Where to start?
In one of my previous roles the release cycle was very long. This was not because we didn't want to release more often. It was simply because the system was very large and there were only few customers. Typically the upgrades would require significant manual intervention anyways. On the other hand, quality was a real issue and starting the improvements in that direction was a good choice by introducing a set of new tools, new designs, new technologies, new equipment, and new process. It was very focused on the inside of the development team.
In my current role we moved from one major release per year to monthly release cycles earlier this year. And although there were some concerns with it we were able to mitigate the impact in such a way that our clients can choose their own upgrade cycle. Whenever there is a feature of interest in a new release they can upgrade from their current version to the latest version in a one-step process. There is no need any longer to upgrade to the any of the versions in between. So, while we still offer new features each month, no client is force to upgrade on a monthly basis. There are, though, some clients who do, and each month there are clients who upgrade to that monthly release.
With this background it has become clear that just moving to monthly releases wasn't enough. Instead we combined it with significant efforts to simplify the upgrade process for our clients. And the feedback we get from clients in different geographies is very positive. Therefore we will continue improving the upgrade process so that it becomes even easier for our clients to move to later and even better versions of our software. With this ever-improving upgrade process in place we have established a delivery mechanism that allows us shipping new features faster to the market place. New features are picked up sooner and we receive feedback and suggestions faster as well. Our clients benefit from earlier availability of new features that in the turn allow them to run their business more efficiently.
In the second example I focused on the delivery process first - short release cycle combined with easier upgrades - while in the first example I focused on an improved engineering environment first. In the second example think of this: What if you had the perfect product but it would be a nightmare to upgrade? It would be very difficult to get improved versions installed on client's sites. If on the other hand you have a very simple upgrade process (and hence delivery process) you can roll out product improvements much faster.
There is no hard and fast rule what to do in each scenario. The key learning is that you need to identify what the determining factors are for your team's environment. Then create options and see how they would address the biggest challenges in your situation. Start in one place, and start small. Then observe and take the next step. And make sure you line up your team members. In particular their creativity and innovation are key elements to selecting the right starting point and to successfully move from there.