One of my favorite topics to discuss with my boss is the need for maintenance work, doing code updates and refining existing code with new techniques. Especially things like: a new Telerik controls update (got to love breaking changes).
How do you convince your boss?
Simply - my boss knows that there are new customer requests, new bugs are being found in our software, we need more features to stay on market, operating systems add new requirements for software to work properly (DEP, UAC created the need to change something). With packed software you always need maintenance.
Really hard to do because a lot of bosses are of the "if it ain't broke, don't fix it" mentality, which from a business perspective, makes sense. You need to tell them how your new changes are going to save them money in the long run, even though in the short run it will cost them a pretty penny.
Plus if you can clearly demonstrate the benefits of fixing vs keeping the old system (in addition to monetarily), they may be subject to changing their mind.
Do some reading on the subject to learn some hard and fast reasons for doing it (it's called "refactoring", by the way). It's pretty quantifiable, as much as such things can be, and quantifiability is the best way to convince.
http://en.wikipedia.org/wiki/Code_refactoring
Martin Fowler's book is a pretty good start also.
If my mechanic told me about these new modifiable bucket seats made for astronauts that fit in my car, I would ask: What is in it for me? What is it worth? If it isn't worth the return, I probably will not get it done.
Only things that have appreciable ROI to the business get worked on.
You can sometimes tie small tech updates to those things.
The large ones are only approved if they bring in the moolah.
G'day,
You might like to have a read of this short article "The ROI Variable" which I happened to read just yesterday. It's from the excellent book "97 Things Every Software Architect Should Know" (sanitised Amazon link) which is an excellent read covering all sorts of topics.
It gives an example of a typical argument to use to support your case of the need for such work.
Edit: I forgot to say that this is pretty much how I go about convincing people about this need BTW. Managers are numbers people, convince them of the benefits and you'll get their support along with providing them with ammo for any arguments they may have from higher up!
HTH.
'Avahappy.
I usually try to talk in terms of being proactive vs. reactive. Most managers understand that working in a strictly reactive mode is much more expensive than being proactive.
Relate maintenance and updates to being proactive and its a hard argument to lose.
I agree with Rob Wells, to convince the "average" boss, you need to talk in terms they can understand. I have good experience using the "technical dept" metaphor. It is something even nontechnical people can understand and it allows them to understand things like why one can get away without cleanup for a short time, but the longer the program will need to be maintained, the more important a cleanup is" (long running dept with interest is expensive).
Might be worth a try.