Is it better to start with the biggest issues, then work out the ancillary or other smaller issues? Or will you be better off sorting out a bunch of smaller issues before taking on the big one? Here’s how to decide.

Starting with a big issue
The upside of starting with the biggest issue in conflict resolution is that ancillary issues may turn out not to matter much once the primary issues are resolved, or they’ll feel easier to sort out.
The downside is that big issues are often the most difficult, so starting there could lead to early frustration, deadlock, and temptation to throw in the towel.
Starting with small issues
The upside of starting with smaller issues is that a series of “quick wins” together can set a solid foundation of teamwork and hope for tackling the bigger issue(s). If you read my first book, Making Mediation Your Day Job, you may recall a story by my friend and colleague, Susanne Terry, called The Thousand-Link Crossing. It’s about the way a series of small yesses can lead to resolution.
The downside of starting with smaller issues is that it can feel like you’re postponing the “real” work and leave participants feeling like they’re not accomplishing a great deal.
How to decide
There is, as you see, no rule, not even a rule of thumb. It’s a judgment call based on the participants and the situation.
Here are some guidelines for deciding:
Is the big issue potentially explosive or really overwhelming? Start with small issues to help them build success before tackling the big issue.
Is the big issue so big they can’t see past it to work on smaller issues? Start with the big issue, then.
Are the participants generally in good spirits with each other, but just stuck? Then it may not matter and starting with a big issue might feel very relieving to them.
Are the participants quite ugly with each other? Probably best to build momentum with a series of small successes before tackling bigger issues.
What are they inclined to do? You don’t have to carry the weight of the decision. They may well have an opinion about where to start and if they agree on that, start there.
And if you realize you picked wrong, no one will leap out of the woodwork and force you to continue on that path. Change direction, setting aside the initial issue for now, and move on.