Drive AI Adoption By Using It Yourself On A Real Problem
Executives using the tool daily on their own real problems beats any top-down mandate or think-piece
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 4
- Confidence
- 87%
Prasanna's method for driving company-wide AI adoption: leaders — including the CEO — must use the tools themselves, every day, on their own real problems. This teaches the tool's actual strengths, weaknesses, and ergonomics far better than reading think-pieces, and only then can you credibly reshape your organization's workflow. The accelerant is picking a specific personal problem you genuinely want solved, which makes the learning real and motivating.
Origin
Prasanna's approach at Block; reinforced by CEO Jack Dorsey's 'learning-first company' ethos and co-articulated with host Lenny Rachitsky ('stop reading about it, just build some stuff').
Core principles
- 01Adoption is driven by leaders using the tool, not mandating it — Jack, the exec team, and Prasanna all use Goose daily
- 02Direct use reveals strengths, weaknesses, and ergonomics that no think-piece can
- 03A specific personal problem you actually want solved makes the learning real and motivating
- 04Give the tool flexibility to try, fail, back up, and try another route
- 05Be a 'learning-first' organization: judge experiments by what you learned, not only whether you got the right answer
How to run it
- 1
Get leadership using it daily
Have the CEO and executive team personally use the AI tools every single day, not delegate or observe.
Pro tip 'Jack uses goose, I use goose, our executive team all have used goose... every single day' — this is how adoption spread.
Watch out Reading think-pieces on LinkedIn or HBR then pushing teams to follow will not teach you your own workflow changes.
- 2
Pick a specific real problem you want solved
Choose an actual personal pain point — it motivates you and makes the tool's behavior concrete.
Pro tip Lenny's example: 'build an app where I can give you a Google doc URL and let me download the images' via Lovable.
- 3
Let the tool try, fail, and reroute
Give the agent flexibility to attempt approaches, and when it fails, back up and try a different route until it makes progress.
Pro tip Goose collated scattered receipts (PDFs, screenshots) into a single Apple Notes note as HTML that synced to phone — using AppleScript it discovered on its own.
- 4
Translate personal learning to org workflow
Only after feeling the tool's strengths and weaknesses firsthand, decide how to reshape team workflows and where to deploy it.
Pro tip 'Feel it, understand its strengths and weaknesses and its ergonomics and then figure out how to apply it to your teams.'
In the wild
Prasanna had scattered therapy receipts for his son in various forms (screenshots, PDFs) across Google Drive and needed to collate them for his wife to claim from insurance. He described the problem to Goose; it tried several approaches, failed, rerouted, and settled on AppleScript to gather everything into a single Apple Notes note converted to HTML so it synced to his phone.
→ A workflow he 'just never would have thought of' got solved end-to-end — teaching him a concrete strength (agentic reroute + desktop control) he could then apply organizationally.
Rather than mandating adoption, Block's CEO Jack Dorsey, Prasanna, and the executive team all use Goose and other AI programming assistants every single day.
→ This firsthand executive usage is what Prasanna credits for driving most of Block's company-wide AI adoption.
Common mistakes
Learning about AI from think-pieces instead of using it
Reading LinkedIn/HBR articles and pushing teams to follow teaches you nothing about your own workflow; only daily hands-on use reveals real strengths and ergonomics.
Mandating adoption top-down without personal use
Directing teams to adopt AI while executives don't use it lacks the credibility and firsthand insight that drove Block's adoption when leadership used Goose daily.
Is it for you?
Best for
Executives and team leads trying to drive genuine AI adoption across an organization
Not ideal for
Leaders unwilling to spend hands-on time with the tools, or contexts where no relevant personal problem exists to practice on
From the transcript
“the way in which I think we've been able to drive most of the adoption is Jack uses goose, I use goose, our executive team…”
“that's going to tell you so much more about how are you going to change your organization's workflow than if you're reading a bunch of…”
“have a specific task or problem you want to solve for yourself because that really motivates you and makes it very real”
“if it tries a few things and fails, it'll back up and it'll try a different route and it'll just keep going until it makes…”
From the episode
How Block is becoming the most AI-native enterprise in the world
Dhanji R. Prasanna