1Build an AI that remembers how you manage
Turn Cowork into a system that learns your voice, your preferences, your team's context, and your standards over time.
live workshop · rsvp open
Claude Cowork 201: Turn your chat into a chief of staff
Dave Kline Leadership Coach & Founder
Most managers use AI for the easy stuff. Here's how to point it at the hardest part of the job: developing your people.
- When
- Wednesday, September 30, 2026 · 2:00 PM EDT Wed, Sep 30 · 2:00 PM EDT
- Length
- 1 hour 30 minutes
About this live course
Most managers use AI for the easy stuff: drafting emails, summarizing notes. The hardest part of the job, developing people, gets none of that leverage. Every chat starts from zero, so nothing sticks.
Cowork changes that. It remembers your team, learns your style, and runs real work in the background. In this session, Dave builds a working setup live, aimed at frontline managers who want an AI chief of staff rather than a smarter autocomplete. In about an hour you'll see how memory, skills, connectors, and scheduled tasks turn one prep session into a system that runs itself each week.
In this session, you'll learn
5 outcomes2Turn your best thinking into a repeatable Skill
Build a Skill once from real work you've already done, then run it the same reliable way every time.
3Automate your weekly prep
Connect your calendar and memory and schedule a Skill so next week's prep is done before you sit down.
4Wire the pieces together
Projects, the Chrome extension, and voice mode that talks back, connected into one working system.
5Point it at your team
Steer the setup toward accountability, follow-through, and developing your people, not just clearing your own tasks.
What to expect
Live on YouTube
Come back to this page when the session starts and join with one click.
Hands-on workflows
Real setups you can copy, not slideware.
Open Q&A
Bring the AI workflows you are trying to make more dependable.
Replay for 48 hours
The recording lives on this page for 48 hours after the session, with an AI summary PDF.
A preview of what we'll cover
- The one-off chat problem: why nothing sticks when every conversation starts from zero
- Projects and memory that hold your team's context between conversations
- Building a Skill from work you've already done
- The Chrome extension and voice mode, and when each earns its place
- Scheduling a Skill so prep runs on its own
- Using the system for accountability and developing your people
Tools used in this session
Claude Cowork
Your instructor
Dave Kline Leadership Coach & FounderFor 20+ years, Dave Kline led high-performing divisions at Bridgewater and Moody's, and has trained thousands of leaders on how high-performance teams actually run. Today he's an executive coach for eight- and nine-figure CEOs at rapidly scaling companies.
