In the arcane world of duplicate bridge* there is an adage that if your opponents never make the contracts you double, you are aren't doubling enough.
* [Duplicate is one of my favorite recreational pastimes—there's something deliciously weird about being at a major tournament where you're in a hotel ballroom for three hours straight with hundreds of card tables chock-a-block with players and no one is speaking above a whisper.]
The operational principle here has an analog in cooperative group dynamics: if you're never sporting any arrows in your chest, you're probably being too wimpy. Mind you, I'm not advocating assholery—there's plenty enough of that without my being a cheerleader for it. Rather, I'm talking about having the courage to speak up when someone does something than seems off in the context of a group you're both in.
While it's no doubt worthwhile learning how to voice feedback in ways that are less likely to be provocative, there are no guarantees. At the end of the day, if you're regularly speaking up, then you're occasionally triggering reaction. It goes with the territory.
To be sure, there are number of ways that giving feedback can land awkwardly:
1. You may have misunderstood what happened
Perceptions, amazingly enough, are not the same as reality. While I think reactions are a decent motivation for speaking up, it can be embarrassing when you got it wrong, and you're reaction is out of line.
2. You may not know the full context
Even when there's no discrepancy about what happened, or what was intended, you may not know enough of the background or the specifics of the situation to understand the choices being made and what they mean to the key players. Maybe you only heard or saw part of the exchange. Simply put, your reaction may be out to lunch and not helpful. At a minimum, it'll be irrelevant; at worst, it can be trigger a secondary first that's more dangerous than the one you thought you were putting out.
3. Your group may not have any agreements—or even understandings—about acceptable ways to deliver feedback or to work constructively with tension
As a consequence you're on your own when speaking up. The default for most of us is to deliver feedback as we would want it to be given to us, which, unfortunately, may have no bearing whatsoever to how the other person prefers to receive it. In short, it's a crap shoot and good intentions alone will not necessarily see you safely across No Man's Land.
4. You may get creamed for calling someone out
Voicing critical concerns can result in your being the target of backlash criticism ("How dare you question what I did?"), even if there are agreements in place that what you did is "supposed to be OK." In all probability, the theory about how your group wants to support feedback was developed while people we're responding from their mammalian brain; the reaction comes from a dynamic moment that is being processed by their reptilian fight-or-flight brain. Uh oh.
One of the key measures of a group's maturity is the environment it creates for constructive feedback. When people get punished for speaking up, it's a bad sign. When there's curiosity in the presence of upset, that's gold.
In such a dynamic, you'll likely have a multi-car accident and it can be awkward knowing where to start and a challenge keeping the focus in one spot long enough to ease tension there before the second intrudes upon the first. Here's how it works: Let's say Jesse is upset with something that Kim did (or didn't do) and that upset leaks into the way Jesse gives feedback to Kim. Now, in addition to Jesse's original upset, you also have Kim irked with how Jesse delivered the news. What to do?
Pick one of the two (probably whichever seems the most upsetting) and work that through before getting to the other one, promising all parties that everyone will get a turn being heard and having their concerns addressed. Hint: In the example above, if you start by focusing on the aggressive way that Jesse gave feedback (Kim's reaction), you'd likely begin by hearing from Kim about how the feedback landed, which would not be comments about the behavior that triggered Jesse; it would be about how Kim felt attacked by Jesse. Then, when you asked what Jesse heard, you'd be looking for a reflection, not why the forcefulness of the criticism (an attack) was justified by Kim's original behavior. In short, you need to keep the focus on one thing a time, and not let the examination devolve into a ping pong match, where the protagonists are exchanging salvos instead of information.
It can be done! Really.