Even when we do it well, asserting ourselves often has a social cost. For this reason, we need to choose our battles wisely. To speak up or not to speak up – that decision can create a lot of anxiety; yet the answer may become clear simply by taking out a piece of paper, drawing a line down the middle, and listing the pros and cons. If that doesn’t do it, try running it through a risk assessment with expected values. Simply assign values and probabilities to your potential outcomes for each alternative and compare the bottom line.

Let’s say, for example, that Lu would like to ask her very touchy VP, Kim, to communicate better with another VP whom Kim dislikes. If Lu could put a dollar figure on what having a successful discussion with Kim about it was worth, Lu might decide “My work would be easier and I might achieve my bonus worth $10,000 if they could get along better”. Unfortunately, Lu believes that the probability of a successful discussion with Kim is about 10%. In fact, even asking for it might result in “punishing” behavior because Kim might think Lu is taking the other VP’s side and that’s worth $3,000 to avoid – just to put a number on it. There’s about a 75% chance of a punishing response. Then the net expected value of this decision is negative. That is, Lu is likely to make things worse just by asking. Now clearly those numbers are not real but they might help Lu compare the order of magnitude of the two alternatives – but she’s not done yet.

Such an analysis may show that sometimes it’s not worth it to speak up but don’t give up too soon. Ask yourself, what you can do to reduce the risk? Look at each element in your table. Can you add more pros, reduce cons, do something to affect the significance of the values or change the probabilities?

Overall, two things you can do to improve your odds of a successful conversation with anyone are to leverage relationships and master Deliberate Dialogue^(R). The more you invest in building relationships with people and the better your communication skills, the more likely the expected value of a difficult conversation will be positive.

For an Excel spreadsheet that helps you conduct an expected-value analysis like this, click here: Choose your battles