Leaders Use the Tools

Drive AI adoption by having executives personally use the tools daily, not by mandating adoption

Dhanji R. Prasanna
How Block is becoming the most AI-native enterprise in the world

Leaders Use the Tools

"Really try and use these tools yourself... 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 all have used Goose and use it regularly... we do it every single day." - Dhanji R. Prasanna

What It Is

Leaders Use the Tools is Block's approach to driving AI adoption: rather than mandating usage or reading about AI, executives personally use AI tools daily and learn from firsthand experience. This creates authentic advocacy, surfaces real insights about tool capabilities, and demonstrates commitment that permeates through the organization.

Dhanji contrasts this with the alternative—reading "think pieces on LinkedIn or Harvard Business Review" and then trying to get teams to follow suit. That approach fails because leaders can't speak authentically about tools they don't use and can't understand how to apply them to their organization's specific workflows.

How It Works

Why top-down usage works:

  1. Authentic advocacy - When executives speak about AI from personal experience, it carries more weight than theoretical enthusiasm

  2. Workflow insight - Using tools personally teaches leaders how their own workflows can change, which informs organizational workflow changes

  3. Signal of commitment - If the CEO and CTO use these tools daily, it signals AI isn't optional

  4. Faster learning - Leaders who use tools can evaluate claims, identify real use cases, and spot limitations without waiting for reports

Block's example:

  • Jack Dorsey (CEO) uses Goose daily
  • Dhanji (CTO) writes code every day using AI tools
  • The executive team all use Goose and other AI tools regularly
  • This isn't occasional experimentation—it's daily practice

The alternative that fails:

Reading about AI → Theorizing about potential → Mandating adoption → Wondering why it doesn't work

This fails because:

  • Leaders can't answer real questions about the tools
  • They don't understand actual capabilities and limitations
  • Teams sense the disconnect and don't take mandates seriously
  • Use cases remain theoretical rather than practical

How to Apply It

  1. Start with yourself:

    • Install the AI tools you want your organization to use
    • Use them daily, not occasionally
    • Solve real problems, not just toy examples
    • Track what works and what doesn't

  2. Use tools for real work:

    • Dhanji: "I write code every day"
    • His example: Using Goose to organize receipts, convert to HTML, sync to Apple Notes
    • Not: Playing with tools in spare time

  3. Get your executive team involved:

    • Block's executive team all use Goose regularly
    • This creates collective experience to share
    • Multiple perspectives surface different use cases

  4. Share learnings authentically:

    • Talk about specific problems you solved
    • Be honest about limitations you encountered
    • Describe surprising capabilities you discovered

  5. Connect personal experience to organizational change:

    • "So we learn a lot about how our own workflow can change, and that's going to tell you so much more about how you're going to change your organization's workflow"

What to Try

Dhanji suggests finding real problems to solve:

  • He used Goose to gather his son's therapy receipts from various sources (PDFs, screenshots, Google Drive), convert them to a single HTML note, and share with his wife
  • This was a real problem he needed to solve, not a demo

The more real the problem, the more you learn about actual tool capabilities.

When to Use It

  • When adopting any significant new technology across an organization
  • When AI adoption is stalling despite good tools being available
  • When there's skepticism about whether AI tools actually provide value
  • When leaders are removed from how their teams actually work

Source

  • Guest: Dhanji R. Prasanna
  • Episode: "How Block is becoming the most AI-native enterprise in the world"
  • Key Discussion: (00:54:04) - Leaders using tools themselves to drive adoption
  • YouTube: Watch on YouTube

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