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!


Why You Should Cultivate Buyer Empathy

After two years of pitching and selling, I found myself on the other side: as a buyer of a similarly complex, expensive, and strategic service — needing to make an immensely important purchasing decision.

I recently embarked on a Buyer’s Journey to find a marketing agency to help grow our company, Retriever.

This experience has helped me build empathy for “the buyer”: what goes through their heads as they do their diligence to survey the market of outsourced sales development services, to find the one that’s best for their business. Being the buyer is hard!

I wanted to share this insight with other sales leaders, so that you too can empathize with your buyer — better understand their psychology, and win more deals.

Here’s our Buyer Journey, and principles of effective sales tactics that I learned along the way.

Stage 1. Problem/Need Recognition

For us, the first step of the Buyer Journey was realizing that we had a need. We wanted to generate an inbound pipeline of marketing leads to supplement our sales efforts.

Since Retriever’s inception, we’ve grown by “dogfooding”: i.e. using our own service: outbound sales via LinkedIn.

And in less than a year, we’ve grown with outbound from a team of 3 to 20. 100% bootstrapped. I’m quite proud of what we’ve built with zero outside funding.

But as I began planning strategic initiatives for Retriever in 2020, I wanted to diversify our go-to-market — to generate inbound leads through paid ads and content. That was the first step in our buyer journey.

Stage 2. Consideration

Now that we knew we wanted to scale our marketing, we needed to answer two questions:

1. what marketing agencies are out there?

2. which agency would be the best fit for Retriever?

To answer the first question, one of our teammates researched and reached out to about 10 marketing agencies, scheduling calls with them to learn more about them.

Those calls offered amazing insight into how I can improve my pitch.

Here are some principles that I noticed:

Buyer Empathy Insight #1: Be clear and articulate

When people sound like they have their pitch nailed down, I feel like they’ve done it before, they’re professionals — veterans. “They know what they’re doing.”

Inarticulate explanations, bumbling, and rambling, sapped my confidence in them. One vendor said “page on time” referring to “time on page”, making me wonder, “is this person not used to discussing these metrics? I should hope not!”.

When the lead asks a question, answer first, then give context!

e.g.) cost? => not having a clear answer makes me think either 1. they don’t know (they’ve never sold this before!?) or 2. they’re being unnecessarily obscure (which breeds distrust)

Buyer Empathy Insight #2 Dig deep to understand your prospect

I felt more confidence in the vendors who asked detailed questions to understand my business model, my goals for growth, and other relevant constraints: my budget, my timeline, other go-to-market initiatives, specifics on our target customers, etc.

Shallow questions made me feel like they’re inattentive, not customized to our particular needs and constraints, and made me worry that they wouldn’t understand the business well enough to run marketing for us.

Further, I wanted a detailed proposal from these vendors. Working backwards, then, they needed to ask detailed questions about us, so that they could personalize their proposal for us.

Buyer Empathy Insight #3 Qualification is about the lead — not about you

One vendor spent most of his call with us figuring out whether we had authority and budget, and not asking specific questions to determine what we needed.

In BANT* speak, it was all “Budget” and “Authority” and no “Need” and “Timing”.

[*BANT = qualifying leads by determining their Budget, Authority, Need, and Timing.]

BANT is fine as a qualification framework. But it should startwith the Need. Understand why this person is on the phone with you? What pain are they feeling?

From the “Buyer Journey” perspective, what was the “Problem” or “Need” that they recognized? Dig into that before trying to tick every checkbox on your qualification list.

Buyer Empathy Insight #4 Be an Expert: Recommend a Specific Strategy

After asking specific questions: put your expert hat on.

I spend a bulk of my day leading people: leading my team in meetings, leading my prospects. As a buyer, I want to be led!

I want the vendor to expertly guide me through the process. Once they’ve asked all the questions that they need to create a strategy — a prescription, tailored to the prospect’s needs — I want it laid out perfectly for me.

High level: Help the prospect understand the lay of the land. Explain the universe of possible solutions, and what factors determine which is the best fit. This is sort of like a high-dimensional Gartner Magic Quadrant.

Low level: Zoom in on particulars of the strategy that you recommend. Draw upon your experience implementing that strategy.

What does the first week look like? The first month? What’s the time to ROI? Flesh out a picture of what this looks like, that the prospect can easily imagine for themselves.

Stage 3. Decision

By this point, your prospect likely has all the information that they need to make a decision.

They’ve solicited proposals from multiple vendors. They’ve gotten an understanding of the competitive landscape, their budget and expected ROI, and are deciding i) Which strategy to implement, ii) Which vendor is the best fit to implement that strategy.

By this point, there’s little you can do to further influence the decision.

So as a vendor, the best thing you can do is work backwards to win in the decision stage. In the consideration stage, you’ll need to make the best case that you can for (i) and (ii) above.

First: convince them that your proposed strategy is the best one (i).

Second: convince them that your company is the best fit to implement that strategy (ii).

If you do both of those things, you’ll maximize the probability of winning the deal in the Decision Stage.


Would love to hear your thoughts / feedback on this.

And if you want to talk more about sales, drop me a line: stedman at retriever dot co.