A Manager's Guide to Claude, Six Months Later

Back in February I wrote a manager’s guide to working with Claude. In that guide I described Slack as my command center, generating automated briefings and team summaries, as well as a wish list that was mostly limitations. Some of my wishes came true, some didn’t, and some of my automations were sunsetted. In other words, my usage is evolving and this blog post is to document the evolution.

A Wish Granted

Our Claude in Slack solution got write access to Google Docs. As a result, my briefings and summaries can now keep schedules, persist deadlines for later, and remind me as we approach those deadlines. Write access also enabled automated working backwards documents. The team simply feeds it one or multiple epics with pointed stories and the skill will generate a delivery timeline against several different resourcing options. All of this of course using actual team delivery metrics to estimate velocity.

Feature Flags That Clean Up After Themselves

In February this workflow was half-built. The automated release schedule would remind me of previously launched features and ask if a PR should be cut to remove it. It would create the PR but I would need to run a series of tests to ensure functionality didn’t regress and post the PR up on Claude’s behalf for code-review. This has now been nearly automated for some of our software. Claude will cut a pull-request and post that PR to a dedicated pull-request slack channel after running a series of UI regression tests to ensure application functionality. For the vast majority of our feature launches, I trust it without a second look.

I’m quietly most proud of this automation because feature flag cleanup is precisely the kind of work that will never get prioritized.

The Early Warning System

The newest Slack workflow is an early warning system that warns us when business decisions in other channels will impact our software. We now look for these decisions in the background and warn the team on a regular cadence. The goal of this process isn’t to provide context of those discussions or decisions, but rather to notify us ahead of time so we can make appropriate proactive adjustments if necessary.

Tabloids and Other Fun

These workflows are helpful, but they are also dull, mostly informative, and lack any human spirit. So we made it fun. The daily briefing now gets a tabloid newspaper mostly designed to be fun. The skill is set up to be as snarky as possible. It’ll use the information from the daily briefings, summaries, and metrics to create a snarky tabloid. Sometimes it too is dull and lacking human spirit. But at least one a week is gold and quite funny.

Closing Thoughts

Iterating on my Claude automations has been fun. It’s a challenge of sorts to see how much of the daily toil I can take away from my daily tasks and how much of the valuable information I can surface to myself and our product partners every morning. And Slack is the perfect place for all of this automation work.