What behaviors does he reward?

Just like anyone else, your boss values some behaviors more than others. When it comes to your work style or behavior, do you know what he likes and doesn’t like? This insight is critical to establishing a good working relationship. Obviously, if you’re doing things that annoy him, that’s not going to create a solid foundation. You need to learn his preferences and try to work within those boundaries. Yes, that might mean adapting your style a bit, but if you want to improve the relationship, you need to figure out what he wants from you, and make adjustments.

For example, how does he feel about being on time for meetings? Is it acceptable to call and ask for more time on an assignment? Does he like you to run ideas by him, or does he let you make decisions? Does he want to know where you are throughout the day? Does he want you to e-mail back immediately, or do you have until the end of the day? How does he feel about you working from home? Does he want you to stay in touch when you’re on vacation? What does he think of your work space?

These may seem like trivial examples, but I’ve seen every one of these become a big issue. There are dozens of boss preferences you have to learn, from presentation routines and travel habits to meeting behavior and clothing styles. The problem is, your boss won’t always say, This is a big deal to me—and often, he wants you to figure it out. So if he gets annoyed by late arrivals, be on time for the meeting (in that exact moment, this is what your boss wants from you). If he likes immediate e-mail replies, respond to his question as soon as possible. If he tells you, Don’t even think about the office while you’re on vacation (but you know he doesn’t really mean it), trust your instincts and check in occasionally.

I see this “preferences disconnect” all the time in mycoaching practice. I worked with Harriet, who had arranged to start work early in the morning, allowing her to leave at 4:00 p.m. The boss agreed to this arrangement, even though the rest of the team worked a more traditional work schedule. Sure enough, when I was collecting feedback, the boss told me he was concerned about Harriet’s habit of leaving early. This is a perfect example of the boss using preferences to judge performance (in this case, favoring people who stayed late). The hours and output were the same, but he was having a difficult time overcoming his own biases. The only recourse for Harriet was to remind him of their agreement and prompt him to stay open-minded about his commitment. But she has to stay alert to his mood on this issue, and be proactive about addressing it.

Another example is Robert, whose boss insisted he copy him on all e-mails sent to any VP (and above) in the organization. The explanation had something to do with “alignment” or “mission clarity” but the underlying reason was pure paranoia. The boss was a control freak and afraid of being left out of the loop. Robert tried to reason with the boss, but wasn’t successful—this was his standing e-mail edict. So Robert had two choices: find another role in the company, or learn to live with this relatively minor annoyance. He chose to live with it, and eventually established his own credibility with his boss’s peers.

Of course, the flip side of what he prefers is what he doesn’t want you doing. Developing a close relationship with one of his peers is often frowned upon. Some bosses don’t want you to speak to their boss without them in the room. Others don’t want you asking questions in all-hands meetings or volunteering for extra work around the company. Some bosses don’t want you going to industry events; others don’t want you becoming a known player in your field. Frankly, there are just as many“don’ts” as there are “do’s” when it comes to what behavior your boss wants from you. The bottom line is that you have to learn both the positive and negative preferences—what he tends to reward and what he disapproves of—in order to truly understand his attitude or actions. I recommend making a do-and-don’t list and checking it with a trusted peer. Don’t get hung up on whether these preferences are right or wrong, or logical or paranoid. Oftentimes they are just minor irritations, but if you ignore them, they can turn into bigger issues for you.

My advice is to study the results, not just the stated direction. In other words, trust what you see, not what he says. Study how he rewards or punishes certain behaviors, and you’ll learn his preferences. Pay attention to what happens to people who meet or miss those preferences. Don’t ignore the clear signs or clues out there; he is sending dozens of signals each day about what he wants from you. All you have to do is raise your level of awareness and react in a way that best serves your overall goal, which is improving the relationship.