OPERATOR FEEDBACK · DIAGRAMMO · 2026-04-30

Diagrammo — 30-min operator friction test (the smash-back, continued)

A single operator tried to build a factory map in Diagrammo today. Hit 30 minutes of UX friction before getting to the actual diagram. This is the brain dump — what tripped me up, and what I'd ship to fix it. Written in the spirit of helping Diagrammo ship better.

PJ Zonis Single operator · SideGuy Solutions · Encinitas · Operator-translation layer for tools like Diagrammo — about →

TL;DR: Diagrammo by Demian Neidetcher (VP at MLB, built with Claude Code) is a beautiful diagram-as-code tool. After shipping an operator-onboarding page for it this morning, I tried to use the tool myself to build a real production diagram (the SideGuy factory map). I hit 30 minutes of friction before getting to the actual diagram work — most of it on first-file creation. Below: 7 specific pain points + the fixes I'd ship if this were my tool. Written as operator-tier real-use feedback, in the spirit of the smash-back doctrine: take the thing, use the thing, ship better than they did.

Context: I shipped an operator-onboarding page for Diagrammo earlier today as the first move in the SideGuy "smash-back doctrine" — when a builder ships something gorgeous, you don't pitch them, you USE it and ship something better than the README on top.

Step two was: build my own production diagram (the SideGuy factory map) IN Diagrammo and ship that as a second proof point. That's the test that hit friction.

This isn't a critique. It's the kind of feedback I'd want if Diagrammo were mine — written by someone who actually tried to use it, not someone who skimmed the marketing site.

The 7 friction points (in order of pain)

1Folder-create vs file-create icons look identical

What happened: I clicked the "+" icon on the left toolbar to create a new diagram file. It made empty folders instead. Clicked again. More empty folders. Ended up with 4 unwanted "New Folder", "New Folder (2)", "New Folder (3)" entries before realizing the file-create button is a separate icon I never identified.

Fix: Distinct icons for new-file vs new-folder (or text labels under them). Hover tooltips on every icon — currently the toolbar is icon-only with no labels, so first-time users guess. Add a clear "Create your first diagram" CTA when the working set is empty.

2Cmd+N opens a new browser window, not a new diagram

What happened: Tried Cmd+N (the universal "new" shortcut). Got a new browser tab/window — the browser intercepted the shortcut before Diagrammo could.

Fix: Bind a non-conflicting shortcut for new file (e.g., Cmd+Shift+N or Cmd+Option+N — Notion uses these). Or intercept Cmd+N when Diagrammo has focus (modern web apps can do this with preventDefault on the keydown event).

3Share-link URL puts you in a read-only view with no obvious "back to editor" path

What happened: Clicked something that put me on a URL like online.diagrammo.app/?dgmo=MQAg6gpgN.... Suddenly everything was grayed out. The diagram was visible but I couldn't edit. Took me 2-3 minutes to figure out I was in a share-link preview mode and needed to go back to the base URL.

Fix: When in share-link view, show a clear banner at top: "You're viewing a shared diagram. Click here to copy it to your library and edit." That single banner removes the entire confusion.

4No clipboard-paste detection in the editor

What happened: I had a fully-formed .dgmo snippet on my clipboard (from a prepared starter). My instinct was to just paste it somewhere and have Diagrammo say "want me to make a new file from this?" — that's how Notion, Linear, and Figma all behave. Instead I had to find the new-file button first, then paste.

Fix: When the user pastes .dgmo-shaped content (starts with boxes-and-lines or similar) anywhere in the app, prompt: "New diagram from clipboard?" One-click create. Bonus: drag-and-drop a .dgmo file onto the working-set sidebar to import.

5SVG export not available in browser version (PNG only)

What happened: Wanted to embed the diagram on my domain. Tried to export as SVG (preferred for sharp scaling + searchable text). Diagrammo browser-version only offered PNG.

Fix: Add SVG export to the browser version — the diagram is already vector under the hood, the export should be one-line. SVG is the format operators want for embedding (Apple, Stripe, Linear all use SVG diagrams on their docs).

6Empty state on a fresh load is the welcome doc, not a CTA

What happened: Fresh user lands on Diagrammo. Sees the welcome doc as the default file. Tries to figure out where to start. The welcome itself doesn't auto-prompt "Click here to make your first diagram" — it explains how but doesn't do.

Fix: Big primary CTA button on the welcome doc itself: "Create Your First Diagram." One click → new untitled file → cursor in the editor → ready to type. The welcome doc text can still be there as reference, but the CTA does the action.

7No visible undo / no obvious "delete this folder I just made by mistake"

What happened: After accidentally creating 4 empty folders, I couldn't easily delete them. Right-click didn't give me a delete option I could find. Had to leave them there.

Fix: Right-click any item in the working set should give: Rename, Delete, Duplicate. Plus a global Cmd+Z undo for sidebar actions (folder/file create, rename, delete) for the last ~10 actions.

What I would have built (if I'd gotten past the friction)

For reference, here's the SideGuy factory map I tried to render — the actual operating system behind the SideGuy single-operator AI shop. This is the .dgmo source I had ready to paste, before I gave up on the file-creation step:

boxes-and-lines
direction TD

[Capture]
  News Radar
  Inbound DM
  Featured Form
  Public Comments

[Generate]
  News Take
  Personal Page
  Custom Shareable
  Listing Read

[Publish]
  Shareable Wall
  LinkedIn Post
  X Post
  HN Post

[Distribute]
  Sniper DM List
  Touch Sequence
  Comment Threads

[Convert]
  Lead in CSV
  Tier Match
  Paid Engagement

[Compound]
  Receipts Page
  Doctrine Essay
  Cross-Links

[Background Agents]
  3am swarm-improver
  7am morning-snapshot
  9am improve-bot

News Radar -> News Take
News Take -> Shareable Wall
Shareable Wall -> LinkedIn Post
LinkedIn Post -> Inbound DM
Featured Form -> Personal Page
Public Comments -> Inbound DM
Inbound DM -> Lead in CSV
Personal Page -> Lead in CSV
Lead in CSV -> Custom Shareable
Lead in CSV -> Listing Read
Custom Shareable -> Touch Sequence
Listing Read -> Touch Sequence
Sniper DM List -> Touch Sequence
Touch Sequence -> Paid Engagement
Touch Sequence -> Comment Threads
Comment Threads -> Inbound DM
Paid Engagement -> Receipts Page
Receipts Page -> Shareable Wall
9am improve-bot -> Cross-Links
3am swarm-improver -> Cross-Links
7am morning-snapshot -> News Radar
Cross-Links -> Shareable Wall

If Diagrammo's UX clears the 7 friction points above, this would have rendered in 30 seconds. As-is, I never got it on screen. (Demian — if you want, paste this into a fresh Diagrammo file on your end and the diagram is yours to use as a public demo.)

Why I'm shipping this as a public page instead of a private DM

Two reasons:

One: the smash-back doctrine says shipping the artifact is the move, not the conversation about it. A public page is a permanent reference Demian can quote, link to, or send to investors as proof "operators tried it for real." Private DM = lost forever in LinkedIn.

Two: other builders watching this play see SideGuy as the operator-translation layer for tools like theirs. Public friction-test feedback IS the offering — that's literally what the new Project Launch Catch-all tier ships.

Shipping in public is the way the leverage compounds for both sides.

Built by: Demian Neidetcher — VP at Major League Baseball, shipped Diagrammo with Claude Code. Diagrammo is a clean, principled diagram-as-code tool. The friction above is first-30-min onboarding stuff, not the core product. The core product is genuinely good.

The doctrine, restated

When a builder ships something, USE it before you praise it
If you hit friction, write down the friction — don't just bounce
Ship the friction notes as a public artifact on your domain — they're more valuable than another LinkedIn comment
Specific fixes > vague feedback. "I'd add tooltips" beats "needs better UX"
Frame it as helping the builder ship better, not as a review
The single-operator-with-taste who actually USED the thing is the rarest, highest-trust feedback any builder can get

Builder shipping a tool that operators bounce on?

The Project Launch Catch-all tier ships exactly this kind of operator-translation layer for builder tools. Onboarding pages, distribution posts, sniper DM lists — and yes, real-use friction tests when warranted.

See the Launch Catch-all tier → 📲 Text PJ

— PJ · SideGuy Solutions · Encinitas · The operator-translation layer for tools like this