Catch the SaaS spend nobody is watching, ramp every hire on a real plan, and never walk into a meeting cold. ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
DeskTheory / archive →
ISSUE 06 · THE THURSDAY 3 2026.06.11
DeskTheory

Three workflows that put you in the top 1% of CEOs.

WORKFLOW / 01

Find the money leaking from your software stack

> OUTCOME

A ranked cancel-and-renegotiate list built from twelve months of transactions: the duplicate tools, the prices that quietly crept up, and the recurring charges nobody on your team can explain. I've run this on my own companies and been annoyed every time; one pass found a tool we'd been paying for since before a reorg that nobody had logged into in a year. Most companies waste 25 to 40 percent of their software spend. This is how you find your share.

> SETUP

A Claude Project on a business plan, plus a twelve-month transaction export from Ramp, Brex, your card statements, or your accounting system. The four-part audit prompt in the article groups every recurring charge by vendor, flags duplicates and price creep, and ranks it all by annual dollars.

> WHAT TO DO NEXT

Export a year of transactions, drop them into the prompt, and send the "do we still need this?" shortlist to your team leads. Watch the number annoy you.

Full step-by-step instructions _
WORKFLOW / 02

Onboarding plans that write themselves

> OUTCOME

You spend six weeks obsessing over a hire, then hand them a laptop and a Slack invite. I've been that CEO. This workflow drafts a role-specific 30/60/90 from the job description: weekly milestones, who to meet and why, and what success at day 90 looks like. Their manager edits a complete draft instead of authoring one from scratch (which usually means it never gets written). Every hire ramps on a real plan.

> SETUP

A Claude Project loaded with your org context. Feed it the JD and the manager's first-quarter goals, then load the milestones into Rippling or BambooHR so the day-30 and day-90 check-ins fire on their own.

> WHAT TO DO NEXT

Run the prompt on your newest hire's JD and hand the draft to their manager to own. Watch day one go differently.

Full step-by-step instructions _
WORKFLOW / 03

Never walk into a meeting cold again

> OUTCOME

I used to sit down in meetings and quietly search my own email under the table to remember who I was talking to. This workflow ends that. Claude reviews your week, flags the Tuesday double-booking while it's still fixable, proposes two focus blocks before meetings find the gaps, and briefs you on every external call: who they are, your last touch, the loop you forgot to close. You walk in prepared and you did zero prep.

> SETUP

Claude with the Google Workspace connector, plus Granola so it has context on who you're meeting. Read-only on day one: it proposes fixes, it never touches the calendar.

> WHAT TO DO NEXT

Connect your calendar read-only, run the weekly review prompt from the article, and book the focus blocks it finds as real holds. Defend them.

Full step-by-step instructions _
Andrew
1:1 · operator to operator $1,000 · limited spots

Get my eyes on your AI setup.

I'm opening a few 1:1 working sessions. 60 minutes, screen-share, operator to operator. We start with where you are and what you want to achieve, then map the highest-leverage systems and workflows for your business from there, and fix whatever is blocking your setup. You leave with a concrete plan you can run that week.

$1,000 a session, and spots are limited. If it's not worth it, you don't pay.

Reserve a session →
./books · the self-serve path

Prefer to go it alone first?

The three guides take you from "never opened a terminal" to running real workflows end to end. $99 each, or $199 for all three.

Get the guides →

Not sure they're for you? Read the full argument first →

desktheory.com · archive · written by Andrew Lissimore
ISSUE 06 · 2026.06.11