I built a Claude Cowork scheduled task that runs each week across my recent meeting transcripts and written communications, looking for patterns in how I communicate.
There is a little setup behind it, but once that is in place, it can review a week of meetings, emails and documents together. Claude first needs access to the tools where those communications live, through connectors, and meetings need to be transcribed by whatever recording tool you use. The transcripts then need to be stored somewhere Claude can reach, such as Google Drive.
This flow was not designed to tell me what was decided or pull out my action items. I have other workflows for that. This was designed to help me get better.
It tells me where I was clear. Where an idea I pitched landed. Where I helped move a conversation forward. And where I over-explained, softened a point too much or talked too much. The point is not just to generate an interesting personality assessment. I have asked Claude to use real examples as coaching material: show me the sentence, explain what it did, and suggest how I might handle a similar moment more deliberately next time.
Claude noticed that I change register depending on the relationship without sounding like a different person. It described some of my communication as "a strategist wearing a woollen jumper". Warm and fairly casual on the surface, but still asking the right questions, testing assumptions and intentionally nudging toward decisions.
Other observations have given me some work to do. Claude noticed how often I make myself flexible. I'll say "no rush", offer to work around someone else's schedule or suggest we start and assess as we go. That can lower the pressure and make it easier for someone to engage, but it can also lead to ambiguity, decision paralysis and schedule delays.
A single email or meeting wasn't going to be enough, but across several weeks, my repeated habits become much easier to see and Claude has some real patterns to base the analysis off. This private coaching is already helping me understand what my communication style is, identify the habits that make my communication less effective and target something specific to improve on each week.