In response to some queries about how chevruta should work, I want to post some thoughts on how you might approach this powerful Jewish learning methodology.
Both partners should arrive at the learning session having read the text.
Both partners should bring a copy of the text they are studying. Trade off reading out loud to one another, one bit at a time. Sometimes this bit will be a whole paragraph, sometimes just a sentence, and sometimes even just a word. It depends on what you find in it.
After you've read the paragraph or sentence, go back over it to make sure you've understood the most basic meaning. What is the author saying?
If you are the kind of person who is quite shy, make sure you are contributing to the conversation. If you are the kind of person who loves to talk and is brimming over with thoughts about the text, make sure you make plenty of space in the conversation for your partner to participate.
Keep in mind that every person has something unique to bring to the text. If you hold back your insights, or if you prevent your partner from participating, you are silencing the insights, culled from a lifetime of experience of being a human, that are waiting to come out.
What are your reactions to the text? Do you agree with it? Does it resonate with other things you believe? Do you disagree? Why? How does one paragraph connect to the next - is there an argument that is being built? What are the assumptions of the text? What assertions about human nature are being made? What assertions about God are being made?
What are your emotional responses to the text (this may not always apply, of course)? Chevruta study doesn't have to be a mere intellectual exchange. If you find your anger swelling at a certain passage, or if you are particularly moved by a particular passage, that's important. Delve deeper to find out what about the passage is hitting you so hard.
The conversation should be informed by your life experience. The conversation should absolutely drift from the text at times so you or your partner can "open up" or clarify a certain passage with insights from personal experience. How far afield you run will depend on your judgment, and your partner's, as to how valuable the conversation is. However, you should avoid the temptation to read one paragraph and then have it become a schmooze session. Make time to schmooze afterward. Make sure you return to the text.
Don't feel that the primary purpose is to get through the entire chapter. All things being equal, if you have enough time, or if you are meeting more than once between classes, this is the best thing. But if you are rushing through the text just to finish, you are shutting down all the best parts of the conversation. At the same time, if you only cover one paragraph in the session, you won't really have a chance to engage with the work.
It is 'ok' not to agree with the text. Keep in mind that Orchot Tzaddikim is 550 years old! You need to avoid simply giving up on the text. This wouldn't be giving kavod to this teaching which has touched so many lives.
Make notes about the parts that bother you. There can often be great insights that emerge from disagreeing with a passage if you can be patient enough to stick with the text and explore where it is coming from and then articulate where you are coming from.
You and your partner may disagree about the value of a passage, or even about its meaning. It is important to explore those disagreements. But do so with a sense of respect and humility. The point of chevruta is very much NOT to convince the other person that they are wrong. I would expect that many disagreements will simply be left unresolved.
Your book should look messy with pencil marks, underlines, marginal notes, and questions when you are done.
There are some further resources here.