives.
    • Furthermore, as CEO, my job is to keep this company aligned and moving in a unified direction.
      • Companies are like boats. Every time you change directions, you lose speed (focus, alignment, and subsequently, execution). Suppose we’re trying to sail north, and we find ourselves a few degrees off course. I’d rather continue slightly off course, and maintain our speed, rather than re-route to True North and lose speed in the process.
    • That said! Sometimes I’m unduly conservative. If you feel that I’m flippant or dismissive, please flag it. I don’t want to be negative or closed-minded. I just want to protect the overall company’s trajectory.
    • Finally, I can take a while to come around to new ideas/proposals. If you come to me excited with a new idea, don’t take my initial deadpan response as dismissal. I’m just trying to wrap my brain around it.
  • Process
    If you’re in charge of something — from a Client’s outbound campaigns to managing a team at Retriever — I want to see that you have process. We are a “Business Process Outsourcing” company: “process” is literally in the name! It’s crucial that we create deterministic processes in our company — rather than be running on habit, whim, and fickle memory.
  • Scale yourself.
    Follow these two rules:
    1. try to pass off as much responsibility to your direct reports as they can handle.
    2. If you’ve done that, and you’re at capacity, let your manager know.If everyone follows these two rules, we will be ensuring that everyone on the team is as highly-leveraged as possible.
    • Is there a meeting you don’t think you need to be part of? Ask your manager if you can be removed from it, or made optional. That’s why we have meeting minutes 🙂
    • Is something repetitive crowding out time you could be spending on higher ROI activity? Let your manager know, and you can work together to find an efficiency gain.
  • Getting in the Weeds
    When considering strategic questions, I often jump too quickly to implementation details. Try to help me stay high-level and abstract until we need to address implementation.
  • Language
    I use a lot of acronyms. I also have an annoying habit of using bigger words than necessary.
    • If you catch me saying a word that is unnecessarily esoteric weird, please let me know.
    • If I use an acronym that you don’t know, please ask me what it means. I’m probably using it because it’s important enough of a concept that we need to reference it often + quickly, so you should know it too. A short list:
      • ICP: ideal customer profile; target market
      • ACV: annual contract value; how much a year’s worth of something costs
      • ROI: return on investment
      • LTV: lifetime value of a customer; how much profit we make from a single customer
      • SG: sounds good
      • RN: right now
      • BTCHESA: “best team capitalism has ever seen assembled”; i.e. the Retriever team 🙂
  • Growth vs fixed mindset
    • I believe in my capacity to grow and improve.
    • As part of this User Guide, I listed some of my blind spots and shortcomings. But I’m still actively working on improving these things. So much so that I anticipate removing them from this User Guide once I’ve overcome them.
    • Likewise, I believe that you can grow and improve! If I flag an area of weakness for you, that’s not an eternal sentencing. I have confidence that you will be able to improve upon it — if you want it badly enough! Related:
  • Decision-making
    I often need a while to think through big decisions. Don’t expect me to make decisions on the spot. Let me talk/ramble through them plz , as that’s how I can best think through them.
  • Personal growth through feedback
    Personal growth is one of my 3 core principles (along with “creating impact” and “having fun”). So please, please, please don’t hold back the constructive criticism. It’s your greatest potential gift to me! I promise I will not be offended or upset, and I will be indebted to you for the insight. I’m particularly interested in feedback on my communication style: how can I be a more effective communicator? Am I using “um” too much? Do I come off as impatient? Is there something I’m doing in our interaction that makes you want to avoid interacting with me in the future?


Here are some other articles and resources that I found helpful while constructing my User Guide:

Questions to get you started

Questions focused on yourself:

- What are some honest, unfiltered things about you?
- What drives you nuts?
- What are your quirks?
- How can people earn an extra gold star with you?
- What qualities do you particularly value in people who work with you?
- What are some things that people might misunderstand about you that you should clarify?

Questions focused on how your interact with others:

- How do you coach people to do their best work and develop their talents?
- What’s the best way to communicate with you?
- What’s the best way to convince you to do something?
- How do you like to give feedback?
- How do you like to get feedback?

Hope this helps!


Leave a Reply