When your Engineering team makes significant changes, they are likely producing alongside it the proper process to accommodate everyone involved (if not, contact me). They will make sure to communicate it via emails and relevant Slack channels. Wiki pages will be created, revised, and spread. They will create deployment plans, contingencies, and updates for the on-call personnel. After all, expecting things to work without due preparation would be ludicrous, won’t it?

Now, consider what tends to happen in your organization when non-technical changes are in order: the making of new managers, work processes with Product, feedback framework, promotion to managing managers, and many other scenarios. Many organizations are prone to putting things into motion without setting up the needed support framework to make it likely to succeed and stick.

How can you expect your cross-functional teams experiment to work if no one understands who they should be reporting to, and each person is doing it differently? Why will your post-mortems provide any valuable lessons if everyone is essentially sitting there twiddling their thumbs, not knowing what a good one looks like?

I believe this is called winging it. People do not spontaneously gain knowledge. We are not Neo plugged into the Matrix. No one will sit up after 5 minutes saying “I know OKRs.” Teach your organization how to teach things. Provide the guidance and support needed to make things easier without waiting for questions. By preempting the need and anticipating the issues, you will make it OK to ask questions, and of course, make success likely.