Saying the quiet part out loud : a missing stair

The only other time I’ve written something like this was 10 years after leaving an abusive relationship, to describe what it was like to try to get over it and how I still carried it with me in some ways. I tried hard to be compassionate to Corey, even then. I’m less interested in being compassionate in this post about Gunner. Corey at least had youth to pin things on, could still possibly change. I have sat down with Gunner to talk to him about all this, and while he didn’t get defensive in the moment, it seems he’s up to his old games still, I’ve offered to meet with him again, and I’m frankly pretty sick of this dead weight on the tech justice space.

I had written a very long-form thing to get all my feels out. Receipts there if you ask me for a password and agree not to share outwards, but it boils down to this: Gunner is pathologically unable to move from ideation space into execution, and does this at very high cost to the marginalized people he surrounds himself with, who have built their prior careers on being able to execute. Gunner has a great nose for potential, and taps into that potential, but then absolutely destroys your potential if you try to realize your dreams around him. He does this while making it your fault. This tendency has slowed (stopped, in some cases) the social justice technology space he is involved with. We no longer have time for this, and so I’m deciding to speak up.

I am confident enough of this that I will buy you dinner, wherever you are, with or without my company, to talk through it if you have hard data to the contrary. This only applies to people of a marginalized identity, not other white dudes or people in a funding position; and must be about executing on something, not just the ideation stage.

This is not a call to cancel someone. This is a call to be cautious about what sorts of ideas you bring to him, and what sorts of work you try to do with him.

The first 30 days

I’ve now been at GoFundMe for 30 days! Hooray! In an act of reestablishing how I like to learn and share, I asked if I could write blog posts about my experiences in learning to manage, and got a thumbs-up. Here’s what I’ve gotten up to!

Setting up support

There are a bunch of lovely folk in my life who I respect who also manage. I have put them into a Signal thread where I can ask questions. Yes, they’re all pretty spicy and I’m worried about the fights that might happen. Yes, also I have slept with all of them. Yes, it’s already proven pretty invaluable.

I also asked explicitly for a mentor at GFM who’s established there and could counter balance what I have blind spots in. I’ve been set up with someone and we’re off to a good start.

Read a fucking book

There’s a lot to read out there (and I’m making my way through a fair amount of it, mostly recommended by an infosec Slack I’m in), but I also wanted a focused book for this time. My brother recommended The First 90 Days and it’s been REALLY good so far. The parts that are useful are really useful, the parts that are less useful are easy to skip over.

So far, I’ve learned to separate out focus areas into political, cultural, and technical things, and to check in with those around me about which lane I should be focused in most. I’ve also learned to think about if folks are better at sustaining or being a hero, and at what stage of a business. This is all helping as I get to know new folks, I can plug them into my little database of people.

Get to know the people

I’m not just paying attention to the folks that report to me, or the people further up in the chain. I’m also getting to know peers near and far. As we talk, I ask each person if there’s anyone else I should be talking to. Sometimes they have someone not already on my list, but often not. I take notes and structure the data so we can start our next conversation in a more advanced place. Plus, it’s way better to say hello to someone BEFORE something is on fire.

Hack my own tendencies

The first while at a new job should be about learning the terrain and people. Learning what not to step in. Learning root causes to what might seem like disparate problems.

Problem is, if I don’t have a thing to do, I will FIND something to do, and that’s not great for this period of onboarding. So I have found a low-stakes project that touches a lot of what I’m getting up to, plus some interactions with nearby teams, in order to give me a thing to focus on while I move more slowly elsewhere. You probably guessed this, but I’m organizing our documentation and starting to come up with a stronger onboarding story.

Start to make a plan

I’ve started laying out where I think we are, and where I think we can get to next. I’m waiting to bring this to my reports until I have it pretty well dialed in and have broad categories in place. I want a strong story to tell. But I am testing bits and pieces for readiness and accuracy in most conversations I’m having, regardless of with who.

I’m excited! This seems to be really promising.

Lying to people about time

I’m not a good liar. I don’t enjoy it, although I seem to be good at it when the need has arisen. Games like Werewolf frankly make me sick to my stomach and I play up how much I don’t want to lie as a mechanic for when I do have to lie in those games. However, in two areas of my life, I lie my ass off: facilitation and program management. But I only lie about one thing in both of these contexts: time.

Most people need to feel a sense of urgency in order to get anything done, and also a sense of spaciousness to really be thoughtful about outcomes. Both of these are necessary to facilitate a good conversation, and both are necessary to help guide a project well. It’s a balance navigated with nuance, intuition, and experience.

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How I think about retrospectives

I believe in self-improving systems, and retrospectives are a core way of reflecting and then changing behavior accordingly. There’s a lot out there on what a retrospective is, formats to use, and other techniques, so I’ll just highlight my facilitation thoughts on them here. This is influenced by the CAST handbook and my own facilitation background.

Must be blame-free / a psychologically safe space

People will not open up and be actually present and interrogative if they don’t feel safe. It is your responsibility when setting up, facilitating, and debriefing to make sure the system is what is being critiqued, not the humans within it. The humans made the best possible choice they could given the circumstances they were in, so let’s change the circumstances in the future. Make this explicit early and often. As Charity says on the sticker on my megaphone, “communicate positive intent.”

A picture of a megaphone focused on a sticker in Lisa Frank obnoxiously bright styling, "communicate positive intent." Additional stickers that are visible are the Priceless Baroot, the edge of a pleading taco emoji, and one that seems to ready "...necessarily a crime."

Must be scoped well

If people don’t know what they’re talking about, they won’t talk about the same thing, and getting to concrete outcomes will become nearly impossible. Focus on a specific project, timeline, or outcome. Communicate this early and often.

Should encourage creative thinking

Whatever format you pick should be mildly novel (not so novel that it disrupts how people approach things, but novel enough to edge them out of their comfort zone). Use a different prompt set or a different tool, but rarely both at the same time. Ask more of people to engage and challenge them into someplace new.

Needs to lead to concrete, actionable tweaks

If you don’t arrive at experiments that will change how you’re behaving, you have wasted everyone’s time. I like to set aside about 1/4 of the time of the retro to listing, refining, and then selecting one or two these experiments. I ask the following questions:

  • What will change if we take this action?
  • What would prevent us from making the change?
  • How will we know if we’re successful or not?
  • When should we check back?
  • What is our next step, and who is responsible for it?

I only pick up 1-3 concrete steps to take after each retro. I track them just like any project, and I report back on them before the next retro to show that the time and vulnerability is worth it.

One goal should be building trust with the team

A core part of the system is team trust, and in improving the system, we should be focused on building that part of it. By being blame free, enacting suggestions, and pushing people to engage more, we build that trust. If something about the retro process is eroding trust, pause and reassess your approach.

Historical income

So I found some of my old tax documents and figured I’d map what the income trajectory has been like for me since I started working at 16. I often held 2-3 jobs at a time before moving into a nonprofit career, before deciding I was tired of the constant stress of paying rent and moved to the private sector.

Chart of income over time, boxed out for what was going on in life at certain points. Boiled-down summary follows in blog post.


Moving to full time work with an undergrad degree 3-4x’d my income.
Moving from jobs to a career tripled it.
Moving to the private sector doubled that again.
Leveling up to senior increased by about 50%.

The job hunt

So I’ve just signed to start in mid-December as the manager of the AppSec team at a well-known platform. I’m REALLY excited for this for many reasons I’ll get into after I’ve actually started and it feels real. I’m really excited to be able to talk about this part of my life again.

I’ll do a separate post about how I structured my consulting because that’s it own fun setup, but I wanted to take a moment here to talk about how grueling the job hunt is right now and to offer some scaffolding, because being intentional about things is how I stay sane when in a chaotic situation.

This is long because I have a lot to say on keeping track, experiments in approach, and what actually worked this time.

Resources mentioned in here:

  1. Job hunt tracking spreadsheet
  2. Sankey HTML file and associated page/image
  3. Financial burn-down spreadsheet
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Dimming my own light

I’ve always enjoyed being under the influence. Whether alcohol or more illicit things, I usually have a good time, even when the times aren’t particularly good.

This is absolutely not a “drugs are bad” post. I still enjoy drugs (including alcohol), in the right context. More research is being done on the usefulness of drugs ranging from run-of-the-mill THC to ketamine to hallucinogens. No, this post is about why I used a specific drug to dim my own light (by which I mean “exercising my mind and expecting great things from other people exercising theirs”), where it got me to, and where I’m at now.

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Distributed playbook

While I was at Truss, I helped move us from a dozen people in the Bay Area to nearly a hundred across 20 states. Through monthly meetings to run experiments in improving our practices, we came up with the Distributed Playbook. It’s since changed format enough that I missed the original version, so I’ve ported it over from Github to a page on this blog. It, along with the onboarding guide, are two of the things of which I’m most proud from my time at Truss. Hope they can help you out, too!

Onboarding documentation the most important documentation

Originally posted on the Truss blog

Most of us rely on documentation in one way or another. In this blog post, we attempt to make the following points:

  1. Most documentation should be treated as if it is onboarding someone to an organization, project, process, etc.
  2. Involving multiple people of different practice areas increases the quality and context of the documentation.
  3. Documentation can help a growing/large organization stay in sync with itself.
  4. Truss’s onboarding documentation is great and you should check it out.

Onboarding documentation is the most important documentation

“Documentation” is the media object (text, video, images, etc) which explains how to do something. Docs can take the form of descriptive policy, READMEs, How-Tos, welcoming, etc. 

Documentation is nearly always worth having, but if you only have time to get one piece of documentation in place, it should be made on the assumption it’s being used to onboard someone to the project, organization, process, etc to which it relates. A person rarely looks at the whole project, organization, process, etc as a whole as that is overwhelming. They instead look for signposts that provide context and support in understanding the system they’re about to interact with. 

When I got started at Truss long long ago in 2017, we had an onboarding manager checklist but no real guidance for the new Trussel outside of that human contact. Ari, who at the time was doing onboarding (and is now an engineer), is an incredibly high-touch, welcoming human. However, if she or another person helping with the process had a more pressing thing to be doing (which was often the case at a suddenly and rapidly growing consultancy), a new Trussel would stall out and be left in a sea of tasks, new tools, and new people, with a sense of “what even do I do?” And when one doesn’t have a clear path forward, one can feel useless, which is not a good feeling when you’re just getting started somewhere and want to prove your worth.

This was because we had documentation about how things worked, but not from the perspective of the person being onboarded to the organization. If we were to get this in place, a new Trussel would feel more welcomed and solid in their footing.

Luckily(?) I compulsively document things. So as I learned about bits and pieces of the organization, I wrote down in one place what others should also expect as they came in. Oh, we do have a document about PTO? Link it up and give a quick summary. We don’t have one on role definition? Could I help make one? I tried to set it up so when something was unclear or incorrect in the docs, a new person would feel safe enough to ask questions and empowered enough to edit the docs when they learned the answer. This generated a surprisingly long document which was complete enough, but also incredibly overwhelming.

Pouring the firehose into drinkable cups

Documentation takes a bunch of different people of different practices to make it good. Sharing the load also makes creating and maintaining the docs a lighter lift and a shared source of truth and object worth maintaining together.

Our document was way too burdensome, so we called on our design content strategists James and Kaleigh, who suggested it be reformatted into phases of onboarding time. Delivery Manager Amy tried this format out first on her project, and then I expanded it into the MilMove project. When it stuck well enough, we did a card sorting exercise for who wanted to know about which parts of our operations, and when it made sense to learn about them. We also started linking out to external documents when a section got too long or convoluted. This allows people to focus on the big picture, and dive in deeper when something is relevant to them. Then we took our honking document and rearranged it and edited it down to a mere 28 pages.

Just as people had started asking to have new policy or reference docs put into the emerging guide, everyone also helped edit for clarity. It became a thing for more folk to reference and make use of. And just as Nelz, Jeri, Andrew (all engineers), and Mallory (designer) have held my hand in multiple ways to migrate the Guide from a Google Doc to GitHub Pages, many other folk have also refined the Guide to make it what it is. Including our general counsel Burstein writing the best damn disclaimer you ever did see and otherwise making sure we’re not just witty but also reasonable legally.

We have all done this in the spirit of being a warm, welcoming place for new Trussels. All those folk named here (and those I have forgotten 💔) have demonstrated our values in order to make it an easier transition for others to also represent those values.

If you are working on onboarding documents, call in help! Ask tenured folk to verify knowledge is represented, newer folk that it’s clear, content specialists to review structure, etc. 

Being able to document something requires understanding it

Growing and large organizations are often accused of “the left hand not knowing what the right is doing.” This has to do with the functions of the different hands not being clear to the other. Enter (you guessed it): onboarding documentation! By describing how different components of a system work, the system itself has opportunities to become more aligned.

One thing that came up time and time again as we worked on the Trussels’ Guide were points of inconsistency or lack of clarity around internal workings. As we grew from 14 to 90 Trussels during the development of the Guide, our processes were also scaling. We became more robust and more formal. But importantly, we always did so with an eye to being comprehensible to an incoming Trussel. Docs shouldn’t only be intelligible in the context of the whole — each should stand on its own in a meaningful way. While most Trussels can’t (and shouldn’t have to) know about every tiny detail of how the business operates, they should be able to look up the details and/or who to ask if they start to care.

As an aside, there’s also this great piece about how you can’t fix a product (or a process) by having good words. The thing you’re describing has to be good, too.

Documenting can surface where things are out of alignment and provide a route to bringing them back into sync with each other. This is important for your organization, project, or process to be functional within the context of itself and the larger systems of which it is part.

A quick how-to

What’s worth documenting? I start documenting when roughly three people ask me the same sort of question. Rather than respond to each separately, I 

  1. try to write it down with the first’s help, 
  2. talk through it with the second, and 
  3. ask the third to try to self-serve with the document created. 

This allows emergent areas of interest, guided by our new Trussels, to determine some of the aspects of the business we next define more clearly. 

We’re proud of how we do things at Truss and want to share them

So now we are ready, dear reader, to show you how we work at Truss and, as importantly, how we talk about how we work. And so I introduce to you the Trussels’ Guide to Truss. In it are the ways we are kind to each other, how the business functions, some of the decisions we’ve made, and how we embed assumptions into our work.

We hope you’ll have a look, take what works for you, leave what doesn’t, and continue to engage in the conversation of how to build great businesses together. Also, if this seems like the place for you, we’re hiring!