The Drawing Test

Here's a simple exercise: grab a piece of paper and draw how your tools connect.

Put each tool your organization uses in a box. Then draw lines showing how data flows between them.

If you're like most leaders, you'll discover something uncomfortable: you can't complete the exercise.

Why This Matters

If you can't visualize your tech stack, you can't:

  • Diagnose problems — When something breaks, you don't know where to look
  • Plan improvements — You don't know what depends on what
  • Onboard people — You can't explain something you don't understand
  • Make decisions — Every tool choice affects the whole system

The Mapping Exercise

Set aside 30 minutes and follow this process:

Step 1: List Every Tool

Write down every tool your organization uses. Include:

  • Core business tools (CRM, project management, etc.)
  • Communication tools (email, chat, video)
  • Financial tools (accounting, invoicing, payroll)
  • Marketing tools (website, social, email marketing)
  • Operational tools (scheduling, documentation, file storage)

Don't worry about organization yet—just get everything on paper.

Step 2: Identify Data Flows

For each tool, ask:

  • What information goes INTO this tool?
  • What information comes OUT of this tool?
  • Where does that information come from/go to?

Draw arrows showing these flows.

Step 3: Mark the Integrations

Identify which connections are:

  • Automated — Data flows automatically between tools
  • Manual — Someone has to copy/paste or re-enter information
  • Broken — Data should flow but doesn't

Use different colors or line styles for each type.

Step 4: Find the Hubs

Look for tools that have many connections. These are your hubs—the critical pieces of infrastructure that everything else depends on.

Step 5: Identify the Gaps

Look for places where:

  • Data has to be manually transferred
  • Information gets stuck
  • Different tools have conflicting data
  • No one knows who's responsible

What You'll Likely Find

Most organizations discover:

Too Many Tools

The average small business uses 50+ different tools. Many are redundant. Some are forgotten. Few are fully utilized.

Manual Bridges

Critical data often relies on someone remembering to copy it from one place to another. These manual bridges are fragile and error-prone.

Single Points of Failure

One tool—or worse, one person—often serves as a critical hub. If that fails, everything stops.

Data Inconsistency

The same information exists in multiple places with different values. No one knows which version is correct.

What to Do With This Map

Once you have a visual representation:

1. Eliminate Redundancy

If multiple tools do the same thing, consolidate. Every tool is a maintenance burden.

2. Automate Manual Bridges

Those lines you marked as "manual"? Those are opportunities. Look for integrations or automation tools that can eliminate human data entry.

3. Strengthen Critical Hubs

Your hub tools need extra attention. Ensure they're reliable, well-documented, and not dependent on a single person's knowledge.

4. Create Data Authority

For each type of information, designate one tool as the "source of truth." Everything else syncs from that source.

The Ongoing Practice

Your tech stack map isn't a one-time exercise. Things change. Tools are added. Integrations break.

Schedule a quarterly review to update your map and identify new issues before they become problems.

The Bottom Line

You can't manage what you can't see. Taking the time to visually map your tech stack reveals complexity you didn't know existed—and that's the first step to simplifying it.

Grab that paper. Start drawing.