Colin Cox - Work Smarter Company

AI Bootcamp: Session 2

Make it yours: a smarter Cowork, context files, skills on a schedule, and the quality bar.

The Work Smarter Company01

Session 1, as reported at the water cooler

A teammate10:00 AM

Me before AI Bootcamp: Caveman SpongeBob

Me after AI Bootcamp: Handsome Squidward

25 3

Accurate. But handsome is not a one-time upgrade, it is a habit.

Today: how to stay Handsome Squidward when the novelty wears off.

The next hour

Four parts, three live demos, and one challenge you can finish by Friday.

01Cowork has leveled up
What changed since Session 1, and how to push through a bad first draft
02Context files
Stop re-introducing yourself in every chat
03Skills and scheduled tasks
Teach it once, put it on a schedule, let it come to you
04Preventing AI slop
The quality bar before anything leaves your desk

Then Q&A, and one action to take before Friday.

Part 01 of 0415 min

Cowork has leveled up

The tool you learned in Session 1 has been quietly getting stronger. Four upgrades change how you should work with it, starting today.

Runs while you sleep

Scheduled tasks no longer need your laptop open or your PC on.

Chat vs Cowork

Two modes, two jobs. Knowing when to flip the toggle is half the skill.

Three dials for hard problems

Subagents, models, and effort: more thinking power when it matters.

Pushing through

What to do when the first output is bad. Hint: not giving up.

Part 01: Cowork Has Leveled Up

Your automations no longer need you awake

The biggest change since Session 1: scheduled tasks now run in the cloud. Close the laptop, shut down the PC, go on vacation. The work still happens.

Before

Your scheduled task was tied to your machine. Laptop closed at 7am? The 7am task never ran. The automation was only as reliable as your charging cable.

Now

Tasks run in the cloud on their schedule, whether your machine is awake, asleep, or in a bag. Results are waiting for you when you show up.

Why this matters: Anything worth doing weekly is now worth scheduling. The excuse "I forgot to run it" is officially retired.

Part 01: Cowork Has Leveled Up

Chat or Cowork? Pick the right mode

Same brain, two working styles. The toggle at the top is the most underused control in the product.

Chat

A conversation. You stay in the loop.

Quick questions, summaries, and explanations.

Drafting and editing where you want to steer each round.

Thinking out loud: pressure-testing an idea before a meeting.

Cowork

A delegation. It works, you review.

Multi-step jobs: research, build, and assemble in one run.

Anything touching files: documents, spreadsheets, decks, folders.

Long tasks you would rather not babysit. Set it going, come back.

Rule of thumb: if you would forward it to a capable assistant, it belongs in Cowork.

Part 01: Cowork Has Leveled Up

Three dials for hard problems

Default settings are tuned for everyday work. When the problem is genuinely hard, you can turn up the machine. All three dials exist in Claude Cowork and Claude Code.

Subagents

Parallel workers on one job. One researches, one drafts, one checks. Big tasks stop being serial.

Models

Pick the heavyweight for the hard call, the fast one for the routine sweep. Match the brain to the problem.

Effort

Let it think longer before it answers. Cheap insurance on decisions you will live with for months.

When to reach for them: Ambiguous, high-stakes, or multi-part work: dial up. Reformatting a table: leave the dials alone. Matching horsepower to the job is what separates power users from tourists.

When the first output is bad

It will happen. What you do next is the whole game.

Caveman SpongeBob

Gives up. Or worse, ships it.

Tries once, gets a mediocre result, declares AI overrated.

Never says what was actually wrong with the output.

Starts from zero next time and gets the same mediocre result.

Handsome Squidward

Treats it like feedback, not failure.

Tells it exactly what is wrong, in plain language.

Has it write the lesson into its memory or its skill.

Runs it again. The next version, and every version after, is better.

The first output is the start of the conversation, not the verdict.

Live demo

From bad first draft to solid v2, live

We build something real, it comes out rough, and we fix it in front of you. No edited highlights: this is the actual loop you will use every day.

What to watch for

01
The first version comes out mediocre. That is normal, not broken.
02
I critique it the way I would critique a junior's draft: specific, direct, no code words.
03
It updates its own memory and skill so the lesson sticks.
04
The rerun is visibly better, and tomorrow's first draft starts from there.

Part 02 of 0410 min

Context files: stop re-introducing yourself

Every great prompt you have ever written had one thing in common: context. A context file means you write that context once, and every conversation starts warm.

The re-prompting tax

Why pasting the same background into every chat is costing you the output quality you want.

What a context file is

A document the AI reads automatically: your role, your standards, your world.

Live build

We create one for writing style from real samples, and watch the output start sounding like you.

The re-prompting tax

A context file is a document the AI reads at the start of every conversation. Write the background once, never type it again.

Caveman SpongeBob

Re-introduces himself every single chat.

Types 'I'm a customer success manager at a payroll company...' for the 40th time.

Forgets half the background, gets generic output, blames the AI.

Every conversation starts cold.

Handsome Squidward

Wrote it down once.

Role, team, product, audience, and standards live in a context file.

Every chat starts already knowing his world.

His prompts are one sentence long and his outputs are specific.

Good context is why two people get wildly different results from the same AI.

Live demo

Build a context file for your writing style

We feed it two or three things I actually wrote, have it extract the style, then generate something new. The goal: output that sounds like me, not like AI.

What to watch for

01
I give it real samples, not adjectives. 'Professional but friendly' tells it nothing.
02
It extracts the patterns: sentence length, rhythm, words I use, words I never use.
03
We save that as a context file, one time.
04
The new draft sounds like me on a good day, and it will tomorrow too.

Part 02: Context Files

Three context files worth building this week

Writing style is just the opener. Each of these takes 15 minutes to build and pays you back on every conversation after.

Your role

What you own, who you work with, what good looks like in your job. Suddenly its suggestions fit your actual responsibilities.

Your team's product

Features, jargon, pricing, roadmap. It stops explaining your own product back to you incorrectly.

Your customer's voice

Who they are, what they worry about, how they talk. Everything you draft lands closer to what they need to hear.

Pick one. Build it before Friday. That is half of today's homework already done.

Part 03 of 0415 min

Skills and scheduled tasks

A context file tells the AI who you are. A skill tells it how you do a specific job. Put a skill on a schedule and you have built your first real automation, without writing a line of code.

Build a skill, live

Meeting notes in, tight recap out: owners, dates, house style. Built from one good example.

Put it on a schedule

The skill runs on a cadence you set, and per Part 1, your laptop can stay closed.

It comes to you

The output shows up ready for review. You went from doing the work to approving it.

Live demo

Build a skill from scratch

Meeting notes go in, a tight recap comes out: decisions, owners, due dates, in house style. We teach it once, then rerun it on fresh notes to prove it stuck.

What to watch for

01
A skill is just instructions written down. If you can explain the job to a new hire, you can build one.
02
We build it from one good example of the output we want.
03
Rerun on brand new notes: same quality, zero extra effort.
04
The skill is shareable. Your whole team inherits your best process.

Part 03: Skills and Scheduled Tasks

Now put it on the calendar

A skill you have to remember to run is still a chore. A skill on a schedule is an employee.

1. Teach

Build the skill once, from one good example. Correct it until the output is right.

→

2. Schedule

Make it a recurring task in Cowork: every Friday at 4pm, every morning at 7.

→

3. Receive

It runs in the cloud and the result lands in front of you, ready to review and send.

The compounding part: Every correction you make (Part 1) improves the skill. The Friday report you get in week four is better than the one you got in week one, and you did not touch it in between.

Teach it once.
Schedule it.
Done.

That is a personal automation. No ticket, no engineer, no budget line.

Part 04 of 0410 min

Preventing AI slop

AI made content nearly free to produce. It did not make it free to read. The last part of this session is about the quality bar: what has to happen before AI output leaves your desk.

What slop is

Unreviewed AI output shipped to a coworker as if it were finished work.

The burden math

Easy to generate, expensive to consume. Someone always pays; the question is who.

Three rules

Trim it, add your judgment, and never let it look like AI wrote it.

Two ways to ship AI work

Same tools, same hour of effort. Completely different reputation six months from now.

Caveman SpongeBob

Ships AI slop.

Generates 10 pages, skims none of them, hits send.

Makes his coworkers do the reviewing he skipped.

Everyone quietly starts ignoring what he sends.

Handsome Squidward

Instructs, plans, then inspects and verifies.

Briefs the AI properly, with context and a plan.

Inspects the output line by line and checks the claims.

Ships two tight pages he would put his name on. Because he did.

When you pass raw AI output to a coworker, you are not saving time. You are billing them for it.

Part 04: Preventing AI Slop

Easy to generate, expensive to consume

The math of shipping a raw AI document to your team, in round numbers:

30 min

You saved by not editing the 10 pages down.

5 x 20 min

Five readers each spend 20 minutes wading through it to find the four sentences that matter.

The rule that falls out of the math: The reviewer's time is more expensive than your time saving. Compression is a courtesy you owe the people you send things to, and they can tell whether you paid it.

Part 04: Preventing AI Slop

Three rules before you hit send

01
Trim it before you share it
Ten pages can almost always be two. Cut it down to what the reader actually needs, then cut again.
02
Add the judgment only you have
Your read on the client, the political context, the call you would make. That is the part AI cannot do, and the part your name is for.
03
At minimum: do not let it look like AI
Kill the telltale headers, the bullet avalanches, the 'delve' and 'moreover'. If it reads like a bot, it gets treated like spam.

Q&A

What is in the way of you using this tomorrow morning?

One action before Friday

Not a study plan. Two small builds, both demoed today, both under 20 minutes.

One context file

Your writing style, your role, or your product. Pick the one you repeat most often.

One scheduled skill

Teach it one job you do weekly, put it on a cadence, and let it run with your laptop closed.

Friday you is counting on Wednesday you.

Stuck? Post in your internal AI channel.

Want more? A hands-on power user session is coming.

AI Bootcamp: Session 2

AI Bootcamp: Session 2

Session 1, as reported at the water cooler

The next hour

Cowork has leveled up

Your automations no longer need you awake

Chat or Cowork? Pick the right mode

Three dials for hard problems

When the first output is bad

From bad first draft to solid v2, live

Context files: stop re-introducing yourself

The re-prompting tax

Build a context file for your writing style

Three context files worth building this week

Skills and scheduled tasks

Build a skill from scratch

Now put it on the calendar

Teach it once.
Schedule it.
Done.

Preventing AI slop

Two ways to ship AI work

Easy to generate, expensive to consume

Three rules before you hit send

Q&A

One action before Friday

Contents

Keyboard

AI Bootcamp: Session 2

Session 1, as reported at the water cooler

The next hour

Cowork has leveled up

Your automations no longer need you awake

Chat or Cowork? Pick the right mode

Three dials for hard problems

When the first output is bad

From bad first draft to solid v2, live

Context files: stop re-introducing yourself

The re-prompting tax

Build a context file for your writing style

Three context files worth building this week

Skills and scheduled tasks

Build a skill from scratch

Now put it on the calendar

Teach it once.Schedule it.Done.

Preventing AI slop

Two ways to ship AI work

Easy to generate, expensive to consume

Three rules before you hit send

Q&A

One action before Friday

Contents

Keyboard

Teach it once.
Schedule it.
Done.