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The steps of (re)positioning

As a humble reminder, we’re out at a conference this week. We’ll be back the week of May 19.

We’re aware that our positioning towards software is the most important technological event of the past century, and as a result, some people have questions about how we did it. We’ve undertaken a few initiatives, some done, some still in progress:

  • Rework our website to reflect our new focus on software, which we wrapped up last week.

  • Start from basics. Paid members have already received a couple of lessons on pricing & onboarding, with more to come.

  • Outline a few years of new lessons on increasingly granular topics. Hoping to do this on the plane in a couple of days.

  • Relationship building. Figure out where to speak next, who to talk to, etc.

Let’s talk about lesson planning. Content ideas are shockingly easy to brainstorm; you just need to make the writing prompts to get you going when you’re in front of a blank screen. I got this idea from Naomi Dunford at IttyBiz and have adapted it for our use.

First, come up with a few primary topics that fit your positioning. For us, that involves:

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#197
May 6, 2025
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What is the baseline anatomy of an onboarding sequence?

First, our monthly office hours for paid members is coming up! Join us on Tuesday, May 13 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!


Onboarding is massively important, but it usually doesn’t lend itself well to specific design patterns, since the goal is to create a specific outcome that is specific to your product’s value. In this lesson, then, we’ll talk about some of the principles that onboarding should follow, and dive into some examples.

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#196
May 1, 2025
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The advisory role

They say that a pilot earns their paycheck every tenth landing. The theory: the plane mostly flies itself when everything goes well*. When you need to do something more complex – like, say, fly into ORD mid-derecho, as I’ve had the unfortunate fate of experiencing – then that’s where your expertise kicks in.

I have had the good fortune of earning my paycheck this past month, for all of my clients, for reasons both obvious and not obvious. One client watched a vendor turn usurious with a day to go in the contract; another lost a key staff member; a third shared with me a big, intractable problem around onboarding. In each of these, we flew into the storm, stuck the landing.

The common thread is advisory, brought about through establishing the expert position ahead of time. Expertise can be publicized in the form of whitepapers, process documents, surveys, books, and reports. Most of you know we’re experts in what we do, but many others, including some who hire us(!), need a little budging.

Because what we do is value-based design, but how we create value is through advisory. It doesn’t take long for people to start asking us bigger strategic questions that, on face, have nothing to do with the actual practice. But they have everything to do with the way the business works, and there’s always something deeper to explore.

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#195
April 29, 2025
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What is the baseline anatomy of a pricing page?

Now that we’re focused on software, it’s time to turn our attention back toward a big topic: pricing pages. In this lesson, we’ll outline the baseline anatomy of a pricing page, so you can make sure yours is doing as well as possible before you start to break rules or make improvements.

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#194
April 24, 2025
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How many designers does it take to change a light bulb?

Why did we put a light bulb there? What is the point of a light bulb? Where are we attempting to put light, exactly? Are people really asking for light here in the first place? Could this be more easily solved by simply cutting a hole in the ceiling and putting a skylight in there? Do we need light when it’s dark out?

Why did the light bulb fail? Don’t we have LED lighting now? You can just buy a light that lasts for 15,000 hours and be done with it, so if the light failed and it is LED, why? Faulty wiring? A power spike? Do we need to make a warranty claim? Do we need to open up the ceiling and figure out what happened? If the light isn’t LED, why do we have incandescent or CFL bulbs in the first place?

What was the temperature of the light? Why? What is the function of the space? Are we talking a nice cozy home, or an office, or a hospital? Or maybe it’s a design consultancy where we need fully neutral 5000K daylight bulbs everywhere, so people can make sure their colors render properly?

What is our prior knowledge of this light? What value are people getting from this light? Have we talked to anyone? Why not?

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#193
April 22, 2025
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How will value-based designers respond to current market conditions?

Oh lawd, we’re talking about tariffs.

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#192
April 17, 2025
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Draft’s Employee of the Month for April 2025

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here. If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.

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New event alert! I’m pleased to announce that I’ll be doing live teardowns at MicroConf Remote in May. Come through! Submit your site! I promise to be firm but kind as I lovingly rip your work to shreds.


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#191
April 15, 2025
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How do you connect sources of truth when defining, adapting, and measuring processes?

In our previous lesson, we defined & discussed process design. In this week’s paid lesson, we’ll connect that lesson with our evergreen piece on sources of truth go in depth about how we can connect sources of truth to yield deeper insight.

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#190
April 10, 2025
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Winter 2 (what’s next for design)

Many wild events have happened in Draft’s history, and you could conceivably pick a few to qualify as the wildest. My consistent pick for the wildest happened in 2023, when design began the deepest winter in the industry’s whole history while we also had our second-best year ever.

Four things happened all at once:

  1. We came to a global consciousness that design is a form of leveraged power, and those in power took it from us.
  2. People in power wanted everything to happen faster, and since design frequently slows things down, design got cut.
  3. Other tools appeared that appeared to make design more efficient to those in power. Whether or not this is true remains an open debate, but I think nobody is debating that people in power think the tools make design more efficient.
  4. Global fascism, which has caused numerous tech workers to go on strike from the industry.

None of which are great! But again, we also had our second-best year ever – because prospective clients recognized the value of our work, and decided to take a chance on us.

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#189
April 8, 2025
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A short-but-sweet guide to process design

In our previous two lessons, we set forth the idea of executional velocity and described why it’s important for teams to pursue, especially those that are beginning to scale. Usually that happens through the intentional creation of structured process.

In this lesson, we’ll talk about how to design a process, and how to apply your design skills to the creation of generous execution in any organization.

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#188
April 3, 2025
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Notes on the rework (avoid deck chair moves)

First, our monthly office hours for paid members is coming up! Join us on Tuesday, April 15 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!


We are never not reworking the stupid website. The world changes; you change; you adapt. Since we’re usually busy serving our clients – and since we’ve been fully sold out since 2022 – I don’t know if we make changes often enough, but we eventually get around to it. Last week we got around to it. We got rid of some things, reworded some other things, and scrubbed a position that was no longer working for us.

The goal is correct plumage. You are signaling to a person in a way that solves their urgent, expensive problem. You do so in a way that reads the room & meets the moment. When it works well, you find kindred spirits. When it works poorly, you try to do everything for everyone, and you bungle your positioning.

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#187
April 1, 2025
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More questions on executional velocity

In last week’s masterpiece, we coined the term executional velocity and answered a few questions about it:

  • What is executional velocity?

  • What’s the difference between executional velocity & productivity?

  • How can we identify the main operational issues that harm executional velocity?

This week, we’re going to answer a few more questions:

  • Why isn’t executional velocity discussed more broadly?

  • What’s the relationship between executional velocity & key business goals?

  • Under what circumstances might additional executional velocity not be desirable?

  • What are some of the ways that we can address normalized deviant practices that actively harm executional velocity?

Let’s begin.

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#186
March 27, 2025
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How to practice value-based design in a smaller team

I printed a few copies of our WTF notebook, and I’m seeking beta testers. Hit reply with your mailing address if you’re able to use it for a bit and provide me with brutal, unflinching feedback in return.


Our recent paid lessons have focused on some of the dynamics that occur in teams that are over, oh, say, 7 people. By that point, roles are defined, people wear fewer hats, responsibility gets meted out, and power structures become more readily apparent.

Most businesses are this large, but what if yours isn’t? How does value-based design manifest in smaller teams, or with solo practitioners?

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#185
March 25, 2025
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What is executional velocity?

I’ve been lucky enough to watch several dozen growing businesses from the inside over the course of my career. Some have been successful, scaling effectively and growing into new markets. Some have been… less successful. And really, the thing that separates the two is execution. What defines the ability for a team to do things, and do them well?


The rest of this post is available to members. Upgrade now to get:

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#184
March 20, 2025
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Contemporary design is a messy human problem

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here. If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.


We wrote a brief guide to why we use email when communicating with people. This joins a few other explainer bits that outline our principles & motivations.

Precisely three of you wanted a WTF notebook. I may print some as zines for my close people. We love a fun side project.

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#183
March 18, 2025
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How do you incorporate called experiments into your existing prioritization?

First, our monthly office hours for paid members is coming up! Join us on Tuesday, March 18 to ask me anything about value-based design & getting an impact with your work. These vary in attendance from 1 to 10 people, and they’re always helpful for you and for me. Signup link after the jump!


Let’s say you ran an experiment, and it had a notable result. Win or lose, doesn’t matter: you felt something. Surely it will affect the prioritization of your existing work.

In this paid lesson, we’ll talk about how – and what to do about it.

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#182
March 13, 2025
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WTF

I was recently at dinner with a dear friend who went independent after a decade of working in a consultancy. One day a while back, the consultancy got a new CEO. For their first few months, the CEO would walk around with two notebooks. One was the regular ol’ black notebook that you expect every knowledge worker to have. The other was red, and it had the letters WTF written on the front.

Every time the CEO heard something that sounded absurd or horrible to them, they would put their regular notebook away and write it down in the WTF notebook. As you would expect, being the CEO of a new-to-them company, they rapidly filled the notebook.

I think of this often as a consultant. I am frequently called to be present in WTF situations. Some are obvious, but most are not, or they would have been addressed without me in the room, right? It’s incumbent on me to figure out the real reasons I’m hired, which are frequently subtle, requiring some digging. You ask questions, poke around corners, pull on threads, and find an expensive WTF.

Dan Luu’s immortal, essential “Normalization of deviance”, a URL I have memorized, speaks to this issue:

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#181
March 10, 2025
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How do you address the Big Problem?

There is always a Big Problem. Sometimes the Big Problem is stated; sometimes you must figure it out yourself.

Your goal as a value-based designer is to laser-focus on the Big Problem until it is comprehensively solved. Then, you either find yourself another Big Problem, or you run out of them and show yourself out. In this lesson, we’ll cover some example Big Problems, layout the process for identifying them, and provide next steps.

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#180
February 20, 2025
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Good software is as little software as possible

Our monthly office hours for paid members is today! Join us at 1p Central Time to chat about all things value-based design. Happy to answer any questions or pressing issues you may currently have. Find out what 1p Central Time is in your time zone here. If you’re a paid member, our meeting link is at the end of this email. If you sign up between now and 1p, we’ll send the meeting link your way.


After some current events, it’s come to my attention that some of you might want to know more about my tech stack.

I hold a few key principles in order to remain in right relationship to software:

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#179
February 18, 2025
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Money sent, thanks

There’s a meme in my consulting circles:

$500 client: “I just feel as though with this investment I am about to make in you, that we should understand how our lives are about to change and I need results and you need to bring them, I am entrusting you with our livelihood and lives.”
$50,000 client: “Money sent, thanks”

In this week’s paid lesson, we’ll talk about how to generate more of the latter for you.

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#178
February 13, 2025
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