When coaching teams you want to use appropriate time to understand the current reality. Not too little, lest decisions are based on fantasy. Not too much, lest talk fails to turn into action. How much is enough? This is actually a wrong question. It is not about the time you use to dissect the situation, it is the manner. Here are the things you want the team to see:
1. The big picture.
You want the coachees to see the situation beyond their usual point of view. You want them to consider how the different problems they have fit together. For example, the fact that the build monitor is nearly constantly red, and the fact that customer never seems satisfied with the sprint results may be tied. If so, it is important to notice and understand the systemic relationship. Otherwise the team a naive solution to one problem may make the other problem even worse.
2. Just enough details.
Avoid going to too much details. The right level of discussion is such that everyone can follow and understands what we are talking about. There is a tendency to talk about individual tools or people. If a specific tool or person really is a problem, then go ahead and discuss it. But almost always, the actual problem lies elsewhere.
3. Both the team and the environment affect the situation.
Teams tend to blame others of their problems. This is usually fruitless and should be avoided. However, it is not good to deny the current reality. The constraints of the environment (including other people) must be understood, and taken into account. Otherwise the team will bump into problems very soon when they try to change things.
4. Improvement is possible.
The aim is always to turn understanding into action. The team must not be overwhelmed by the trouble. It is not the size or the amount of problems, it is how they are viewed. A myriad of problems becomes reachable, when you see the connections between them. A depressing problem becomes an exhilarating challenge when the teams believes in its ability.
5. This is interesting and important.
What form the above suggestions take in coaching depend entirely on situation. For example the number of people involved: it is practically impossible to reach a common deep understanding with a conversation of, say, twenty people. In that case you may will want to talk to individuals beforehand so you understand the situation very well when the whole group meets. On the other hand, with four people, you can actually have a fruitful discussion right then and there.
Good coaching captivates people, makes them feel the things are important and they are important.