At least once a year, Twilio CEO Khozema Shipchandler’s right hand cramps up from a few hours of writing. He’s not signing copies of a book.

The pain, instead, comes from penning personalized notes to every member of the technology company’s 80-plus-person leadership team ahead of their annual retreat.

“After every 10, I have to take a 30-minute break,” Shipchandler told Business Insider of the deliberately analog ritual, which is rooted partly in his own memories of being a more junior employee at GE and how special it felt to have a senior leader take notice of him.

“I have no idea what the words were, I can’t remember, but I definitely…