Author: Brendon

Using AI skill files to review bylaws

I’m in conversation with an Oregon nonprofit about senior leadership role, and part of my preparation was reading their bylaws. They were in good shape: recently revised, thorough, and clearly written by a board that takes governance seriously. They also included requirements tied to a specialized program area I don’t know well.

I’ve reviewed bylaws the old way. It takes a highlighter, extra coffee, and a growing suspicion that Article VII contradicts Article IV. This time I tried something I’ve been recommending to other people. I downloaded the Bylaws & Policy skill from the Nonprofit AI Skill Library and attached it to a Perplexity request along with the bylaws, which the organization posts publicly on its website. Then I typed “Review the attached bylaws using this skill.” That was the whole prompt.

Five and a half minutes and about $1.42 in credits later, I had a list of about half a dozen places where the bylaws appear to conflict with state or federal requirements. They were sorted into tier one conflicts with Oregon law and tier two specialty compliance gaps. It isn’t a legal opinion, and the skill is marked “expert required” for a reason. It’s still a much better starting list for a conversation with counsel than anything my highlighter ever gave me. If I end up in that role, I’ll bring the list and we’ll start there.

A skill file is a plain text document that gives an AI agent the frameworks, steps, and common mistakes for a specific kind of work. With the right one(s) attached, it’s like having a skilled paraprofessional next to you who has done this particular task many times. I think nonprofit leaders should learn to use them, and I built the library partly to make that easier. It’s free and open source, with 102 skills covering governance, finance, fundraising, programs, and more.

If you’re on a board or run an organization, take your own bylaws and run the same check. It costs about as much as a vending machine snack, and it’s a lot more useful.

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Announcing Nonprofit-Skills.ai

My new project launched today, and I’m quite proud! I don’t know how long skill files will be relevant but this was a fun learning experience and I hope it can be a useful addition to the nonprofit community. There are 11 categories and 63 distinct skill files. I hope the community extends the project.

The quick explainer is that it’s a bunch of Markdown files meant to be used with your AI agent of choice to help nonprofit leaders make better decisions. The files are hosted on GitHub which will allow very transparent and public version history. I have been creating and using skills with my AI agent of choice, currently Perplexity, and I recently ran across Anil Dash’s better-documents skill. I used that in some writing stacks to good effect. Later, I ran into Corey Haines’ collection of marketing skills and was inspired to create this project.

I learned a lot while doing this! I’d browsed GitHub in the past but I’m not a developer and really had no need for it. Microsoft and Google are the heavy hitters in the nonprofit space and their document creation and editing tools have version history, which was always what I thought was GitHub’s main selling point. Anyway, learning GitHub was super interesting for me. I also learned a lot about the development of skills.md files, Markdown, and website development.

Right now my plan is just to release this to the world, but I am also considering how I might leverage the project to extend my impact in the nonprofit community.

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Backcountry progress

Last year (’22-’23 season) I invested in a splitboard, skins, bindings and boots. I hadn’t been snowboarding for a few years because I found resort crowds and expense increasingly annoying. I started heading up easy local trails with the splitboard to get accustomed to the mechanics and cadence of transitioning from uphill to downhill modes. I loved that I could just wander anywhere in the snow.

This year I invested in the education of a Mazamas backcountry touring class and it was a huge boost to my knowledge and experience. I’ve got better avalanche awareness and I’m making informed decisions in the backcountry. I also found some new adventure friends which is pretty nice too.

Today I planned a trip to ride the Lower White River Bowl, which is a couple of miles up the White River Canyon on Mt. Hood. I’d done the approach once before with the Mazamas class, so it felt familiar. I was surprised that we were the first tracks after a couple of days of snow. The conditions on the run were a little soft since it’d been in direct sun all morning, but still fun riding!

Our trip was about 3.5 hours car to car, 1,400′ of elevation gain, and 4.7 miles round trip. It was a quick one, but definitely built some confidence. I’m looking forward to many more years of doing this.

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Calling in thanks

Recently I participated in a “thank a thon”, where I called a list of donors to thank them for their gifts of time and money during the past year. This is a common tradition among nonprofit organizations. I was provided a template script for live calls and for voicemail messages. Both scripts seemed to hit the right notes of gratitude but for some reason I had difficulty with them. I knew I just needed to lend my own words to the basics of the script but it felt forced. I was better by the last call, but I can’t say I felt proud of any of the calls I made.

Having a little time off for the holidays I found myself reflecting again on my discomfort with those calls. In an attempt to release my mind from the recursive discomfort, I considered what I would have said if I’d taken the time to think through my own version of those scripts. I don’t have a story about how affordable housing made a difference in my life. I was briefly a renter as a young adult, but otherwise was raised in homes my parents owned, and I’ve owned four of my own. I have been literally sheltered by privilege.

I am truly grateful to participate in the building of a healthy society. That’s how I think of my work. Every effort matters, every effort moves us closer to completing the next home. Big dollar donors are participating in the effort, folks who volunteer their time and labor with us are participating in the effort, even the person who donates their old screwdriver to one of our retail stores is participating in the effort. I am grateful for all of them.

Our donors fund community building. When donors support efforts to create affordable housing, they are actively backing communities that foster stability, well-being, and opportunities for all. Healthy communities are foundational for healthy societies. This is work to be proud of.

Our donors fund generational impact. Safe and affordable housing is directly correlated with social benefits that are almost too many to number. Reduced trauma over housing insecurity, reduced exposure to environmental hazards, academic performance improves, graduation rates rise, greater resilience to disasters, reduced homelessness, and on and on. It really is the basic stuff that shows how a civil society cares for its citizens.

Our donors fund generational wealth building. The homes we build are permanently affordable, meaning each time the home is sold the price will always be affordable to an average income buyer. And each owner benefits from home equity and market growth when they sell. These opportunities can reverberate through generations of a family. Donor support helps make that possible.

I know it’s unlikely that any of the folks on my call list will read this post, but it’s a reminder to me at least that as difficult and frustrating as the work can get, I am forever grateful to be doing it.

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Nondual leadership

2021-03-22 update: After a lot of contemplation about this post, I believe there is nothing special about ‘nondual leadership’. The idea of nondualism, in my mind anyway, can too often be a distraction from the present moment. Which is ironic since the concept of nondualism is a pointer to the idea that there is no separation between self and experience. It can become a distraction when the focus is on the concept rather than the direct experience. Leaders should be rooted in the present moment, and not distracted by whether they are sufficiently grounded in nondual practice, process, or feelings. My interest in nondualism led me to recognise that the present moment is all that is available to us. The present moment cannot be improved upon, it simply is. We may not like what we are experiencing in the present moment, but it cannot be different. We may decide that we want different outcomes in the future, and that’s great. It just doesn’t change what is right now. Coming to this understanding was helped along by a book called The Ten Thousand Things, by Robert Salzman.

As part of my commitment to cultivating a deeper practice of meditation, I have been investigating and learning about nondualism. Nondualism, in a nutshell (and to my layman’s understanding), is the state of consciousness that recognizes no edges to experience. The concept of subject/object loses meaning; all is one.

There is a recognition among nondualists that at some level one must continue to attend to the perceived world, and not simply bathe in transcendental understanding. I suspect there is also an understanding that interaction with the perceived world is necessarily influenced by nondual knowledge. Put simply, when you find no edges to experience and all is one, it is a natural extension to care for others (because they are not actually “other”, but only the continuation of what can be called Experience (as opposed to lower case experience)). Other names I have seen for this include Consciousness, Witnessing Awareness, Awareness, and Nature.

As I learned more, I have become increasingly interested in how nondual awareness might influence the practice of leadership, mine in particular. One difficulty with this line of questioning is that nondual awareness itself implies no value system; it is simply witness to experience (or, when concepts sufficiently collapse, simply Experience). This state of valuelessness may worry critics who foresee anarchy and chaos on the (nondual) horizon. I strongly suspect benign neglect is more likely. Anarchy requires a value system.

Less experienced nondual leaders may, ironically, have two distinct experiences of the world. One is the transcendental experience of witnessing the dissolution of the border between self and world. The other is the world as the nondual leader has been historically conditioned to experience. Assuming continued inquiry into nondual awareness, I assume this condition is temporary and eventually collapses into a singular Experience. In this singular Experience the nondual leader is able to behave in the perceived world with great fidelity toward nondual awareness.

My curiosity revolves around whether expressions of nondual leadership take on a particular cast or bend in a particular arc. As mentioned above, I suspect the policy outcomes of nondual leadership will generally avoid expressions of “isms” and will tend to share power if not outright decentralize it.

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Wisdom

Wisdom too often never comes, and so one ought not to reject it merely because it comes late.

—Justice Felix Frankfurter

I read this quote recently and it struck a nerve. Over the last few months my eyes have been opened to what it means to be a white man in America. Having been a white man in America for decades now, this seems like an odd realization. I am a natural navel-gazer, and I’ve spent a lot of time mining the depths of my own mind and psyche. I haven’t spent a lot of time understanding where I fit in society. I read widely, so I certainly had heard of “white privilege” prior to doing the deep work with diversity, equity, and inclusion.

Like many white guys, the first time I heard the phrase I mentally recoiled. Who was telling me I had privilege? How dare they paint me with such a broad brush! What did they know about my life, my troubles, my struggles? And besides, how could someone be anti-racist while racializing something like privilege? Wasn’t that hypocrisy? WTF!

Over time I learned the true meaning of white privilege, but it remained an abstract intellectual concept. It wasn’t until I was able to see and internalize the ways in which society blocks progress for people of color, and for black men in particular, that I began to understand what it means to be a white man in America.

I suppose once white people begin to have a recognition of their privilege, they have some choices about what to do with that knowledge: engage with it and try to reshape spheres of influence; shove it way down deep and pretend you still don’t know any better; embrace the privilege and the inherent racism that accompanies it. And it is important to note here that only white people get these choices—another privilege. 

Back to the original quote because I don’t want to make this post too long. DEI wisdom is arriving late for me, and I do not reject it.

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Why we start with race

Our organization has been engaged with training around diversity, equity, and inclusion (DEI) for several months. As C.O.O., I’m the person who got the ball rolling, though this goal was present on our 5 year plan prior to my arrival at the organization.

Though I have always had an interest in equality and inclusion, I had not had much education or training around it. These past few months have been nothing short of transformational for me. I believe the work we are doing will also be transformational for our organization, though that will take more time.

One of the fundamental ideas that I’ve learned is that DEI (or EDI if you prefer) begins with race. We begin with race because that work can be leveraged to impact other marginalized identities, commonly referred to as “intersectionality”.

Speaking from my own experience, beginning with race helped me see the world around me with fresh eyes. This education has made me feel embarrassed by my own previous assumptions, and humbled to learn a new way of viewing society in general, and my own privilege in particular.

I am convinced that a deep understanding of diversity, equity, and inclusion is a non-negotiable leadership competency. Leaders must be educated in this work, and must maintain that education. Whatever a leader’s speciality—finance, m&a, HR, IT, whatever—their work must not only acknowledge the importance of DEI, but must center on it.

Centering our work on DEI does not necessarily mean we become trainers, though that role may make sense for some. It means that we are able to articulate organizational strategy in ways that expose, interrupt, and sidestep the currents of white supremacy in our organizations, and in the culture at large.

I feel strongly that leaders who understand DEI are obligated to work only with organizations that also demonstrate an understanding of the importance of interrupting inequitable cultures. Do not join organizations, as employees, board members, or volunteers, if the organizations do not clearly demonstrate a commitment to racial equity.

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Convenience vs privacy

I am not an expert in either convenience nor privacy. But I do read about such things, and I have an Amazon Echo Dot in the kitchen. Mostly it’s a fancy voice activated tea timer. And we recently got a smart plug so we can tell Alexa to turn off the Christmas tree without being bothered to bend over and unplug the thing. I feel surprisingly powerful when I make the Christmas tree lights turn off and on with just my voice.

I am certain that Amazon collects the voice snippets I direct at Alexa. I’m convinced (a very different standard from ‘certain’) that Amazon collects everything else I say, regardless of whether it is preceded by the ‘Alexa’ keyword. Nothing weird has happened at our house, I’ve just read enough reports of weird things, and reports from terminated Amazon contractors. Also, if Amazon could gather that data and parse it in a meaningful way to help nudge your buying patterns on their website, I assume they would certainly assess the risk of getting caught against the value of the activity.

Anyway, I guess I let ‘em listen in. Turning off the Christmas tree with just my voice is apparently worth it.

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More (time, distance, resistance)

The last post was about how I’ve lost weight by tracking calories. I’ve also been paying attention to how much I move each day. I have a tendency to jump into a routine and go too hard, which makes me really sore and provides a convenient excuse to stop doing the thing. It’s a dumb cycle that took too long to identify.

Anyway, these days I’m walking the dog. Literally. I wake up at 5am and have a quick self-talk in the vein of Marcus:

“At dawn, when you have trouble getting out of bed, tell yourself: “I have to go to work — as a human being. What do I have to complain of, if I’m going to do what I was born for — the things I was brought into the world to do? Or is this what I was created for? To huddle under the blankets and stay warm?”

Marcus Aurelius, Meditations

I’ve got a backpack1 that I use for pretty much everything, and once I finally roll out of bed I dump out the iPad and keyboard and throw in a 45lb2 plate. I take the dog for a 3 mile walk with the backpack. Takes about 55 minutes which, for me, equals about 6,500 steps. Since I’m a sedentary office drone and I don’t move much once I’m at work, this is a great way to get some movement and steps. I usually end up with somewhere north of 9k steps each day.

Generally speaking, our human bodies seem to adapt well to whatever we throw at them. In my case, just walking the dog, even with a weighted backpack, eventually becomes the new normal. When that happens, or to delay that adaptation, I try to mix up my walking approach with changes to time, distance, and resistance. I’ll try to walk the usual route a little faster, adding in some jogging. I’ll try a longer route, but throw the weighted pack on my back. That kind of stuff. I don’t plan it out, but I do try to get more time/distance on the weekends.

1. I use a 26L GR1 from GoRuck. They are expensive, though I got mine on eBay for a decent discount. These bags are bombproof, so there should be no hesitation buying a used one. For the last 18 months or so, I‘ve used mine daily, with 45lbs in it, and it’s in great shape. If it ever blows out can’t be repaired, I’ll get another one. GoRuck stands behind their gear, so if it ever does blow out I’ll send it to them first to see if it can be repaired. ↩

2. I got a 45lb plate on Amazon instead of directly from GoRuck. GoRuck’s manufacturing process is compelling though. For me, there wasn’t enough of a distinction between the American-made plates and the plates from who-knows-where to justify the difference in price. They both just get shoved in the backpack. ↩

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One way to lose weight

There are lots of ways to lose weight. I recently dropped 30 pounds over the course of about 4 months. I started by trying Noom, but the whole model around Noom is very high-touch, and that annoyed me. I just wanted to suffer silently and alone. I switched over to LoseIt and did.

LoseIt pretty much leaves you alone to do what you need to do. At its core, it’s just calorie counter and has a very good database of food. It is easy to add your own food as well. It also has a low-key goals function that I found helpful. I set my goal weight and told the app how fast I wanted to go (1lb/week). After that it’s just a matter of tracking everything you eat.

I can get a little obsessive with details on things like this, but this time I just wanted to keep everything casual. If the food database didn’t have the exact thing I just ate, I’d throw in whatever seemed closest and I always leaned toward the database item that had more calories that I figured I’d eaten. I also tried to come in below my calories for the day, and was mostly successful with that. On the few days I came in over budget, I just accepted the day and did better the next day.

I did not intentionally change the stuff I ate. No keto, no low/slow carb, no weird fasting schedule. I did notice that by only tracking calories, I naturally adjusted the food I was eating in order to feel full longer. That means I ate more salads, not because of some plan, but because they were low calorie and made my stomach feel satisfied. I usually just have coffee with cream for breakfast, a salad from 7-Eleven, and whatever dinner the family was eating that night. Also beer.

Another thing I like about LoseIt is that it connects to other services pretty well. I use a Garmin watch which tracks my movement, and LoseIt is able to pull in that data and adjust my daily caloric goals. It also connects to my WiFi scale and pulls in my morning weigh-in to track progress against the goal. I don’t do much more than step on the scale and input my food.

I do try to move my body during the day, and I have some specific routines and gear that I use. I’ll save that detail for another post.

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