Note: we've since moved off on Clockwise because while there was value the pricing model didn't work for our team as we scaled. We've switched over to Motion which handles what Clockwise and Calendly both used to do for us and does it much better.
A crucial aspect of receiving a benefit is knowing that it happened. When software does magic, and you don't notice, it might appear that you received nothing. This introduces an interesting problem for software creators: their product might have gotten too good in some ways.
Clockwise, a product billed as "a smart calendar assistant that frees up your time so you can focus on what matters" offers an example of this phenomenon. A few teammates recently said they "don't use Clockwise" and that they "wouldn't be disappointed if we stopped paying for it."
Upon inspection, it turned out that Clockwise is being used and helping them—they just aren't touching the software! Clockwise is cleaning up calendars and rearranging meetings to be more convenient without them noticing. It's similar to how a Roomba robot vacuum autonomously cleans up the floor of a room with one significant difference: the vacuum is better at making its presence, and therefore its benefit, known to the user.
Your involvement in the operation of software ensures that you understand any benefit that it may generate. I'm not sure I have the perfect solution for best emphasizing value generated automatically without user input. Perhaps software needs to be a tiny bit more visible—enough for you to remember it exists and helps you do better work.
Thank you to Harry Qi for the discussion that inspired this.
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