Here's a great post that discusses how Monsanto is not only managing their technical debt but turning it into an asset.
From the start, the author of this post discusses how he realized that their system had to be scale the codebase. Monsanto had at one point invested very heavily in 'grow platforms, but this in turn resulted in a lot of technical debt. In their code base, there wasn't sufficient investment for the future due to this. In order to resolve this situation a new program was implemented called: Modernize, Secure, and Scale. This was meant to improve cybersecurity, platforms and assets, as well as encourage the migration of work to cloud. All of the components of this program work well to reduce technical debt and increase a system's efficiency.
Along with these items, it was necessary to this making sure that Monsanto's network was able to hold the amount of data that at $15 billion corporations has to deal with. Here is where the logic of looking into the future was necessary - the network needed to be refreshed but not just with enough effort that would only push it last another year or two, and then put the organization in the same place where it was to begin with. In order to do this, questions like what investments need to be made in order to develop such a foundation and platform, need to be asked.
This leads to another important factor to consider is total cost of ownership. When developing a feature, simply thinking about whether you will be able to get a return on that investment isn't enough, you need to know whether you can sustain it as well. If you developed a feature the quickly in order to get it to market quicker and have lower costs associated it for launch, you have to realize that over time the cost of that feature will only increase as working on it becomes difficult due to technical debt.
Ultimately, what has to be done in order to make sure that technical debt can be used as an asset rather than have it become an impediment to your organization's success is discipline in delivering what was promised. The CIO of Monsanto, in this post, discusses the mindset necessary for creating maintainable software. This meant providing the executive team quarterly reports on progress going on with respect to modernization of scalability of the codebase. This allows a dialogue to emerge between business and technical stakeholders on the success of a project and on new issues that emerge at any given moment. Having a proper dialogue makes issues of technical debt more real for business stakeholders who may otherwise not understand the issues that IT teams face on a daily basis.
Making software development and the issues that come along with it a topic of conversation is essential for making technical debt an asset, because it allows for proper funding on future endeavours and understanding on the issues associated with them.