Should I Write, Upload or Generate My AI Agent's First Skill?
Four choices sit under the add menu for skills. What I said about each one, and the check I make before I upload a skill I did not write.
Generate it. I create my skills inside the builder, so each one is personalized for me and the way that I work. I only recommend writing skill instructions yourself if you are super tech-savvy, and I'm very hesitant to copy a skill I can't read first.
In my skills setup video I mouse over the plus icon next to the word add in the Skills section, and a menu opens. Which choice you pick decides who writes the first draft of the skill.
The builder in that video is Gumloop. On my relationship to Gumloop, I said this:
From the recording, 33:22. I don't work for Gumloop. I found this tool over the summer through Lenny's podcast, and I started using it and have since made myself an ambassador for them. I've created a relationship with Gumloop. I am not an employee.
More on that is in Do you work for Gumloop? (the answer from the session).
What are the four choices?
From my setup video. So, there are a couple of ways to create skills inside of Gumloop. If you're mousing over the plus icon and the word add, you get a four-menu drop-down option. You can create your skill with AI, you can upload a skill, write skill instructions, or add existing skills.
What I said about each:
| Choice | What I said | Where I land | |---|---|---| | Create with AI | We select option one, and create the skill inside Gumloop "so it's personalized for us and the way that we work." | My choice, by voice | | Upload a skill | "You can download it there and upload it here," from a tool like Claude, as a markdown file. | Only after I can read it | | Write skill instructions | "I only recommend this if you're super tech-savvy to write your own instructions." | Only if you are super tech-savvy | | Add existing skill | "If you have a skill in your library already for Gumloop, that's where you add the existing." | When the skill is already in my library |
Checked on 2026-11-05 against Gumloop's AI agent documentation, which lists the same four choices under the Skills section: Create With AI, Upload Files, Write Skill Instructions and Add Existing Skill. It says Upload Files turns a document or .zip into a skill. My video says "upload a skill," and screens change.
Why do I generate my first one?
In the video I create the skill right inside the builder, and I say why.
From my setup video. so it's personalized for us and the way that we work.
In the live session I made the same call, at 36:49.
From the recording, 36:49. The best way to create skills inside of Gumloop is to come back to the dictate feature.
My prompt asks the AI agent to question me before it writes anything.
From the recording, 37:10. Ask me three or four questions to customize my agent's skills.
The dictation, start to finish, is in How Do I Teach an AI Agent My Vetting Process by Voice?. The steps for the session build are in How Do You Create Skills for an AI Agent?.
What do I check before I upload a skill I did not write?
I read it first. I said so when I paused the session to give a word of caution about skills from the internet.
From the recording, 34:47. I am very hesitant to copy someone's skill offline if I don't have access to read it before I download it.
A skill can be pages long, and I told the group how I use a skills site to decide what's worth opening (35:38 to 36:28). I showed it as something to have in my back pocket, not to use that day. That part is in How Do You Vet an AI Agent Skill Before You Download It?.
- 01
Open the file and read it all the way through before you upload it.
- 02
If you cannot read it, do not copy it.
- 03
After the AI agent adds the skill, double-click into it and read it again (42:34).
What goes wrong
A skill you can't read can give away access to data you didn't mean to share.
From the recording, 34:59. People can write any set of instructions in a skill and you can inadvertently give away access to data that you don't feel comfortable with.
What my video doesn't show: the upload screen itself, or what happens to a file that has a problem in it.
Where this comes from
This article grows from the session I taught live with Women Applying AI on October 7, 2026, and from my published setup video on YouTube, whose captions were pulled on October 31, 2026. The quoted passages are my own words, taken verbatim from the recording and the video. The steps, tables and checklists around them were drafted by my team's AI agents from those words and my published pages, and checked against the recording before publishing.
Build Your First AI Agent in One Hour: the full session with the clips, the prompts and the transcript.
Related reading: How Do You Create Skills for an AI Agent?, How Do You Vet an AI Agent Skill Before You Download It?, and What Is an AI Agent Skill?.
Frequently asked questions
Which option do I pick for a first skill?
Create with AI. I speak the job into the dictate button, so the skill fits how I work.
When do I write the skill instructions myself?
Only if you are super tech-savvy. That's the only case I recommend it for.
Can I upload a skill from another tool?
In my video I said you can download skills from Claude as a markdown file and upload them in the builder. I read the file before I upload it.
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