# Plan your software stack before you buy

> A skill that interviews you about your work, then recommends the tools you actually need, what they cost, and the order to set them up.

- Type: skill
- Access: free, no account needed
- Category: Strategy & Planning
- Tags: Strategy & Planning
- Added: 2026-11-08

## What it is

Most small operations end up with a pile of subscriptions bought in a hurry. One tool for bookings, another for invoices, two for email, a project board nobody opens. This skill turns that mess into a short list.

You answer a handful of questions about how you work. The skill works out which categories of software you genuinely need, names a sensible pick for each, gives a rough monthly cost, and tells you which one to set up first. It also flags overlaps, so you can see where two tools are doing the same job.

It is a planning skill, not a shopping bot. It does not sign you up for anything. It gives you a plan you can argue with and then act on.

## When to use it

Run it when you are starting something new and need a baseline. Run it again when the bill feels too high and you cannot say why. It is also useful before a busy season, when you want to know whether your current setup will hold or whether one more piece is worth adding.

Skip it if you already know your stack and just want a cheaper plan for one specific tool. This works at the level of the whole stack.

## How to use it

1. Install the skill in your assistant of choice and start a session.
2. Describe your work in plain terms: what you sell, who buys it, how many clients you handle in a month, and whether you work alone or with others.
3. List what you pay for today, with rough amounts. Include the free tools you lean on, since they count.
4. Answer the follow-up questions. Expect ones about how you take payment, how you talk to customers, and where your files live.
5. Read the output in two passes. First check the recommended categories. Then check the cost column against what you actually spend.
6. Ask it to cut the list. A good prompt is: "Drop anything I could replace with a spreadsheet for the next six months."
7. Work through the setup order it gives you, one step at a time.

## What a good result looks like

You get a table with four columns: what the tool is for, a suggested option, an estimated monthly cost, and a setup order. Below it, a short note on what you can cancel or postpone.

A strong plan is boring. Five or six lines, not twenty. Every line maps to something you said you do. The first item is the thing that unblocks everything else, usually payments or a place to keep client details.

If the answer comes back with a dozen tools, push back. Ask which three matter in the first month. The point is to spend less and set up faster, not to collect a longer list.

HTML version: https://websitespa.net/library/plan-your-software-stack-before-you-buy