How do you keep transitioning to the next set of tools?

Pontifications

For example, I would argue that gmail was the right call in 2004 but now slack is better (at least internally).
How do you a) find the next set of tools b) move successfully there
e.g. slack will one day be legacy and cruft. how do you identify slack.next?
My guess: have a very small group of tastemaker trailblazers who try things out and continuously roll out new things to progressively larger groups. Extremely difficult because this group can become moribund itself. I guess you need to get new folks into the group or find a way to have decentralized small groups and/or have a way to do things more than one way inside an organization. This is hard because a lot of folks only want one tool, one way. I say the more the better as long as you get the right things done at the right time. Again extremely hard!

This post was inspired by:Tools as a catalyst for culture change:

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"Fostering continuous learning

One risk of a strong internal community is that you may become cut off from improvements in the world outside your company. One of the underlying premises of Jeff’s “find what best looks like” principle is that in a world with more than 6 billion people, there’s inevitably someone doing whatever you’re doing better thank you. As a leader, you should recognize and reward your employees for adopting and promoting better ideas from outside your company. Also, it’s powerful to put your money where your mouth is and invest in your people’s external learning, by funding their travel to visit other excellent companies and investing in their continuing education. One of the investments I’ve been most happy with is our subscription to Safari Books Online, which gives our employees access to a vast library of excellent books as well as the ability to watch replays from all O’Reilly conferences, where top industry experts share their most recent insights and practices."

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