You also know too much persistence can strain a relationship. So you hesitate to persist even when you know it's your only chance.
Most people ask themselves if they're pushing too little or too much. That's not the most effective question to ask yourself.
More effective is to ask:
What can I do to make my persistence work so they'll appreciate it?
In business, I hustle and I value relationships. I've experimented a lot in this area and found a few things that work and build relationships at the same time.
You've had people persist and annoy you, but you've also had people persist so you appreciated their effort. How do you make sure you're the latter?
Involve them in the process with magic phrase No. 1.
When I wonder if I might be pushing someone too much, I use my strategy: How do you decide when your decision affects other people? Involve them in the process. In this case I've developed a way to ask the other person in a manner that has elicited positive responses every time I've used it.
I have put the following question countless times, basically verbatim:
Am I persisting too much, too little, or just right?
The other person has always answered. The most common response begins by thanking me (an amazing turnaround when what prompted my writing it is usually anxiety) and telling me I persisted just right.
Often they'll ask me to persist more.
Politely surprise them with magic phrase No. 2.
I'm writing this post because I just used magic phrase No. 2 and it worked successfully, the same as every other time I've used it.
Sometimes someone doesn't respond. You don't think they're trying to blow you off, but they aren't writing back, either. How do you engage them?
My second magic phrase works in this context:
I hope I haven't said or written anything offensive.
I copied that verbatim from a recent email to someone who hadn't responded to three emails. We're working on a project together, and I depended on him doing something for me. He didn't depend on me, so I had little leverage, making it difficult to ask him to do more or even respond.
He responded basically the way everyone does:
No, Joshua, what you wrote wasn't offensive, but it brought to light what seems to be a misunderstanding.
He then explained the misunderstanding that he had been sitting on until then. We resolved it, and collaboration continued.
You know your relationships better than anyone else. You know how to communicate with your people.
These phrases have worked for me each time I've used them. I can't guarantee they will for you. They aren't the whole email. You have to fit them into the context of the rest of your communication.
I recommend trying them, though, because they help change the question from "Does persistence pay off?" or "Am I pushing too much?" to "How do I persist so everyone benefits?"
Then you become someone people thank for motivating them.