Tips on Running an AI Hackathon

~ Sasha ~ Leave a comment

Last Friday we hosted an AI Hackathon at 60 Decibels, and it was a roaring success. In case you want to borrow the idea, here’s a look into how we did it.

First, the why: getting our team to go from asking questions of AI tools to getting these tools to solve real problems and do real work for them. My impression is that 80%+ of our team (including me) were in the first camp, and our goal was to jumpstart getting 80%+ of our team in the second camp faster.

We knew from experience that what matters is doing, not talking or reading or watching.

We laid out dedicated time for this: a half day starting AM, with three different groups to account for time zones (India / Kenya + Europe / Americas). Each region had a leader, who was someone who had more experience with AI tools and could serve as an internal expert / troubleshooter / problem-solver, as well as a second facilitator. Each team worked together, on Zoom.

The logistics were important. Here were some elements we put in place:

  • Dedicated time per regional team
  • Crowdsourcing ideas of things to work on in advance (Google sheet) — anyone can add
  • Advance sign-up to confirm participation (Google sheet), and confirmation if people wanted to work alone or in a group
  • Zoom call for each of the regional teams, with a everyone in the same room for the introduction and ‘idea pitch’, then breakout rooms for each team. The ‘experts’ were always accessible to answer questions during the session in the main Zoom room.
  • We set up a dedicated private Slack channel for the planning group (~8 people), about a week before the Hackaton, and repurposed another public AI channel for all other comms and day-of communication
  • We got IT issues / logins sorted in advance: made sure we had enough pro accounts across the tools we wanted to use (primarily Claude); confirmed logins available to these tools; confirmed that a person in each region had the admin access to buy more tokens if we ran out / access to extra accounts if something went sideways.
  • Worked with our IT support to pre-load whatever apps we needed onto people’s laptops before the Hackaton (again, primarily Claude), because many people don’t have admin rights to download new software
  • (aside: a few folks did get ground to a halt on the Claude Cowork installation on PCs the day of…I assume Claude will work this out shortly)
  • Reminded our teams in advance of our safe use policy for all tools

We created and shared a document with background reading—definitely the sort of thing AI can create for you. It covered everything (agenda, safe use policy, ‘What is AI really?’, Choosing the Right AI Tool(s), How to Talk to AI, Agentic AI for Beginners, Suggested Reading). The suggested pre-reading / watching was:

In terms of what happened, the team did incredible things.

  • They generated 58 ideas of meaningful business problems to work on, and worked on 20+ of these across three time zones.
  • These were big and small—many at the core of some of the most difficult problems we have as a business, some much smaller, nagging issues that bug just one person.

Best of all was seeing the energy and the enthusiasm of the team, people jumping in to help each other, people feeling empowered to tackle issues themselves or in teams. We’re definitely going to do it again!

The Global Majority Data Project

~ Sasha ~ Leave a comment

I’ve been quietly working on an idea that I’m very excited about. It’s an initiative that will bring more of 60 Decibels data to life and will make this data—and the lived experience of the people it represents—more useful to more people.

The basic concept is that AI is being trained on data from a narrow slice of humanity. The voices of billions are missing.

This initiative, called The Global Majority Data Project, will build the infrastructure to make the lived experiences of the world’s most underserved communities both vivid and accessible, so that these experience can influence how decisions are made.

I’m in the early stages of fundraising for this work, and I’ve been talking about it with folks I know in the AI for good space.

After a few great conversations last week, the thought occurred to me: a nice website for this initiative would help move it forward.

But who has time to build a website? Certainly not me (time, or know-how).

And then I thought about the AI Hackathon we’re doing this Friday at 60 Decibels and realized it was time to eat my own cooking.

I had the idea for the website at the end of the day on Friday.

On Saturday, I sat down at noon with Claude CoWork.

At 3pm the site was live.

This is a massive step change in leverage for me (and it could be for you).

What I had on hand at noon was a whitepaper describing the project and existing branding from 60 Decibels.

Three hours of conversation with Claude (including a decent amount of waiting, because it was ‘thinking,’ so I cleaned up the kitchen) to make a high-quality website.

Think of what else it can do.

For those of you who have been using these tools, this is not a surprising outcome. For those who haven’t, I hope this serves as a concrete example of what is now possible.

Normally I’d end the post here, but I thought some specificity would help.

If you’d like to read on, here’s a detailed summary of what I told Claude and how the whole process unfolded.

I hope you’ll take this as inspiration to go build something meaningful.

And if you have ideas for folks who might want to make this idea come to life, please send them my way! (the contact form is on the website).

My Claude Prompts to build globalmajoritydata.com

  1. My initial prompt

OK I want your help building a website to support the Global Majority Data Project. Here’s the white paper that it is based on.

I already have a company – 60 decibels – so I don’t need this to be a new company,

it is an initiative of 60 decibels. I am raising money for this and want to see if I can make a decent website easily. Ultimately I expect that if it’s good, the pages will move to the 60decibels.com domain, but I just purchased globalmajoritydata.com on GoDaddy.

So what I want to do is:

  1. I’ll share the brief
  2. I’ll share a few websites that look like what I’m interested in – obviously the branding should mostly align with 60 decibels
  3. I want you to give me some options for how to approach this, ask questions, etc…I don’t want you doing too much work building until we are aligned on how it’s going to be structured and what it will look like
  4. I’ll want you to create the structure of the site and the draft copy for me to approve
  5. Once that’s sorted, we’ll work on look and feel
  6. Then you’ll do the homepage
  7. Finally, you’ll do the rest of the site

How does that sound?

Any questions?

  1. Claude asked two rounds of clarifying questions—tone, structure, site size, audience, etc.—which I answered. I also uploaded my existing Global Majority Data Project whitepaper.
  2. I had to fiddle with the Chrome for Claude extension, which wasn’t behaving. Claude suggested skipping it; I insisted we fix it. We did.
  3. With Step 1 done, Claude asked for reference sites (Step 2). I shared a few. It reflected back what it inferred from them and proposed two structures: single long scroll or multi-page.
  4. I reacted to the structure, added a missing page, and outlined what it should contain.
  5. Claude drafted full-site copy, page by page. I reviewed it, gave specific comments, and it incorporated them.
  6. It asked for images. I found ~30 from internal documents and from various 60dB published assets and uploaded them.
  7. It produced a first draft of the site. Some of it was jaw-droppingly ugly. I gave pointed feedback. We went ~4 rounds on design, then I did smaller copy tweaks.
  8. The site was nearly ready. Claude generated HTML pages for browser preview with no images. It said mine were too low-res, so I bundled them into a PPT and re-uploaded.
  9. A few more rounds of feedback about the images on the site: adding variety, eliminating repetition, tightening a few style choices.
  10. (Fun moment.) I said, “Looks great, let’s publish.” Claude replied, “You’ve flagged a style issue three times that I haven’t fixed. Want me to try another approach?” I said yes.
  11. I asked how to publish. It gave instructions, which I followed. I was mostly lost at this step, but it walked me through them (with me pasting a bunch of screen shots and saying, ‘what does this mean’?). I had a handful of DNS issues that took some time to resolve.

And that was that. The site is live. Pretty cool, huh?

 

Turning the Corner on AI

~ Sasha ~ 1 Comment

The context for AI has changed.

If you haven’t yet, I’d encourage you to read Something Big is Happening, by Matt Schumer.

It clearly explains the AI revolution taking place right in front of us. Here’s how the essay starts:

Think back to February 2020.

If you were paying close attention, you might have noticed a few people talking about a virus spreading overseas. But most of us weren’t paying close attention. The stock market was doing great, your kids were in school, you were going to restaurants and shaking hands and planning trips. If someone told you they were stockpiling toilet paper you would have thought they’d been spending too much time on a weird corner of the internet. Then, over the course of about three weeks, the entire world changed. Your office closed, your kids came home, and life rearranged itself into something you wouldn’t have believed if you’d described it to yourself a month earlier.

I think we’re in the “this seems overblown” phase of something much, much bigger than Covid.

Once you read that, I’d encourage you to look at this webinar announcing Claude CoPilot (40 mins full speed—but you can get through it in ~15 if you really want to).

It starts with this statement (paraphrasing): “most people are using AI to ask questions; the people who are going to stand out are the ones who get it to do things.”

I am in the category of “good at using AI to ask questions, but I don’t use AI to do things.” That’s not where I want to be so I’m going to make a new, more concerted effort to cross the next chasm—and we’re holding an AI Hackathon at 60 Decibels next week to jump start our next phase of usage of these tools. According Boris Cherny at Anthropic (from the webinar), he has CoPilot doing his project management for him, and he used it to unsubscribe from a ton of services he wasn’t using. (I appreciated the honesty of his top two use cases).

AI isn’t going anywhere. If you sit near anyone whose job used to be writing code, you know that they’ve mostly stopped writing code and are now having AI tools do that work for them. Their leverage is 2-10x (and increasing).

That’s where we all could be.

And, as they say, the best time to jump in was 5 years ago, but the next best time is today.

(friendly reminder: for all of these tools, you want the paid version. It makes all the difference).

The Problem with AI Writing

~ Sasha ~ Leave a comment

“Writing and reading is a way of underscoring that human connection is important. That you can know my mind and I can know your mind — which is a vastly consoling idea…So may times in my life, I felt a more articulate version of myself emerge after a period of writing. And when that happens, the world changes.”

– George Saunders, author of 13 books and a recipient of the National Book Foundation’s medal for Distinguished Contribution to American Letters

George Saunders, author of Lincon in the Bardo and many other works, is an acclaimed author and essayist who has also been called “the ultimate teacher of kindness and of craft.”

I’ve been casting about for an explanation of what’s worrying me when I read more and more AI-generated content. Saunders’ explanation—you can listen the whole conversation here—gets to the heart of the matter.

The question is: what is writing, really? And Saunders’ answer is anchored in the idea of two people knowing each others’ minds, and the beauty in that connection.

That’s the thing that’s tripping me up with all the AI-generated writing, a doubly confusing experience I’m also finding my own AI helper(s) to be radically useful: as brainstorming partners, as “I think this thing isn’t quite right, but I’m not sure how to make it better,” as a project planners… but very rarely as a writer, and never as a writer of this blog.

Like George Saunders, I’m writing for two reasons: to figure something out (a sharpening of my understanding that comes from sitting with and articulating an idea), and to personally connect with readers.

And something breaks when I’m not the person writing the words, and when I’m reading words not written by a person.

I’m sure you’re having this experience as often as I am: working your way through an article or an email or some other document, and you come across a sentence or a phrase that is so stylistically ChatGPT that you stop…and in that moment, feel a strong sense of disconnection.

For example, I was reading this interesting post about searching job listings and pay rates to understand what skills AI firms are paying for to feed their models (answer: “the bottleneck for AI is no longer information (facts); it is expert reasoning (process).) While the research and the conclusions in the article are interesting, the writing is so clearly authored by ChatGPT that I quickly disengaged.

The reason for that disengagement Saunders’ severing of human connection.

It’s as if there’s an implicit equation that I’m carrying around in my head, something about balancing:

The author’s effort in getting the words just right =  My effort as a reader to sit with and deeply understand what the author is saying.

Because when the author cares enough to toil over every word, that means that they are carrying around an idea that matters deeply to them.

If the author truly cared, if the author takes the work personally, then I do too.

(aside: if I’m reading something equivalent to a textbook. If I just am acquiring knowledge or skills, I’m fine with the computer writing most of that text).

Whereas, if my effort in deciphering a 1,000 word post is greater than what it took the author to create it…something feels fundamentally off. I feel like I’m being had, that that essay is part of the mountain of words generated by a computer model that doesn’t mean much, really, to the person who “wrote” it.

What’s curious is that the models will get better and this moment will pass. What happens when it’s impossible to tell the difference?

I don’t know how to answer that with confidence, but I’ll stand by my view that I’m reading because I want to see through a window into the mind of another person—whether it’s fiction or nonfiction, analysis or some fantastical world.

The intent and the human behind the words are the reason writing comes alive. It isn’t just words on a page, it is the effort, struggle and care of one person opening up their mind and heart. That’s why I’ve rewritten this post four times in 12 hours 🙂

We write what we believe, what we care about, what we’ve thought about, and then we share that with others. The connection is personal, the words are the medium.

The moment that connection is severed, I find it much harder to show up as a reader with my full attention.

Fast, Intentional, and Grounded

~ Sasha ~ 1 Comment

I keep on thinking about the question Abby posed last week: how do we move quickly without rushing?

The dilemma, and the assumptions behind it, can be illustrated like this:

We all know the Fast and Rushing quadrant well.

It’s a version of “OMG I have SO much homework…” “No I have SO MUCH HOMEWORK!” that surfaced sometime in school. Busy becomes a way of life, and we get hooked on the buzzing tension. That rushing, frantic feeling can accompany getting a lot done. But often, we start to unconsciously equate fast with frenzy, and it’s no surprise that we often end up at a breaking point.

Ironically, it’s also possible to take that same energy into the “slow” quadrant: fear takes hold of us, and we cannot face reality. The tasks we are able to  accomplish pale in comparison to everything that needs to be done, so we do less. Yet we still find ourselves expending a tremendous amount of energy on worry and fear. We are paralyzed.

That, to me, is the main difference between the top and bottom half of this graph: not the amount we get done, but the amount of mental energy we spend cycling through worry.

We know how it feels to end up in this place: no matter how much we accomplished, it’s feels impossible to truly stop at the end of the day.

We can’t stop our minds from churning even when we’ve closed the laptop.

We’ve gotten on such a stimulation high—maybe, even, from crushing it all day—that we spend the rest of the night stimulating ourselves more, scrolling or finding other ways to get a dopamine hit.

As our brains gets used to this pattern, the pattern itself strengthens. We get to a point where, thanks to long stretches (months, years) of both moving fast and being frenzied, we assume that “fast” and “frenzied” are inseparable.

Think, for a moment, what fast and intentional looks like: maybe a professional athlete, or an animal in the wild that knows exactly where it’s heading.

There’s an efficiency of movement, a calm focus, no wasted energy, and a power that comes from a lethal combination of relaxation, clarity, and aggression.

“How much we do” and “how we do what we do” move on independent axes.

To be clear, I’m as likely as the next person to get caught up in worry, in unproductive cycling through “what if’s,” of a sense that if I slow down for even 20 minutes to sit and really think about something that I’ll have fallen behind.

But that mode makes me neither more effective nor happier, so I’m trying to observe it to see if I can let it go.

When I come up short, bouts of intense exercise and moments of unbridled laughter and joy with loved ones are a great way to reset.

How to Move Quickly in 2026

~ Sasha ~ 1 Comment

My 2026 started with a blanket of snow: six inches of unexpected, fresh powder in the Vermont mountains.

I was there on a surprise 3-day snowboarding trip with my 14-year-old daughter. We braved single-digit (F) temperatures, ignoring the impacts of an ice storm that had blanketed (read: ruined) the mountain just a few days prior.

The half a foot of snow was dumb luck—a ‘dusting’ was expected—and it was amazing.

We were on the first lift at 8:01am, in 5 degree weather, and had the most perfect four hours to start off 2026.

2025 was not an easy year for so many of us. So many things that we took for granted shifted or disappeared, and I, at least, spent a tremendous amount of energy fighting to stand still.

The good news is: we are here today, stronger for what we have endured, and more confident in our resilience for having made it through 2025.

The snow that started this year is a fresh, clean, undisturbed canvas.

It’s not a canvas that lasts forever. And, yes, that sheet of hard, unforgiving ice might be just below the surface.

But we can allow ourselves the space to start again, and we can believe in the possibility of renewal and new possibility.

My friend Abby Falik writes a newsletter called Taking Flight. In her most recent post, she poses the question:

Sometimes, when I’m running late, I play an inner game: Can I move quickly without rushing?  The grip loosens. Breath returns. A possibility cracks open and I’m more likely to arrive present.

I have no illusion of approaching 2026 in low gear, no pretense that it won’t be challenging and intense.

Rather than hiding from that, my goal is to pull strength from the knowledge of what I achieved in 2025—despite all the challenges—coupled with a commitment, thanks to Abby’s nudge, to move quickly without rushing.

I remind myself: the speed and quantity of what I do can be high without the frenzy that comes from rushing. I can be fast and thoughtful, speedy and intentional, and grounded throughout.

So can you.

Happy 2026.

Quality is Non-Linear

~ Sasha ~ Leave a comment

Imagine a scale for “quality” that goes from 0 to 100, where quality is “anything that makes something good or special.”

As a novice, I look at that scale and trick myself into thinking it is linear: the difference between what it takes to be able to produce a quality of 40 vs a 30 might be the same as the difference between what it takes to go from 90 to 100.

As in: when I started played guitar, I couldn’t reliably pluck the string I wanted to, let alone do it rhythmically.  (0 to 10)

Then, I could find the string most of the time, but I only plucked down, not up and down. (10 to 20).

Now that I can do that well, and now that I’ve mastered ten other plucking skills, I’ve been told that my picking technique has too much wrist, I’m holding my pick perpendicular to the string when it should be at a slight angle, I should be executing a relaxed figure 8 pattern over each string….all this just my first year of lessons. Imagine what next year will hold!

The expert knows that, as we make progress, we learn about nuance and details that were previously invisible.

This is why quality is not linear, it is logarithmic: the closer we get to “great” the more skill, will, and effort it takes to improve a little bit more.

This means that the move from 40 to 41 could take as much time and effort as getting from 0 to 10: because improvement at the beginning was relatively easy, it was the work of going from terrible to OK, and maybe all the way to decent.

But good to really good? Really good to great? Great to exceptional? Exceptional to best in class?

Each of those is a full journey: being open to the idea that better exists; taking the time to understand what it entails; building that new skill on top of your already-strong foundation; having the attention and patience to master the next micro-skill and the one after that.

This is why greatness is both expensive and rare. It’s why, at the 3-star Michelin restaurant Sukiyabashi Jiro, apprentices, who train for 10 years, aren’t allowed to touch the fish for the first few years. The same goes for expert watchmakers, knifemakers, and makers of F1 racecars.

If we’ve had the patience and discipline to develop mastery of any skill in any domain, we understand this intuitively, because we’ve walked that path. We just need to retain the humility to see that each new journey, each new skill, will have as much depth and nuance as the skill we’ve already mastered.

And if we work with people who haven’t yet developed mastery—of other skills or these skills—it can be difficult to communicate clearly about “the distance from here (where you are) to there (where you’d like to be).”

As in: we’ve all met the bright-eyed newbie who “wants to do strategy” as if that’s something that is 6 months away and just requires “good analytical skills”—when the reality is that good strategic decision-making is the accumulation of years analyzing, thinking, putting yourself on the hook, making the tough call, being right or wrong, living with the consequences, and doing it all over again.

The job of the expert, then, is to cultivate curiosity in the novice, to point out all the progress he’s made, and, also, to show, with patience and a commitment to detail, the difference between “90% there” and “100% there.”

And the job of the novice is to have the humility to say “I got to this point quickly, it’s possible that I don’t fully understand what it takes to be great, but I’m willing to keep being curious and keep on putting in the work.”

 

What Are We More Afraid to Miss?

~ Sasha ~ Leave a comment

Which scares us more:

  • Missing something, or
  • Not devoting enough time to the important things.

To explore this question, here’s a short parable of modern work life: how I manage my Inbox.

Starting 15 years ago, I established my current approach to my Inbox. It is based on the philosophy that there are two kinds of emails:

  1. Ones I need to act on
  2. Ones I don’t need to act on

The approach is brutally simple:

  1. The first group is unread
  2. The second is read.

No filing of any kind. Search works great. Zero inbox is meaningless; zero unreads is not. Voila!

This approach, plus ruthless use of the “mark as spam / block sender” functionality in my Gmail interface, has served me well for years.

Last week, for the first time in ages, I decided I needed to adjust my system.

I think it’s because of an explosion of workflow-related emails: Calendar updates, Calendly updates, Zoom meeting updates, Docusign updates, Box updates, AI recording updates, etc.

Combine this with the general flotsam of subscriptions of varying degrees of usefulness, and the ratio of must read:optional to read emails in my Inbox had gotten out of whack.

My solution to this is that I caved in to using filters in Gmail (I’m sure there are many better solutions (Superhuman, etc.).

What’s interesting is the experience of setting up those filters: it’s the task of taking every nonessential but interesting email and putting it somewhere other than my Inbox—the only part of my email world that I’ve looked at consistently for more than a decade.

The feeling is the same one I have when there’s an “internal meeting I could join but maybe don’t have to join.” You know the one: the content is important, you will probably learn something and maybe will make the meeting a little better. But do you absolutely need to be there?

The same goes for the Slack channel that’s been there forever that I rarely read; the client call that might be helpful to join even though someone else is running the meeting; the conference that I always attend, even though I can’t show concrete business results.

Most of us feel short on time—including time to be unproductive. We ache for open space, time to be generative, time to do the things that matter most… “once all this stuff is out of the way.” We tell ourselves that there’s no real way to create this kind of space.

One way to explore if this is true is to experience the fear of missing something: that essential email, that meeting where a wrong decision gets made, that photo op at the conference….

Perhaps that fear is justified, and the consequences would be significant.. Maybe success is defined by you getting to everything right on time; you being present to optimize each and every decision; you seeing all the edge cases and fixing them immediately. That might be what we need most from you.

Or it might be that there’s more resilience in the system than you expect.

That the cost of tracking and sifting through everything is real.

That setting a different bar for “what requires me” would create such a seismic, structural shift in your days and your weeks that it would be a little bit, or even a lot, disorienting.

This is what the sixth stage of Kevin Kelly is all about: “finding those things to which you are uniquely suited, and doing only those things.”

Not the places you can add value, not the things you are best at. The things that only you can do.

It’s a really high bar, and it cuts against the culture in most organizations.

It’s also worth exploring.

Podcast Alert: Patrick Thean

~ Sasha ~ Leave a comment

Patrick is an author, CEO coach and mentor, and I was happy to get the chance to join his podcast recently. Our discussion covered topics that will be familiar to readers of this blog and, as always, I discovered that talking about a topic helps me understand the topic better.

If I had to summarize my reflections from the conversation, they are:

  1. How we do anything is how we do everything
  2. One way to learn how we do anything is by digging into new domains we are exploring

What follows is a conversation that starts with 60 Decibels,  my motivation for doing work in the social sector and my Generosity Experiment; but quickly turns to learning to play the guitar, my favorite AI use cases, and the attitude Patrick and I would suggest towards getting over your lingering AI resistance.

You can listen to the full podcast here (20 mins):

• Apple: https://bit.ly/3GB5W0P
• iHeart Radio: https://bit.ly/40eTeLU
• Spotify: https://bit.ly/4lqkhfM

The Road Runner

~ Sasha ~ Leave a comment

My son, who has been lifting weights regularly, has a 12 week cycle. 12 weeks of doing the same exercises in the same order before you switch.

He told me that there’s some science that says that the first 8 weeks of improvements are just your body getting used to doing these movements— muscles firing more in conjunction, tendons adjusting —and meaningful change in strength at the level of muscle fibers only happens in the last 4 weeks.

It’s a useful metaphor for all changes: the first steps in the process are just getting used to doing the new thing. I don’t need to be stronger or faster to improve, I just need to spend regular time in the activity, and all my existing abilities will come together more effectively to produce a better output.

So if I’m trying to run more, I just need to run more, even if that’s a tiny bit every day. The every day is what matters the most, much more than effort or time or the perfect coaching.

Consistency –> New habits –> Reordering of our internal systems –> Improvement

The amount of “improving” we need to do is less than we think and easier to achieve than it appears.

We just have to remember to form new habits, and it all starts with the mantra:

That thing that’s terribly hard for me today will be easier for me tomorrow if I just do it today.