In last week’s entry, we discussed the importance of considering the situation when evaluating someone’s behavior rather than attributing the behavior solely to a personal trait. In this entry, we will zero in on three of the most important situational factors to consider so you can increase the likelihood of conversational success.

Although there are an infinite number of situational factors that you could consider (such as the location, the lighting, the seating arrangement, the time of day, and so on), the three factors with the greatest impact on goal attainment are: what motivates, what frustrates, and what is the most opportune time for the conversation.

Look for what motivates.

Consider again the employee who can’t get to work on time but somehow manages to be sitting in the swamp at 4:30 a.m. during hunting season. Our intrepid predawn duck hunter is certainly demonstrating that he could show up to work on time, so it very likely that something in the work environment is causing his tardiness. Perhaps something about the way the job is structured is stifling his motivation. You could try to adjust the employee’s work schedule—he might be motivated to arrive to work on time if he could avoid morning traffic. The point is that a chronically tardy employee who can be sitting in a swamp by 4:30 a.m. on Saturday is telling you something about the work situation and something about himself. Both of these pieces of information are useful.

Look for what frustrates.

In addition to identifying factors that motivate, identify and avoid factors that frustrate. Two of the most common frustration triggers are specific people and particular topics. Some people just don’t mesh, and if you put them together in a conversation your chances of reaching your conversation goal will plummet. The same is true for certain topics. Start with the most obvious frustrations and, over time, increase your precision. If you know that your boss strongly dislikes Steve from accounting and that she also reacts negatively to last-minute travel requests, keep Steve miles away from her and submit your travel requests on time.

Build on these rudimentary observations and, over time, see if you can develop your observations more completely. Is there something about Steve that you can generalize to other people (maybe your boss doesn’t like aggressive, flashy young men). Maybe she doesn’t like last minute travel requests because she thinks that the company is wasting too much money on travel, or maybe she’s under fire from her boss for too much departmental spending. There are often insights that can guide your interaction strategies behind the things that frustrate.

In important work relationships, you will often have months or even years to accumulate information and to learn about the things that frustrate and the things that motivate key people in your work life. Watch and learn—this represents an important investment in your situational understanding. Once you have a good understanding of these main situational factors, do one more thing—select an opportune time for your important conversations.

Then, choose your time.

People fail to choose the most opportune time for a conversation not because they don’t know that the moment is not right, but because they don’t feel like waiting. Said differently, most people have the brains to figure out a good time for a conversation—they just don’t have the conversational discipline to act on this knowledge. Remember this conversational rule of thumb (and slight exaggeration): If you are dying to have a conversation, it’s probably going to kill you.

Most of the conversations you are itching to have actually do not have a legitimate conversational goal—your mind is rationalizing a fake goal to justify the emotionally fueled words you want to say. We will discuss conversational goals (and fake goals) in next week’s entry, but for now just remember that conversations that you are itching to have are probably going to rub the other person the wrong way. When it comes to evaluating the situation, look for what motivates, look for what frustrates, and then choose an opportune time to talk. Doing these three things will increase your odds for conversational success.