How do you know if and when to start working with a demon?

Hi! I am deep in debate with working with a specific demon.

I'll spare you the details but at my current state I am a disaster who needs to get my life together, and I need someone to flay me into shape.

And although this demon isnt quite known for this domain, I have a strong feeling he's the guy to help.

But I don't know *if* I should. I've tried every divination method under the sun, all I get is mixed messages and maybes/probablies.

So far I've asked for a sign... and that's it. I dont know if it's a mistake getting into this particular demon.

I'd hate to go in blind and do something rash. How did you guys know with your demons, 'This is what I should be doing.'

Thanks in advance!