Like many others have said, this is a terrible LPT. You're just wasting time and goodwill which will result in you not getting what you want. If you aren't thrown back into queue, the person you get to will 'warm xfer' you to the other dept. The 'warm xfer' is first agent calling 2nd agent and saying something like "this joker called me to get out of the system to talk about a refund so handle accordingly (nudge nudge"). 2nd agent will take call and then deny your request because you were basically trying to be sneaky and waste others time. See how that works? So just use the system and get to the right person. That's what it's designed for. If you don't like the system or can't xfer, then use chat or email.

Here's a copy/paste of my answer to another "LPT" about automated systems.

I built these systems for a couple decades and these LPTs are getting annoying. There is no secret to any of it. It all depends on the individual design choices. Some companies don't want you to talk to an agent so no amount of pressing 0 or * or # will get you there.....ever.

It's not like there is a documented set of ISO design standards for IVRs. Sure there are best practices, but management will ultimately decide when/if you talk to someone.

Edit: Ok, rant over. You want tips from a designer?

Tip 1: try using the system. You might be surprised at how much time it could save you. It also helps keep costs lower by reducing operating costs of having much more expensive agents handle your rote transaction.

Tip 2: Option not available in the IVR? Ok, listen for the option to transfer. If it's not there, then try 0. If using a speech reco system, say agent or representative or person. In speech reco, you have to pass or fail a defined grammar of responses. A well designed system might have these. I say might because if the company doesn't want you to transfer, you won't no matter what you say or push.

Tip 3: You will likely have to fail 2 or 3 times. Many of these systems are designed to handle your error and prompt again, and again. That's right, there's error handling and call recovery designed in.

Tip 4: As someone else said, some of these systems do sentiment analysis. If you sound angry or frustrated, they will detect that prompt accordingly (maybe next prompt will ask if you want to speak to someone). These are likely companies with lots of money and focus on customer service....so not that many. This feature is pretty expensive.

TL;DR there's no one trick that works because each system is uniquely designed and has unique feature set. Don't like the phone system? Use email or chat instead.