2 Claude skills I use every day

In last week’s article, we showed you a skill to find skills for Claude Cowork.

But I didn’t mention the ones I use almost every day.

And they are not specifically related to investing or asset management.

They are more general in scope.

So let’s look at 2 of my favorite Claude skills. (To install these skills, just copy-paste the URL inside Claude Cowork and ask it to install it)

I build tools and systems to enhance my investing process. So this first skill is the grill-me skill from Matt Pocock.

It’s simple and genius. When you build or do something, be it in Cowork or Claude Code, grill-me will, well, grill you. It will start asking deep questions to fully understand exactly what you want.

Here’s an example:

In the past, I mentioned the AskUserQuestion tool, which is always a good idea: let Claude ask you lots of questions so it can build the best context.

Grill me goes a step further.

Here are 2 examples of questions it asked: Where to pull the data:

And for example: A question on the components of the dashboard itself.

And it went on and on. Grilling me until it was satisfied.

In total, Claude asked me 10 questions. Which is more than he typically would without the skill.

And what did I do?

Yep, I went for a second round.

Better context → Better final quality

The problem: When you’re working in Claude, sometimes you’re running out of a session. You’ve consumed your entire context window.

And even if you haven’t consumed everything, performance degrades when your session gets long. The model has trouble “remembering”.

In those 2 situations, you need to be able to stop your session cleanly, and then hand it over to a next session

(Note: There are techniques to limit token usage inside a session; we wrote about it here).

The skill that solves this is the handoff skill.

Everything that happened in your session is saved to a file named HANDOFF.md at the project root, which contains Goal, Current Progress, What Worked, What Didn’t Work, and Next Steps. It reads any existing HANDOFF.md first so updates chain across sessions rather than overwriting context.

In addition, it will append a “suggested skills” section telling the next agent which skills to invoke. (Because without this, the agent might not know in a fresh session).

I had a project where I was building a 10k reader. I almost used the full 1M context window with Opus, so I used /handoff

What is this assisted10kreader?

You’ll see that in a couple of weeks.

May the markets be with you, always!

Kevin