How do you ensure all your stakeholders are always kept informed on a regular basis?
I think the most important and first step here is to really understand who your stakeholders are, and what methods work best based on timezones, priorities, projects, etc.
As a product marketer, I typically find my stakeholders spread between 3 main groups - product, sales and marketing. Of course there are other stakeholders like program management, data teams, research teams etc - but I try to prioritize defining how I will manage my relationships with my core 3 internal groups.
With my marketing counterparts, it tends to be a bit easier - we sit in the same team meetings, we share tools, and there tends to be more visibility naturally, so that is supplemented with 1:1s where it makes sense.
With product counterparts, there tends to be a bit more to be done to build relationships. Historically we don't always share the same tools so documentation has been important as a source of truth between our teams. In the best case scenarios, its helpful to join specific meetings that help provide context, and leave room for feedback. And this is also supported through 1:1s where it makes sense.
On the sales side, finding meeting time can be harder when it means taking sales folks off the floor - so 1:1s may be less often, and we lean on asynchronous ways to share information, and plugging into existing channels where it makes sense.
These are just a few anecdotal examples, it really depends on your specific environment, but start with understanding your stakeholders and their needs and you can't go wrong.
Keeping stakeholders informed on a regular basis can involve a variety activities, including:
Sharing updates in broader company forums (all hands updates, OKR updates, Slack / Teams / email updates)
Regular syncs with key functional leaders
Regular syncs between product area owners
Documentation on ongoing trackers or project management tools